Synthesis of a Bi-Quaternary Ammonium Salt from Rosin and its Inhibition to some Wood Decay Fungi

2012 ◽  
Vol 174-177 ◽  
pp. 478-482 ◽  
Author(s):  
Thi Thanh Hien Nguyen ◽  
Shu Jun Li ◽  
Jian Li ◽  
Yan Jin ◽  
Nan Xue Liu

An anti-fungal derivative of rosin, bi-quaternary ammonium salt (B-QAS) was synthesized. First, rosin was modified by acrylic acid. Then using this modified rosin reacted with an intermediate quaternary ammonium (epoxy propyl triethyl ammonium chloride) which was the reaction product of triethylamine and epichlorohydrin. The final product was bisN-(3-rosin acyloxy -2-hydroxy) propyl-N, N triethyl ammonium chloride. The chemical structure of the product and its functional groups was characterized by Fourier transform infrared spectroscopy (FTIR). Its yield of greater than 80% was conformed by high performance liquid chromatography (HPLC) and gravimetric analysis. Its anti-fungal activity was determined in vitro with a paper-disc method. B-QAS presented significant inhibitory effect for Trametes versicolor, Gloeophyllum trabeum and Postia placenta when its concentration was 0.5 mg/mL, whereas for Irpex lacteus the inhibitory effect was a little poor.

2011 ◽  
Vol 685 ◽  
pp. 291-297 ◽  
Author(s):  
Yan Jin ◽  
Shu Jun Li ◽  
Tao Liang ◽  
Zhi Jun Chen

Many pine trees could secrete oleo-resin when they were wounded. The oleo-resin was a mixture of turpentine and rosin. After evaporation of volatile turpentine, rosin remained and covered the wound to protect wood from fungi and insects. From this point, rosin protects wood naturally. However, rosin is not bioactive against most wood decay fungi. In this report, a bioactive rosin derivated, quaternary ammonium salt (QAS), was synthesized and its bioactivity against some wood decay fungi was tested. Firstly, the rosin was esterified by epoxy chloropropane with the mole ratio of 1:2, the reaction time of 3.5h at 90°C. The intermediate was 3-rosin acyloxy-2- hydroxypropyl chlorine. Then, the intermediate reacted with demethylamine to produce N-(3-rosin acyloxy- 2-hydroxyl) propyl-N, N dimethylamine at the following conditions: their mole ratio of 1:2, reaction temperature of 80°C and reaction time of 2.5h. Finally, the N-(3-rosin acyloxy-2-hydroxyl) propyl-N, N dimethylamine was quaternized by epoxy chloropropane with the mole ratio of 1:1, the reaction time of 3h at 90°C, and the yield was 72.8%. The chemical structure of the product was identified by FTIR and 1H NMR. The QAS content of the product was characterized by gravimetric analysis with sodium tetraphenylborate as its precipitation reagent, and liquid chromatography analysis (LC) analysis. The antifungal activity of the product was determined by paper-disc method with wood decay fungi such as Trametes versicolor, Gloeophyllum trabeum and wood stain fungi such as Aspergillus niger and Paecilomyces variot Bainier. The anti-fungal experiment results signified that the QAS of rosin is active to these fungi, especially Gloeophyllum trabeum. Since it is produced easily from rosin, which is renewable and not expensive, QAS of rosin could be a potential wood preservative. Further study is planning.


2019 ◽  
Vol 9 (1) ◽  
Author(s):  
Sanjay Kumar Tiwari ◽  
Xiao Guo ◽  
Yannan Huang ◽  
Xuedong Zhou ◽  
Hockin H. K. Xu ◽  
...  

2012 ◽  
Vol 174-177 ◽  
pp. 1433-1436 ◽  
Author(s):  
Zong Cheng Miao ◽  
Fang Wang ◽  
Deng Deng ◽  
Yong Ming Zhang ◽  
Xiao Ping Huo ◽  
...  

