留言板

尊敬的读者、作者、审稿人, 关于本刊的投稿、审稿、编辑和出版的任何问题, 您可以本页添加留言。我们将尽快给您答复。谢谢您的支持!

姓名
邮箱
手机号码
标题
留言内容
验证码

染料/颜料封装技术及评价方法

张铁男 毛晓庆 张娜

张铁男, 毛晓庆, 张娜. 染料/颜料封装技术及评价方法[J]. 复合材料学报, 2024, 42(0): 1-17.
引用本文: 张铁男, 毛晓庆, 张娜. 染料/颜料封装技术及评价方法[J]. 复合材料学报, 2024, 42(0): 1-17.
ZHANG Tienan, MAO Xiaoqing, ZHANG Na. Dye/pigment encapsulation technology and evaluation method[J]. Acta Materiae Compositae Sinica.
Citation: ZHANG Tienan, MAO Xiaoqing, ZHANG Na. Dye/pigment encapsulation technology and evaluation method[J]. Acta Materiae Compositae Sinica.

染料/颜料封装技术及评价方法

基金项目: 国家重点研发计划(2021YFD2100902-3);哈尔滨商业大学横向课题(HSDHX202104061);黑龙江省“双一流”学科协同创新成果项目(LJGXCG202080;LJGXCG202083)
详细信息
    通讯作者:

    张铁男,讲师,研究方向为微球封装技术 E-mail:102615@hrbcu.edu.cn

  • 中图分类号: TQ317;TB332

Dye/pigment encapsulation technology and evaluation method

Funds: National Key Research and Development Program of China (2021YFD2100902-3); Harbin Business University Horizontal Project (HSDHX202104061); Heilongjiang Province "Double First-Class" Discipline Collaborative Innovation Achievement Project (LJGXCG202080; LJGXCG202083)
  • 摘要: 近年来,彩色微球(CMS)的开发和应用越来越受到关注,它是一种微纳米级高分子聚合物,具有粒径小、比表面积大、单分散、稳定和色泽明亮等特点,在环保、医药、电子、农业、食品、化妆品等制造业领域具有广泛的应用。目前,关于影响CMS封装效果关键因素的综合分析尚属空白。同时,我国CMS的种类和应用与国外相比还有较大差距。因此加强CMS的基础研究和技术攻关成为重中之重。染料/颜料(D/P)的封装在CMS的合成过程中是非常重要的环节,除了考虑CMS的稳定性和色泽亮度的基本性能外,还需要对D/P的封装效果进行科学的评价。本文介绍了D/P在溶液中的聚集机制及排列形式,D/P与微球(MS)基材相互作用对封装的影响及作用机制,重点从聚合方法、D/P结构、MS基材等方面综合阐述了CMS合成过程中影响封装的关键因素及机制,并总结了目前较为成熟的D/P封装效果评价方法。最后,预测了CMS的D/P封装技术的未来研究方向。

     

  • 图  1  彩色微球的应用领域示意图

    Figure  1.  Schematic diagram of the application field of colored latex

    图  2  (a)激子理论-吸收波长位移示意图[133];(b)激子-激子湮灭过程的能级示意图[18];(c)聚集体与单分子动态平衡示意图[134]

    Figure  2.  (a) Exciton Theory-Schematic diagram of absorption wavelength shift[133]; (b) Schematic diagram of the energy level of the exciton-exciton annihilation process [18]; (c) Schematic diagram of the dynamic equilibrium of aggregates and single molecules [134]

    图  3  (a)乳化剂分子胶束的形成示意图[135];(b)细乳液中助稳定剂的作用机制[136]

    Figure  3.  (a) Schematic diagram of the formation of emulsifying agents [135]; (b) Mechanism of action of co-stabilizers in fine emulsions [136]

    图  4  球磨-细乳聚合封装过程示意图[72]

    Figure  4.  Schematic diagram of ball milling-fine milk polymerization and encapsulation process[72]

    图  5  (a)静置沉降示意图;(b)浓硫酸稀释颜色变化示意图[72];(c)超离心沉降示意图[72] ;(d)彩色微球的TEM示意图

    Figure  5.  (a)Schematic diagram of static settlement; (b)Schematic diagram of dilution color change of concentrated sulfuric acid (b)[72]; (c)Schematic diagram of ultracentrifugal sedimentation[72]; (d)Schematic diagram of TEM of colored microspheres

    图  6  (a)染料和彩色微球的紫外吸收谱图[55];(b)染料和彩色微球的XRD分析谱图[107]

    Figure  6.  (a) Ultraviolet absorption spectra of dyes and colored latex[55]; (b) XRD analysis of dyes and colored latex [107]

    图  7  (a)染料TGA热图;(b)空白微球的TGA热图;(c)CMS的TGA热图[72];(d)CMS的DSC图谱[115]

    Figure  7.  (a)Dye TGA heatmap (a); (b)TGA heat map of blank latex; (c)TGA heat map of colored latex [72]; (d)DSC spectrum of color latex [115]

    表  1  彩色微球的封装方法及特点

    Table  1.   Encapsulation methods and characteristics of colored polymers

    Polymerization method Performance characteristics Name of dye/pigment References
    Miniemulsion polymerization High encapsulation rate;
    Good repeatability;
    Gentle reaction rate;
    Highly tunable microsphere
    size and structure;
    Sudan black B [47]
    Solvent red;solvent blue;solvent yellow [82]
    PB15:3 [53]
    PB15:3;styrene-based dyes [14]
    Disperse yellow 201;oil yellow 129 [62]
    Solvent red;yellow; blue;green [55]
    Solvent yellow43 [73]
    Perylene orange [119]
    Carbon black [46]
    Disperse red 60 [120]
    Pigment yellow 13 [72]
    Fluorescein [118]
    PB15:3 [107]
    PB15:3 [121]
    C.I. 60752;
    Disperse yellow 211;
    Disperse blue183;

