CN111519438A - Antibacterial and antiviral finishing agent and preparation method and use method thereof - Google Patents
Antibacterial and antiviral finishing agent and preparation method and use method thereof Download PDFInfo
- Publication number
- CN111519438A CN111519438A CN202010371528.5A CN202010371528A CN111519438A CN 111519438 A CN111519438 A CN 111519438A CN 202010371528 A CN202010371528 A CN 202010371528A CN 111519438 A CN111519438 A CN 111519438A
- Authority
- CN
- China
- Prior art keywords
- glycyrrhetinic acid
- beta
- modified
- antibacterial
- cation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 47
- 230000000840 anti-viral effect Effects 0.000 title claims abstract description 47
- 238000000034 method Methods 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title abstract description 27
- -1 cation modified 18 β -glycyrrhetinic acid Chemical class 0.000 claims abstract description 51
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 48
- 239000004744 fabric Substances 0.000 claims abstract description 24
- 239000003242 anti bacterial agent Substances 0.000 claims abstract description 16
- 239000002994 raw material Substances 0.000 claims abstract description 16
- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- MPDGHEJMBKOTSU-YKLVYJNSSA-N 18beta-glycyrrhetic acid Chemical class C([C@H]1C2=CC(=O)[C@H]34)[C@@](C)(C(O)=O)CC[C@]1(C)CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@H](O)C1(C)C MPDGHEJMBKOTSU-YKLVYJNSSA-N 0.000 claims description 47
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 32
- MPDGHEJMBKOTSU-UHFFFAOYSA-N Glycyrrhetinsaeure Natural products C12C(=O)C=C3C4CC(C)(C(O)=O)CCC4(C)CCC3(C)C1(C)CCC1C2(C)CCC(O)C1(C)C MPDGHEJMBKOTSU-UHFFFAOYSA-N 0.000 claims description 24
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 20
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 20
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 239000012224 working solution Substances 0.000 claims description 16
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical group [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 150000004714 phosphonium salts Chemical group 0.000 claims description 10
- 230000003213 activating effect Effects 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 229910001961 silver nitrate Inorganic materials 0.000 claims description 7
- 150000001408 amides Chemical class 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 230000032050 esterification Effects 0.000 claims description 5
- 238000005886 esterification reaction Methods 0.000 claims description 5
- 238000007730 finishing process Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 239000012046 mixed solvent Substances 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical group CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 claims description 4
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical group C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 claims description 4
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 4
- 230000004913 activation Effects 0.000 claims description 2
- 230000009435 amidation Effects 0.000 claims description 2
- 238000007112 amidation reaction Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229960004198 guanidine Drugs 0.000 claims 11
- KTAKAALUQFRMOJ-UHFFFAOYSA-M triphenyl(propoxycarbonyl)phosphanium bromide Chemical group [Br-].CCCOC(=O)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 KTAKAALUQFRMOJ-UHFFFAOYSA-M 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 4
- 230000008859 change Effects 0.000 abstract description 3
- 230000005764 inhibitory process Effects 0.000 abstract description 3
- 241000588724 Escherichia coli Species 0.000 abstract description 2
- 241000191967 Staphylococcus aureus Species 0.000 abstract description 2
- 230000000052 comparative effect Effects 0.000 description 23
- 238000001514 detection method Methods 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 238000012544 monitoring process Methods 0.000 description 6
- 229910052709 silver Inorganic materials 0.000 description 6
- 239000004332 silver Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 239000004753 textile Substances 0.000 description 5
- 125000002091 cationic group Chemical group 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 241000700605 Viruses Species 0.000 description 3
- 238000002845 discoloration Methods 0.000 description 3
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 238000002390 rotary evaporation Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 238000005189 flocculation Methods 0.000 description 2
