A kind of betaine type antibacterial finishing agent and preparation method thereof

An antibacterial finishing agent and betaine technology, which is applied in the field of betaine antibacterial finishing agent and its preparation, can solve the problems of easy dissolution of quaternary ammonium salts, poor stability of reactive groups, lack of reactive functional groups, etc., and improve air permeability and moisture permeability , improve the hydrophilic performance, and the effect of simple synthesis method

Active Publication Date: 2019-06-07
JIANGNAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, the commonly used antibacterial finishing agents mainly include inorganic antibacterial agents (nano TiO 2 , nano Ag and their ions, etc.), organic antibacterial agents (quaternary ammonium salts, haloamine compounds, etc.), natural antibacterial agents (chitosan and its derivatives, etc.), but these antibacterial agents have various problems that limit their application
Heavy metals and their ions (Ag, Cu, etc.) are easy to dissolve, causing heavy metal pollution and affecting the surface color of materials; photocatalytic metal oxides (TiO 2 ) only have antibacterial properties under ultraviolet light irradiation conditions, and may also cause fabric degradation; quaternary ammonium salt antibacterial agents have poor compatibility with anionic additives, poor heat resistance, and are prone to yellowing and discoloration of fabrics, and unfixed quaternary ammonium antibacterial agents Ammonium salts are easy to dissolve, which may cause drug resistance; haloamine compounds need to be regenerated, and residual chlorine on textiles will produce odors and damage fibers; chitosan and its derivatives are only antibacterial under acidic conditions, durability, and heat resistance Poor resistance and water solubility, and affect the fabric feel
[0004] Marty Ward et al. (Marty Ward, Sanchez M, Elasri M O, et al. Antimicrobial activity of statistical polymethacrylic sulfopropylbetaines against gram-positive and gram-negative bacteria [J]. Journal of Applied Polymer Science, 2006, 101(2): 1036–1041 .) Prepared a series of sulfobetaine polymer antibacterial agents, the minimum inhibitory concentration MIC to E. Lack of reactive functional groups, unable to chemically bond with the material surface, poor antibacterial durability and bring endless pressure to the environment
Shiguo Chen et al. (Chen S, Chen S, Jiang S, et al.Environmentally Friendly Antibacterial Cotton Textiles Finished with Siloxane Sulfopropylbetaine[J].Applied Materials&Interfaces,2011,3(4):1154-1162.) prepared a reaction The organosilicon sulfobetaine antibacterial agent with sexual functional group, the silanol group formed after the hydrolysis of the siloxane group can react with the hydroxyl group on the cotton fiber, and form a stable antibacterial coating on the surface of the cotton fabric, which is effective against Escherichia coli (E.coli ) and Staphylococcus aureus (S.aureus) have an antibacterial rate of more than 99%, but the presence of Si-O causes the antibacterial agent to self-polymerize easily, and the stability of the reactive group is poor, so it is not resistant to long-term washing
In this regard, Shiguo Chen et al. (Chen S, Yuan L, Li Q, et al. Durable Antibacterial and Nonfouling Cotton Textiles with Enhanced Comfort via Zwitterionic Sulfopropylbetaine Coating [J]. Small, 2016, 12(26): 3516–3521.) have developed A high-efficiency broad-spectrum antibacterial antibacterial agent was prepared by using the reaction principle of -NCO and -OH and the ring-opening reaction of propane sultone and tertiary amine to prepare isocyanate sulfobetaine and apply it to the antibacterial effect of cotton fabrics Finishing, the isocyanate group (-NCO) and the hydroxyl group (-OH) on the cotton fabric are chemically bonded, so that the betaine antibacterial agent is fixed on the surface of the cotton fiber and is not easy to dissolve, but the preparation process of the antibacterial agent is complicated. Fabric reaction conditions are too harsh
Liang He et al. (He L, Gao C, Li S, et al.Non-leaching and durable antibacterial textiles finished with reactivezwitterionic sulfobetaine[J].Journal of Industrial&Engineering Chemistry,2017,46(4):373-378.) developed Triazine sulfobetaine antibacterial agent, using the covalent reaction of triazine group and cellulose hydroxyl group to prepare antibacterial cotton fabric with long-lasting antibacterial activity, the antibacterial rate of E.coli and S.aureus after 30 times of washing Still as high as more than 95%, but the preparation process of the triazine betaine is long and difficult for industrial application

Method used

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  • A kind of betaine type antibacterial finishing agent and preparation method thereof
  • A kind of betaine type antibacterial finishing agent and preparation method thereof
  • A kind of betaine type antibacterial finishing agent and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Weigh 0.6mol (51.1g) dimethylacrylamine【CH 2 =CHCH 2 N(CH 3 ) 2 】Put it into a round-bottomed flask equipped with mechanical stirring, nitrogen inlet tube, condensing reflux tube and thermometer, raise the temperature to 50°C, feed high-purity nitrogen gas for 30 minutes to remove oxygen, and slowly add propane sultone dropwise with a constant pressure funnel【 Abbreviated as 1,3-PS] 0.6mol (73.2g, dissolved in 600mL of absolute ethanol), reacted for 2 hours after the dropwise addition, and obtained a white precipitate, which was purified by rotary evaporation to obtain the product betaine monomer, whose structural formula is CH 2 =CHCH 2 + N(CH 3 ) 2 (CH 2 ) 3 SO 3 — .