    [122]
    PB15:3 [9]
    Fluorescent yellow R [90]
    Pigment yellow 74;
    Pigment violet 19;
    PB15:3;

    [61]
    PB15:3 [84]
    Emulsion polymerization High encapsulation rate;
    Good encapsulation pattern;
    Good dispersion stability;
    Low system viscosity;
    Short reaction period;
    Uniform particle size;
    Basic red 9 [67][124]
    Double-bonded anthraquinone dyes [124-125] [127]
    Carbon black [89]
    PB15:3 [126]
    Pigment red 112; [72]
    Emulsifier free emulsion
    polymerization
    Emulsifier free;
    Clean product ;
    Good monodispersity;
    Carbon black [41]
    Disperse red 60;
    Disperse blue 60;
    Disperse yellow 114;
    Disperse black;
    [75]
    Disperse red 60;
    Disperse blue 60;
    Disperse yellow 114;
    [112]
    Disperse red 60 [4]
    Disperse red 343 [117]
    Reactive red 24;
    Reactive blue 49;
    Reactive yellow 95;
    Reactive black 5;
    [128]
    Sudan red 7 B [10]
    Seeding polymerization High encapsulation rate;
    Uniform particle size distribution;
    8301 blue FFG [129]

    In-situ polymerization
    Good stability;
    Strong controllability;
    Excellent performance;
    Carbon black [130]
    Notes:PB15:3 is the ceresbluebhr.
    下载: 导出CSV

    表  2  染料/颜料用量对封装过程的影响

    Table  2.   Effect of dye dosage on the encapsulation process

    Dye/pigment amount Mechanisms of influence References




    Excessive
    amout
    Increased proportion of nitrogen and thinning of the PS; [47]
    Enhanced intermolecular interactions and hydrophobicity of D/P promote phase separation; [82]
    D/P cannot be dispersed uniformly and precipitation occurs during polymerization. [131]
    Excessive D/P kernel, thinning of PS thickness; [72]
    Increase in the number of D/P molecules leads to an increase in entropy and an increase in the
    chances of intermolecular collisions, which enhances D/P aggregation;
    [49]
    Lesser amount The distance between molecules is far, the intermolecular force is weak, and the monomer
    polymerization rate is fast, thus it is difficult to realize phase separation between PS and D/P;
    [82]
    CMS color is too low; [120]
    Easily appear blank irregular MS; [42]
    CMS yield is too low. [132]
    Notes:The PS is a polymer layer; D/P is the dye/pigment; CMS is the color microsphere;MS is the microsphere.
    下载: 导出CSV
  • [1] WANG F, LI J, LU L, et al. One-step mini-emulsion copolymerisation of waterborne polysiloxane-modified polyacrylate/pigment hybrid latex and its application in textile pigment printing[J]. Coloration Technology, 2022, 138(3): 291-303. doi: 10.1111/cote.12591
    [2] ELSHEMY N S, El-SAYAD H S, ABD EI-RAHMAN A A, et al. Optimization and characterization of prepared nano-disperse dyes via a sonication process and their application in textile dyeing and printing[J]. Fibers and Polymers, 2019, 20: 2540-2549. doi: 10.1007/s12221-019-9135-1
    [3] YANG Y, YIN M, SHENG M, et al. Ink-Jet Printing of Colored Latex Inks with a “Soft” Core–“Hard” Shell Structure[J]. ACS Applied Polymer Materials, 2023.
    [4] SONG Y, FANG K, BUKHARI M N, et al. Disperse dye/poly (styrene-methacrylic acid) nanospheres with high coloration performance for textiles[J]. Journal of Cleaner Production, 2020, 263: 121538. doi: 10.1016/j.jclepro.2020.121538
    [5] FEMIA A L, GONZALEZ V D G, GARCIA V S, et al. Carboxyl fuchsine-based colored particles for application to immunodetection[J]. International Journal of Polymeric Materials and Polymeric Biomaterials, 2022, 71(9): 656-668. doi: 10.1080/00914037.2021.1876056
    [6] FANG K , REN B . A facile method for preparing colored nanospheres of poly(styrene-co-acrylic acid)[J]. Dyes and Pigments, 2014, 100 50-56.
    [7] NGUYEN D, HUYNH V, LAM M, et al. Encapsulation by Directed PISA: RAFT-Based Polymer-Vesiculated Pigment for Opacity Enhancement in Paint Films[J]. Macromolecular Rapid Communications, 2021, 42(10): 2100008. doi: 10.1002/marc.202100008
    [8] NORTH SM, ARMES SP. Aqueous one-pot synthesis of well-defined zwitterionic diblock copolymers by RAFT polymerization: an efficient and environmentally-friendly route to a useful dispersant for aqueous pigments. Green Chem. 2021;23(3): 1248-¬1258.
    [9] LU L, LI J, WANG F, et al. Fluorosilicone modified polyacrylate/pigment hybrid latex: Synthesis, properties, and application in binder-free pigment printing of polyester fabrics[J]. Polymers for Advanced Technologies, 2022, 33(3): 904-914. doi: 10.1002/pat.5566
    [10] 杨承凤, 周梦圆, 李智, 等. 单分散彩色聚合物微球的制备及应用[J]. 冶金与材料, 2021, 41 (05): 1-3.