- 230000016615 flocculation Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 241000712461 unidentified influenza virus Species 0.000 description 2
- 238000004383 yellowing Methods 0.000 description 2
- GDPNZLVMHDCVHD-UHFFFAOYSA-N CCCOC(C(C=CC=C1)=C1P(C1=CC=CC=C1)C1=CC=CC=C1)=O.Br Chemical compound CCCOC(C(C=CC=C1)=C1P(C1=CC=CC=C1)C1=CC=CC=C1)=O.Br GDPNZLVMHDCVHD-UHFFFAOYSA-N 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- 206010069767 H1N1 influenza Diseases 0.000 description 1
- 241000588747 Klebsiella pneumoniae Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- MGIYRDNGCNKGJU-UHFFFAOYSA-N isothiazolinone Chemical compound O=C1C=CSN1 MGIYRDNGCNKGJU-UHFFFAOYSA-N 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000007102 metabolic function Effects 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 230000004202 respiratory function Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 201000010740 swine influenza Diseases 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- ICUTUKXCWQYESQ-UHFFFAOYSA-N triclocarban Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC1=CC=C(Cl)C(Cl)=C1 ICUTUKXCWQYESQ-UHFFFAOYSA-N 0.000 description 1
- 229960001325 triclocarban Drugs 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
-
- 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
- D06M11/58—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 nitrogen or compounds thereof, e.g. with nitrides
- D06M11/64—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 nitrogen or compounds thereof, e.g. with nitrides with nitrogen oxides; with oxyacids of nitrogen or their salts
- D06M11/65—Salts of oxyacids of nitrogen
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Textile Engineering (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses an antibacterial and antiviral finishing agent and a preparation method and a using method thereof, the finishing agent is prepared from the following raw materials, by weight, 20-50 parts of cation modified 18 β -glycyrrhetinic acid, 10-20 parts of silver ion antibacterial agent and 30-60 parts of water, wherein the cation modified 18 β -glycyrrhetinic acid has the following structural formula:
Description
Technical Field
The invention relates to a finishing agent and a preparation method and a using method thereof, in particular to an antibacterial and antiviral finishing agent and a preparation method and a using method thereof.
Background
Due to climate warming and the like, the transmission of bacterial viruses increasingly threatens the health of people, and textiles are the main medium for the propagation and transmission of the microorganisms. In recent years, textile sanitation finishing (antibacterial and deodorant finishing or microbial finishing) attracts attention and has rapidly developed. There are many brands of antibacterial textiles on the market, but most of them only have antibacterial efficacy and do not meet the antiviral requirements. The antibacterial and antiviral finishing agent can be divided into two categories of natural products and synthetic products. The natural finishing agent has the greatest advantages of good safety to human bodies and the defects of low antibacterial and antiviral efficiency and high cost. The finishing agent of the composition mainly comprises quaternary ammonium salt, triclocarban, isothiazolinone, silver ion compound and the like. The cationic antibacterial agent such as quaternary ammonium salt can be combined with negative charges on the cell surface to destroy the transport function, metabolic function and respiratory function of substances inside and outside the cell membrane; but the cationic antibacterial agent has a weak antiviral effect and a slow rate. Silver ions can disrupt the protein replication of bacteria and viruses. The silver ion has two difficulties for antibacterial and antiviral finishing, and firstly, the silver ion has good inhibition effect on gram-negative bacteria, gram-positive bacteria and viruses, but has unsatisfactory antifungal effect; secondly, silver ions encounter substances such as oxygen, sulfur and the like in the air and generate obvious color change after being heated or stored for a long time.
Disclosure of Invention
The purpose of the invention is as follows: the first purpose of the invention is to provide an antibacterial, antiviral and oxidation discoloration-resistant antibacterial and antiviral finishing agent, the second purpose of the invention is to provide a preparation method of cation modified 18 beta-glycyrrhetinic acid, the third purpose of the invention is to provide a preparation method of the finishing agent, and the fourth purpose of the invention is to provide a use method of the finishing agent.
