交联剂TETS的合成与应用研究
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摘要
本论文提出了一种新型的交联剂TETS，对交联剂TETS的合成与应用性能进行了系统的研究。
TETS(N，N，N-三乙胺硫代硫酸酯钠盐)是一种本特盐类交联剂，由TES(N，N，N-三乙胺硫酸酯钠盐)和Na_2S_2O_3在一定的条件下反应而成，其分子结构中含有三个本特基和一个叔胺基，可在碱性条件下与纤维素纤维分子上的羟基或蛋白质纤维分子上的氨基等发生交联，交联能力强，储存稳定性好，合成工艺简单，易溶于水，应用方便，合成和使用过程中不释放甲醛等有害物质。
论文采用毛细管电泳技术对TETS合成反应过程进行跟踪控制，验证合成反应机理，确定最佳合成条件，监测分离提纯效果，分析样品水解程度，对目标产物进行定性和定量分析。合成中提出了一种新型的分离方法—“先热后冷乙醇溶液过滤法”，解决了目标本特盐产物难以与反应副产物硫酸钠分离的难题，最后综合运用毛细管电泳、拉曼光谱等手段对目标产物进行了表征。
论文对TETS的热稳定性、酸碱稳定性以及水解稳定性进行了分析，并根据前人对其他相近反应所做的研究结果推测了交联剂TETS与纤维素纤维交联反应的机理，认为TETS分子首先在碱性条件下依次脱去三个离去基(硫代硫酸基)生成氮丙啶环正离子，之后亲核试剂(纤维素纤维上的羟基、蛋白质纤维上的氨基等)进攻氮丙啶环正离子上的中心碳原子使之开环，进而完成TETS与纤维间的亲核取代反应。通过红外分析、氮元素分析、硫元素分析手段验证了交联反应的发生。
论文系统研究了交联剂TETS在棉织物的免烫整理、纤维素纤维胺化交联改性染色、牛皮纸以及瓦楞纸等纸品的湿强整理、Lyocell纤维的抗原纤化整理、竹纤维的湿增强整理、真丝织物的抗皱整理、蚕蛹蛋白／粘胶纤维的防脱落整理等领域的应用性能，提出了一些相关的测试方法，摸索了最佳工艺条件，对有关现象进行了理论分析，为交联剂的开发与应用提供了一些新的途径。主要应用研究结果简述如下：
1)棉织物经TETS整理后产生了优良的抗皱免烫性能：织物的弹性可达到传统树脂整理产品所具有的水平，折皱回复角高达270°：织物的强力保留率明显提高，为75％左右；织物的耐洗性好于传统树脂；但白度稍有下降。
正交实验确定TETS对棉织物免烫整理的最佳工艺：TETS浓度100g／L，轧液pH值9.5，焙烘温度为170℃，焙烘时间为3min。
论文探讨了交联剂TETS能够使免烫整理后的织物具有较高强力保留率的原因。通过实验证明了传统的酸性交联工艺对织物的降强是两方面的结果造成的，一是交联降强，二是酸性降强。TETS的碱性交联条件避免了酸性催化水解纤维素使强力的下降，从而具有较高的织物强力保留率。
2) TETS是一种具有交联作用的胺化改性剂，棉织物经TETS改性后大大提高了纤维素纤维活性染料的染色性能。改性织物染色后，得色量明显加深，吸尽率和固色率大大提高，织物的摩擦色牢度明显提高，耐洗牢度有所改善；但日晒牢度有所降低，移染性变差，匀染性降低，对此有待于今后进一步研究。
论文采用DMF剥色实验证明了活性染料在中性(或酸性)无盐条件下染色仍与纤维分子生成了共价键结合。
实验表明改性方法对TETS改性效果影响很大，采用焙烘工艺比采用湿蒸工艺改性效果好得多。
交联剂TETS改性处理为纤维素纤维胺化改性提供了一条新的途径。它不仅能使活性染料染色具有节约染料、减少染色污水的优点，更有可以进行酸性(或中性)、无盐(或低盐)染色的优势，对解决传统活性染料存在的固色率低、大量无机盐促染造成的环境污染问题具有重要的现实意义。
3) TETS对纸品进行湿强整理后，纸张的湿抗张强度提高显著，牛皮纸的湿抗张强度提高5-6倍，湿／干强度比高达50-60％(未经处理的仅有9％)；但纸的伸长率有所降低；纸的耐折度下降明显。
牛皮纸TETS湿强处理的最佳工艺条件为：TETS浓度150g／L、pH值9.5、焙烘温度170℃、焙烘时间3min。
TETS整理后的湿／干强度比大于传统的六羟树脂和F-CL树脂，而且干抗张强力和耐折度也都高于六羟树脂和F-CL树脂。TETS在瓦楞原纸、混合废纸挂面纸板、普通滤纸上也有良好的整理效果，湿／干强度比从整理前的10％以下提高到25％以上，在瓦楞纸上的湿强度甚至增加了8倍；耐折度下降程度较小。因此，TETS有望成为纸张湿强剂的一个新品种。
4)在TETS用于Lyocell织物的抗原纤化整理中，用织物起毛起球仪使织物原纤化，之后借用烧毛等级评定法来评判抗原纤化效果。Lyocell纤维经TETS整理后，抗原纤化等级明显提高，从处理前的1-2级提高到处理后的3-4级。
5)在竹纤维针织物的湿增强整理中，用顶破强力的变化来衡量整理效果。实验表明经TETS处理后，竹纤维针织物的干、湿顶破强力均比未处理的高，尤其是湿顶破强力提高了近20％，湿／干强度比从45.3％增加到64.6％。
6) TETS用于蚕蛹蛋白纤维的防脱落整理，对水煮、碱煮和酸煮三种仿染整加工处理都有一定的防脱落效果，纤维失重率和强力损失率都有所下降。
