咪唑类离子液体的合成、对纤维素和木粉的溶解性能及其在高分子中的应用
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摘要
本文合成了一系列咪唑类离子液体,研究了其对纤维素和杉木粉的溶解性能;以离子液体为介质,用丙烯酰胺接枝溶解的微晶纤维素或杉木粉制备了改性絮凝剂,考察了絮凝剂对污水的絮凝性能;采用原位方法制备了离子液体/杉木粉/酚醛树脂复合胶粘剂,探讨了离子液体和杉木粉对复合胶性能的影响。主要研究内容如下:
1.以N-甲基咪唑、N-乙基咪唑、N-乙烯基咪唑和氯丙烯、氯乙醇等为原料,采用一步法合成了一系列咪唑类离子液体:[BMIM]Cl、[AMIM]Cl、[HeMIM]Cl、[AEIM]Cl、[HeEIM]Cl和[HeVIM]Cl等,并用红外和氢核磁表征了离子液体的化学结构。侧链基团对离子液体物理性质有很大的影响,侧链越长,粘度越大,电导率和表面张力越小;侧链含有双键基团的离子液体,电导率较高;含有羟基的离子液体表面张力较大。与水或一般有机溶剂相比,合成的咪唑类离子液体的密度、粘度和沸点都比较高,表面张力都比较低。
2.采用不同浓度的碱溶液在不同工艺条件下(常温常压、微波和高压罐)分别对纤维素和杉木粉进行预处理。处理后的纤维素和杉木粉的氢键作用均被削弱,相对结晶度均被降低。在高压罐(140℃)中分别浸渍棉纤维、微晶纤维素和杉木粉的最佳NaOH溶液浓度分别是30%、15%和25%。处理前后棉纤维聚合度由1180降低到632,结晶度由82.6%降到53.3%,微晶纤维素聚合度由306降到153,结晶度由92.0%降到49.2%,杉木粉相对结晶度由61.0%降到2.4%。
3.采用微波加热法或传统加热法对处理过的纤维素和杉木粉进行溶解,考察了离子液体的溶解性能,探讨了溶解工艺、溶解温度等对纤维素和杉木粉的溶解率的影响。以N-乙基咪唑、氯乙酸和氯化亚砜为原料,合成带有酰氯基团的离子液体中间体,再与棉纤维酰氯酯化制备了离子化纤维素酯,并考察其溶解性能。微波加热法的溶解效果远远优于传统加热法,且最佳溶解温度为90℃左右。离子液体[HeVIM]Cl的溶解效果最好,溶解后得到的再生纤维素或木粉残渣相对结晶度变小,热稳定性降低,表观形貌发生变化。与离子液体相比,制备的离子化纤维素酯对纤维素的溶解能力更佳,但对纤维素的降解作用也很大。
4.以离子液体为介质,用微波(400w, 90℃)溶解过的微晶纤维素或杉木粉和单体丙烯酰胺接枝共聚分别制备了改性的纤维素絮凝剂和木素絮凝剂,考察了改性絮凝剂对煤泥水和陶土污水的絮凝性能。离子液体为介质制备的絮凝剂性能远远优于水介质。当离子液体与纤维素的质量比为25:1,聚合温度为45℃时,制备的纤维素絮凝剂(AM-g-MCC)性能最优。当单体质量百分数为25%,离子液体与木粉的质量比为30:1,木粉与单体质量比为1:4时制备的木素絮凝剂(AM-g-Wood)性能最好。改性絮凝剂均具有较好的絮凝效果,其中木素絮凝剂更适合处理细粒级的陶土污水。
5.用离子液体在微波条件下(400w, 90℃)预先溶解杉木粉,再与苯酚甲醛共混制备了离子液体/杉木粉/酚醛树脂的复合胶粘剂,探讨了杉木粉对复合胶游离醛的捕捉作用及离子液体对胶合性能的影响。侧链带有羟基的离子液体制备的复合胶的性能最佳,当离子液体[HeVIM]Cl与木粉质量比为10:1时,复合胶粘剂游离醛从1.76%降低到0.16%,拉伸剪切强度从2.16MPa提高到8.38MPa,随着离子液体的量的增加,复合胶粘剂的强度也逐渐增大,且固化后复合胶不龟裂,透明度高,光泽性好,热分解温度提高,但残碳率降低。
A series of imidazolium ionic liquids were synthesized and their solubilities for cellulose and fir powder were discussed; Modified flocculants were prepared by grafting dissolved cellulose or fir powder with acrylamide (AM) in ionic liquids and the flocculations for waste water were studied. Besides, ionic liquid/fir powder/phenol-formaldehyde composite adhesive was prepared in situ and the effects of the ionic liquids and fir powder on the performance of the composite adhesive were researched.