The technical scheme is as follows: the antibacterial and antiviral finishing agent is prepared from the following raw material components, by weight, 20-50 parts of cation modified 18 beta-glycyrrhetinic acid, 10-20 parts of silver ion antibacterial agent and 30-60 parts of water, wherein the cation modified 18 beta-glycyrrhetinic acid has the following structural formula:
the preparation method of the cation modified 18 beta-glycyrrhetinic acid comprises the following steps: firstly, combining organic guanidine and 30-site carboxyl of 18 beta-glycyrrhetinic acid to generate amide to prepare organic guanidine modified 18 beta-glycyrrhetinic acid, and then esterifying 3-site hydroxyl of quaternary phosphonium salt and organic guanidine modified 18 beta-glycyrrhetinic acid to prepare cation modified 18 beta-glycyrrhetinic acid.
Further, the amidation of the 30-position carboxyl of the organic guanidine and 18 beta-glycyrrhetinic acid comprises the following steps: dissolving 18 beta-glycyrrhetinic acid in a mixed solvent of ethanol and dimethyl sulfoxide, adding an activating agent and a condensing agent for activation for 1-2h, adding organic guanidine for reaction for 18-24h, recrystallizing with acetone after the reaction is finished, and drying in vacuum, wherein the mass ratio of the 18 beta-glycyrrhetinic acid to the organic guanidine is 2: 5-10.
Further, the esterification of quaternary phosphonium salt and 3-hydroxyl of 18 beta-glycyrrhetinic acid modified by organic guanidine comprises the following steps: dissolving quaternary phosphonium salt in dimethylformamide, adding organic guanidine modified 18 beta-glycyrrhetinic acid, adding pyridine, heating and refluxing for 2-4h, cooling after the reaction is finished, concentrating, purifying, and concentrating again, wherein the mass ratio of the quaternary phosphonium salt to the organic guanidine modified 18 beta-glycyrrhetinic acid is 5: 1-3.
The preparation method of the antibacterial and antiviral finishing agent comprises the following steps: mixing the cation modified 18 beta-glycyrrhetinic acid and water, and adding the silver ion antibacterial agent.
The use method of the antibacterial and antiviral finishing agent comprises the following steps: preparing the antibacterial and antiviral finishing agent into working solution of 30-60g/L, and adding the working solution in the after-finishing process of the fabric.
Has the advantages that: compared with the prior art, the invention has the following remarkable advantages:
(1) polyhexamethylene guanidine adopted for modifying 18 beta-glycyrrhetinic acid in the antibacterial and antiviral finishing agent is a cationic antibacterial agent with excellent water solubility, can remarkably increase the water solubility of 18 beta-glycyrrhetinic acid, and creates conditions for dyeing and finishing processing; meanwhile, a quaternary phosphonium salt antibacterial agent (3-propylcarboxyl) triphenyl phosphine bromide is introduced, so that the antibacterial property of the 18 beta-glycyrrhetinic acid can be synergistically improved; after the cation modified 18 beta-glycyrrhetinic acid and the silver ion antibacterial agent are compounded, the antiviral activity and the antiviral rate of a system can be effectively improved; the 18 beta-glycyrrhetinic acid has excellent reducing effect, and the 11-carbonyl group has chelating effect on silver ions, so that the stability of the silver ions can be improved, and the problem of oxidative discoloration of fabrics after the cationic antibacterial agent and the silver ion antibacterial agent are used for finishing cloth surfaces is effectively solved;
(2) the preparation method is simple to operate and easy to realize;
(3) the finished fabric has quick and excellent antibacterial and antiviral effects, has obvious inhibition effects on escherichia coli, staphylococcus aureus, klebsiella pneumoniae, candida albicans, H1N1 influenza virus and H3N2 influenza virus, has no color change risk after long-term storage of the finished fabric surface, and has no influence on the whiteness of the bleached fabric.
Detailed Description
The technical solution of the present invention is further illustrated by the following examples.
Example 1
The antibacterial and antiviral finishing agent is prepared from the following raw material components, by weight, 20 parts of cation modified 18 beta-glycyrrhetinic acid, 10 parts of silver nitrate and 30 parts of water, wherein the cation modified 18 beta-glycyrrhetinic acid has the following structural formula:
the preparation method of the cation modified 18 beta-glycyrrhetinic acid comprises the following steps: firstly, 30-site carboxyl of PHMG and 18 beta-glycyrrhetinic acid is combined to generate amide, and then CPTPPB and 3-site hydroxyl of PHMG modified 18 beta-glycyrrhetinic acid are esterified to prepare cation modified 18 beta-glycyrrhetinic acid.
