新型吡啶季铵盐抗菌剂和抗菌性阳离子活性染料的合成、表征及应用性能研究
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摘要
本论文研究内容包括两大部分;一是高效吡啶季铵盐抗菌剂的合成、表征、结构与抗菌性能的关系,以及对羊毛纤维及棉纤维的抗菌机理研究;二是具有抗菌功能的阳离子活性染料的合成、表征及其对棉纤维、羊毛、腈纶及尼龙的染色性能和抗菌性能研究。
论文第一章论述了选题背景及其意义,介绍了国外纺织品抗菌整理的研究现状,重点介绍了季铵盐类抗菌剂和抗菌性阳离子活性染料的国内外研究成果。
论文第二章是具有不同烷基碳链长度的氨基吡啶季铵盐抗菌剂的合成、表征及抗菌性能研究。本工作采用一步法和三步法分别合成出了三种含有不同碳链长度(分别为4个碳、8个碳和12个碳原子)的氨基吡啶季铵盐抗菌剂,并采用核磁共振(1~H-NMR和(13)~C-NMR)、红外光谱(FT-IR)和差热分析仪(DSC和TGA)对产物进行了精确表征,比较了两种方法的产率,初步探索了叔胺的烷基化机理及合成工艺条件。对大肠杆菌E coli的抗菌机理研究表明碳链长度对季铵盐的抗菌性能具有重要的影响。具有不同烷基链长度的季铵盐抗菌性能不同。本工作为高效抗菌季铵盐抗菌剂的合成提供了重要实验依据和实验方法。
论文第三章采用合成的氨基吡啶季铵盐抗菌剂对羊毛纤维进行了抗菌性能研究。研究了三种不同碳链长度的氨基吡啶季铵盐对羊毛纤维的反应机理和动力学,发现阳离子季铵盐抗菌剂可以通过离子键和疏水键与羊毛纤维结合,从而使羊毛织物获得具有一定耐久性的抗菌性能。实验测定了包括最大吸附速率和最大吸附量等动力学参数,以及整理工艺条件pH值、抗菌剂浓度、整理温度以及季铵盐分子中的疏水碳链长度对动力学参数的影响。羊毛纤维上的季铵盐抗菌剂采用FT-IR行了分析。羊毛织物对大肠杆菌E coli的抗菌研究结果表明,碳链中含有十二个碳原子的季铵盐抗菌剂具有优异的抗菌性能和良好的耐洗涤性。该研究提供了阳离子季铵盐抗菌剂对羊毛纤维、锦纶纤维和腈纶纤维的改性动力学模型,为设计和研制适合该类纤维的高效抗菌剂提供了理论依据。
为了进一步提高季铵盐的抗菌性能,对季铵盐的抗菌机理有更加全面、深入地认识,开发高效季铵盐类抗菌剂,论文第四、五章对季铵盐的结构与抗菌性能的关系进行了深入研究。
论文第四章在前两章研究基础上,研究了季铵盐的结构尤其是分子中的疏水基团对其抗菌性能的影响。成功合成了在季铵盐吡啶环4位上含有不同疏水性基团的季铵盐化合物,并采用1~H-NMR、(13)~C-NMR和FT-IR行了结构表征,三种季铵盐分别是4-乙酰氨基十二烷基氯化吡啶(AADPC)、4-苯甲酰氨基十二烷基溴化吡啶(BADPB)和4-(1-萘酰)氨基-十二烷基溴化吡啶(NADPB),并对大肠杆菌Ecoli和金黄色葡萄球菌S aureus进行了抗菌实验。这些季铵盐具有相同的烷基链长度但不同的疏水基团。抗菌研究表明,四种季铵盐都具有很强的抗菌性能,但抗菌性能不同,季铵盐分子中含有的疏水性基团(如苯环和萘环)越大,抗菌性越强。研究表明,吡啶环上4位的疏水基团可以提高吡啶季铵盐的抗菌性能,即季铵盐分子中的疏水基团对季铵盐的抗菌性能具有增效作用。本研究内容国内外文献未有相关报道。该研究结果有助于设计、开发高效季铵盐抗菌剂。
论文第五章是关于季铵盐抗菌剂ALPC、BADPB和NADPB对棉纤维的抗菌整理研究。分析了活性和直接染料染色的棉纤维进行抗菌整理时季铵盐分子与纤维素分子之间的化学键类型。结果表明经过含有磺酸基(-SO_3H)和羧酸基(-COOH)阴离子染料染色的棉纤维,由于引入了阴离子基团,可以与季铵盐类整理剂形成离子键结合,棉织物对大肠杆菌E coli和葡萄球菌S aureus的抗菌性能优异且耐久。染料分子中的磺酸基团通过与季铵盐分子之间的离子键结合,封闭了季铵盐的水溶性基团,同时由于季铵盐分子量的增大,提高了与纤维之间的作用力,降低了水溶性,使得季铵盐在纤维上的抗菌耐久性提高,染料分子对季铵盐的抗菌耐久性起到了增效作用。