In order to obtain some novel cationic surfactants with high surface activity, n-octadecyldimethylamine and epichlorohydrin were used to synthesize 2-hydroxy-1, 3-dis (chloride octadecyl dimethyl ammonium) propane, which was a kind of gemini quaternary ammonium salt. N-octadecyldimethylamine and epichlorohydrin were used to prepare active epoxy intermediate glycidyloctadecyldimethyl ammonium chlorided, and then glycidyloctadecyldimethyl ammonium chlorided was reacted with octadecyldimethyl amine hydrochloride to synthesize the gemini cationic surfactant. FTIR and 1H NMR were used to represent structure of the gemini cationic surfactant. The interface characteristics were studied in detail. The critical micellar concentration (CMC) was determined by surface tension test to obtain the values of CMC and surface tension at CMC. The foam ability and foam stability of the gemini cationic surfactant were also discussed through contrast octadecyltrimethyl ammonium chloride and cetyltrimethyl ammonium chloride.


1986 ◽  
Vol 55 (01) ◽  
pp. 058-060 ◽  
Author(s):  
A M Cumming ◽  
R T Wensley ◽  
I W Delamore

SummaryFactor VIII coagulant activity (VIII: C) has been shown by several investigators to exhibit increased stability in vitro when physiological levels of plasma ionized calcium are maintained by anticoagulation with heparin rather than citrate. An increase in initial activity of VIII: C in heparin over that of VIII: C in citrate has been reported but this has not been confirmed. In order to assay VIII :C in heparinized plasma, the heparin anticoagulant effect must be excluded without interfering with the validity of the assay. A one-stage clotting assay for VIII: C has been developed where heparin is neutralized by Polybrene®, a synthetic polymerized quaternary ammonium salt. VIII :C may be accurately measured by this method which satisfies the requirements for a valid assay of parallelism and linearity.


2016 ◽  
Vol 87 (6) ◽  
pp. 759-765 ◽  
Author(s):  
W Zhang ◽  
JJ Zhou ◽  
XL Dai

The water soluble and reactive O-methyl acrylamide quaternary ammonium salt of chitosan (NMA-HTCC) was prepared with a view to develop an antibacterial finishing on cotton fabric. 2-hydroxypropyltrimethyl ammonium chloride chitosan (HTCC) was synthesized by the chemical reaction of chitosan and 2,3-epoxypropyltrimethyl ammonium chloride. Then, NMA-HTCC with reactive groups was synthesized by the chemical reaction of HTCC and N-(hydroxymethyl) –acrylamide, and its chemical structure was characterized by the Fourier transform infrared spectroscopy and nuclear magnetic resonance (NMR). The antibacterial activities of chitosan and NMA-HTCC were tested and compared by the minimal inhibitory method. Cotton fabrics were finished by NMA-HTCC under the alkalinity condition using sodium bicarbonate as the catalyst. The antibacterial activity of cotton fabric before and after finishing was measured by the oscillation flask method. The results showed that both chitosan and NMA-HTCC had a significant antibacterial effect on staphylococcus and coli, and the antibacterial activity of NMA-HTCC was better than that of chitosan. The antibacterial activity of cotton fabric to staphylococcus and coli were significantly improved after finishing by chitosan and NMA-HTCC, and the antibacterial activity of the cotton fabric finished by NMA-HTCC was better than that finished by chitosan.


Author(s):  
Ewa Obłąk ◽  
Andrzej Gamian ◽  
Ryszard Adamski ◽  
Stanisław Ułaszewski

AbstractWe investigated the action of the quaternary ammonium salt (QAS) called IM (N-(dodecyloxycarboxymethyl)-N,N,N-trimethyl ammonium chloride) on Saccharomyces cerevisiae yeast cells. Changes in the yeast cell ultrastructure were confirmed by electron microscopy. We treated resistant mutant cells with QAS, and confirmed destruction of the mutant cytoplasm, an increase in the thickness of the cell wall, separation of the cell wall from the cytoplasm, and the accumulation of numerous lipid droplets. We also observed a relatively high production of lipids in the cells of the parental wild-type strain Σ1278b and in its IM-resistant (IMR) mutant in the presence of the QAS. The IMR mutant showed increased sensitivity to CaCl2 and SDS, and resistance to ethidium bromide, chloramphenicol, erythromycin and osmotic shock. It also tolerated growth at low pH. We suggest that the resistance to IM could be connected with the level of permeability of the cell membrane because the IMR mutant was sensitive to this compound in vivo in the presence of SDS and guanidine hydrochloride, which cause increased permeability of the cell plasma membrane.


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