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

2011 ◽  
Vol 685 ◽  
pp. 291-297 ◽  
Author(s):  
Yan Jin ◽  
Shu Jun Li ◽  
Tao Liang ◽  
Zhi Jun Chen
Keyword(s):  
Reaction Time ◽  
Ammonium Salt ◽  
Quaternary Ammonium ◽  
Quaternary Ammonium Salt ◽  
Wood Decay ◽  
Wood Preservative ◽  
Gravimetric Analysis ◽  
Gloeophyllum Trabeum ◽  
Decay Fungi ◽  
Wood Decay Fungi

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.

Synthesis and Characterization of BisN-(3-rosin acyloxy-2-hydroxyl) propyl-N,N dimethylamine

2010 ◽  
Vol 113-116 ◽  
pp. 2197-2200 ◽  
Author(s):  
Shuang Yue Li ◽  
Jing Wang ◽  
Shu Jun Li ◽  
Zhi Jun Chen ◽  
Bing Tian ◽  
...  
Keyword(s):  
Aspergillus Niger ◽  
Chemical Structure ◽  
Wood Decay ◽  
Wood Preservative ◽  
Gloeophyllum Trabeum ◽  
Decay Fungi ◽  
Wood Decay Fungi ◽  
Anti Fungal ◽  
Paper Disc

An anti-fungal derivative of rosin was synthesized. First, rosin was modified by acrylic acid and the modified rosin was esterified by epoxy chloropropane with the mole ratio of 1:3 for 3.5h at 90°C. The intermediate was bis 3-rosin acyloxy-2- hydroxypropyl chlorine and the degree of esterification was 98.81%. Then, bisN-(3-rosin acyloxy-2-hydroxyl) propyl-N,N dimethylamine was made from the intermediate under the following conditions: the intermediate and dimethylamine mole ratio of 1:2, reaction temperature of 80°C and reaction time of 2.5h. The chemical structure of the product was identified by Fourier transform infrared spectroscopy (FTIR). The anti-fungal 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 bisN-(3-rosin acyloxy-2-hydroxyl) propyl-N, N dimethylamine is active vs. these fungi, but less effective with Aspergillus niger. Since it is produced easily from rosin, which is renewable and not expensive, this product has a promising future as a potential wood preservative.

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
Keyword(s):  
Ammonium Chloride ◽  
Ammonium Salt ◽  
Quaternary Ammonium ◽  
Quaternary Ammonium Salt ◽  
Inhibitory Effect ◽  
Gravimetric Analysis ◽  
Irpex Lacteus ◽  
Decay Fungi ◽  
Anti Fungal

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.

Synthesis, Characterization and Properties of Tri-n-octylmethyl-ammonium Methyl Carbonate

2013 ◽  
Vol 781-784 ◽  
pp. 263-271
Author(s):  
Kui Fang Zhang ◽  
Zuo Ying Cao ◽  
Gui Qing Zhang ◽  
Lian Sheng Xiao ◽  
Xiao Zhou Zhou
Keyword(s):  
Reaction Time ◽  
Ammonium Salt ◽  
Reaction Temperature ◽  
Quaternary Ammonium ◽  
Quaternary Ammonium Salt ◽  
Dimethyl Carbonate ◽  
Volume Fraction ◽  
Feed Solution ◽  
Molar Ratio ◽  
Methyl Carbonate

The tri-n-octylmethyl-ammonium methyl carbonate was synthesized via a high pressure process with tri-n-octylamine(tri-C8) and dimethyl carbonate(DMC) in the catalysis of tri-n-octylmethyl-ammonium bromine, and its chemical structure was confirmed using FTIR spectroscopic analysis. The influence of reactants molar ratio, reaction temperature, solvent, catalyst and reaction time on the quaternization reaction were examined, and the optimal conditions were that dimethyl carbonate(DMC):tri-n-octylamine(tri-C8)=5.6:1(molar:molar), methanol:tri-n-octylamine (tri-C8)=1:2 (volume:volume), catalysts 5% of the weight of reactant mixtures(materials fraction), reaction temperature 110°C and reaction time 8 h. Under the optimum conditions, the highest conversion rate of tri-n-octylamine(tri-C8) could reach 99.57%. A type of SO42- quaternary ammonium salt was prepared by the reaction between the product and H2SO4, and its properties on extracting vanadium in the feed solution from autoclave-soda leach solution of stone coal was researched, demonstrating that with 8% the type of SO42- quaternary ammonium salt(QAS) and 5% sec-octyl alcohols dissolved in 87% sulphonated kerosene as extractant (volume fraction), the saturated loading capacity for V2O5 reaches 14.32 g/L.