通过以上四章的研究工作,得到了高效季铵盐抗菌剂的结构特征、抗菌性能及对常用纤维的吸附性能,从而为抗菌型阳离子活性染料的研究奠定了基础。
论文第六章设计并合成了具有抗菌功能的蒽醌型季铵盐类阳离子活性染料。该染料以葸醌作为染料母体,是基于葸醌的化学稳定性好、适合开发不同颜色的染料品种;活性基为一氯或一氟均三嗪,有利于中高温进行固色反应,提高染料的扩散性能和水溶性;季铵盐不但可以赋予染料的水溶性,还使染料具有抗菌性能。该新型染料的结构采用FT-IR、1~H-NMR和(13)~C-NMR进行了精确表征;采用λax和εmax研究了染料在水溶液中的颜色特点;采用最小抑制细菌浓度(minimuminhibitory concentration,MIC)研究了染料的抗菌性能;同时采用差热分析仪(DSC)和热重分析仪(TGA)对染料的热稳定性进行了研究。结果表明,根据所设计的实验方法可以成功合成出一种新型抗菌型阳离子活性染料,该染料由于蒽醌和均三嗪基团的疏水性,较传统季铵盐抗菌剂具有优异的抗菌性能。
第七章进一步研究了多功能性阳离子活性染料对棉、羊毛、锦纶和腈纶纤维的染色性能。重点研究了染料对棉纤维染色时电解质浓度、染色温度和染色时间对上染百分率和固色率的影响。结果表明阳离子活性染料对棉纤维染色时,不需要中性电解质的促染就可以获得高的上染百分率和固色率,该染料可以进行无盐染色,可以获得高的上染百分率和固色率,同时棉织物还具有优良的抗菌功能和一定的耐久性。此外,阳离子活性染料对羊毛、锦纶和腈纶染色的研究表明,染料对这些纤维表现出良好的染色性能,所有染色织物具有优异的抗菌(E coli和S aureus)性能。
综上所述,以高效吡啶季铵盐抗菌剂的合成及应用研究为基础,所合成的具有抗菌功能的阳离子活性染料是集染色与功能整理于一体的新型功能性染料。该染料对常用纤维具有高的亲和力,可以采用传统染色方法将染色与整理一次完成。该研究成果为活性染料的无盐染色和多组分纤维纺织品的一浴法染色提供了一种可能的技术途径。
The content of the thesis covers two parts.One is the synthesis and characterization of the aminopyridinium salts and their antimicrobial mechanism in the finishing of wool,nylon,acrylic,and cotton fabrics.The other is the synthesis and the antimicrobial efficacy of the antimicrobial cationic reactive dye and its performance in the dyeing of cotton,nylon,wool,and acrylic fibers.
In foreword the background of topic selection of the thesis is described.In chapter 1 the recent progress in the world of studies on the antimicrobial finishing of textiles is introduced.The research works of the antimicrobial pyridinium salts and the antimicrobial dyes are majorly mentioned.