    YANG Chengfeng, ZHOU Mengyuan , LI Zhi, et al. Preparation and application of monodisperse color polymer microspheres[J]. Metallurgy and Materials, 2021, 41 (05): 1-3. (in Chinese)
    [11] ROHATGI K K, SINGHAL G S. Nature of bonding in dye aggregates[J]. The Journal of Physical Chemistry, 1966, 70(6): 1695-1701. doi: 10.1021/j100878a002
    [12] HOEBEN F J M, JONKHEIJM P, MEIJER E W, et al. About supramolecular assemblies of π-conjugated systems[J]. Chemical reviews, 2005, 105(4): 1491-1546. doi: 10.1021/cr030070z
    [13] ZHAO X, ZHOU S, CHEN M, et al. Supramolecular architecture, spectroscopic properties and stability of CI Basic Violet 10 (Rhodamine B) at high concentration[J]. Dyes and Pigments, 2009, 80(2): 212-218. doi: 10.1016/j.dyepig.2008.07.003
    [14] TAKASU M, SHIROYA T, TAKESHITA K, et al. Preparation of colored latex containing oil-soluble dyes with high dye content by mini-emulsion polymerization[J]. Colloid and Polymer Science, 2003, 282: 119-126. doi: 10.1007/s00396-003-0902-5
    [15] YONG Q , RUYI X , AIHONG Y , et al. Effect of ethylene glycol and its derivatives on the aggregation properties of reactive Orange 13 dye aqueous solution[J]. RSC ADVANCES, 2020, 10 (57): 34373-34380.
    [16] GAN Z, LIU Y, WANG L, et al. Distance makes a difference in crystalline photoluminescence[J]. Nature Communications, 2020, 11(1): 5572. doi: 10.1038/s41467-020-19377-6
    [17] HONG Y, RUDOLF M, KIM M, et al. Steering the multiexciton generation in slip-stacked perylene dye array via exciton coupling[J]. Nature communications, 2022, 13(1): 4488. doi: 10.1038/s41467-022-31958-1
    [18] MAY V. Kinetic theory of exciton–exciton annihilation[J]. The Journal of Chemical Physics, 2014, 140(5).
    [19] HERZ A H. Aggregation of sensitizing dyes in solution and their adsorption onto silver halides[J]. Advances in Colloid and Interface Science, 1977, 8(4): 237-298. doi: 10.1016/0001-8686(77)80011-0
    [20] NEUMANN B . On the Aggregation Behavior of Pseudoisocyanine Chloride in Aqueous Solution as Probed by UV/vis Spectroscopy and Static Light Scattering[J]. The journal of physical chemistry, B. Condensed matter, materials, surfaces, interfaces & biophysical, 2001, 105 (34): 8268-8274.
    [21] BROOKER L G S, KEYES G H, SPRAGUE R H, et al. Color and constitution. X. 1 Absorption of the merocyanines2[J]. Journal of the American Chemical Society, 1951, 73(11): 5332-5350. doi: 10.1021/ja01155a096
    [22] JELLEY E E. Spectral absorption and fluorescence of dyes in the molecular state[J]. Nature, 1936, 138(3502): 1009-1010. doi: 10.1038/1381009a0
    [23] SHAO , FENG , ZHANG , et al. Encapsulation of organic yellow pigment particles via miniemulsion polymerisation procedure and their application in electrophoretic displays[J]. Materials Research Innovations, 2013, 17 (6): 403-407.
    [24] ERDEM B , SUDOL D E , DIMONIE L V , et al. Encapsulation of inorganic particles via miniemulsion polymerization. I. Dispersion of titanium dioxide particles in organic media using OLOA 370 as stabilizer[J]. Journal of Polymer Science Part A: Polymer Chemistry, 2000, 38 (24): 4419-4430.
    [25] 马光辉, 苏志国. 高分子微球材料[M]. 化学工业出版社, 2005.

