Synthesis And Properties Of Rosin-based Gemini Surfactants

With the fast development of society and economy and the increasingly deterioration of entiroment, the worse efficiency and deocomposing traditional surfactant hasn't met with the need of economy of nation and life of people.Consequently, it is urgen affair of chemist researching and developing the efficient and environment friendly surfactant. Gemini surfactant honored"nouveau surfactant"with superior performance of physics and chemistry emerges as the times require. With the increment concerning of enviroment and resource and people's pursue of sustainable develop, producing high value products through chemical modification of main component of natural resource is the important direction of natural product research. Rosin is an important natural resource of China, pine resin acids are the main components of rosin, they have been attracted great interest for their specian chemical structures and wide rang of biological activities. In this paper, several series of rosin-based Gemini surfactants were synthesized from pine resin acids and their derivatives. The main results are asfollows:1 Several kinds of cationic gemini surfactants, anionic gemini surfactants and nonionic gemini surfactants 16 compounds contained tricyclic diterpene structure were synthesized by using of dehydroabietic acid and dehydroabietylamine andα,ω-dibromoalkane through the idea of connecting of active groups. The 16 compounds have not been reported in the literatures. Their structures were characterized by IR, 1H NMR and 13C NMR spectroscopy. The optimized methods of synthesis were determined by discussing the factors affecting reactions. The cationic gemini surfactants with hydrophenanthrene structure was synthesized from dehydroabietic acid by conventional thermal condition and microwave irradiation, respectively. It had been found that microwave assisted synthesis is an efficient way for the synthesis of this cationic gemini surfactant with shorter reaction time and higher yield.2 Their critical micelle concentration(CMC) values,the surface tension at their cmc(γcmc) values, emulsifying power(EP, with benzene), foaming power(FP), krafft's point(KP), turbid point(TP), lime soap dispersing power (LSDP), hydrophile-lipophile balance number(HLB), calium ion stability (CIS) and the contact angles of the solutions of them on sheet glasses were measured. Results show that cationic gemini surfactants have high surface activities with ccmc value up to 10-5 mol?L-1 orders of magnitude,γcmc value at below 30.267 mN?m-1. N,N, N′,N′-tetramethyl-N, N′-diethanolamine dehydroabietate butyldiamine dibromide (TDDBD), N,N, N′,N′-tetramethyl- N, N′- dehydroabietate ethylenediamine dibromid(eTDED)and N,N, N′,N′-tetramethyl - N, N′- dehydroabietate octadiamine dibromide(TDOD) have higher emulsifying power (with benzene) reached above 4 days, respectively.They showed the strongest emulsify ability which is better than that of an aqueous monomeric counterpart N′- dehydroabietate-N,N-dimethyl-N-ethanolamine amine dibromide (57min). The anionic gemini surfactants(SDDE,SDDB,SDDH,SDDO)have also higher surface active:their ccmc values were 3.2×10-4, 2.9×10-4, 1.8×10-4and 1.3×10-4 mol·L-1,γcmc values 31.0 , 28.6, 29.4 and 28.1mN·m-1 respectively. The contact angles of the solutions of the series sulfonate gemini surfactants on sheet glasses were smaller and had better property of surface wettability than that of K12 and TLS. N, N′-diglucose, didehydroabietate- 1,8- octadiamine(DDO)of nonionic gemini surfactants has higher surface active:its ccmc value was 6.5×10-4 mN·m-1,γcmc values 34.3 mol·L-1 respectively.Its surface activity is close to that of non-ionic gemini surfactants based on nonylphenol which were reported in literature.3 The behaviors of gemini surfactants synthesized by using as bacterostasis and emulgents were evaluated. The bioactivity test showed that cationic gemini surfactants possessed good antimicrobial activities towarding the seven tested bacteria.Among them,the minimal bacteriostatic concentration of TDDED,TDDBD,TDDHDT and DDOD against S. epidermidis were all 16μg·mL. Their antimicrobial activities approach to that of geramine. The emulsifleatlons of rosin ester prepared by using TDDBD,TDED as emulgent have a small and uniform particle diameter and have a better stability with no deposition appeared for six month. They have better stability than that of emulsifleatlon prepared by special emulsifier(SX-1)for emulsifying rosin ester.