The main contents as follows:
1. A series of imidazolium ionic liquids, [BMIM]Cl, [AMIM]Cl, [HeMIM]Cl, [AEIM]Cl, [HeEIM]Cl and [HeVIM]Cl, were synthesized using N-methyl imidazolium, N-ethyl imidazolium, N-ethylene imidazolium, allyl chloride and chloroethanol as raw materials, and chemical structures of the ionic liquids were characterized by FTIR and 1H NMR. The side chains had great effects on ionic liquids’physical properties. The longer side chain of the ionic liquid was, the greater was its viscosity and the smaller was its conductance rate and surface tension. Ionic liquids containing double bond on its side chain had a higher conductance rate, while the ionic liquids containing hydroxyl group had a higher surface tension. It was shown that the ionic liquids had higher density, viscosity, boiling point and lower surface tension compared with water or organic solvents.
2. Cellulose and fir powder were pretreated with different concentrations of NaOH under various technologies (normal temperature and pressure, microwave and high pressure pot) respectively. Hydrogen bonding actions of cellulose and fir powder were all weakened greatly after treatment and the crystallinity of them were also decreased. The most effective concentrations of NaOH were 30%, 15% and 25% to dip cotton fibre, microcrystalline (MCC) and fir powder respectively in the high pressure pot (140℃). Degree of polymerization (DP) of cotton fibre after treatment was decreased from 1180 to 632 and crystallinity was changed from 82.6% to 53.3%, DP of MCC was decreased from 306 to 153 and crystallinity was changed from 92% to 49.2%, relative crystallinity of fir powder was degreased from 61.0% to 2.4%.
3. Cellulose and fir powder after treatment were dissolved in ionic liquids by microwave heating and traditional heating. The solubilities of the ionic liquids were studied, the effects of dissolving methods and temperatures on dissolving rate of cellulose were discussed. Intermediate of ionic liquid with carbonyl group was synthesized with thionyl chloride, N-ethyl imidazolium and chloroacetic acid, and then reacted with cellulose to prepare ionization cellulose ester, whose solubility was also examined. The soluble effect of microwave heating was far superior to traditional heating, and the most suitable temperature was 90℃. The solubility of [HeVIM]Cl was best, crystallinity and thermostability of regenerated cellulose and fir powder residue after dissolved were decreased and morphology of them was changed greatly. Compared with ionic liquids, ionization cellulose ester had better solubility for cellulose due to its strong degradation of cellulose.
4. Modified flocculants were prepared in ionic liquids by grafting AM onto MCC or fir powder, which were dissolved by microwave heating at first. The flocculations of the flocculants were studied by treating with coal slurry water and argil waste water. The performances of the flocculants prepared in ionic liquid were far superior to aqueous medium. The performance of cellulose flocculant (AM-g-MCC) was best when the polymerization temperature was 45℃and the mass ratio of ionic liquid to MCC was 25:1. While the performance of wood flocculant (AM-g-Wood) was best when the mass fraction of AM was 25%, the mass ratio of ionic liquid to fir powder was 30:1 and the mass ratio of wood to AM was 1:4. Both cellulose flocculants and wood flocculant had good flocculations, the wood flocculant was more suitable for treating with tiny particles of argil waste water.
5. Fir powder was dissolved in ionic liquids by microwave heating (400w, 90℃) at first, then reacted with phenol and formaldehyde to prepare ionic liquid/fir powder/phenol-formaldehyde composite adhesive. Effects of fir powder and ionic liquids on performances of the adhesive were studied. The performance of the adhesive prepared by ionic liquid with hydroxyl was best, free formaldehyde of the adhesive decreased from 1.76% to 0.16% compared to common PF, the tensile shear strength increased from 2.16MPa to 8.38MPa when the mass ratio of [HeVIM]Cl to fir powder was 10:1. Besides, the tensile shear strength increased with the mass of ionic liquid increasing, and the cured composite adhesive had higher transparence and better luster, its thermal decomposition temperature was increased, while the content of residual carbon was decreased.