    MA G F, SU Z G. Polymer microsphere materials [M]. Chemical Industry Press, 2005.
    [26] ROEBUCK H S, BON S A F. Cross-linked primer strategy for pigment encapsulation. 1. encapsulation of calcium carbonate by emulsion polymerization[J]. Industrial & Engineering Chemistry Research, 2019, 58(46): 21130-21141.
    [27] GHARIEH A, KHOEE S, MAHDAVIAN A R. Emulsion and miniemulsion techniques in preparation of polymer nanoparticles with versatile characteristics[J]. Advances in colloid and interface science, 2019, 269: 152-186. doi: 10.1016/j.cis.2019.04.010
    [28] KALIA S, HALDORAI Y. Organic-inorganic hybrid nanomaterials.[J]. ORGANIC-INORGANIC HYBRID NANOMATERIALS, 2015, 267 1-385.
    [29] VAN HERK, ALEX M. , et al. Chemistry and technology of emulsion polymerisation[M]. John Wiley & Sons, 2013.
    [30] NAUMAN N, ZAQUEN N, JUNKERS T, et al. Particle size control in miniemulsion polymerization via membrane emulsification[J]. Macromolecules, 2019, 52(12): 4492-4499. doi: 10.1021/acs.macromol.9b00447
    [31] LI J, FAN J, CAO R, et al. Encapsulated dye/polymer nanoparticles prepared via miniemulsion polymerization for inkjet printing[J]. ACS omega, 2018, 3(7): 7380-7387. doi: 10.1021/acsomega.8b01151
    [32] GAO F, WU X, WU D, et al. Preparation of degradable magnetic temperature-and redox-responsive polymeric/Fe3O4 nanocomposite nanogels in inverse miniemulsions for loading and release of 5-fluorouracil[J]. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2020, 587: 124363. doi: 10.1016/j.colsurfa.2019.124363
    [33] SCHORK F J. In Support of Commercial Applications of Miniemulsion Polymerization[J]. Industrial & Engineering Chemistry Research, 2022, 62(5): 2329-2335.
    [34] BECHTHOLD N, TIARKS F, WILLERT M, et al. Miniemulsion polymerization: applications and new materials[C]//Macromolecular Symposia. Weinheim: WILEY-VCH Verlag, 2000, 151(1): 549-555.
    [35] GHOSH D C, SEN P K, PAL B. Evidence of formation of dye–surfactant ion pair micelle in the anionic surfactant mediated alkaline fading of methyl violet carbocation[J]. International Journal of Chemical Kinetics, 2021, 53(11): 1228-1238. doi: 10.1002/kin.21528
    [36] TAJ M B, NOOR S, JAVED T, et al. Effect of nonionic surfactant on micellization thermodynamics and spectroscopic profile of dye-surfactant aggregation[J]. Journal of Dispersion Science and Technology, 2023, 44(4): 669-678. doi: 10.1080/01932691.2021.1960169
    [37] BABAEI M, COPTY N K. Numerical modelling of the impact of surfactant partitioning on surfactant-enhanced aquifer remediation[J]. Journal of contaminant hydrology, 2019, 221: 69-81. doi: 10.1016/j.jconhyd.2019.01.004
    [38] LI J, LIU W, LIAO G, et al. Chemical migration and emulsification of surfactant-polymer flooding[J]. Journal of Chemistry, 2019, 2019: 1-8.
    [39] YAMAUCHI N, IINO H, OBINATA S, et al. One-pot formation of sugar-immobilized monodisperse polymethylmethacrylate particles by soap-free emulsion polymerization[J]. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2019, 580: 123754. doi: 10.1016/j.colsurfa.2019.123754
    [40] ZHANG Y, BEI W, QIN Z. Preparation and characterization of soap-free vinyl acetate/butyl acrylate copolymer latex[J]. Materials, 2020, 13(4): 865. doi: 10.3390/ma13040865
    [41] YAMAMOTO T, ARAKAWA K, TAKAHASHI Y, et al. Antimicrobial activities of low molecular weight polymers synthesized through soap-free emulsion polymerization[J]. European Polymer Journal, 2018, 109: 532-536. doi: 10.1016/j.eurpolymj.2018.10.047
    [42] MAITI J , BASFAR A A . Encapsulation of carbon black by surfactant free emulsion polymerization process[J]. Macromolecular Research, 2017, 25 (2): 120-127.
    [43] ZHANG C, LI J, CUI N, et al. Polymer/CI Pigment Red 170 hybrid latexes prepared by RAFT-mediated surfactant-free emulsion polymerization[J]. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2021, 629: 127409. doi: 10.1016/j.colsurfa.2021.127409
    [44] LI J, ZHONG S, CHEN Z, et al. Fabrication and properties of polysilsesquioxane-based trilayer core–shell structure latex coatings with fluorinated polyacrylate and silica nanocomposite as the shell layer[J]. Journal of Coatings Technology and Research, 2018, 15: 1077-1088. doi: 10.1007/s11998-018-0044-9
    [45] STEIERT N , LANDFESTER K . Encapsulation of Organic Pigment Particles Via Miniemulsion Polymerization[J]. Macromolecular Materials and Engineering, 2007, 292 (10-11): 1111-1125.
    [46] TIARKS F , LANDFESTER K , ANTONIETTI M . et al. Encapsulation of Carbon Black by Miniemulsion Polymerization[J]. Macromolecular Chemistry and Physics, 2001, 202 (1): 51-60.
    [47] ZHAO X , ZHOU S , CHEN M , et al. Effective encapsulation of Sudan black B with polystyrene using miniemulsion polymerization[J]. Colloid and Polymer Science, 2009, 287 (8): 969-977.
    [48] ZHANG K, XIE R, FANG K, et al. Effects of reactive dye structures on surface tensions and viscosities of dye solutions[J]. Journal of Molecular Liquids, 2019, 287: 110932. doi: 10.1016/j.molliq.2019.110932
    [49] ZhANG X, FANG K, ZHOU H, et al. Enhancing inkjet image quality through controlling the interaction of complex dye and diol molecules[J]. Journal of Molecular Liquids, 2020, 312: 113481. doi: 10.1016/j.molliq.2020.113481
    [50] CONG Y, DU C, KE X, et al. Research on solubility modelling of actarit in different solvents: Solvent effect, Hansen solubility parameter, molecular interactions and solution thermodynamics[J]. Journal of Molecular Liquids, 2022, 347: 117965. doi: 10.1016/j.molliq.2021.117965
    [51] CAO C, ZHAO Z, QI Y, et al. Effects of alkanolamine solvents on the aggregation states of reactive dyes in concentrated solutions and the properties of the solutions[J]. RSC advances, 2021, 11(18): 10929-10934. doi: 10.1039/D0RA10656A
    [52] XU F, GONG K, LIU D, et al. Enhancing photocurrent of dye-sensitized solar cells through solvent modulating aggregation of dyes[J]. Solar Energy, 2022, 240: 157-167. doi: 10.1016/j.solener.2022.05.032
    [53] LELU S, NOVAT C, GRAILLAT C, et al. Encapsulation of an organic phthalocyanine blue pigment into polystyrene latex particles using a miniemulsion polymerization process[J]. Polymer International, 2003, 52(4): 542-547. doi: 10.1002/pi.1029
    [54] OUYANG J, LIU L, ZHOU L, et al. Solubility, dissolution thermodynamics, Hansen solubility parameter and molecular simulation of 4-chlorobenzophenone with different solvents[J]. Journal of Molecular Liquids, 2022, 360: 119438. doi: 10.1016/j.molliq.2022.119438
    [55] HU Z, XUE M, ZHANG Q, et al. Nanocolorants: A novel class of colorants, the preparation and performance characterization[J]. Dyes and pigments, 2008, 76(1): 173-178. doi: 10.1016/j.dyepig.2006.08.026
    [56] ONAIZI S A. Dynamic surface tension and adsorption mechanism of surfactin biosurfactant at the air–water interface[J]. European Biophysics Journal, 2018, 47(6): 631-640. doi: 10.1007/s00249-018-1289-z
    [57] NI K, FANG H, YU Z, et al. The velocity dependence of viscosity of flowing water[J]. Journal of Molecular Liquids, 2019, 278: 234-238. doi: 10.1016/j.molliq.2019.01.055
    [58] 陈荣圻. 有机颜料的聚合物包覆改性处理[J]. 染整技术, 2021, 43(11): 4-8. doi: 10.3969/j.issn.1005-9350.2021.11.002