The 30-position carboxyamidation of PHMG and 18 beta-glycyrrhetinic acid comprises the following steps: dissolving 2g of 18 beta-glycyrrhetinic acid in 50mL of mixed solvent of ethanol and dimethyl sulfoxide, wherein the volume ratio of the ethanol to the dimethyl sulfoxide is 1:1, adding an activating agent 1-hydroxybenzotriazole HOBt and a condensing agent diisopropyl carbodiimide DIC, activating at room temperature for 1h, adding 5g of PHMG, reacting at room temperature for 18h, monitoring the reaction by TLC, recrystallizing with acetone after the reaction is finished, and drying in vacuum to obtain a water-soluble white solid with the yield of 79%.
The esterification of 3-hydroxyl of CPTPPB and PHMG modified 18 beta-glycyrrhetinic acid comprises the following steps: dissolving 10g of CPTPPB in 50mL of DMF, adding 2g of PHMG modified 18 beta-glycyrrhetinic acid, adding pyridine, heating and refluxing for 2h, monitoring the reaction by TLC, naturally cooling after the reaction is finished, concentrating the solution, purifying by silica gel column and chromatography, carrying out rotary evaporation and concentration on petroleum ether/ethyl acetate (4:1, v/v) under the chromatography condition to obtain a water-soluble white or light yellow solid, wherein the yield is 72%, the polymerization degree n of PHMG is 50, and the molecular weight of PHMG is 8000.
The preparation method of the antibacterial and antiviral finishing agent comprises the following steps: mixing the cation modified 18 beta-glycyrrhetinic acid and water, and adding the silver ion antibacterial agent.
The use method of the antibacterial and antiviral finishing agent comprises the following steps: the antibacterial and antiviral finishing agent is prepared into 30g/L working solution, and the working solution is added in the fabric after-finishing process.
Example 2
The antibacterial and antiviral finishing agent is prepared from the following raw material components, by weight, 50 parts of cation modified 18 beta-glycyrrhetinic acid, 20 parts of silver nitrate and 60 parts of water, wherein the cation modified 18 beta-glycyrrhetinic acid has the following structural formula:
the preparation method of the cation modified 18 beta-glycyrrhetinic acid comprises the following steps: firstly, 30-site carboxyl of PHMG and 18 beta-glycyrrhetinic acid is combined to generate amide, and then CPTPPB and 3-site hydroxyl of PHMG modified 18 beta-glycyrrhetinic acid are esterified to prepare cation modified 18 beta-glycyrrhetinic acid.
The 30-position carboxyamidation of PHMG and 18 beta-glycyrrhetinic acid comprises the following steps: dissolving 2g of 18 beta-glycyrrhetinic acid in 50mL of mixed solvent of ethanol and dimethyl sulfoxide, wherein the volume ratio of the ethanol to the dimethyl sulfoxide is 1:5, adding an activating agent 1-hydroxybenzotriazole HOBt and a condensing agent diisopropyl carbodiimide DIC, activating at room temperature for 2h, adding 10g of PHMG, reacting at room temperature for 24h, monitoring the reaction by TLC, recrystallizing with acetone after the reaction is finished, and drying in vacuum to obtain a water-soluble white solid with the yield of 92%.
The esterification of 3-hydroxyl of CPTPPB and PHMG modified 18 beta-glycyrrhetinic acid comprises the following steps: dissolving 10g of CPTPPB in 50mL of DMF, adding 6g of PHMG modified 18 beta-glycyrrhetinic acid, adding pyridine, heating and refluxing for 4h, monitoring the reaction by TLC, naturally cooling after the reaction is finished, concentrating the solution, purifying by silica gel column and chromatography, carrying out rotary evaporation and concentration on petroleum ether/ethyl acetate (4:1, v/v) under the chromatography condition to obtain a water-soluble white or light yellow solid, wherein the yield is 89%, the polymerization degree n of PHMG is 100, and the molecular weight of PHMG is 15000.
