金属络合交联染料的合成和应用
摘要
本文设计合成了多胺型可交联金属络合染料,即将含有四乙烯五胺的邻,邻'-二羟基偶氮交联染料与金属离子通过络合反应制得,利用交联染料分子中的氨基、亚胺基的高反应性及同一染料分子上存在多个可反应基团的优点,渴望通过交联染色和固色实现染料在纤维上的超高固色率,实现染色的绿色化;同时通过引入金属离子,期望提高四乙烯五胺型交联染料的耐光稳定性。
论文以3-氨基-4-羟基苯磺酸为重氮组份,分别与偶合组份1-苯基-3-甲基-5-吡唑啉酮和1-(4'-磺酸基)苯基-3-甲基-5-吡唑啉酮进行重氮偶合反应合成了染料母体1a-2a。以2-氨基-4-硝基苯酚为重氮组分,分别与偶合组分1-(4'-磺酸基)苯基-3-甲基-5-吡唑啉酮和2-羟基萘-3,6-二磺酸钠(R盐)进行重氮偶合反应生成了染料母体3a-4a。用质谱、红外光谱和核磁共振氢谱证明了磺酸基染料1a-4a的结构正确。
论文采用氯化亚砜为氯化试剂,DMF为催化剂,将四支染料结构中的磺酸基进行磺酰氯化,合成了活性较高的磺酰氯化合物1b-4b。利用质谱、红外光谱和核磁共振氢谱证明了磺酰氯基染料1b-4b的结构正确。考察了反应温度、反应时间、溶剂用量和催化剂用量等条件对磺酰氯化反应的影响。在四氢呋喃溶剂中将磺酰氯染料与四乙烯五胺进行胺解反应合成四支多胺型可交联染料1c-4c,用红外光谱证明了多胺型可交联染料结构中磺酰胺基团和四乙烯五胺的存在。
论文将四支多胺型可交联染料母体1c-4c分别与铬盐和铁盐进行络合反应,合成了四支铬络合交联染料1d-4d和四支铁络合交联染料1e-4e。用红外光谱和原子吸收光谱证明了八支金属络合交联染料的结构正确。利用紫外可见光谱研究了可交联染料络合前后的光谱特性。
论文以铜酞菁为原料,通过氯磺酸和二氯亚砜对铜酞菁进行氯磺化处理后,与四乙烯五胺发生胺解反应合成了铜酞菁交联染料5。利用红外光谱证明了铜酞菁交联染料中磺酰胺基团和四乙烯五胺的存在。考察了氯磺化反应中铜酞菁、氯磺酸和二氯亚砜的摩尔比以及反应温度对铜酞菁磺酰氯中磺酰氯基团个数的影响。考察了反应时间、反应温度、磺酰氯基与四乙烯五胺的摩尔比、溶剂用量等条件对胺解产物产率和溶解性的影响。
论文利用无盐浸染的清洁染色工艺将所合成的多胺型可交联金属络合染料用于丝绸与羊毛纤维的染色,研究了染浴pH值、染色温度、浴比和色度等条件对染料分别在丝绸和羊毛上染色性能的影响。部分铁络合交联染料在丝绸和羊毛上的竭染率最高可分别达99%和97%。染色纤维通过交联剂DAST进行了固色,考察了固色pH值和交联剂浓度等条件对交联固色的影响,发现铁络合交联染料的交联率最高可达98%以上,在丝绸和羊毛上的最终固色率最高可分别达97%和95%以上。通过比较,发现铁络合交联染料的染色性能与铬络合交联染料的染色性能相当,完全可以用环境友好的铁络合交联染料取代铬络合染料,来实现在丝绸和羊毛上良好的交联染色性能。考察了染色纤维的牢度性能,与相应结构的交联染料母体染色的纤维相比,铁络合交联染料染色纤维的日晒牢度提高了2-3级,水洗牢度有所提高,两者的摩擦牢度相当。铁络合交联染料具有与铬络合交联染料相当的牢度性能。分子结构中引入四乙烯五胺的铜酞菁交联染料在丝绸和羊毛上的染色实现了良好的染色性能和牢度性能。
In this thesis, metal-complexed crosslinking dyes containing polyamine groups were designed and synthesized. They were prepared by introducing the metal ions onto the molecules of crosslinking dyes which contained the reactive amino and imine groups. As the dyes contain a certain number of reactive groups, a super-high dye fixation on fibre is expected to be achieved through crosslinking dyeing and fixation, and the greenization of the dyeing process may be realized. At the same time, the light fastness of the crosslinking dyes is expected to be improved due to the existence of metal ions within the dye molecules.