7)真丝织物在碱性条件下经TETS抗皱整理后，织物的干、湿回复角都有所提高，但提高不大。
本论文的创新点体现在以下几个方面：一是所提出的交联剂TETS结构，至今未见有报道；二是在合成中采用了毛细管电泳分析手段对合成反应进行监控，这在国内纺织化学领域中尚属首创；三是较为系统地研究了此交联剂在纺织纤维、印染、纸张等整理中的应用，提供了一些新型的整理途径和工艺。
A novel crosslinking agent TETS was proposed and the synthesis & applications ofthe crosslinker were wholly studied in this paper.
Crosslinker TETS (2,2',2"-nitrilo-triethylthiosulphate) is a kind of Bunte salt. Itcould be prepared from the reaction of TES (2,2',2"-nitrilo-triethylsulphate) andthiosulphate (Na_2S_2O_3). There are three Bunte groups and a tertiary amine group in themolecule. TETS easily takes the crosslinking reaction with the hydroxyl group incellulosic fibre or the amino group in protein fibre in alkaline condition. It features strongcrossing ability, good stability of storage, simple process of synthesis, easily soluble inwater, and non- formaldehyde & other harmful substances during its synthesis andapplication.
Capillary electrophoresis analysis (CE) was used to trace and control the syntheticreaction, confirm the synthetic mechanism, optimize the process, monitor the separationeffect, analyze the hydrolysis of samples, quantify and characterize the aim resultant. Aseparation method namely "hot and cold filtration with ethanol" was proposed whichresolved the problem of separating TETS from the side resultant sulphate. The objectiveproduct was obtained successfully in the end. By combining the CE and Raman spectraanalysis, the objective substance TETS was characterized and identified.
The stabilization to heat, alkali, acids, and hydrolysis of TETS were studied. Themechanism of cross reaction between TETS and cellulosic fibre was speculated accordingto the similar researches from literatures. It is assumed that TETS molecule firstlygenerates an aziridinum ring by eliminating the three leaving groups (-OSO3- groups)sequentially in alkaline environment. Then, the nucleophiles (hydroxyl in cellulose fibreor amino group in protein fibre) would attack and open the aziridinium ring, finishing thesubstitution reaction between TETS and fibres. The crosslinkage bond is testified byinfra-red analysis, element analysis for nitrogen and sulphate.