The preparation method of the antibacterial and antiviral finishing agent comprises the following steps: mixing the cation modified 18 beta-glycyrrhetinic acid and water, and adding the silver ion antibacterial agent.
The use method of the antibacterial and antiviral finishing agent comprises the following steps: the antibacterial and antiviral finishing agent is prepared into 60g/L working solution, and the working solution is added in the fabric after-finishing process.
Example 3
The antibacterial and antiviral finishing agent is prepared from the following raw material components, by weight, 40 parts of cation modified 18 beta-glycyrrhetinic acid, 15 parts of silver nitrate and 40 parts of water, wherein the cation modified 18 beta-glycyrrhetinic acid has the following structural formula:
the preparation method of the cation modified 18 beta-glycyrrhetinic acid comprises the following steps: firstly, 30-site carboxyl of PHMG and 18 beta-glycyrrhetinic acid is combined to generate amide, and then CPTPPB and 3-site hydroxyl of PHMG modified 18 beta-glycyrrhetinic acid are esterified to prepare cation modified 18 beta-glycyrrhetinic acid.
The 30-position carboxyamidation of PHMG and 18 beta-glycyrrhetinic acid comprises the following steps: dissolving 2g of 18 beta-glycyrrhetinic acid in 50mL of mixed solvent of ethanol and dimethyl sulfoxide, wherein the volume ratio of the ethanol to the dimethyl sulfoxide is 1:3, adding an activating agent 1-hydroxybenzotriazole HOBt and a condensing agent diisopropyl carbodiimide DIC, activating at room temperature for 1.5h, adding 7g of PHMG, reacting at room temperature for 20h, monitoring by TLC, recrystallizing with acetone after the reaction is finished, and drying in vacuum to obtain a water-soluble white solid with the yield of 85%.
The esterification of 3-hydroxyl of CPTPPB and PHMG modified 18 beta-glycyrrhetinic acid comprises the following steps: dissolving 10g of CPTPPB in 50mL of DMF, adding 4g of PHMG modified 18 beta-glycyrrhetinic acid, adding pyridine, heating and refluxing for 3h, monitoring the reaction by TLC, naturally cooling after the reaction is finished, concentrating the solution, purifying by silica gel column and chromatography, carrying out rotary evaporation and concentration on petroleum ether/ethyl acetate (4:1, v/v) under the chromatography condition to obtain a water-soluble white or light yellow solid with the yield of 80 percent, the polymerization degree n of PHMG of 70 and the molecular weight of PHMG of 11000.
The preparation method of the antibacterial and antiviral finishing agent comprises the following steps: mixing the cation modified 18 beta-glycyrrhetinic acid and water, and adding the silver ion antibacterial agent.
The use method of the antibacterial and antiviral finishing agent comprises the following steps: the antibacterial and antiviral finishing agent is prepared into 45g/L working solution, and the working solution is added in the fabric after-finishing process.
Comparative example 1
In the comparative example, the cation modified 18 beta-glycyrrhetinic acid is 18 parts, and other raw materials, the proportion, the preparation method and the detection method are the same as those in the example 1.
Comparative example 2
In the comparative example, the cation modified 18 beta-glycyrrhetinic acid is 52 parts, and other raw materials, the proportion, the preparation method and the detection method are the same as those in the example 1.
Comparative example 3
In the comparative example, 8 parts of silver nitrate is used, and other raw materials, proportion, preparation methods and detection methods are the same as those in example 1.
Comparative example 4
In the comparative example, 22 parts of silver nitrate is used, and other raw materials, proportion, preparation methods and detection methods are the same as those in example 1.
Comparative example 5
In the comparative example, 4g of PHMG was used, and the other raw materials, compounding ratio, preparation method and detection method were the same as those in example 1.