Dye parents la and 2a were synthesized through diazotization and coupling reaction by using 3-amino-4-hydroxy benzenesulfonic acid as diazo component, and 3-methyl-1-phenyl-2-pyrazolin-5-one and 4-(4-hydroxy-3-methyl-1H-pyrazol-1-yl)benzenesulfonic acid as coupling componds, respectively. Dye parents 3a and 4a were synthesized through diazotization and coupling reaction by using 2-amino-4-nitrophenol as diazo component, and 4-(4-hydroxy-3-methyl-1H-pyrazol-1-yl)benzenesulfonic acid and 2-hydroxynaphthalene-3,6-disulfonic acid as coupling componds, respectively. The structures of these dye parents were characterized by IR, ~1H NMR and API-ES mass spectroscopy.
Four chlorosulfonyl-containing azo compounds (1b-4b) were synthesized by the reactions of the corresponding sodium sulfonate of acid dyes and thionyl chloride in the presence of a catalytic quantity of DMF. Their structures were confirmed by IR, ~1H NMR and API-ES mass spectroscopy. The effects of reaction time and the amounts of the solvent and DMF on the reaction were discussed. Four polyamine crosslinking dyes 1c-4c were synthesized from the prepared chlorosulfonyl-containing compounds and tetraethylenepentamine. The structures of dyes 1c-4c were characterized by IR spectroscopy.
Four metal-free crosslinking dyes 1c-4c were complexed with chromium salt and iron salt, respectively, to get four new Cr-complexed crosslinking dyes ld-4d and four new Fe-complexed crosslinking dyes 1e-4e. The structures of these metal-complexed crosslinking dyes were confirmed by IR and atomic absorption spectroscopy (AAS). The visible spectra of the crosslinking dyes before and after the complex reaction were studied by UV-Vis spectroscopy.
Copper phthalocyanine (CuPc) crosslinking dye was synthesized through the reaction of chlorosulfonyl-containing copper phthalocyanine dye with tetraethylenepentamine. Its structure was confirmed by IR spectroscopy. The effects of reaction temperature and the molar ratio of CuPc to HSO_3Cl to SOCl_2 on the amount of chlorosulfonyl group in CuPc were discussed. The effects of reaction time, temperature, the molar ratio of the amount of chlorosulfonyl group in CuPc to tetraethylenepentamine and the amount of the solvent on amination reaction were studied.
Some polyamine crosslinking metal-complexed dyes were used to dye silk and wool through salt-free exhaustion dyeing. The effects of pH value, temperature, the liquor ratio and the concerntration of dyes on the dyeing performance were discussed. The exhaustion of some Fe-complexed crosslinking dyes on silk reached 99% and on wool reached 97%, respectively. With use of DAST as fixation agent, the effects of pH value and the concerntration of DAST on fixation were discussed. The crosslinking reaction of Fe-complexed crosslinking dyes on silk and wool all reached 98%. The fixation ratio of Fe-complexed crosslinking dyes on silk and wool reached 97% and 95%, respectively. The light fastness of Fe-complexed crosslinking dyes on silk and wool was 2-3 grade higher than that of the corresponding metal-free crosslinking dyes. The wash fastness of Fe-complexed crosslinking dyes was a little higher than that of the corresponding metal-free crosslinking dyes. The rub fastness of Fe-complexed crosslinking dyes was comparable with that of the corresponding metal-free crosslinking dyes. The dyeing performance and fastness properties of Fe-complexed crosslinking dyes were comparable with that of Cr-complexed crosslinking dyes. The exhaustion of the dyed silk and wool using copper phthalocyanine crosslinking dye was high. The lightfastness, wash fastness and rub fastness of the copper phthalocyanine crosslinking dye on silk and wool were satisfactory.