A proposed accelerated field stake test for rapid assessment of wood preservative systems

Holzforschung ◽  
2010 ◽  
Vol 64 (5) ◽  
Author(s):  
Tor P. Schultz ◽  
Darrel D. Nicholas
Keyword(s):  
Field Test ◽  
Rapid Assessment ◽  
Wood Decay ◽  
Wood Preservative ◽  
Exposure Period ◽  
Test Method ◽  
Short Exposure ◽  
Ground Contact ◽  
Decay Fungi ◽  
Wood Decay Fungi

Abstract A ground-contact field test which would yield faster deterioration data when testing new wood preservative systems would be useful. This paper reports on an accelerated field test concept where wood samples are treated with a proposed preservative and a reference system with known efficacy, with the treated samples installed next to ground-contact wood feeder stakes that are already infected with wood decay fungi. This method was employed to compare decay efficacies of wood treated with four copper systems commonly available in the US. Two preliminary short-term studies show that this test method can provide differentiation between preservatives systems after only a short exposure period.

scholarly journals Preservative effect of Tetraclinis articulata and Cedrus atlantica wood extractives against fungal decay

2020 ◽  
Vol 26 (3) ◽  
Author(s):  
Noura Salhi ◽  
Abdelwahed Fidah ◽  
Mohamed Rahouti ◽  
My Rchid Ismaili ◽  
Bouselham Kabouchi ◽  
...  
Keyword(s):  
Treated Wood ◽  
Wood Decay ◽  
Wood Preservative ◽  
Fungal Decay ◽  
Decay Fungi ◽  
Plant Essential Oils ◽  
Cedrus Atlantica ◽  
Mass Losses ◽  
Tetraclinis Articulata ◽  
Wood Decay Fungi

Testing environmentaly-friendly plant essential oils for their ability to protect non-durable wood against wood decay fungi is a research topic of current interest. In this study, wood preservative potential of extracts from the wood of the durable species, Tetraclinis articulata and Cedrus atlantica were assessed on non-durable maritime pine sapwood, Pinus pinaster var atlantica, after exposure to three wood decay fungi, according to the EN 113 Standard. Significant differences were observed between treatment effects of these extracts, between fungal decay levels and between oils concentrations. Overall, mean mass losses of treated wood specimens were above 8%. T. articulata root burl extract gave the best protection level for this type of wood against Gleophyllum trabeum and Rhodonia placenta but only at test concentrations above 0.1%v/v. However, efficacy levels of both extracts’ treatments, applied at the tested concentrations, were judged insufficient on the basis of the NF EN 113 standard used.

Nanoparticles for the Controlled Release of Fungicides in Wood: Soil Jar Studies Using G.Trabeum and T. Versicolor Wood Decay Fungi

Holzforschung ◽  
2003 ◽  
Vol 57 (2) ◽  
pp. 135-139 ◽  
Author(s):  
Y. Liu ◽  
P. Laks ◽  
P. Heiden
Keyword(s):  
Controlled Release ◽  
Wood Decay ◽  
Maximum Amount ◽  
Pressure Treatment ◽  
Gloeophyllum Trabeum ◽  
Decay Fungi ◽  
Aqueous Dispersions ◽  
Wood Decay Fungi ◽  
Yellow Pine ◽  
Southern Yellow Pine

Summary Nanoparticles containing a fungicide, tebuconazole or chlorothalonil, were prepared as aqueous dispersions to treat sapwood of southern yellow pine (SYP) and birch using conventional pressure treatment methods. The maximum amount of active ingredient (a.i.) delivered into wood was ca. 2 kg a.i./m3 wood with tebuconazole-containing and 1.6 kg a.i/m3 wood with chlorothalonil-containing nanoparticles. Nanoparticles were prepared using polyvinylpyridine (PVPy) and polyvinylpyridine-co-styrene with 10% styrene (PVPy-10%-Sty) and with 30% styrene (PVPy-30%-Sty) as matrices. Soil jar tests were performed where nanoparticle-treated SYP was exposed to Gloeophyllum trabeum for 16 weeks and nanoparticle-treated birch was exposed to T. versicolor for 12 weeks. Following exposure to G. trabeum, SYP lost ca. 5% of its mass when treated with tebuconazole-containing nanoparticles (PVPy, PVPy-10%-Sty, PVPy-30%-Sty) with a tebuconazole content of ca. 0.5 kg a.i./m3 SYP. Similar results were obtained with chlorothalonil-treated SYP (0.5 kg a.i./m3) with PVPy-10%-Sty and PVPy-30%-Sty. Birch exposed to T. versicolor lost ca. 5% mass when tebuconazole (in PVPy and PVPy-30%-Sty) was ca. 0.5 kg a.i./m3, while similar results were found with chlorothalonil (PVPy, PVPy-10%-Sty, PVPy-30%-Sty) only at a biocide content of ca. 1.6 kg/m3 wood.