Comparative example 6
In this comparative example, PHMG was 11g, and other raw materials, compounding ratio, production method and detection method were the same as those in example 1.
Comparative example 7
In the comparative example, the amount of the PHMG-modified 18 beta-glycyrrhetinic acid is 1g, and other raw materials, mixture ratio, preparation methods and detection methods are the same as those in example 1.
Comparative example 8
In the comparative example, the amount of the modified 18 beta-glycyrrhetinic acid PHMG is 7g, and other raw materials, mixture ratio, preparation methods and detection methods are the same as those in example 1.
Comparative example 9
The concentration of the working solution in the comparative example is 20g/L, and other raw materials, mixture ratio, preparation method and detection method are the same as those in example 1.
Comparative example 10
The concentration of the working solution in the comparative example is 70g/L, and other raw materials, mixture ratio, preparation method and detection method are the same as those in example 1.
The fabric antibacterial performance detection method refers to GB/T20944.2-2013 textile antibacterial performance evaluation part 2: absorption method; the fabric antiviral performance detection method refers to ISO 18184 and 2019 determination of textile antiviral activity; the solubility of the system and the discoloration condition of the fabric are both determined by visual inspection, and the detection results are shown in Table 1.
TABLE 1 antibacterial and antiviral property test results of fabrics
Compared with the example 1, the antibacterial and antiviral finishing agent has lower content of the cation modified 18 beta-glycyrrhetinic acid, is not enough to completely chelate silver ions, and is easy to produce flocculation or precipitates in a system. In addition, the finished fabric has the risk of blackening and yellowing due to oxidation.
Compared with the example 1, the content of the cationic modified 18 beta-glycyrrhetinic acid in the antibacterial and antiviral finishing agent is higher than the saturated solubility, and the cationic modified 18 beta-glycyrrhetinic acid cannot be completely dissolved in a formula system.
Compared with the example 1, the antibacterial and antiviral finishing agent has lower silver ion content, and the antiviral activity value of the finished fabric can not meet the standard requirement.
Compared with the example 1, the content of silver nitrate in the antibacterial and antiviral finishing agent is higher, more free silver ions exist in the system, and flocculation or precipitates are easy to produce. In addition, the finished fabric has the risk of blackening and yellowing due to oxidation.
Compared with the example 1, the comparative example 5 has less PHMG grafted on the 30-carboxyl of the 18 beta glycyrrhetinic acid, and the solubility of the modified 18 beta glycyrrhetinic acid is not ideal, so that the subsequent preparation requirement cannot be met.
Compared with the example 1, the comparative example 6 has the advantages that more PHMG is grafted on the carboxyl at the 30-site of the 18 beta glycyrrhetinic acid, the obtained cation modified 18 beta glycyrrhetinic acid has stronger ionic property, and the cloth surface after finishing is seriously yellowed.
Compared with the example 1, the CPTPPB grafted on the hydroxyl at the 3-position of the PHMG-modified 18 beta glycyrrhetinic acid is more, the CPTPPB is water-insoluble, and the solubility of the obtained cation-modified 18 beta glycyrrhetinic acid is not ideal, so that the subsequent preparation requirement cannot be met.
Compared with example 1, the CPTPPB grafted on the hydroxyl at the 3-position of the PHMG-modified 18 beta glycyrrhetinic acid is less, and the obtained cation-modified 18 beta glycyrrhetinic acid has poorer antibacterial property.
Compared with the working solution of the embodiment 1, the working solution concentration of the comparative example 9 is low, and the antibacterial rate and the antiviral activity value of the finished fabric are not ideal and do not meet the standard requirements.
Compared with the working solution in the example 1, although the concentration of the working solution is increased, the antibacterial rate and the antiviral activity of the finished fabric are not increased any more, and the hand feeling of the fabric is also affected by the increase of the content of the auxiliary agent in the fabric.
