Study On Synthesis Of Three Quaternary Ammonium Salts From Rosin And Its Inhibition To Some Wood Decay Fungi

Wood is a kind of nature renewable resource. The exploration and the use of wood are environmentally safe, however, wood is low decay resistance. With the need of wood increasing, wood protection becomes an important way of saving the forest resources.In this paper, rosin is used as raw material to synthesize some kinds of rosin derivatives which have anti-fungal activity and surface activity. Synthesis based on rosin not only can make full use of this renewable resource and can increase greatly its additional value but also can prompt the industry of deep processing development of rosin. Wood preservatives from rosin are renewable, active and environment-friendly.i.Rosin was used as raw material to prepare N-(3- rosin acyloxy-2-hydroxyl) propyl-N, N dimethylamine chloride. Firstly, the rosin was esterified by epoxy chloropropane with the mole ratio of 1:2, the reaction time of 3.5h at 90℃. 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℃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℃. The content of the product was characterized by gravimetric analysis with sodium tetraphenylborate as its precipitation reagent and the yield was 72.8%. There are many impurities in the rosin, so N-(3-dehydrogenated rosin acyloxy-2-hydroxyl) propyl-N, N dimethylamine chloride was synthesized in the same mechanism used to characterize the structure of N-(3-rosin acyloxy-2-hydroxyl) propyl-N, N dimethylamine chloride. The chemical structure of the product was identified by FTIR,HPLC,1H-NMR.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 N-(3-rosin acyloxy-2-hydroxyl) propyl-N, N dimethylamine chloride, is active to these fungi, especially Gloeophyllum trabeum.. The concentrations of the product are 16 mg/mL,32 mg/mL and 64 mg/mL. The weight-loss method was used to detect the performance of N-(3-rosin acyloxy-2-hydroxyl) propyl-N, N dimethylamine chloride on wood protection. The result show that when the concentration of N-(3-rosin acyloxy-2-hydroxyl) propyl-N, N dimethylamine chloride is 64 mg/mL, the resistence to Trametes versicolor, Gloeophyllum trabeum is on the first grade of the wood protection.2. Rosin was used as material to prepare bisN-(3-rosin acyloxy-2-hydroxyl) propyl-N, N dimethylamine chloride firstly, the rosin was modified by acrylic acid and a carboxylic acid group was introduced to the rosin. Secondly, the modified rosin reacted with the epoxy chloropropane, the intermediate I was obtained by the way. Thirdly, the intermediate reacted with dimethylamine. By this way the intermediateⅡwas synthesized. Finally the intermediate II reacted with the epoxy chloropropane in the mole ratio of 1:3, the reaction time of 4.5h at 80℃. The content of the product was characterized by gravimetric analysis with sodium tetraphenylborate as its precipitation reagent and the yield was 92.8%. The chemical structure of the product was identified by FTIR,HPLC,1H-NMR. The antifungal activity of the product was determined by paper-disc method with wood decay fungi such as Coriolus versicolor Gloeophyllum trabeum Irpex lacteas and Postia placenta. The anti-fungal experiment results signified that the bisN-(3-rosin acyloxy-2-hydroxyl) propyl-N, N dimethylamine chloride, is active to these fungi, especially Irpex lacteas and Postia placenta. The concentrations of the product are 16 mg/mL,32 mg/mL and 64 mg/mL. The weight-loss method was used to detect the performance of bisN-(3-rosin acyloxy-2-hydroxyl) propyl-N, N dimethylamine chloride on wood protection. The result show that when the concentration of bisN-(3-rosin acyloxy-2-hydroxyl) propyl-N, N dimethylamine chloride is 64 mg/mL, the resistence to Trametes versicolor, Gloeophyllum trabeum is on the first grade of the wood protection. BisN-(3-rosin acyloxy-2-hydroxyl) propyl-N, N dimethylamine chloride has a critical micellar concentration (CMC) of 8×10-3mol/L, a surface tension of 39.381mN/m, an emulsification activity of 56min, a height of foam of 250 mm, and a foam stability of 200 mm.BisN-(3-rosin acyloxy-2-hydroxyl) propyl-N, N triethylamine was synthsised by three steps. Firstly, the modified rosin was synthesised by the reaction of rosin and acryl acid. Secondly, the modified rosin was esterified with epoxy chloropropane with the mole ratio of 1:3, the product was 3-rosin acyloxy-2-hydroxypropyl chlorine. Finally, the intermediate reacted with epoxy propyl triethyl ammonium chloride to produce bisN-(3-rosin acyloxy-2-hydroxyl) propyl-N, N triethylamine. The content of the product was characterized by gravimetric analysis with sodium tetraphenylborate as its precipitation reagent and the yield was 87.7%. The chemical structure of the product was identified by FTIR,HPLC. Antifungal assays of bisN-(3-rosin acyloxy-2-hydroxyl) propyl-N, N trimethylamine chloride were performed based on the method of Chang et al. (1999) with slight modifications with wood decay fungi such as Coriolus versicolor Gloeophyllum trabeum Irpex lacteas and Postia placenta. The anti-fungal experiment results signified that the bisN-(3- rosin acyloxy-2-hydroxyl) propyl-N, N trimethylamine chloride is active to these fungi, when the concentration of the product is 0.5 mg/mL, the resistence to Coriolus versicolor Gloeophyllum trabeum and Postia placenta was obvious, when the concentration of the product is 1.0 mg/mL, the resistence to Irpex lacteas was obvious.