In chapter 2 the research work is about the synthesis and characterization of the antimicrobial aminopyridinium salts with different alkyl chain length.As an effort to develop antimicrobial surface treatment agents for wool fibers,three antimicrobial 4-aminopyridinium salts were synthesized by using two different processes.The structures of the salts were fully characterized by using FT-IR,1~H-NMR and (13)~C-NMR analysis.Besides,their thermal stability was also conducted by using DSC and TGA.The yields of two synthesis processes were also compared.The antimicrobial efficacy of these compounds was evaluated by using a minimum inhibitory concentration(MIC)as an indicator.All of the synthesized aminopyridinium salts showed antimicrobial activities against gram-negative bacterium,but in different levels depending on their structures.The salts possessing longer alkyl chain length demonstrated better antimicrobial functions.The research result provided the theory and method guidance for the synthesis of novel antimicrobial quaternary ammonium salts.
In chapter 3 the synthesized quaternary aminopyridinium salts were employed in antimicrobial finishing wool fabrics.All the finished wool fabrics exhibited antimicrobial efficacy against E coli.The quaternary ammonium salts could form ionic interactions with anionic groups on wool,which contribute to durable antimicrobial functions.The effects of alkyl chain length in the salts,pH conditions of finishing baths,finishing time and temperature,and salt concentrations were investigated.The absorption rate and the exhaustion percent of salts on the fibers were also measured.The incorporated quaternary aminopyridinium salt molecules on wool were characterized by FT-IR.The salt with the longest alkyl chain(12-C)showed the best antimicrobial performance and the washing durability of antimicrobial functions on the finished wool fabrics.The research provided a kinetics model for the antimicrobial finishing of wool fibers,acrylic fibers,and nylon fibers with quaternary ammonium salts.And it also provided an theory guidance for designing and synthesizing of biocides with high antimicrobial efficacy.
The antimicrobial mechanisms of the aminopyridinium salts are further explored in chapter 4 and chapter 5 for a comprehensive understanding of it. Based on the research works of chapter 2 and chapter 3,chapter 4 was aimed to explore the relationship between chemical structure and antimicrobial activities of quaternary ammonium salts,particularly the impact of hydrophobicity of the salts on antimicrobial functions.Four quaternary ammonium salts(QASs),i.e. 4-aminododecylpyridinium chloride,4-acetylaminododecylpyridinium chloride, 4-benzoylaminododecylpyridinium bromide,and 4-(1-Naphthoyl) aminododecylpyridinium bromide were employed in antimicrobial tests against both gram-negative and gram-positive bacteria,E coli and S aureus.These four QASs possess the same long alkyl chain but different hydrophobic group at the 4-amino groups.Antimicrobial activity of QASs was measured in liquid phases by growing bacterial cultures in the presence and absence of the QAS.The most hydrophobic compound exhibited the strongest antimicrobial activity than other salts.All of the quaternary pyridinium salts exhibited significantly antimicrobial activities but in different extents according to their hydrophobicity at the 4-amino position.QASs which have larger hydrophobic groups were significantly more effective than that with smaller groups.This research revealed that hydrophobic and aromatic ring structures at 4-amino position on quaternary aminopyridinium ring could improve antimicrobial activity of the salts.The results could assist understanding and development of antimicrobial quaternary ammonium salts.Besides,the ionic bounds between the dyes and the salts could increase the antimicrobial durability of pyridinium salts.
In chapter 5,three quaternary ammonium salts,namely 4-amino-laurylpyridium chloride(ALPC),4-benzoylamino-1-dodecylpyridinium bromide(BADPB),and 4-(l-naphthoyl)amino-l-dodecylpyridinium bromide(NADPB)were employed in antimicrobial finishing of cotton fabrics.The intermolecular interactions between the dyes and the aminopyridinium salts and their impact on the exhaustions of salts on the direct and reactive dyed fabrics were discussed.The quaternary ammonium salts could form ionic forces with sulfonate groups on the dyed cotton fibers,which contribute to higher exhaustion uptakes of the salts and better antimicrobial activities against E coli and and S aureus of the dyed cotton fabrics compared to that of the undyed sample.The fabrics also exhibited antimicrobial durability.