Claims (10)
1. An antibacterial and antiviral finishing agent is characterized by comprising the following raw material components, by weight, 20-50 parts of cation modified 18 beta-glycyrrhetinic acid, 10-20 parts of silver ion antibacterial agent and 30-60 parts of water, wherein the cation modified 18 beta-glycyrrhetinic acid has the following structural formula:
2. the antibacterial and antiviral finish according to claim 1, characterized in that: the silver ion antibacterial agent is silver nitrate.
3. A method for preparing the cation-modified 18 β -glycyrrhetinic acid of claim 1, comprising the steps of: firstly, combining organic guanidine and 30-site carboxyl of 18 beta-glycyrrhetinic acid to generate amide to prepare organic guanidine modified 18 beta-glycyrrhetinic acid, and then esterifying quaternary phosphonium salt and 3-site hydroxyl of the organic guanidine modified 18 beta-glycyrrhetinic acid to prepare cation modified 18 beta-glycyrrhetinic acid.
4. The method for preparing the cation-modified 18 β -glycyrrhetinic acid according to claim 3, wherein the amidation of the 30-position carboxyl group of the organic guanidine and 18 β -glycyrrhetinic acid comprises the steps of: dissolving 18 beta-glycyrrhetinic acid in a mixed solvent of ethanol and dimethyl sulfoxide, adding an activating agent and a condensing agent for activation for 1-2h, adding organic guanidine for reaction for 18-24h, recrystallizing with acetone after the reaction is finished, and drying in vacuum, wherein the mass ratio of the 18 beta-glycyrrhetinic acid to the organic guanidine is 2: 5-10.
5. The method for preparing the cation-modified 18 β -glycyrrhetinic acid according to claim 4, characterized in that: the activating agent is 1-hydroxybenzotriazole, and the condensing agent is diisopropylcarbodiimide.
6. The method for preparing the cation-modified 18 β -glycyrrhetinic acid according to claim 4, characterized in that: the volume ratio of the ethanol to the dimethyl sulfoxide is 1: 1-5.
7. The method for preparing the cation-modified 18 β -glycyrrhetinic acid according to claim 3, wherein the esterification of the quaternary phosphonium salt with the hydroxyl group at the 3-position of the organic guanidine-modified 18 β -glycyrrhetinic acid comprises the steps of: dissolving a quaternary phosphonium salt in dimethylformamide, adding organic guanidine modified 18 beta-glycyrrhetinic acid, adding pyridine, heating and refluxing for 2-4h, cooling after the reaction is finished, concentrating, purifying, and concentrating again, wherein the mass ratio of the quaternary phosphonium salt to the organic guanidine modified 18 beta-glycyrrhetinic acid is 5: 1-3.
8. The method for preparing the cation-modified 18 β -glycyrrhetinic acid according to claim 3, characterized in that: the organic guanidine is polyhexamethylene guanidine hydrochloride, the polymerization degree of the organic guanidine is 50-100, and the molecular weight of the organic guanidine is 8000-15000; the quaternary phosphonium salt is (3-propyl carboxyl) triphenyl phosphonium bromide.
9. A process for preparing the antibacterial and antiviral finishing agent according to claim 1, comprising the steps of: mixing the cation modified 18 beta-glycyrrhetinic acid with water, and adding a silver ion antibacterial agent.