    CHEN Rongqi. Polymer coating modification of organic pigments[J]. Dyeing and Finishing Techniques, 2021, 43(11): 4-8(in Chinese). doi: 10.3969/j.issn.1005-9350.2021.11.002
    [59] BECHTHOLD N, TIARKS F, WILLERT M, et al. Miniemulsion polymerization: applications and new materials[C]//Macromolecular Symposia. Weinheim: WILEY-VCH Verlag, 2000, 151(1): 549-555.
    [60] SHIMODE M, MIMURA M, URAKAWA H, et al. Interaction between the dyestuff aggregates in aqueous solution[J]. Sen'i Gakkaishi, 1996, 52(6): 301-309. doi: 10.2115/fiber.52.6_301
    [61] STEIERT N, LANDFESTER K. Encapsulation of organic pigment particles via miniemulsion polymerization[J]. Macromolecular Materials and Engineering, 2007, 292(10-11): 1111-1125.
    [62] TAKASU M, SHIROYA T, TAKESHITA K, et al. Improvement of the storage stability and photostability of colored latex prepared by miniemulsion polymerization[J]. Colloid and Polymer Science, 2004, 282: 740-746. doi: 10.1007/s00396-003-1008-9
    [63] LI B, SHEN J, JIANG Y, et al. Preparation and properties of covalently colored polymer latex based on a new anthraquinone monomer[J]. Journal of applied polymer science, 2013, 129(3): 1484-1490. doi: 10.1002/app.38848
    [64] POLPANICH D, ASAWAPIROM U, THIRAMANAS R, et al. Self-colored nanoparticles containing naphthalene-bisimide derivatives: Synthesis and protein adsorption study[J]. Materials Chemistry and Physics, 2011, 129(1-2): 495-500. doi: 10.1016/j.matchemphys.2011.04.050
    [65] 王东伟, 房宽峻, 刘秀明, 等. 彩色聚合物微球的制备及其在纺织品印染中应用的研究进展[J]. 纺织学报, 2019, 40(3): 175-182.

    WANG Dongwei , FANG Kuanjun , LIU Xiuming , et al. Research progress on the preparation of colored polymer microspheres and their application in textile printing and dyeing[J]. Journal of Textile Research, 2019, 40(3): 175-182. (in Chinese)
    [66] FEMIA ANABELA L. ; GONZALEZ VERÓNICA D. G. ; GARCIA VALERIA , et al. Polymerizable dye for colored particles synthesis with potential use in immunoassays[J]. International Journal of Polymeric Materials and Polymeric Biomaterials, 2020, 69 (12): 798-809.
    [67] BECHTHOLD N, TIARKS F, WILLERT M, et al. Miniemulsion polymerization: applications and new materials[C]//Macromolecular Symposia. Weinheim: WILEY-VCH Verlag, 2000, 151(1): 549-555.
    [68] HAKEIM O , DIAB H , ADAMS J . Preparation and characterization of UV curable-encapsulated phthalocyanine blue pigment[J]. Progress in Organic Coatings, 2015, 84 70-78.
    [69] NGUYEN D, ZONDANOS H S, FARRUGIA J M, et al. Pigment encapsulation by emulsion polymerization using macro-RAFT copolymers[J]. Langmuir, 2008, 24(5): 2140-2150. doi: 10.1021/la7027466
    [70] AGBO C, JAKPA W, SARKODIE B, et al. A review on the mechanism of pigment dispersion[J]. Journal of Dispersion Science and Technology, 2018, 39(6): 874-889. doi: 10.1080/01932691.2017.1406367
    [71] BADGUJAR N , BHOGE Y , DESHPANDE T , et al. Ultrasound assisted organic pigment dispersion: advantages of ultrasound method over conventional method[J]. Pigment & Resin Technology, 2015, 44 (4): 214-223.
    [72] DING Y, YE M, HAN A, et al. Preparation and characterization of encapsulated CI pigment yellow 12 via ball-milling and mini-emulsion polymerization[J]. Progress in Organic Coatings, 2018, 117: 69-75. doi: 10.1016/j.porgcoat.2018.01.009
    [73] 刘杰, 张丽平, 田安丽等. 利用细乳液聚合由溶剂黄43制备纳米微球荧光颜料[J]. 精细化工, 2015, 32 (09): 1067-1071.

    LIU Jie, ZHANG Liping , TIAN Anli, et al. Nanosphere fluorescent pigments were prepared by polymerization of fine emulsion from solvent yellow 43[J]. Fine Chemicals, 2015, 32 (09): 1067-1071. (in Chinese)
    [74] BULIGA D I, DIACON A, CALINESCU I, et al. Enhancing the light fastness of natural dyes by encapsulation in silica matrix[J]. Journal of Photochemistry and Photobiology A: Chemistry, 2022, 432: 114085. doi: 10.1016/j.jphotochem.2022.114085
    [75] 曾佳. CMS的制备及其应用[D]. 无锡: 江南大学, 2013

    ZENG J. Preparation and application of CMS [D]. Wuxi: Jiangnan University, 2013.
    [76] ZHANG K, YE M, HAN A, et al. Preparation and properties of Styrene-Butyl Acrylate resin co-encapsulated Pigment Red 48: 2 and Oxidized Polyethylene wax composite nanoparticles[J]. Journal of Applied Polymer Science, 2020, 137(38): 49150. doi: 10.1002/app.49150
    [77] WANG J, LI B , JIN Q , ET al. Preparation of covalently colored polymer latex through miniemulsion polymerization based on a polymerizable dye[J]. Designed Monomers and Polymers, 2015, 18 (7): 611-619.
    [78] 徐保律, 吴伟, 钟毅等. 有机溶剂对液体活性染料分散和水解稳定性影响的模拟研究[J]. 纺织学报, 2021, 42(2): 113-121.