1.以N-甲基咪唑、N-乙基咪唑、N-乙烯基咪唑和氯丙烯、氯乙醇等为原料,采用一步法合成了一系列咪唑类离子液体:[BMIM]Cl、[AMIM]Cl、[HeMIM]Cl、[AEIM]Cl、[HeEIM]Cl和[HeVIM]Cl等,并用红外和氢核磁表征了离子液体的化学结构。侧链基团对离子液体物理性质有很大的影响,侧链越长,粘度越大,电导率和表面张力越小;侧链含有双键基团的离子液体,电导率较高;含有羟基的离子液体表面张力较大。与水或一般有机溶剂相比,合成的咪唑类离子液体的密度、粘度和沸点都比较高,表面张力都比较低。
2.采用不同浓度的碱溶液在不同工艺条件下(常温常压、微波和高压罐)分别对纤维素和杉木粉进行预处理。处理后的纤维素和杉木粉的氢键作用均被削弱,相对结晶度均被降低。在高压罐(140℃)中分别浸渍棉纤维、微晶纤维素和杉木粉的最佳NaOH溶液浓度分别是30%、15%和25%。处理前后棉纤维聚合度由1180降低到632,结晶度由82.6%降到53.3%,微晶纤维素聚合度由306降到153,结晶度由92.0%降到49.2%,杉木粉相对结晶度由61.0%降到2.4%。
3.采用微波加热法或传统加热法对处理过的纤维素和杉木粉进行溶解,考察了离子液体的溶解性能,探讨了溶解工艺、溶解温度等对纤维素和杉木粉的溶解率的影响。以N-乙基咪唑、氯乙酸和氯化亚砜为原料,合成带有酰氯基团的离子液体中间体,再与棉纤维酰氯酯化制备了离子化纤维素酯,并考察其溶解性能。微波加热法的溶解效果远远优于传统加热法,且最佳溶解温度为90℃左右。离子液体[HeVIM]Cl的溶解效果最好,溶解后得到的再生纤维素或木粉残渣相对结晶度变小,热稳定性降低,表观形貌发生变化。与离子液体相比,制备的离子化纤维素酯对纤维素的溶解能力更佳,但对纤维素的降解作用也很大。
4.以离子液体为介质,用微波(400w, 90℃)溶解过的微晶纤维素或杉木粉和单体丙烯酰胺接枝共聚分别制备了改性的纤维素絮凝剂和木素絮凝剂,考察了改性絮凝剂对煤泥水和陶土污水的絮凝性能。离子液体为介质制备的絮凝剂性能远远优于水介质。当离子液体与纤维素的质量比为25:1,聚合温度为45℃时,制备的纤维素絮凝剂(AM-g-MCC)性能最优。当单体质量百分数为25%,离子液体与木粉的质量比为30:1,木粉与单体质量比为1:4时制备的木素絮凝剂(AM-g-Wood)性能最好。改性絮凝剂均具有较好的絮凝效果,其中木素絮凝剂更适合处理细粒级的陶土污水。
5.用离子液体在微波条件下(400w, 90℃)预先溶解杉木粉,再与苯酚甲醛共混制备了离子液体/杉木粉/酚醛树脂的复合胶粘剂,探讨了杉木粉对复合胶游离醛的捕捉作用及离子液体对胶合性能的影响。侧链带有羟基的离子液体制备的复合胶的性能最佳,当离子液体[HeVIM]Cl与木粉质量比为10:1时,复合胶粘剂游离醛从1.76%降低到0.16%,拉伸剪切强度从2.16MPa提高到8.38MPa,随着离子液体的量的增加,复合胶粘剂的强度也逐渐增大,且固化后复合胶不龟裂,透明度高,光泽性好,热分解温度提高,但残碳率降低。
A series of imidazolium ionic liquids were synthesized and their solubilities for cellulose and fir powder were discussed; Modified flocculants were prepared by grafting dissolved cellulose or fir powder with acrylamide (AM) in ionic liquids and the flocculations for waste water were studied. Besides, ionic liquid/fir powder/phenol-formaldehyde composite adhesive was prepared in situ and the effects of the ionic liquids and fir powder on the performance of the composite adhesive were researched.