10. A method of using the antibacterial and antiviral finish of claim 1, comprising the steps of: preparing 30-60g/L working solution from the antibacterial and antiviral finishing agent, and adding the working solution in the fabric after-finishing process.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010371528.5A CN111519438A (en) | 2020-05-06 | 2020-05-06 | Antibacterial and antiviral finishing agent and preparation method and use method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010371528.5A CN111519438A (en) | 2020-05-06 | 2020-05-06 | Antibacterial and antiviral finishing agent and preparation method and use method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN111519438A true CN111519438A (en) | 2020-08-11 |
Family
ID=71907044
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010371528.5A Pending CN111519438A (en) | 2020-05-06 | 2020-05-06 | Antibacterial and antiviral finishing agent and preparation method and use method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111519438A (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101200488A (en) * | 2007-12-07 | 2008-06-18 | 北京润德康医药技术有限公司 | Novel biogastrone acid derivatives, preparation method and medical uses thereof |
| CN101747404A (en) * | 2009-12-17 | 2010-06-23 | 中国海洋大学 | Glycyrrhetinic acid cyclic phosphonate ester derivative and preparation method thereof |
| CN103668544A (en) * | 2013-12-11 | 2014-03-26 | 浙江华峰氨纶股份有限公司 | Polyurethane elastic fibers with multielement functionality and preparation method thereof |
| CN106758216A (en) * | 2016-12-02 | 2017-05-31 | 辽东学院 | A kind of processing method of antibacterial, uvioresistant bafta |
-
2020
- 2020-05-06 CN CN202010371528.5A patent/CN111519438A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101200488A (en) * | 2007-12-07 | 2008-06-18 | 北京润德康医药技术有限公司 | Novel biogastrone acid derivatives, preparation method and medical uses thereof |
| CN101747404A (en) * | 2009-12-17 | 2010-06-23 | 中国海洋大学 | Glycyrrhetinic acid cyclic phosphonate ester derivative and preparation method thereof |
| CN103668544A (en) * | 2013-12-11 | 2014-03-26 | 浙江华峰氨纶股份有限公司 | Polyurethane elastic fibers with multielement functionality and preparation method thereof |
| CN106758216A (en) * | 2016-12-02 | 2017-05-31 | 辽东学院 | A kind of processing method of antibacterial, uvioresistant bafta |
Non-Patent Citations (1)
| Title |
|---|
| 周莹等: "植物源抗菌剂在纺织工业中的应用及前景", 《现代纺织技术》 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN109608554B (en) | Preparation method of antibacterial cationic nano-fibrillated cellulose | |
| CN102492182B (en) | Biofilms of rare-earth element contained chitosan and/or derivatives of chitosan | |
| CN104878589A (en) | Preparation method of finishing agent of textiles | |
| CN108468211B (en) | Anti-yellowing agent and preparation method thereof | |
| CN111519438A (en) | Antibacterial and antiviral finishing agent and preparation method and use method thereof | |
| CN1036727C (en) | Antibiotic health fabric and its prepn method and application | |
| CN111364115A (en) | Antibacterial polyester fiber and fabric | |
| CN115262227B (en) | Antibacterial finishing agent and preparation method and application thereof | |
| JPH09157113A (en) | Antimicrobial agent | |
| CN112042673B (en) | Silver fulvate antibacterial agent, preparation method and application thereof, and nylon material | |
| CN109369910A (en) | Antibacterial monomer and its preparation method and application based on polyethyleneimine-modified | |
| CN113981563A (en) | Antibacterial polyester high stretch yarn and preparation method thereof | |
| CN113152089A (en) | Preparation method of antibacterial fabric | |
| CN112790195B (en) | Mildew-proof adhesive and preparation method and application thereof | |
| JP2976261B2 (en) | Antibacterial protein | |
| CN111440674A (en) | Liquid detergent with mite removing effect | |
| CN111957266B (en) | Antibacterial surfactant and antibacterial and bacteriostatic application thereof in daily chemical products | |
| CN110313487B (en) | Novel leather mildew-proof nursing agent and preparation method and application thereof | |
| CN110352959B (en) | Antibacterial preservative film and preparation method and application thereof | |
| JPH10237320A (en) | Antimicrobial resin composition and antimicrobial resin molded product using the same | |
| CN111574710B (en) | Dendritic tryptophan compound, preparation method thereof and application thereof as antibacterial agent | |
| CN117063933B (en) | Kasugamycin organic acid salt, pesticide composition containing kasugamycin organic acid salt and application of kasugamycin organic acid salt | |
| CN108071049A (en) | A kind of super-strong moisture absorbing paper handkerchief with antibiotic property | |
| DE2357278B2 (en) | Ampholytes, processes for their production and detergents, cleaning agents and disinfectants containing them | |
| CN108976213B (en) | Halamine antibacterial agent containing double active groups and preparation method and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20200811 |