A series of experiments and studies were carried out in the fields of durable-pressfinish of cotton fabric, cellulose modifying to improve dyeing properties, wet strength improving of kraft paper and corrugated paper, anti-fibrillating finish of Lyocell fibre, wetstrength improving of bamboo fibre, wrinkle resistant finish of silk fabric,anti-weight-loss finish of pupa protein fibre etc. Some new testing methods wereproposed. Optimum processes were determined. Theoretical explanations to somephenomena were described. Some novel fields are opened and supplied for thedevelopment and application of the crosslinker TETS.
The main conclusions drawn from researches to TETS application are as follows:
1) Obvious wrinkle resistant properties for cotton fabric are produced after TETSfinishing: The elasticity of the fabric can reach the level as high as the product oftraditional resin finishing and the crease recovery angle is high to 270℃; the retention ofstrength gets more improved and reached 75% or so; washing resistance is better than thatof traditional resin; but the whiteness decreases a little.
The optimum process parameters of TETS treatment to cotton fabric for the durablepress finishing are determined by orthogonal experiments: TETS concentration 100g/L,pH 9.5, baking temperature 170℃, baking time 3 min.
The causes that the fabric treated by TETS has higher strength retention were studied.It is testified that there are two aspects which result in the strength loss in traditional sourcross process: one is the crosslink effect, another is the sour effect. The alkalinecrosslinking of TETS would avert cellulose hydrolysis by the sour catalysis, so higherstrength retention comes into being.
2) TETS is an aminating agent with crosslinking function. The dyeing properties ofcotton fabric modified by TETS will greatly be improved when dyed with reactive dyes:colour yield is obviously higher; percentage of exhaustion and fixation increase a lot;colour fastness to rubbing is improved remarkably; washing resistant is better as well; butlight fastness gets lower; ability of migrating and leveling dyeing deteriorate, which needsto be researched further next.
DMF decolouration experiment shows that the covalence between reactive dyes andcellulose is able to form even dyeing in sour bath and non-salt.
Crosslinker TETS supplies a new way to modify cellulosic fibre by amination. It provides a new method of dyeing in neutral (or sour) and non-salt as well.
3) The wet tensile strength for papers increases greatly after TETS treatment. Thewet tensile strength of kraft paper is 5 to 6 times higher than that of paper untreated byTETS. The wet/dry strength ratio is high to 50-60%, comparing the ratio of 9% foruntreated paper. But the elongation rate and the folding resistance decrease a lot.
The optimum process parameters for TETS wet strength improving finish to Kraftpaper are: TETS concentration 150g/L, pH 9.5, baking temperature 170℃, baking time 3min.
Comparing with the traditional resin such as hexahydroxymethyl trimeric cyanamideand F-CL resin (a modified 2D resin), the wet/dry strength ratio, the dry strength and thefolding resistance of Kraft paper treated by TETS are all higher. Good finish effect wasalso obtained in corrugated paper and common filter paper. The wet/dry strength ratioincreases from less than 10% to above 25%. The wet strength in corrugated paper is even8 times higher than that of untreated paper. The decrease of folding resistance gets lower.So TETS is a promising species in wet strength agents.
4) In anti-fibrillating finish of Lyocell fibre by TETS treatment, a new way tofibrillate the fabric with the fuzzing and pilling device is suggested. The grade ofanti-fibrillation is greatly raised from 1-2 to 3-4 grade after TETS treatment.
5) In TETS wet strength improving of bamboo knitted fabric, the change of burstingstrength after TETS finish was used to evaluate the finish effect. The experiment showsthat both wet and dry bursting strength are higher than those untreated by TETSespecially that the wet strength rises near 20% and the wet/dry strength ratio enhancesfrom 45.3 to 64.6%.
6) In anti-weight-loss finish of pupa protein fibre by TETS, a certain degree ofimprovement was achieved to all the three weight loss treatments with water, base andacid. Both weight and strength loss rate get lower.
7) In wrinkle resistant finish of silk fabric, the wet and dry crease recovery anglesare improved after TETS treatment, but not as obvious as cotton fabric.
The creative points in the paper are as follow: Firstly, the structure of the crosslinkerTETS is novel and hasn't been seen in public journals. Secondly, capillary electrophoresis the synthetic reaction which should be the first time in domestic chemical field. Thirdly,the applications of crosslinker TETS in textile fibre, dyeing and finishing, paper makingare studied systematically that provide some new application fields and processes.
