摘要
为从根本上降低木材胶合制品的甲醛释放对环境和人体健康的危害,本论文选用无毒、低挥发的乙二醛(G)全部或部分替代甲醛(F)合成系列乙二醛-尿素(GU)树脂及乙二醛-尿素-甲醛(GUF)共缩聚树脂。在用量子化学计算方法研究了树脂合成反应及结构形成机理的基础上,研究了反应物料摩尔比、反应pH值、反应温度、反应时间、pH调节剂等合成条件对树脂结构和性能的影响规律,确定树脂较佳的合成工艺条件；主要采用紫外-可见吸收光谱(UV-vis)、傅里叶变换红外光谱(FTIR)、核磁共振碳谱(I3CNMR)、基质辅助激光解吸电离飞行时间质谱(MALDI-TOF-MS)等方法研究树脂的结构及分子量分布情况；并用动态热机械性能分析(DMA)方法研究了系列GUF树脂的固化过程。得出如下主要结论：
(1)分子模拟研究表明,尿素(U)、单羟甲基脲(MMU)、双羟甲基脲(DMU)与乙二醛(G)及2,2-二羟基乙醛(G1)的加成反应较难发生；但与质子化乙二醛(p-G)及质子化2,2-二羟基乙醛(p-G1)的加成反应则很容易发生,生成重要的系列碳正离子C-p-UG、C-p-UG1、C-p-G-MMU、C-p-G1-MMU、C-p-G-DMU和C-p-G1-DMU。在缩聚阶段,主要生成C-N-C和C-O-C键使分子量增加。
(2)以量子化学计算的研究结果为指导,主要选择在弱酸性条件下制备出GU及GUF树脂,用其制备的胶合板干状胶合强度能满足国标GB/T9846.3-2004《普通胶合板通用技术条件》对III类胶合板的要求,可以在干燥状态下使用。
(3)树脂的UV-vis谱图中存在π-π*跃迁的吸收峰,表明树脂结构中存在共轭结构；FTIR表明树脂中的主要官能团为-OH、-NH-、C=O、C-N、C-O等；与反应物进行对比,合成树脂的13CNMR谱中均出现许多新的吸收峰,主要对应于不同取代结构的羰基碳(C=O)和sp3杂化碳。
(4) MALDI-TOF-MS研究表明,原料摩尔比对树脂聚合程度及分子量分布情况影响较大,但主要峰的吸收位置相同,表明不同摩尔比树脂的结构中可能具有相同的重复单元,这些重复单元构成了树脂的基本骨架。MMU、DMU自缩聚产生的吸收峰强度随着摩尔比的增加而增加；即低摩尔比时,体系中G与MMU或DMU的反应占主导地位,但高摩尔比时,MMU或DMU的自缩聚反应占主导地位。因此,在GUF树脂的合成过程中MMU/G或DMU/G的摩尔比不宜太高。
(5)甲醛(F)的亲核反应活性强于乙二醛(G),当G、U、F三者放在一起进行反应时,首先发生U与F的反应,然后体系中主要发生G与剩余U及中间产物MMU的加成反应和后续发生的缩聚反应。GUF树脂较适宜的合成条件为：第二阶段的反应pH为弱酸性,反应时间2h,物料摩尔比为0.7：1：0.7。不同物料摩尔比GUF树脂的峰值温度和E’保持稳定的温度范围基本相同,表明树脂的固化速率和固化后树脂的热稳定性相差不大。
In order to decrease fundamentally the harm of formaldehyde to environment and human health, in this PhD thesis, the low volatile and nontoxic aldehyde, glyoxyal (G) was chosen to substitute for formaldehyde (F) to react with urea (U) to prepare glyoxal-urea (GU) resin and glyoxal-urea-formaldehyde (GUF) cocondensed resin. Firstly, the synthesis reaction and structure formation mechanism were studied by quantum chemical calculations. On the basis of the results of quantum chemical calculations, the optimal synthesis conditions will be determined after investigating the effects of various kinds of synthesis conditions on the resins'structure formation process and properties, including the molar ratios of material, reaction pH, reaction time, reaction temperatures and catalysts. Secondly, the structure and molecular weight distribution of the resins were investigated mainly by nuclear resonance carbon-13spectrum (13CNMR), matrix assisted laser desorption ionization time of flight mass spectrometry (MALDI-TOF-MS), Fourier transform infrared spectroscopy (FTIR) and ultraviolet and visible spectroscopy (UV-vis) metods. Then, the dynamic mechanical analysis (DMA) test was used to investigate the curing process of GUF resins by simulating the hot pressing process in plywood manufacture. The main results obtained from the above study are summarized as follows:
(1) The results of chemical calculation indicates that under weak acid condition, the addition reaction of urea (U), monomethylol urea (MMU) and dimethylol urea (DMU) with glyoxal (G) and2,2-dihydroxyacetaldehyde (G1) is difficulty to take place. However, the addition reaction of urea (U), monomethylol urea (MMU) and dimethylol urea (DMU) with protonated glyoxal (p-G) and protonated2,2-dihydroxyacetaldehyde (p-G1) is easily to occur. And in the these reactions, the important carbocation reactive intermediates C-p-UG and C-p-UG1, C-p-G-MMU and C-p-G1-MMU, C-p-G-DMU and C-p-G1-DMU have been formed, respectively. In the condensation stage, the resins have been produced through the formation of two main chemical bond of C-N-C and C-O-C.