    XUN Baolv L, WU Wei, ZHONG Yi, et al. Simulation of the effect of organic solvents on the dispersion and hydrolytic stability of liquid reactive dyes[J]. Journal of Textile Research, 2021, 42(2): 113-121(in Chinese).
    [79] 张炜, 毛庆楷, 朱鹏等. 乙醇/水体系中改性蚕丝织物的活性染料染色动力学和热力学[J]. 纺织学报, 2020, 41(6): 86-92.

    ZHANG Yi, MAO Qingkai, ZHU Peng, et al. Reactive dye dyeing kinetics and thermodynamics of modified silk fabrics in ethanol/water systems[J]. Journal of Textile Research, 2020, 41(6): 86-92(in Chinese).
    [80] STEIERT N , LANDFESTER K . Encapsulation of Organic Pigment Particles Via Miniemulsion Polymerization[J]. Macromolecular Materials and Engineering, 2007, 292 (10-11): 1111-1125.
    [81] LANDFESTER K. Polyreactions in Miniemulsions[J]. Macromolecular Rapid Communications, 2001, 22(12): 896-936. doi: 10.1002/1521-3927(20010801)22:12<896::AID-MARC896>3.0.CO;2-R
    [82] HU K Z , XUE Z M , ZHANG Q , et al. Controlled preparation of nanocolorants via a modified miniemulsion polymerization process[J]. Journal of Applied Polymer Science, 2007, 104 (5): 3036-3041.
    [83] IRANI M M, NOURMOHAMMADIAN F, BASTANI S, et al. Photophysical properties of novel functionalized fluorescent dyes based on diketopyrrolopyrrole and application in inkjet printing ink[J]. Journal of Luminescence, 2018, 199: 499-508. doi: 10.1016/j.jlumin.2018.03.084
    [84] YIQIAN H , JIAWEN Z , YING C , et al. Encapsulation of organic pigment via a facile dispersion approach and soap-free miniemulsion polymerization[J]. Progress in Organic Coatings, 2021, 159
    [85] 杜起, 李忠辉, 吴秋芳, 高玮, 马新胜. 可聚合乳化剂制备纳米色料的形貌及其影响因素[J]. 功能高分子学报, 2014, 27 (03): 327-332.

    DU Qi, LI Zhonghui, WU Qingfang , et al. Morphology and influencing factors of nanopigments prepared by polymerizable emulsifiers[J]. Journal of Functional Polymers, 2014, 27 (03): 327-332. (in Chinese)
    [86] MACHOTOVA J, KNOTEK P, CERNOSKOVA E, et al. Effect of Fluorinated Comonomer, Polymerizable Emulsifier, and Crosslinking on Water Resistance of Latex Coatings[J]. Coatings, 2022, 12(8): 1150. doi: 10.3390/coatings12081150
    [87] 付高位, 王定坤, 陈日清等. 反应型乳化剂对丙烯酸酯乳液聚合的影响研究[J]. 中国胶粘剂, 2021, 30 (03): 1-6+18.

    FU Gaowei , WANG Dingkun , CHEN Riqing , et al. Study on the effect of reactive emulsifiers on polymerization of acrylate emulsions[J]. Chinese Adhesives, 2021, 30 (03): 1-6+18. (in Chinese)
    [88] ZIWEN X , WANG F, LI J, et al. Nanoscale polymer encapsulated pigment hybrid latexes with high pigment content for binder-free pigment printing of cotton/polyester blend fabrics[J]. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2022, 654: 130107.
    [89] KUO C H, SHIU J W, RWEI S P, et al Preparation and characterization of PMMA encapsulated carbon black for water-based digital jet printing ink on different fibers of cotton and PET[J]. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2022, 648: 129450.
    [90] LI M, ZHANG L, PENG H, et al. Preparation of fluorescent pigment latex and its application on binder-free printing of cotton fabrics[J]. Journal of Applied Polymer Science, 2018, 135(6): 45826. doi: 10.1002/app.45826
    [91] LI M, ZHANG L, QIU M, et al. Dyeing property of fluorescent pigment latex on cationic knitted cotton fabrics[J]. Textile Research Journal, 2019, 89(3): 422-433. doi: 10.1177/0040517517748494
    [92] AUTRAN C, DE LA CAL J C, ASUA J M. (Mini) emulsion polymerization kinetics using oil-soluble initiators[J]. Macromolecules, 2007, 40(17): 6233-6238. doi: 10.1021/ma070916r
    [93] 黄岐善, 翁志学, 黄志明, 等. 引发剂 “笼蔽效应” 的微观动力学解释[J]. 高等学校化学学报, 1999, 20(5): 819-823.

    HUANG Qishan , WENG Zhixue , HANG Zhiming, et al. Microkinetic explanation of the "cage effect" of initiators[J]. Chem. J. Chinese Universities, 1999, 20(5): 819-823. (in Chinese)
    [94] SHANG Y, SHAN G, PAN P. Kinetic and molecular weight modeling of miniemulsion polymerization initiated by oil-soluble initiators[J]. Macromolecular Chemistry and Physics, 2015, 216(8): 884-893. doi: 10.1002/macp.201400563
    [95] TANIGUCHI T, TAKEUCHI N, KOBARU S, et al. Preparation of highly monodisperse fluorescent polymer particles by miniemulsion polymerization of styrene with a polymerizable surfactant[J]. Journal of Colloid and Interface Science, 2008, 327(1): 58-62. doi: 10.1016/j.jcis.2008.08.003
    [96] SHIU J W, CHEN C W, LIU M A, et al. Characterization and Synthesis of 2-Hydroxyethyl Acrylate-Encapsulated Pigments by Emulsion Polymerization with Excellent Color Fastness and Stability[J]. Arabian Journal for Science and Engineering, 2023: 1-16.
    [97] YAWEI S , KUANJUN F , YANFEI R , et al. Inkjet Printable and Self-Curable Disperse Dyes/P(St-BA-MAA) Nanosphere Inks for Both Hydrophilic and Hydrophobic Fabrics.[J]. Polymers, 2018, 10 (12): 1402-1402.
    [98] QUEVEDO A C, Guggenheim E, Briffa S M, et al. UV-Vis spectroscopic characterization of nanomaterials in aqueous media[J]. JoVE (Journal of Visualized Experiments), 2021 (176).
    [99] GRUEN L C. The aggregation of copper phthalocyanine dyes[J]. Australian Journal of Chemistry, 1972, 25(8): 1661-1667. doi: 10.1071/CH9721661
    [100] 陈少刚. 细乳液聚合法制备彩色墨粉用有色微球粒子[D]. 南京: 南京理工大学, 2012.