The characteristics of chemical structure,antimicrobial activities,and the absorption performance on fibers of antimicrobial quaternary ammoniumsalts were finally obtained through the work recounted in the previous four chapters,which settles firm bases for the foundation of the antimicrobial cationic reactive dye.
Based on these works,the major work introduced in chapter 6 was the synthesis, characterization,and antimicrobial activity of the cationic reactive dye. Anthraquinone ring was selected as a major chromophore to connect with quaternary ammonium structures because it is structurally small and widely available in different derivatives and has good chemical stability.The reactive group is three chloride triazine.The chemical structure of the new dye was fully characterized by using 1~H-NMR,(13)~C-NMR and FT-IR analyses.The color features of the dyes were studied in terms ofλmax andεmax in aqueous solutions,and the antimicrobial efficacy of the dye was evaluated by using the minimum inhibitory concentration(MIC)as an indicator.Differential scanning calorimetry(DSC)and thermogravimetric analysis (TGA)were employed in the studying of thermal stabilities.The results showed that a novel antimicrobial cationic reactive dye could be synthesized by following the designed procedure.The hydrophobic group of anthroquinone and triazine can improve the antimicrobial activities of the dye compared to the traditional salts.
In chapter 7,the performance of the dye in the dyeing of cotton,nylon,wool,and acrylic fibers were investigated.The research focused on the effect of electrolyte concentration,dyeing time,and dyeing temperature to exhaustion and fixation of the cationic reactive dye on cotton fibers.It was found that the cationic reactive dye exhibited higher exhaustion and fixation values under free salt dyeing condition. Simultaneously,all the treated cotton fabrics exhibited antimicrobial efficacy against E coli and S aureus and showed promising durability fastness to washing.Besides,the cationic reactive dye could be introduced into wool,acrylic,and nylon fabrics by following traditional cationic dyeing procedures.All the treated fabrics exhibited antimicrobial efficacy against E coli and S aureus.
To sum up,based on the synthesis and application of pyridinium salts,the synthesized novel antimicrobial cationic reactive dye combines the color and function together through suitable chemical linkages.The dye exhibits high affinity to the common fibers and the simultaneous dyeing and finishing can be achieved by simply following the traditional dyeing mechanisms.It is now possible to predict the salt free dyeing of reactive dye and realize the dyeing of multifiber fabrics with one kind of dye.