(2) Based on the quantum chemical calculation results, GU and GUF resin have been synthesized under slightly acid condition. The dry shear strength of the plywoods bonded with the GU or GUF resins could meet the type III grade plywood requirement of GB/T9846.3-2004, and could be used in dry conditions, but their wet dry shear strength has yet to be improved.
(3) In the UV-vis spectrum of GU and GUF resins, the adsorption peak of the π→π*transition appears, which suggests that the conjugated structure exists in the structure of GU and GUF resin. FTIR shows that there are mainly such functional groups as-OH,-NH-, C-N, C=O, etc. and compared with the reactive materials, many new adsorption peaks appear in the13CNMR spectrum of GU and GUF resin, corresponding to the signals of the sp3hybridized carbon and carbonyl (C=O) with different substitution degree in the resins, which indicates that the structure of the resins is probably very complicated.
(4) The MALDI-TOF-MS spectrum show that the materials molar ratio has important effects on the condensation degree and the molecular weight's distribution. The main peaks have appeared at the same adsorption position, but with different adsorption strength, which indicates that there are same repeating units in the resins with different molar ratio of MMU/G or DMU/G. Moreover, the peaks due to the dehydration condensation reaction of MMU or DMU also appear in the spectra and their strength increases with the MMU/G or DMU/G molar ratio, which indicates that at low MMU/G or DMU/G molar ratio much more glyoxal reacted with MMU or DMU and at high MMU/G or DMU/G molar ratio much more MMU or DMU occurs the dehydration condensation reaction, so in the resin's synthesis, the appropriate MMU/G or DMU/G molar ratio is very important.
(5) The results of chemical calculation suggested that the nucleophilic reaction activity of formaldrhyde (F) is higher than that of glyoxal (G), so in the system existing G, U and F, U reacts firstly with F, then G reacts with the unreacted U and intermediate product of MMU, the most important intermediate products in the nucleophilic reaction of U and F, and even the corresponding condensation reaction. The proper synthesis conditions of GUF resin are as follows: the reaction pH in the second stage is weak acid; the reaction time in the second stage is2h; the molar ratio of G/U/F is0.7:1:0.7. The peak temperature, peak E'and stable temperature range of E'of GUF samples with different molar ratio are basically the same, which suggests that the curing rate, the heat stability and the performance of the resins are basically the same.
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