[0040] Take by weighing 0.3mol (62.1g) this betaine monomer and 0.3mol (29.4g) maleic anhydride [ Abbreviated as MAH], dissolved in 350mL deionized water, put into a round-bottomed flask equipped with mechanical stirring, nitrogen gas introduction tube, condensing reflux tube and thermomet...

Embodiment 2

[0046] Weigh 0.5mol (56.5g) diethylpropenylamine【CH 2 =CHCH 2 N(CH 2 CH 3 ) 2 】Put it into a round-bottomed flask equipped with mechanical stirring, nitrogen inlet tube, condensing reflux tube and thermometer, raise the temperature to 40°C, feed high-purity nitrogen gas for 30 minutes to remove oxygen, and slowly add 0.5mol (61.1g, Dissolve 1,3-PS in 500mL acetone), react for 5 hours after the dropwise addition, and obtain a white precipitate, which is purified by rotary evaporation to obtain the product betaine monomer, whose structural formula is CH 2 =CHCH 2 + N(CH 2 CH 3 ) 2 (CH 2 ) 3 SO 3 — .

[0047] Weigh 0.5mol (103.5g) of the betaine monomer and 0.5mol (49.0g) of MAH, dissolve them in 600mL of deionized water, and add them into a round bottom flask equipped with mechanical stirring, nitrogen inlet tube, condensing reflux tube and thermometer , pass through high-purity nitrogen for 30 minutes to remove oxygen, raise the temperature to 80°C, slowly add the...

Embodiment 3

[0050] Weigh 0.4mol (34.1g) dimethylacrylamine【CH 2 =CHCH 2 N(CH 3 ) 2 】Put it into a round-bottomed flask equipped with mechanical stirring, nitrogen inlet tube, condensing reflux tube and thermometer, raise the temperature to 30°C, feed high-purity nitrogen gas for 30 minutes to remove oxygen, and slowly add butane sultone dropwise with a constant pressure funnel【 Abbreviated as 1,4-BS] 0.4mol (54.5g, dissolved in 400mL tetrahydrofuran), reacted for 8 hours after the dropwise addition, and obtained a white precipitate, which was purified by rotary evaporation to obtain the product betaine monomer, whose structural formula is CH 2 =CHCH 2 + N(CH 3 ) 2 (CH 2 ) 4 SO 3 — .

[0051] Weigh 0.6mol (124.2g) of the betaine monomer and 0.6mol (58.8g) of MAH, dissolve them in 750mL of deionized water, and add them into a round bottom flask equipped with mechanical stirring, nitrogen inlet tube, condensing reflux tube and thermometer , pass through high-purity nitrogen for ...

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Abstract

The invention discloses a betaine type antibacterial finishing agent and a preparation method thereof and belongs to the technical field of organic synthesis. A synthetic route of the betaine type antibacterial finishing agent comprises the following steps: firstly, taking olefin containing tertiary amine and a substance with a sulfonic acid or carboxylic acid group to react to generate an intermediate product betaine monomer; then taking the betaine monomer and maleic anhydride to be subjected to addition polymerization reaction to generate a betaine polymer, i.e., a target product. The antibacterial agent disclosed by the invention is green and environmentally friendly and can realize efficient and broad-spectrum antibacterial effects; meanwhile, the betaine type antibacterial finishingagent contains a reactive group, can be subjected to covalent reaction with the surface of a material and has a lasting antibacterial property. Moreover, a preparation technology of the antibacterialagent is simple and industrialization is easy to realize.

Description

technical field [0001] The invention relates to a betaine type antibacterial finishing agent and a preparation method thereof, belonging to the technical field of organic synthesis. Background technique [0002] In recent years, there have been countless cases of severe infection and death caused by pathogenic microorganisms, and the harm to human health and public health is increasing day by day. Endowing materials with antibacterial properties to inhibit the growth and reproduction of microorganisms on their surfaces is one of the effective ways to solve microbial infections and reduce cross-infection in public environments. [0003] At present, the commonly used antibacterial finishing agents mainly include inorganic antibacterial agents (nano TiO 2 , nano Ag and their ions, etc.), organic antibacterial agents (quaternary ammonium salts, haloamine compounds, etc.), natural antibacterial agents (chitosan and its derivatives, etc.), but these antibacterial agents have vari...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F226/02C08F222/06D06M15/356D06M13/463C07C309/14C07C303/32D06M101/06
CPCC07C309/14C08F222/06C08F226/02D06M13/463D06M15/3566D06M16/00D06M2101/06
Inventor 王鸿博周莉杜金梅傅佳佳
Owner JIANGNAN UNIV
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