论文以3-氨基-4-羟基苯磺酸为重氮组份,分别与偶合组份1-苯基-3-甲基-5-吡唑啉酮和1-(4'-磺酸基)苯基-3-甲基-5-吡唑啉酮进行重氮偶合反应合成了染料母体1a-2a。以2-氨基-4-硝基苯酚为重氮组分,分别与偶合组分1-(4'-磺酸基)苯基-3-甲基-5-吡唑啉酮和2-羟基萘-3,6-二磺酸钠(R盐)进行重氮偶合反应生成了染料母体3a-4a。用质谱、红外光谱和核磁共振氢谱证明了磺酸基染料1a-4a的结构正确。
论文采用氯化亚砜为氯化试剂,DMF为催化剂,将四支染料结构中的磺酸基进行磺酰氯化,合成了活性较高的磺酰氯化合物1b-4b。利用质谱、红外光谱和核磁共振氢谱证明了磺酰氯基染料1b-4b的结构正确。考察了反应温度、反应时间、溶剂用量和催化剂用量等条件对磺酰氯化反应的影响。在四氢呋喃溶剂中将磺酰氯染料与四乙烯五胺进行胺解反应合成四支多胺型可交联染料1c-4c,用红外光谱证明了多胺型可交联染料结构中磺酰胺基团和四乙烯五胺的存在。
论文将四支多胺型可交联染料母体1c-4c分别与铬盐和铁盐进行络合反应,合成了四支铬络合交联染料1d-4d和四支铁络合交联染料1e-4e。用红外光谱和原子吸收光谱证明了八支金属络合交联染料的结构正确。利用紫外可见光谱研究了可交联染料络合前后的光谱特性。
论文以铜酞菁为原料,通过氯磺酸和二氯亚砜对铜酞菁进行氯磺化处理后,与四乙烯五胺发生胺解反应合成了铜酞菁交联染料5。利用红外光谱证明了铜酞菁交联染料中磺酰胺基团和四乙烯五胺的存在。考察了氯磺化反应中铜酞菁、氯磺酸和二氯亚砜的摩尔比以及反应温度对铜酞菁磺酰氯中磺酰氯基团个数的影响。考察了反应时间、反应温度、磺酰氯基与四乙烯五胺的摩尔比、溶剂用量等条件对胺解产物产率和溶解性的影响。
论文利用无盐浸染的清洁染色工艺将所合成的多胺型可交联金属络合染料用于丝绸与羊毛纤维的染色,研究了染浴pH值、染色温度、浴比和色度等条件对染料分别在丝绸和羊毛上染色性能的影响。部分铁络合交联染料在丝绸和羊毛上的竭染率最高可分别达99%和97%。染色纤维通过交联剂DAST进行了固色,考察了固色pH值和交联剂浓度等条件对交联固色的影响,发现铁络合交联染料的交联率最高可达98%以上,在丝绸和羊毛上的最终固色率最高可分别达97%和95%以上。通过比较,发现铁络合交联染料的染色性能与铬络合交联染料的染色性能相当,完全可以用环境友好的铁络合交联染料取代铬络合染料,来实现在丝绸和羊毛上良好的交联染色性能。考察了染色纤维的牢度性能,与相应结构的交联染料母体染色的纤维相比,铁络合交联染料染色纤维的日晒牢度提高了2-3级,水洗牢度有所提高,两者的摩擦牢度相当。铁络合交联染料具有与铬络合交联染料相当的牢度性能。分子结构中引入四乙烯五胺的铜酞菁交联染料在丝绸和羊毛上的染色实现了良好的染色性能和牢度性能。
In this thesis, metal-complexed crosslinking dyes containing polyamine groups were designed and synthesized. They were prepared by introducing the metal ions onto the molecules of crosslinking dyes which contained the reactive amino and imine groups. As the dyes contain a certain number of reactive groups, a super-high dye fixation on fibre is expected to be achieved through crosslinking dyeing and fixation, and the greenization of the dyeing process may be realized. At the same time, the light fastness of the crosslinking dyes is expected to be improved due to the existence of metal ions within the dye molecules.