The main contents as follows:
1. A series of imidazolium ionic liquids, [BMIM]Cl, [AMIM]Cl, [HeMIM]Cl, [AEIM]Cl, [HeEIM]Cl and [HeVIM]Cl, were synthesized using N-methyl imidazolium, N-ethyl imidazolium, N-ethylene imidazolium, allyl chloride and chloroethanol as raw materials, and chemical structures of the ionic liquids were characterized by FTIR and 1H NMR. The side chains had great effects on ionic liquids’physical properties. The longer side chain of the ionic liquid was, the greater was its viscosity and the smaller was its conductance rate and surface tension. Ionic liquids containing double bond on its side chain had a higher conductance rate, while the ionic liquids containing hydroxyl group had a higher surface tension. It was shown that the ionic liquids had higher density, viscosity, boiling point and lower surface tension compared with water or organic solvents.
2. Cellulose and fir powder were pretreated with different concentrations of NaOH under various technologies (normal temperature and pressure, microwave and high pressure pot) respectively. Hydrogen bonding actions of cellulose and fir powder were all weakened greatly after treatment and the crystallinity of them were also decreased. The most effective concentrations of NaOH were 30%, 15% and 25% to dip cotton fibre, microcrystalline (MCC) and fir powder respectively in the high pressure pot (140℃). Degree of polymerization (DP) of cotton fibre after treatment was decreased from 1180 to 632 and crystallinity was changed from 82.6% to 53.3%, DP of MCC was decreased from 306 to 153 and crystallinity was changed from 92% to 49.2%, relative crystallinity of fir powder was degreased from 61.0% to 2.4%.
3. Cellulose and fir powder after treatment were dissolved in ionic liquids by microwave heating and traditional heating. The solubilities of the ionic liquids were studied, the effects of dissolving methods and temperatures on dissolving rate of cellulose were discussed. Intermediate of ionic liquid with carbonyl group was synthesized with thionyl chloride, N-ethyl imidazolium and chloroacetic acid, and then reacted with cellulose to prepare ionization cellulose ester, whose solubility was also examined. The soluble effect of microwave heating was far superior to traditional heating, and the most suitable temperature was 90℃. The solubility of [HeVIM]Cl was best, crystallinity and thermostability of regenerated cellulose and fir powder residue after dissolved were decreased and morphology of them was changed greatly. Compared with ionic liquids, ionization cellulose ester had better solubility for cellulose due to its strong degradation of cellulose.
4. Modified flocculants were prepared in ionic liquids by grafting AM onto MCC or fir powder, which were dissolved by microwave heating at first. The flocculations of the flocculants were studied by treating with coal slurry water and argil waste water. The performances of the flocculants prepared in ionic liquid were far superior to aqueous medium. The performance of cellulose flocculant (AM-g-MCC) was best when the polymerization temperature was 45℃and the mass ratio of ionic liquid to MCC was 25:1. While the performance of wood flocculant (AM-g-Wood) was best when the mass fraction of AM was 25%, the mass ratio of ionic liquid to fir powder was 30:1 and the mass ratio of wood to AM was 1:4. Both cellulose flocculants and wood flocculant had good flocculations, the wood flocculant was more suitable for treating with tiny particles of argil waste water.
5. Fir powder was dissolved in ionic liquids by microwave heating (400w, 90℃) at first, then reacted with phenol and formaldehyde to prepare ionic liquid/fir powder/phenol-formaldehyde composite adhesive. Effects of fir powder and ionic liquids on performances of the adhesive were studied. The performance of the adhesive prepared by ionic liquid with hydroxyl was best, free formaldehyde of the adhesive decreased from 1.76% to 0.16% compared to common PF, the tensile shear strength increased from 2.16MPa to 8.38MPa when the mass ratio of [HeVIM]Cl to fir powder was 10:1. Besides, the tensile shear strength increased with the mass of ionic liquid increasing, and the cured composite adhesive had higher transparence and better luster, its thermal decomposition temperature was increased, while the content of residual carbon was decreased.
引文
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