CUI Shuling (Chemistry and chemical engineering)
Supervised by: Prof. SONG Xin-yuan
TETS(N，N，N-三乙胺硫代硫酸酯钠盐)是一种本特盐类交联剂，由TES(N，N，N-三乙胺硫酸酯钠盐)和Na_2S_2O_3在一定的条件下反应而成，其分子结构中含有三个本特基和一个叔胺基，可在碱性条件下与纤维素纤维分子上的羟基或蛋白质纤维分子上的氨基等发生交联，交联能力强，储存稳定性好，合成工艺简单，易溶于水，应用方便，合成和使用过程中不释放甲醛等有害物质。
论文采用毛细管电泳技术对TETS合成反应过程进行跟踪控制，验证合成反应机理，确定最佳合成条件，监测分离提纯效果，分析样品水解程度，对目标产物进行定性和定量分析。合成中提出了一种新型的分离方法—“先热后冷乙醇溶液过滤法”，解决了目标本特盐产物难以与反应副产物硫酸钠分离的难题，最后综合运用毛细管电泳、拉曼光谱等手段对目标产物进行了表征。
论文对TETS的热稳定性、酸碱稳定性以及水解稳定性进行了分析，并根据前人对其他相近反应所做的研究结果推测了交联剂TETS与纤维素纤维交联反应的机理，认为TETS分子首先在碱性条件下依次脱去三个离去基(硫代硫酸基)生成氮丙啶环正离子，之后亲核试剂(纤维素纤维上的羟基、蛋白质纤维上的氨基等)进攻氮丙啶环正离子上的中心碳原子使之开环，进而完成TETS与纤维间的亲核取代反应。通过红外分析、氮元素分析、硫元素分析手段验证了交联反应的发生。
论文系统研究了交联剂TETS在棉织物的免烫整理、纤维素纤维胺化交联改性染色、牛皮纸以及瓦楞纸等纸品的湿强整理、Lyocell纤维的抗原纤化整理、竹纤维的湿增强整理、真丝织物的抗皱整理、蚕蛹蛋白／粘胶纤维的防脱落整理等领域的应用性能，提出了一些相关的测试方法，摸索了最佳工艺条件，对有关现象进行了理论分析，为交联剂的开发与应用提供了一些新的途径。主要应用研究结果简述如下：
1)棉织物经TETS整理后产生了优良的抗皱免烫性能：织物的弹性可达到传统树脂整理产品所具有的水平，折皱回复角高达270°：织物的强力保留率明显提高，为75％左右；织物的耐洗性好于传统树脂；但白度稍有下降。
正交实验确定TETS对棉织物免烫整理的最佳工艺：TETS浓度100g／L，轧液pH值9.5，焙烘温度为170℃，焙烘时间为3min。
论文探讨了交联剂TETS能够使免烫整理后的织物具有较高强力保留率的原因。通过实验证明了传统的酸性交联工艺对织物的降强是两方面的结果造成的，一是交联降强，二是酸性降强。TETS的碱性交联条件避免了酸性催化水解纤维素使强力的下降，从而具有较高的织物强力保留率。
2) TETS是一种具有交联作用的胺化改性剂，棉织物经TETS改性后大大提高了纤维素纤维活性染料的染色性能。改性织物染色后，得色量明显加深，吸尽率和固色率大大提高，织物的摩擦色牢度明显提高，耐洗牢度有所改善；但日晒牢度有所降低，移染性变差，匀染性降低，对此有待于今后进一步研究。
论文采用DMF剥色实验证明了活性染料在中性(或酸性)无盐条件下染色仍与纤维分子生成了共价键结合。
实验表明改性方法对TETS改性效果影响很大，采用焙烘工艺比采用湿蒸工艺改性效果好得多。
交联剂TETS改性处理为纤维素纤维胺化改性提供了一条新的途径。它不仅能使活性染料染色具有节约染料、减少染色污水的优点，更有可以进行酸性(或中性)、无盐(或低盐)染色的优势，对解决传统活性染料存在的固色率低、大量无机盐促染造成的环境污染问题具有重要的现实意义。
3) TETS对纸品进行湿强整理后，纸张的湿抗张强度提高显著，牛皮纸的湿抗张强度提高5-6倍，湿／干强度比高达50-60％(未经处理的仅有9％)；但纸的伸长率有所降低；纸的耐折度下降明显。
牛皮纸TETS湿强处理的最佳工艺条件为：TETS浓度150g／L、pH值9.5、焙烘温度170℃、焙烘时间3min。
TETS整理后的湿／干强度比大于传统的六羟树脂和F-CL树脂，而且干抗张强力和耐折度也都高于六羟树脂和F-CL树脂。TETS在瓦楞原纸、混合废纸挂面纸板、普通滤纸上也有良好的整理效果，湿／干强度比从整理前的10％以下提高到25％以上，在瓦楞纸上的湿强度甚至增加了8倍；耐折度下降程度较小。因此，TETS有望成为纸张湿强剂的一个新品种。
4)在TETS用于Lyocell织物的抗原纤化整理中，用织物起毛起球仪使织物原纤化，之后借用烧毛等级评定法来评判抗原纤化效果。Lyocell纤维经TETS整理后，抗原纤化等级明显提高，从处理前的1-2级提高到处理后的3-4级。
5)在竹纤维针织物的湿增强整理中，用顶破强力的变化来衡量整理效果。实验表明经TETS处理后，竹纤维针织物的干、湿顶破强力均比未处理的高，尤其是湿顶破强力提高了近20％，湿／干强度比从45.3％增加到64.6％。
6) TETS用于蚕蛹蛋白纤维的防脱落整理，对水煮、碱煮和酸煮三种仿染整加工处理都有一定的防脱落效果，纤维失重率和强力损失率都有所下降。
7)真丝织物在碱性条件下经TETS抗皱整理后，织物的干、湿回复角都有所提高，但提高不大。
本论文的创新点体现在以下几个方面：一是所提出的交联剂TETS结构，至今未见有报道；二是在合成中采用了毛细管电泳分析手段对合成反应进行监控，这在国内纺织化学领域中尚属首创；三是较为系统地研究了此交联剂在纺织纤维、印染、纸张等整理中的应用，提供了一些新型的整理途径和工艺。
A novel crosslinking agent TETS was proposed and the synthesis & applications ofthe crosslinker were wholly studied in this paper.