Effects of Cunninghamia lanceolata Heartwood Extracts on the Wood Decay Resistance

2011 ◽  
Vol 183-185 ◽  
pp. 2010-2013
Author(s):  
Jing Wang ◽  
Jian Li ◽  
Shu Jun Li ◽  
Li Jun Zhang
Keyword(s):  
Ethyl Acetate ◽  
Sequential Extraction ◽  
Trametes Versicolor ◽  
Wood Decay ◽  
Gloeophyllum Trabeum ◽  
Decay Fungi ◽  
Antifungal Activities ◽  
Weight Losses ◽  
Wood Decay Fungi ◽  
Extraction Processes

In this study, three extractives from China-fir heartwood were obtained by sequential extraction processes with hexane, ethyl acetate and methanol. The antifungal activities of three extractives against two wood decay fungi (Trametes versicolor and Gloeophyllum trabeum) and two wood stain fungi (Paecilomyces variotii and Aspergillus niger) were evaluated with digging-hole method. The results showed that none of the three extracts had good antifungal activities against these four fungi. Among the three extracts, the hexane one was the most effective and the methanol extract was the second. The ethyl acetate extract, to some degree, stimulated the growth of wood decay fungi. Judging from antifungal activities of extracts, the combination of extracts rather than any single compound is important for China-fir durability. The cubes of China-fir heartwood went through a sequential extraction processes with hexane, ethyl acetate and methanol in Soxhlet extractor. The wood decay resistances of non-extracted and extracted heartwood blocks against Trametes versicolor and Gloeophyllum trabeum were evaluated after steam sterilization according to the Chinese standard method. Non-extracted heartwood blocks were resistant to Trametes versicolor but experienced substantial weight losses when exposed to Gloeophyllum trabeum. Weight losses increased after hexane extraction, but then declined markedly after ethyl acetate extraction. The possible explanation for the declined weight losses of ethyl acetate extracted blocks could be that some components which stimulated the growth of these fungi, especially Trametes versicolor were extracted by ethyl acetate. After extraction with methanol, weight losses of the blocks by Gloeophyllum trabeum increased dramatically but weight losses of the blocks by Trametes versicolor were similar to those of the ethyl acetate extracted blocks.

The effects of subthreshold loadings of tebuconazole, DDAC, and boric acid on wood decay by Postia placenta

Holzforschung ◽  
2010 ◽  
Vol 64 (4) ◽  
Author(s):  
Sara C. Robinson ◽  
Peter E. Laks
Keyword(s):  
Weight Loss ◽  
Boric Acid ◽  
Wood Decay ◽  
Pinus Strobus ◽  
Wood Preservative ◽  
White Pine ◽  
Decay Fungi ◽  
Postia Placenta ◽  
Wood Decay Fungi ◽  
Didecyldimethylammonium Chloride

AbstractTebuconazole, didecyldimethylammonium chloride (DDAC), and boric acid are co-biocides frequently added to copper-based wood preservative systems. Although the performance thresholds of these biocides are well known, there is currently little information on the effects of subthreshold loadings of the co-biocides on common wood decay fungi. We tested five strains ofPostia placentaon white pine cubes (Pinus strobus) treated with subthreshold retentions of tebuconazole, DDAC, or boric acid. No stimulatory effects were observed on blocks treated with DDAC or boric acid. Decay stimulation, as measured by weight loss, occurred between loadings of 1.0×10-5to 1.0×10-3 kg m-3on blocks treated with tebuconazole. This effect should be taken into account during the design and use of wood preservative systems containing this fungicide.

Characterization and Synthesis of Quaternary Ammonium Salt of Chitosan by Open-Loop Method of Epoxy Derivatives

2013 ◽  
Vol 781-784 ◽  
pp. 969-974
Author(s):  
Sheng Zhao Gong ◽  
Jian Hua Cheng
Keyword(s):  
Reaction Time ◽  
Ammonium Salt ◽  
Quaternary Ammonium ◽  
Quaternary Ammonium Salt ◽  
Ph Value ◽  
Influence Factors ◽  
Reaction System ◽  
Open Loop ◽  
Molar Ratio ◽  
Thermal Stabilities

Quaternary ammonium salt of chitosan (HACC) was synthesized by the reaction of chitosan(CTS) and 2, 3-epoxypropyltrimethyl- ammonium chloride(GTA) in isopropanol. The influence factors of the degree of substitution of synthetic reaction, such as the molar ratio of reactants, the reaction time, temperature and so on were discussed by single factor experiments.The results showed that the optimal conditions for the preparation were nGTA: nCTS=4:1, the reaction time 8h, the reaction temperature 75°C, the reaction pH value 7, the alkalization time 14h, the molecular weight of chitosan 320000g/mol, the moisture of reaction system 20%. The structures of HACC and CTS were characterized by infrared spectrum, the appearances of morphology of HACC and CTS were researched by scanning electron microscopy, the thermal stabilities of HACC and CTS were studied by thermogravimetry. The results showed that the substitution reaction mainly occurs on the N element, modified derivatives had significant changes in appearance and size, and lower thermal stability.

Catalyst- and oxidant-free electrochemical para-selective hydroxylation of N-arylamides in batch and continuous-flow

2020 ◽  
Vol 22 (19) ◽  
pp. 6437-6443
Author(s):  
Cheng-Kou Liu ◽  
Meng-Yi Chen ◽  
Xin-Xin Lin ◽  
Zheng Fang ◽  
Kai Guo
Keyword(s):  
Ammonium Salt ◽  
Quaternary Ammonium ◽  
Continuous Flow ◽  
Quaternary Ammonium Salt ◽  
Selective Hydroxylation

A catalyst-, oxidant-, acidic solvent- and quaternary ammonium salt-free electrochemical para-selective hydroxylation of N-arylamides at rt in batch and continuous-flow was developed.

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