论文第一章论述了选题背景及其意义,介绍了国外纺织品抗菌整理的研究现状,重点介绍了季铵盐类抗菌剂和抗菌性阳离子活性染料的国内外研究成果。
论文第二章是具有不同烷基碳链长度的氨基吡啶季铵盐抗菌剂的合成、表征及抗菌性能研究。本工作采用一步法和三步法分别合成出了三种含有不同碳链长度(分别为4个碳、8个碳和12个碳原子)的氨基吡啶季铵盐抗菌剂,并采用核磁共振(1~H-NMR和(13)~C-NMR)、红外光谱(FT-IR)和差热分析仪(DSC和TGA)对产物进行了精确表征,比较了两种方法的产率,初步探索了叔胺的烷基化机理及合成工艺条件。对大肠杆菌E coli的抗菌机理研究表明碳链长度对季铵盐的抗菌性能具有重要的影响。具有不同烷基链长度的季铵盐抗菌性能不同。本工作为高效抗菌季铵盐抗菌剂的合成提供了重要实验依据和实验方法。
论文第三章采用合成的氨基吡啶季铵盐抗菌剂对羊毛纤维进行了抗菌性能研究。研究了三种不同碳链长度的氨基吡啶季铵盐对羊毛纤维的反应机理和动力学,发现阳离子季铵盐抗菌剂可以通过离子键和疏水键与羊毛纤维结合,从而使羊毛织物获得具有一定耐久性的抗菌性能。实验测定了包括最大吸附速率和最大吸附量等动力学参数,以及整理工艺条件pH值、抗菌剂浓度、整理温度以及季铵盐分子中的疏水碳链长度对动力学参数的影响。羊毛纤维上的季铵盐抗菌剂采用FT-IR行了分析。羊毛织物对大肠杆菌E coli的抗菌研究结果表明,碳链中含有十二个碳原子的季铵盐抗菌剂具有优异的抗菌性能和良好的耐洗涤性。该研究提供了阳离子季铵盐抗菌剂对羊毛纤维、锦纶纤维和腈纶纤维的改性动力学模型,为设计和研制适合该类纤维的高效抗菌剂提供了理论依据。
为了进一步提高季铵盐的抗菌性能,对季铵盐的抗菌机理有更加全面、深入地认识,开发高效季铵盐类抗菌剂,论文第四、五章对季铵盐的结构与抗菌性能的关系进行了深入研究。
论文第四章在前两章研究基础上,研究了季铵盐的结构尤其是分子中的疏水基团对其抗菌性能的影响。成功合成了在季铵盐吡啶环4位上含有不同疏水性基团的季铵盐化合物,并采用1~H-NMR、(13)~C-NMR和FT-IR行了结构表征,三种季铵盐分别是4-乙酰氨基十二烷基氯化吡啶(AADPC)、4-苯甲酰氨基十二烷基溴化吡啶(BADPB)和4-(1-萘酰)氨基-十二烷基溴化吡啶(NADPB),并对大肠杆菌Ecoli和金黄色葡萄球菌S aureus进行了抗菌实验。这些季铵盐具有相同的烷基链长度但不同的疏水基团。抗菌研究表明,四种季铵盐都具有很强的抗菌性能,但抗菌性能不同,季铵盐分子中含有的疏水性基团(如苯环和萘环)越大,抗菌性越强。研究表明,吡啶环上4位的疏水基团可以提高吡啶季铵盐的抗菌性能,即季铵盐分子中的疏水基团对季铵盐的抗菌性能具有增效作用。本研究内容国内外文献未有相关报道。该研究结果有助于设计、开发高效季铵盐抗菌剂。
论文第五章是关于季铵盐抗菌剂ALPC、BADPB和NADPB对棉纤维的抗菌整理研究。分析了活性和直接染料染色的棉纤维进行抗菌整理时季铵盐分子与纤维素分子之间的化学键类型。结果表明经过含有磺酸基(-SO_3H)和羧酸基(-COOH)阴离子染料染色的棉纤维,由于引入了阴离子基团,可以与季铵盐类整理剂形成离子键结合,棉织物对大肠杆菌E coli和葡萄球菌S aureus的抗菌性能优异且耐久。染料分子中的磺酸基团通过与季铵盐分子之间的离子键结合,封闭了季铵盐的水溶性基团,同时由于季铵盐分子量的增大,提高了与纤维之间的作用力,降低了水溶性,使得季铵盐在纤维上的抗菌耐久性提高,染料分子对季铵盐的抗菌耐久性起到了增效作用。
通过以上四章的研究工作,得到了高效季铵盐抗菌剂的结构特征、抗菌性能及对常用纤维的吸附性能,从而为抗菌型阳离子活性染料的研究奠定了基础。
论文第六章设计并合成了具有抗菌功能的蒽醌型季铵盐类阳离子活性染料。该染料以葸醌作为染料母体,是基于葸醌的化学稳定性好、适合开发不同颜色的染料品种;活性基为一氯或一氟均三嗪,有利于中高温进行固色反应,提高染料的扩散性能和水溶性;季铵盐不但可以赋予染料的水溶性,还使染料具有抗菌性能。该新型染料的结构采用FT-IR、1~H-NMR和(13)~C-NMR进行了精确表征;采用λax和εmax研究了染料在水溶液中的颜色特点;采用最小抑制细菌浓度(minimuminhibitory concentration,MIC)研究了染料的抗菌性能;同时采用差热分析仪(DSC)和热重分析仪(TGA)对染料的热稳定性进行了研究。结果表明,根据所设计的实验方法可以成功合成出一种新型抗菌型阳离子活性染料,该染料由于蒽醌和均三嗪基团的疏水性,较传统季铵盐抗菌剂具有优异的抗菌性能。
第七章进一步研究了多功能性阳离子活性染料对棉、羊毛、锦纶和腈纶纤维的染色性能。重点研究了染料对棉纤维染色时电解质浓度、染色温度和染色时间对上染百分率和固色率的影响。结果表明阳离子活性染料对棉纤维染色时,不需要中性电解质的促染就可以获得高的上染百分率和固色率,该染料可以进行无盐染色,可以获得高的上染百分率和固色率,同时棉织物还具有优良的抗菌功能和一定的耐久性。此外,阳离子活性染料对羊毛、锦纶和腈纶染色的研究表明,染料对这些纤维表现出良好的染色性能,所有染色织物具有优异的抗菌(E coli和S aureus)性能。
综上所述,以高效吡啶季铵盐抗菌剂的合成及应用研究为基础,所合成的具有抗菌功能的阳离子活性染料是集染色与功能整理于一体的新型功能性染料。该染料对常用纤维具有高的亲和力,可以采用传统染色方法将染色与整理一次完成。该研究成果为活性染料的无盐染色和多组分纤维纺织品的一浴法染色提供了一种可能的技术途径。
The content of the thesis covers two parts.One is the synthesis and characterization of the aminopyridinium salts and their antimicrobial mechanism in the finishing of wool,nylon,acrylic,and cotton fabrics.The other is the synthesis and the antimicrobial efficacy of the antimicrobial cationic reactive dye and its performance in the dyeing of cotton,nylon,wool,and acrylic fibers.