Crosslinker TETS (2,2',2"-nitrilo-triethylthiosulphate) is a kind of Bunte salt. Itcould be prepared from the reaction of TES (2,2',2"-nitrilo-triethylsulphate) andthiosulphate (Na_2S_2O_3). There are three Bunte groups and a tertiary amine group in themolecule. TETS easily takes the crosslinking reaction with the hydroxyl group incellulosic fibre or the amino group in protein fibre in alkaline condition. It features strongcrossing ability, good stability of storage, simple process of synthesis, easily soluble inwater, and non- formaldehyde & other harmful substances during its synthesis andapplication.
Capillary electrophoresis analysis (CE) was used to trace and control the syntheticreaction, confirm the synthetic mechanism, optimize the process, monitor the separationeffect, analyze the hydrolysis of samples, quantify and characterize the aim resultant. Aseparation method namely "hot and cold filtration with ethanol" was proposed whichresolved the problem of separating TETS from the side resultant sulphate. The objectiveproduct was obtained successfully in the end. By combining the CE and Raman spectraanalysis, the objective substance TETS was characterized and identified.
The stabilization to heat, alkali, acids, and hydrolysis of TETS were studied. Themechanism of cross reaction between TETS and cellulosic fibre was speculated accordingto the similar researches from literatures. It is assumed that TETS molecule firstlygenerates an aziridinum ring by eliminating the three leaving groups (-OSO3- groups)sequentially in alkaline environment. Then, the nucleophiles (hydroxyl in cellulose fibreor amino group in protein fibre) would attack and open the aziridinium ring, finishing thesubstitution reaction between TETS and fibres. The crosslinkage bond is testified byinfra-red analysis, element analysis for nitrogen and sulphate.
A series of experiments and studies were carried out in the fields of durable-pressfinish of cotton fabric, cellulose modifying to improve dyeing properties, wet strength improving of kraft paper and corrugated paper, anti-fibrillating finish of Lyocell fibre, wetstrength improving of bamboo fibre, wrinkle resistant finish of silk fabric,anti-weight-loss finish of pupa protein fibre etc. Some new testing methods wereproposed. Optimum processes were determined. Theoretical explanations to somephenomena were described. Some novel fields are opened and supplied for thedevelopment and application of the crosslinker TETS.
