硅橡胶着色用含硅活性分散染料的结构与性能
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摘要
硅橡胶是用途最广的精细功能高分子材料之一,为了达到更好的着色效果,分别以对硝基苯胺为重氮组分,三聚氯氰和1,3,5-吡唑啉酮的一缩物为偶合组分,3-氨丙基甲氧基二甲基硅烷、3-氨丙基二甲氧基甲基硅烷和3-氨丙基三甲氧基硅烷为硅烷偶联剂,合成了一类新型黄色含硅活性分散染料。通过UV-Vis、FT-IR、1H-NMR以及MS等分析测试手段对染料进行表征。将该类染料用于硅橡胶着色,着色橡胶的干、湿摩擦牢度和耐洗牢度均达到4~5级,升华牢度也在4级以上,呈现出优异的牢度性能,且同色染料色光基本一致,着色后的硅橡胶色泽鲜艳饱满,静态力学性能保持不变。
Silicone rubber is one of the fine functional polymer materials with widest applications. For the sake of better coloring effect,a series of novel yellow silicon-containing reactive disperse dyes are designed and synthesized by using p-nitroaniline as diazonium component,the first condensation product between cyanuric chloride and pyrazolone as coupling component and 3-aminopropylmethoxydimethylsilane, 3-aminopropylmethyldimethoxysilane and 3-aminopropyltrimethoxysilane as silane coupling agents.The dyes samples are characterized by UV-Vis,1 H-NMR,FT-IR,and MS.The obtained silicon-containing reactive disperse dyes are used to color silicone rubbers,making the dry/wet rubbing and washing fastnesses of colored silicone rubbers all reach grade 4-5 and the sublimation fastness exceed grade4,which indicates outstanding performance in terms of color fastness.Such colored silicone rubbers show bright and rich colors without affecting its static mechanical properties.
Silicone rubber is one of the fine functional polymer materials with widest applications. For the sake of better coloring effect,a series of novel yellow silicon-containing reactive disperse dyes are designed and synthesized by using p-nitroaniline as diazonium component,the first condensation product between cyanuric chloride and pyrazolone as coupling component and 3-aminopropylmethoxydimethylsilane, 3-aminopropylmethyldimethoxysilane and 3-aminopropyltrimethoxysilane as silane coupling agents.The dyes samples are characterized by UV-Vis,1 H-NMR,FT-IR,and MS.The obtained silicon-containing reactive disperse dyes are used to color silicone rubbers,making the dry/wet rubbing and washing fastnesses of colored silicone rubbers all reach grade 4-5 and the sublimation fastness exceed grade4,which indicates outstanding performance in terms of color fastness.Such colored silicone rubbers show bright and rich colors without affecting its static mechanical properties.
引文
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[26]Dan X,Zhu L,Yu-Xin P,et al.Post-modification of 2-formylthiophene based heterocyclic azo dyes[J].Dyes Pigm,2016,133:143-152.
[27]Xiao-Lei Z,Jiao G,Hui-Fen Q,et al.p H-induced azo-keto and azoenol tautomerism for 6-(3-methoxypropylamino)pyridin-2-one based thiophene azo dyes[J].Dyes Pigm,2017,147:318-326.
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[2]Zhao Q,Liu Q,Xu H,et al.Preparation and characterization of room temperature vulcanized silicone rubber usingα-amine ketoximesilanes as auto-catalyzed cross-linkers[J].RSC Advances,2016,6(44):38447-38453.
[3]Chen W,Zeng X,Lai X,et al.Synergistic effect and mechanism of platinum catalyst and nitrogen-containing silane on the thermal stability of silicone rubber[J].Thermochimica Acta,2016,632:1-9.
[4]Wang D,Klein J,Mejía E.Catalytic systems for the cross-linking of organosilicon polymers[J].Chemistry-An Asian Journal,2017,12(11):1180-1197.
[5]Namitha L K,Sebastian M T.High permittivity ceramics loaded silicone elastomer composites for flexible electronics applications[J].Ceramics International,2017,43(3):2994-3003.
[6]Mei H,Chen G,Zhu Q,et al.Improving properties of silicone rubber composites using macromolecular silane coupling agent(MMSCA)[J].Journal of Applied Polymer Science,2016,133(19):43415.
[7]Liu D,Chen J,Song L,et al.Parameterization of silica-filled silicone rubber morphology:A contrast variation SANS and TEM study[J].Polymer,2017,120:155-163.
[8]Pan Z,Sun R,Zhu S,et al.The synthesis,characterization and properties of silicone adhesion promoters for addition-cure silicone rubber[J].Journal of Adhesion Science and Technology,2018,32(14):1-14.