In foreword the background of topic selection of the thesis is described.In chapter 1 the recent progress in the world of studies on the antimicrobial finishing of textiles is introduced.The research works of the antimicrobial pyridinium salts and the antimicrobial dyes are majorly mentioned.
In chapter 2 the research work is about the synthesis and characterization of the antimicrobial aminopyridinium salts with different alkyl chain length.As an effort to develop antimicrobial surface treatment agents for wool fibers,three antimicrobial 4-aminopyridinium salts were synthesized by using two different processes.The structures of the salts were fully characterized by using FT-IR,1~H-NMR and (13)~C-NMR analysis.Besides,their thermal stability was also conducted by using DSC and TGA.The yields of two synthesis processes were also compared.The antimicrobial efficacy of these compounds was evaluated by using a minimum inhibitory concentration(MIC)as an indicator.All of the synthesized aminopyridinium salts showed antimicrobial activities against gram-negative bacterium,but in different levels depending on their structures.The salts possessing longer alkyl chain length demonstrated better antimicrobial functions.The research result provided the theory and method guidance for the synthesis of novel antimicrobial quaternary ammonium salts.
In chapter 3 the synthesized quaternary aminopyridinium salts were employed in antimicrobial finishing wool fabrics.All the finished wool fabrics exhibited antimicrobial efficacy against E coli.The quaternary ammonium salts could form ionic interactions with anionic groups on wool,which contribute to durable antimicrobial functions.The effects of alkyl chain length in the salts,pH conditions of finishing baths,finishing time and temperature,and salt concentrations were investigated.The absorption rate and the exhaustion percent of salts on the fibers were also measured.The incorporated quaternary aminopyridinium salt molecules on wool were characterized by FT-IR.The salt with the longest alkyl chain(12-C)showed the best antimicrobial performance and the washing durability of antimicrobial functions on the finished wool fabrics.The research provided a kinetics model for the antimicrobial finishing of wool fibers,acrylic fibers,and nylon fibers with quaternary ammonium salts.And it also provided an theory guidance for designing and synthesizing of biocides with high antimicrobial efficacy.