The main conclusions drawn from researches to TETS application are as follows:
1) Obvious wrinkle resistant properties for cotton fabric are produced after TETSfinishing: The elasticity of the fabric can reach the level as high as the product oftraditional resin finishing and the crease recovery angle is high to 270℃; the retention ofstrength gets more improved and reached 75% or so; washing resistance is better than thatof traditional resin; but the whiteness decreases a little.
The optimum process parameters of TETS treatment to cotton fabric for the durablepress finishing are determined by orthogonal experiments: TETS concentration 100g/L,pH 9.5, baking temperature 170℃, baking time 3 min.
The causes that the fabric treated by TETS has higher strength retention were studied.It is testified that there are two aspects which result in the strength loss in traditional sourcross process: one is the crosslink effect, another is the sour effect. The alkalinecrosslinking of TETS would avert cellulose hydrolysis by the sour catalysis, so higherstrength retention comes into being.
2) TETS is an aminating agent with crosslinking function. The dyeing properties ofcotton fabric modified by TETS will greatly be improved when dyed with reactive dyes:colour yield is obviously higher; percentage of exhaustion and fixation increase a lot;colour fastness to rubbing is improved remarkably; washing resistant is better as well; butlight fastness gets lower; ability of migrating and leveling dyeing deteriorate, which needsto be researched further next.
DMF decolouration experiment shows that the covalence between reactive dyes andcellulose is able to form even dyeing in sour bath and non-salt.
Crosslinker TETS supplies a new way to modify cellulosic fibre by amination. It provides a new method of dyeing in neutral (or sour) and non-salt as well.
3) The wet tensile strength for papers increases greatly after TETS treatment. Thewet tensile strength of kraft paper is 5 to 6 times higher than that of paper untreated byTETS. The wet/dry strength ratio is high to 50-60%, comparing the ratio of 9% foruntreated paper. But the elongation rate and the folding resistance decrease a lot.
The optimum process parameters for TETS wet strength improving finish to Kraftpaper are: TETS concentration 150g/L, pH 9.5, baking temperature 170℃, baking time 3min.
Comparing with the traditional resin such as hexahydroxymethyl trimeric cyanamideand F-CL resin (a modified 2D resin), the wet/dry strength ratio, the dry strength and thefolding resistance of Kraft paper treated by TETS are all higher. Good finish effect wasalso obtained in corrugated paper and common filter paper. The wet/dry strength ratioincreases from less than 10% to above 25%. The wet strength in corrugated paper is even8 times higher than that of untreated paper. The decrease of folding resistance gets lower.So TETS is a promising species in wet strength agents.
4) In anti-fibrillating finish of Lyocell fibre by TETS treatment, a new way tofibrillate the fabric with the fuzzing and pilling device is suggested. The grade ofanti-fibrillation is greatly raised from 1-2 to 3-4 grade after TETS treatment.
5) In TETS wet strength improving of bamboo knitted fabric, the change of burstingstrength after TETS finish was used to evaluate the finish effect. The experiment showsthat both wet and dry bursting strength are higher than those untreated by TETSespecially that the wet strength rises near 20% and the wet/dry strength ratio enhancesfrom 45.3 to 64.6%.
6) In anti-weight-loss finish of pupa protein fibre by TETS, a certain degree ofimprovement was achieved to all the three weight loss treatments with water, base andacid. Both weight and strength loss rate get lower.
7) In wrinkle resistant finish of silk fabric, the wet and dry crease recovery anglesare improved after TETS treatment, but not as obvious as cotton fabric.
The creative points in the paper are as follow: Firstly, the structure of the crosslinkerTETS is novel and hasn't been seen in public journals. Secondly, capillary electrophoresis the synthetic reaction which should be the first time in domestic chemical field. Thirdly,the applications of crosslinker TETS in textile fibre, dyeing and finishing, paper makingare studied systematically that provide some new application fields and processes.
CUI Shuling (Chemistry and chemical engineering)
Supervised by: Prof. SONG Xin-yuan
引文
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