    CHEN S G. Preparation of colored microsphere particles for color toner by fine emulsion polymerization [D]. Nanjing: Nanjing University of Science and Technology, 2012.
    [101] MESKERS S C J, JANSSEN R A J, HAVERKORT J E M, et al. Relaxation of photo-excitations in films of oligo-and poly-(para-phenylene vinylene) derivatives[J]. Chemical Physics, 2000, 260(3): 415-439. doi: 10.1016/S0301-0104(00)00252-4
    [102] KIM J H, SHIN S R, MATSUOKA M, et al. Self-assembling of aminopyrazine fluorescent dyes and their solid state spectra[J]. Dyes and Pigments, 1998, 39(4): 341-357. doi: 10.1016/S0143-7208(98)00017-5
    [103] KIM J H, MATSUOKA M, FUKUNISHI K. Three dimensional molecular stacking and functionalities of aminonaphthoquinone by intermolecular hydrogen bondings and interlayer π–π interactions[J]. Dyes and pigments, 1999, 40(1): 53-57. doi: 10.1016/S0143-7208(98)00029-1
    [104] FABJAN E Š, OTONIČAR M, GABERŠČEK M, et al. Surface protection of an organic pigment based on a modification using a mixed-micelle system[J]. Dyes and Pigments, 2016, 127: 100-109. doi: 10.1016/j.dyepig.2015.12.016
    [105] FEI X, CAO L, LIU Y. Modified CI Pigment Red 170 with a core-shell structure: Preparation, characterization and computational study[J]. Dyes and Pigments, 2016, 125: 192-200. doi: 10.1016/j.dyepig.2015.10.021
    [106] TONG-SHENG C , SHAO-QUN Z , WEI Z , et al. A Quantitative Theory Model of a Photobleaching Mechanism[J]. Chinese physics letters, 2003, 20 (11): 1940-1943.
    [107] FU S, ZHANG K, ZHHANG M, et al. Encapsulated phthalocyanine blue pigment with polymerisable dispersant for inkjet printing inks[J]. Pigment & Resin Technology, 2012, 41(1): 3-8.
    [108] HAKEIM A O , HAROUN A A , TRIF L , et al. Hyperbranched polyester encapsulated phthalocyanine pigments for in situ printing of cellulosic fabrics[J]. Advances in Polymer Technology, 2018, 37 (8): 3123-3135.
    [109] HAKEIM A O , ABDELGHAFFAR F , HAROUN A A . UV-curable hyperbranched polyester acrylate encapsulation of phthalocyanine pigments for high performance synthetic fabrics printing[J]. Dyes and Pigments, 2020, 177 (prepublish): 108307-108307.
    [110] SONG Y, FANG K, REN Y, et al. Inkjet printable and self-curable disperse dyes/P (St-BA-MAA) nanosphere inks for both hydrophilic and hydrophobic fabrics[J]. Polymers, 2018, 10(12): 1402. doi: 10.3390/polym10121402
    [111] SONG Y, FANG K, BUKHARI M N, et al. Disperse dye/poly (styrene-methacrylic acid) nanospheres with high coloration performance for textiles[J]. Journal of Cleaner Production, 2020, 263: 121538. doi: 10.1016/j.jclepro.2020.121538
    [112] YAWEI S , KUANJUN F , NADEEM M B , et al. Improved inkjet printability of dye-based inks through enhancing the interaction of dye molecules and polymer nanospheres[J]. Journal of Molecular Liquids, 2020, (prepublish): 114702-.
    [113] HAKEIM OSAMA A. ; El Gabry Lamiaa K. ; Haggag Karima, et al. Enhanced Pigment Dyeing and UV Protection of Polyester Fabrics Using Sericin Encapsulated PB 15: 3[J]. Fibers and Polymers, 2022, 23 (7): 1934-1946.
    [114] YANG Y, LI M, TANG A, et al. Preparation of Covalent and solvent-resistance colored latex particles and its application on cotton fabric[J]. Fibers and Polymers, 2020, 21: 1685-1693. doi: 10.1007/s12221-020-9990-9
    [115] LU D, LIU S, ZHANG H, et al. Synthesis and characterization of photochromic polyurethane nanoparticles by miniemulsion polymerization[J]. Dyes and Pigments, 2023, 219: 111647. doi: 10.1016/j.dyepig.2023.111647
    [116] 杜起. 细乳液聚合制备聚合物包覆蒽醌溶剂蓝染料的纳米色料与本体法合成 ABS 树脂 [D]. 上海: 华东理工大学, 2014.