The antimicrobial mechanisms of the aminopyridinium salts are further explored in chapter 4 and chapter 5 for a comprehensive understanding of it. Based on the research works of chapter 2 and chapter 3,chapter 4 was aimed to explore the relationship between chemical structure and antimicrobial activities of quaternary ammonium salts,particularly the impact of hydrophobicity of the salts on antimicrobial functions.Four quaternary ammonium salts(QASs),i.e. 4-aminododecylpyridinium chloride,4-acetylaminododecylpyridinium chloride, 4-benzoylaminododecylpyridinium bromide,and 4-(1-Naphthoyl) aminododecylpyridinium bromide were employed in antimicrobial tests against both gram-negative and gram-positive bacteria,E coli and S aureus.These four QASs possess the same long alkyl chain but different hydrophobic group at the 4-amino groups.Antimicrobial activity of QASs was measured in liquid phases by growing bacterial cultures in the presence and absence of the QAS.The most hydrophobic compound exhibited the strongest antimicrobial activity than other salts.All of the quaternary pyridinium salts exhibited significantly antimicrobial activities but in different extents according to their hydrophobicity at the 4-amino position.QASs which have larger hydrophobic groups were significantly more effective than that with smaller groups.This research revealed that hydrophobic and aromatic ring structures at 4-amino position on quaternary aminopyridinium ring could improve antimicrobial activity of the salts.The results could assist understanding and development of antimicrobial quaternary ammonium salts.Besides,the ionic bounds between the dyes and the salts could increase the antimicrobial durability of pyridinium salts.
In chapter 5,three quaternary ammonium salts,namely 4-amino-laurylpyridium chloride(ALPC),4-benzoylamino-1-dodecylpyridinium bromide(BADPB),and 4-(l-naphthoyl)amino-l-dodecylpyridinium bromide(NADPB)were employed in antimicrobial finishing of cotton fabrics.The intermolecular interactions between the dyes and the aminopyridinium salts and their impact on the exhaustions of salts on the direct and reactive dyed fabrics were discussed.The quaternary ammonium salts could form ionic forces with sulfonate groups on the dyed cotton fibers,which contribute to higher exhaustion uptakes of the salts and better antimicrobial activities against E coli and and S aureus of the dyed cotton fabrics compared to that of the undyed sample.The fabrics also exhibited antimicrobial durability.
The characteristics of chemical structure,antimicrobial activities,and the absorption performance on fibers of antimicrobial quaternary ammoniumsalts were finally obtained through the work recounted in the previous four chapters,which settles firm bases for the foundation of the antimicrobial cationic reactive dye.
Based on these works,the major work introduced in chapter 6 was the synthesis, characterization,and antimicrobial activity of the cationic reactive dye. Anthraquinone ring was selected as a major chromophore to connect with quaternary ammonium structures because it is structurally small and widely available in different derivatives and has good chemical stability.The reactive group is three chloride triazine.The chemical structure of the new dye was fully characterized by using 1~H-NMR,(13)~C-NMR and FT-IR analyses.The color features of the dyes were studied in terms ofλmax andεmax in aqueous solutions,and the antimicrobial efficacy of the dye was evaluated by using the minimum inhibitory concentration(MIC)as an indicator.Differential scanning calorimetry(DSC)and thermogravimetric analysis (TGA)were employed in the studying of thermal stabilities.The results showed that a novel antimicrobial cationic reactive dye could be synthesized by following the designed procedure.The hydrophobic group of anthroquinone and triazine can improve the antimicrobial activities of the dye compared to the traditional salts.
In chapter 7,the performance of the dye in the dyeing of cotton,nylon,wool,and acrylic fibers were investigated.The research focused on the effect of electrolyte concentration,dyeing time,and dyeing temperature to exhaustion and fixation of the cationic reactive dye on cotton fibers.It was found that the cationic reactive dye exhibited higher exhaustion and fixation values under free salt dyeing condition. Simultaneously,all the treated cotton fabrics exhibited antimicrobial efficacy against E coli and S aureus and showed promising durability fastness to washing.Besides,the cationic reactive dye could be introduced into wool,acrylic,and nylon fabrics by following traditional cationic dyeing procedures.All the treated fabrics exhibited antimicrobial efficacy against E coli and S aureus.
To sum up,based on the synthesis and application of pyridinium salts,the synthesized novel antimicrobial cationic reactive dye combines the color and function together through suitable chemical linkages.The dye exhibits high affinity to the common fibers and the simultaneous dyeing and finishing can be achieved by simply following the traditional dyeing mechanisms.It is now possible to predict the salt free dyeing of reactive dye and realize the dyeing of multifiber fabrics with one kind of dye.
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