Dye parents la and 2a were synthesized through diazotization and coupling reaction by using 3-amino-4-hydroxy benzenesulfonic acid as diazo component, and 3-methyl-1-phenyl-2-pyrazolin-5-one and 4-(4-hydroxy-3-methyl-1H-pyrazol-1-yl)benzenesulfonic acid as coupling componds, respectively. Dye parents 3a and 4a were synthesized through diazotization and coupling reaction by using 2-amino-4-nitrophenol as diazo component, and 4-(4-hydroxy-3-methyl-1H-pyrazol-1-yl)benzenesulfonic acid and 2-hydroxynaphthalene-3,6-disulfonic acid as coupling componds, respectively. The structures of these dye parents were characterized by IR, ~1H NMR and API-ES mass spectroscopy.
Four chlorosulfonyl-containing azo compounds (1b-4b) were synthesized by the reactions of the corresponding sodium sulfonate of acid dyes and thionyl chloride in the presence of a catalytic quantity of DMF. Their structures were confirmed by IR, ~1H NMR and API-ES mass spectroscopy. The effects of reaction time and the amounts of the solvent and DMF on the reaction were discussed. Four polyamine crosslinking dyes 1c-4c were synthesized from the prepared chlorosulfonyl-containing compounds and tetraethylenepentamine. The structures of dyes 1c-4c were characterized by IR spectroscopy.
Four metal-free crosslinking dyes 1c-4c were complexed with chromium salt and iron salt, respectively, to get four new Cr-complexed crosslinking dyes ld-4d and four new Fe-complexed crosslinking dyes 1e-4e. The structures of these metal-complexed crosslinking dyes were confirmed by IR and atomic absorption spectroscopy (AAS). The visible spectra of the crosslinking dyes before and after the complex reaction were studied by UV-Vis spectroscopy.
Copper phthalocyanine (CuPc) crosslinking dye was synthesized through the reaction of chlorosulfonyl-containing copper phthalocyanine dye with tetraethylenepentamine. Its structure was confirmed by IR spectroscopy. The effects of reaction temperature and the molar ratio of CuPc to HSO_3Cl to SOCl_2 on the amount of chlorosulfonyl group in CuPc were discussed. The effects of reaction time, temperature, the molar ratio of the amount of chlorosulfonyl group in CuPc to tetraethylenepentamine and the amount of the solvent on amination reaction were studied.
Some polyamine crosslinking metal-complexed dyes were used to dye silk and wool through salt-free exhaustion dyeing. The effects of pH value, temperature, the liquor ratio and the concerntration of dyes on the dyeing performance were discussed. The exhaustion of some Fe-complexed crosslinking dyes on silk reached 99% and on wool reached 97%, respectively. With use of DAST as fixation agent, the effects of pH value and the concerntration of DAST on fixation were discussed. The crosslinking reaction of Fe-complexed crosslinking dyes on silk and wool all reached 98%. The fixation ratio of Fe-complexed crosslinking dyes on silk and wool reached 97% and 95%, respectively. The light fastness of Fe-complexed crosslinking dyes on silk and wool was 2-3 grade higher than that of the corresponding metal-free crosslinking dyes. The wash fastness of Fe-complexed crosslinking dyes was a little higher than that of the corresponding metal-free crosslinking dyes. The rub fastness of Fe-complexed crosslinking dyes was comparable with that of the corresponding metal-free crosslinking dyes. The dyeing performance and fastness properties of Fe-complexed crosslinking dyes were comparable with that of Cr-complexed crosslinking dyes. The exhaustion of the dyed silk and wool using copper phthalocyanine crosslinking dye was high. The lightfastness, wash fastness and rub fastness of the copper phthalocyanine crosslinking dye on silk and wool were satisfactory.
引文
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