    DU Q. Preparation of polymer-coated anthraquinone solvent blue dye nano-colors by fine emulsion polymerization and synthesis of ABS resin by native method [D]. Shanghai: East China University of Science and Technology, 2014.
    [117] YAVUZ G, FELGUEIRAS H P, Ribeiro A I, et al. Dyed poly (styrene-methyl methacrylate-acrylic acid) photonic nanocrystals for enhanced structural color[J]. ACS applied materials & interfaces, 2018, 10(27): 23285-23294.
    [118] LI M, ZHANG L, PENG H, et al. Preparation of fluorescent pigment latex and its application on binder-free printing of cotton fabrics[J]. Journal of Applied Polymer Science, 2018, 135(6): 45826. doi: 10.1002/app.45826
    [119] BAIER M C, HUBER J, Mecking S. Fluorescent conjugated polymer nanoparticles by polymerization in miniemulsion[J]. Journal of the American Chemical Society, 2009, 131(40): 14267-14273. doi: 10.1021/ja905077c
    [120] EL-SAYED G M, KAMEL M M, Morsy N S, et al. Encapsulation of nano Disperse Red 60 via modified miniemulsion polymerization. I. Preparation and characterization[J]. Journal of applied polymer science, 2012, 125(2): 1318-1329. doi: 10.1002/app.35102
    [121] CHEN Z, HU X, WANG X, et al. The morphology of poly (terminal vinyl dimethicone-co-methyl methacrylate-co-n-butyl acrylate)/pigment composite film and its application in pigment printing of polyester fabric[J]. RSC advances, 2020, 10(9): 4949-4955. doi: 10.1039/C9RA09888G
    [122] WANG L, CUI S, NI H, et al. New washing-free printing binder based on organosilicon-modified polyacrylate for polyester fabric printing of disperse dyes[J]. Progress in Organic Coatings, 2018, 123: 75-81. doi: 10.1016/j.porgcoat.2018.06.009
    [123] FEMIA A L, GONZALEZ V D G, Garcia V S, et al. Carboxyl fuchsine-based colored particles for application to immunodetection[J]. International Journal of Polymeric Materials and Polymeric Biomaterials, 2022, 71(9): 656-668. doi: 10.1080/00914037.2021.1876056
    [124] DOLLENDORF C, KRETH S K, Choi S W, et al. Polymerization of novel methacrylated anthraquinone dyes[J]. Beilstein Journal of Organic Chemistry, 2013, 9(1): 453-459.
    [125] LI B, SHEN J, LIANG R, et al. Synthesis and characterization of covalently colored polymer latex based on new polymerizable anthraquinone dyes[J]. Colloid and Polymer Science, 2012, 290: 1893-1900. doi: 10.1007/s00396-012-2718-7
    [126] FU S, XU C, DU C, et al. Encapsulation of CI Pigment blue 15: 3 using a polymerizable dispersant via emulsion polymerization[J]. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2011, 384(1-3): 68-74.
    [127] YANG Y, LI M, FU S. Monodispersed colored polymer latex particles with film formation and chemical crosslinking for application on textile binder-free printing[J]. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2021, 619: 126527. doi: 10.1016/j.colsurfa.2021.126527
    [128] FANG K, XIE R , LIU X, et al. Reactive dye/poly (styrene-co-butyl acrylate-co-trimethyl (vinylbenzyl) ammonium chloride) nanospheres with high coloration performance for cleaner dyeing of cotton fabrics[J]. Cellulose, 2019, 26: 5807-5819.
    [129] ZHANG X, ZHONG Y, SUI X, et al. Synthesis of a low-temperature self-crosslinking polyacrylate binder with a core-shell structure and its application in textile pigment printing[J]. Coloration Technology, 2018, 134(4): 299-307. doi: 10.1111/cote.12339
    [130] ZHOU Y, ZHANG Q, LIU Y, et al. Encapsulation and dispersion of carbon black by an in situ controlling radical polymerization of AA/BA/St with DPE as a control agent[J]. Colloid and Polymer Science, 2013, 291: 2399-2408. doi: 10.1007/s00396-013-2982-1
    [131] 赵晓. 有机染料聚集行为及其包覆研究[D]. 上海: 复旦大学, 2009.

    ZHAO X. Research on the aggregation behavior of organic dyes and their coating [D]. Shanghai: Fudan University, 2009.
    [132] EL-SAYED G M, KAMEL M M, MORSY N S, et al. Encapsulation of nano Disperse Red 60 via modified miniemulsion polymerization. I. Preparation and characterization[J]. Journal of applied polymer science, 2012, 125(2): 1318-1329. doi: 10.1002/app.35102
    [133] 张鹏, 郭心洁, 张倩等. 有机染料聚集在光化学传感中的应用[J]. 化学进展, 2020, 32 (Z1): 286-297.

    ZHANG Peng, GUO Xinjie , ZHANG Qian, et al. Applications of organic dye aggregation in photochemical sensing[J]. Advances in Chemistry, 2020, 32 (Z1): 286-297. (in Chinese)
    [134] 闫文璠, 钱惠红, 黄德音. 咪碳菁类染料在溶液中的聚集行为[J]. 感光科学与光化学, 2003, (01): 25-29.

    YAN Wenpan , QIAN Huihong , HUANG Deyin , et al. Aggregation behavior of micarbacyanine dyes in solution[J]. Photosensitive Science and Photochemistry, 2003, (01): 25-29. (in Chinese)
    [135] 高美华. 十二烷基磷酸钠和其苯磺酸溶液聚集行为研究[D]. 济南: 山东大学, 2021.

    GAO M H. Study on the aggregation behavior of sodium dodecyl phosphate and its benzene sulfonic acid solution [D]. Jinan: Shandong University, 2021.
    [136] 钟瑞英, 付长清, 申亮. 细乳液聚合最新研究进展[J]. 涂料工业, 2019, 49 (08): 81-87.

    ZHONG Ruiying , FU Changqing , SHE Liang, et al. The latest research progress in fine emulsion polymerization[J]. Coating Industry, 2019, 49 (08): 81-87. (in Chinese)
  • 加载中
计量
  • 文章访问数:  34
  • HTML全文浏览量:  23
  • 被引次数: 0
出版历程
  • 收稿日期:  2024-02-18
  • 修回日期:  2024-04-17
  • 录用日期:  2024-04-27
  • 网络出版日期:  2024-05-30

目录

    /

    返回文章
    返回