[9]Sun Z,Huang Q,Wang Y,et al.Structure and properties of silicone rubber/styrene-butadiene rubber blends with in situ interface coupling by thiol-ene click reaction[J].Industrial&Engineering Chemistry Research,2017,56(6):1471-1477.
[10]Seyedmehdi S A,Zhang H,Zhu J.Influence of production method,silicone type and thickness on silicon rubber superhydrophobic coatings[J].Progress in Organic Coatings,2016,90:291-295.
[11]Valentini L,Bon S B,Pugno N M.Severe graphene nanoplatelets aggregation as building block for the preparation of negative temperature coefficient and healable silicone rubber composites[J].Composites Science and Technology,2016,134:125-131.
[12]Xue Y,Li X,Zhang D,et al.Comparison of ATH and Si O2fillers filled silicone rubber composites for HTV insulators[J].Composites Science and Technology,2018,155:137-143.
[13]Xiang H P,Rong M Z,Zhang M Q.A facile method for imparting sunlight driven catalyst-free self-healability and recyclability to commercial silicone elastomer[J].Polymer,2017,108:339-347.
[14]Buijssen K J D A,Oosterhof J J H,Basil L,et al.Influence of surface roughness on silicone rubber voice prostheses on in vitro biofilm formation and clinical lifetime in laryngectomised patients[J].Clinical Otolaryngology,2017,42(6):1235-1240.
[15]Ketchum A R,Kappler M P,Wu J,et al.The preparation and characterization of nitric oxide releasing silicone rubber materials impregnated with S-nitroso-tert-dodecyl mercaptan[J].Journal of Materials Chemistry B,2016,4(3):422-430.
[16]Berahman R,Raiati M,Mazidi M M,et al.Preparation and characterization of vulcanized silicone rubber/halloysite nanotube nanocomposites:Effect of matrix hardness and HNT content[J].Materials&Design,2016,104:333-345.
[17]Emelyanenko A M,Boinovich L B,Bezdomnikov A A,et al.Reinforced superhydrophobic coating on silicone rubber for longstanding anti-icing performance in severe conditions[J].ACS Applied Materials&Interfaces,2017,9(28):24210-24219.
[18]Guo X,Huang Y,Cai X,et al.Capacitive wearable tactile sensor based on smart textile substrate with carbon black/silicone rubber composite dielectric[J].Measurement Science and Technology,2016,27(4):045105.
[19]Heo G,Pyo K,Lee D H,et al.Critical role of Diels-Adler adducts to realise stretchable transparent electrodes based on silver nanowires and silicone elastomer[J].Scientific Reports,2016,6:25358.
[20]Yoshimura K,Nakano K,Hishikawa Y.Flexible tactile sensor materials based on carbon microcoil/silicone-rubber porous composites[J].Composites Science and Technology,2016,123:241-249.
[21]Liu P,Liu C,Huang Y,et al.Transfer function and working principle of a pressure/temperature sensor based on carbon black/silicone rubber composites[J].Journal of Applied Polymer Science,2016,133(7):42979.
[22]Guiotti A M,Goiato M C,Dos Santos D M.Comparison of conventional and plant-extract disinfectant solutions on the hardness and color stability of a maxillofacial elastomer after artificial aging[J].The Journal of Prosthetic Prosthet,2016,115(4),501-508.
[23]Eltayyar N H,Alshimy A M,Abushelib M N.Evaluation of intrinsic color stability of facial silicone elastomer reinforced with different nanoparticles[J].Alexandria Dental Dent Journal J,2016,41:50-54.
[24]Mancuso D N,Goiato M CSantos D M.Color stability after accelerated aging of two silicones,pigmented or not,for use in facial prostheses[J].Braz Oral Res Brazilian Oral Research,2009,23(2):144-148.
[25]Al-Harbi F A,Ayad N M,Saber M A.Mechanical behavior and color change of facial prosthetic elastomers after outdoor weathering in a hot and humid climate.The Journal of Prosthetic Dentistry,2015,113(2),146-151.
[26]Dan X,Zhu L,Yu-Xin P,et al.Post-modification of 2-formylthiophene based heterocyclic azo dyes[J].Dyes Pigm,2016,133:143-152.
[27]Xiao-Lei Z,Jiao G,Hui-Fen Q,et al.p H-induced azo-keto and azoenol tautomerism for 6-(3-methoxypropylamino)pyridin-2-one based thiophene azo dyes[J].Dyes Pigm,2017,147:318-326.
[28]Kew-Yu C,Che-Wei C,Hsing-Yang T.1,6-and 1,7-Regioisomers of highly soluble amino-substituted perylene tetracarboxylic dianhydrides:Synthesis,optical and electrochemical properties[J].Materials,2015,8:4943-4960.