脂肪胺基磷腈多功能织物整理剂的合成与性能研究

doi:10.3969/j.issn.2097-2806.2026.03.010

摘要/Abstract

摘要：

以长链的脂肪胺（十二胺和十八胺）和六氯环三磷腈为原料，以四氢呋喃为溶剂，50 ℃条件下经一步反应合成了六（十二胺基）环三磷腈盐酸盐（HDCCP）和六（十八胺基）环三磷腈盐酸盐（HOCCP）油溶性表面活性剂，产率分别为92.34%和86.13%，并利用红外光谱和核磁共振对产物进行了表征。垂直燃烧测试实验发现由HDCCP和HOCCP整理后的棉织物其残碳率分别达到了28.89%和22.46%，具有温和的阻燃性能。抑菌性能测试表明HDCCP对金黄色葡萄球菌、大肠杆菌和白色念珠菌都具有良好的抑菌效果，具有广谱抑菌性。经HDCCP和HOCCP整理后的棉布柔软性能可以达到4~5级，与商用柔软剂的性能相当，结果表明长链脂肪胺基磷腈兼有阻燃、抑菌、柔软的功能。

关键词: 多功能整理剂, 阻燃, 抑菌, 磷氮衍生物

Abstract:

Two novel oil-soluble surfactants, namely hexa （dodecylamino） cyclotriphosphonitrile hydrochloride （HDCCP） and hexa （octadecylamino） cyclotriphosphonitrile hydrochloride （HOCCP）, were successfully synthesized via an one-step reaction at 50 ℃ using tetrahydrofuran （THF） as the solvent. The synthesis involved the nucleophilic substitution of hexachlorocyclotriphosphonitrile with long-chain aliphatic amines （including dodecylamine and octadecylamine）, resulting in yields of 92.34% for HDCCP and 86.13% for HOCCP. The products were characterized by infrared spectroscopy （IR） and nuclear magnetic resonance （NMR）. When they were applied as finishing agents for cotton cloth, the cotton cloths treated with HDCCP and HOCCP demonstrated residual carbon rates of 28.89% and 22.46% in vertical burning test, suggesting that these compounds could effectively enhance the flame resistance of the treated textile. Additionally, antibacterial performance tests indicated that HDCCP exhibited excellent broad-spectrum antimicrobial activity against common pathogens, including Staphylococcus aureus, Escherichia coli and Candida albicans, making it a promising candidate for antibacterial agent for textile. Furthermore, the softness of fabrics treated with HDCCP and HOCCP reached a favorable level of 4-5 in the standard softness test, which was comparable to that achieved by a commercial fabric softener. Therefore, these compounds not only provided flame retardancy and antibacterial effects but also maintained fabric comfort. In conclusion, long-chain alkylamino phosphonitrile derivatives exhibited outstanding properties as multifunctional fabric finishing agents, combining flame retardancy, antimicrobial effects and softness enhancement in a single treatment.

Key words: multifunctional finishing agent, flame retardant, antibacterial, phosphazene derivative

中图分类号:

TQ423

陈立文,王念念,秦勇. 脂肪胺基磷腈多功能织物整理剂的合成与性能研究[J]. 日用化学工业（中英文）, 2026, 56(3): 354-359.

Liwen Chen,Niannian Wang,Yong Qin. Synthesis and performance of alkylamino phosphoronitriles as multifunctional fabric finishing agents[J]. China Surfactant Detergent & Cosmetics, 2026, 56(3): 354-359.

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参考文献 26

[1]	Elfaleh I, Abbassi F, Habibi M, et al. A comprehensive review of natural fibers and their composites: An eco-friendly alternative to conventional materials[J]. Results in Engineering, 2023, 19: 101271.
[2]	Khan A, Awais M, Mohsin M, et al. Sustainable yarns and fabrics from tri-blends of banana, cotton and tencel fibres for textile applications[J]. Journal of Cleaner Production, 2024, 436: 140545.
[3]	Abdelkhalik A, Makhlouf G, Ameen H, et al. A new multifunctional flame-retardant coating for cotton fabric to enhance smoke suppression, and UV shielding properties[J]. Industrial Crops and Products, 2023, 205: 117469.
[4]	Liu C, Shi Y, Feng Y, et al. Design of core-multi shell flame retardant towards fire safe thermoplastic polyurethane composites with low toxic fumes generation[J]. Composites Communications, 2022, 35: 101339.
[5]	Safdar F, Ashraf M, Abid A, et al. Eco-friendly, efficient and durable flame retardant coating for cotton fabrics using phytic acid/silane hybrid sol[J]. Materials Chemistry and Physics, 2024, 311: 128568.
[6]	Kaur I, Verma S K. Living radical polymerization and grafting of diethyl (acryloyloxy) ethylthiophosphoramidate onto cotton fabric to impart flame retardancy[J]. Surface and Coatings Technology, 2010, 205 (7) : 2082-2090.
[7]	Cheng Y, Liu K, Liu Y, et al. A novel durable flame retardant rich in phosphate ester groups for cotton fabrics[J]. Materials Today Chemistry, 2023, 33: 101701.
[8]	Li H, Wen D, Wang S, et al. Durable multifunctional cotton fabric with superior biocidal efficacy and flame retardancy based on an ammonium phosphate N-halamine[J]. International Journal of Biological Macromolecules, 2023, 253: 126812.
[9]	Antoun K, Ayadi M, El Hage R, et al. Renewable phosphorous-based flame retardant for lignocellulosic fibers[J]. Industrial Crops and Products, 2022, 186: 115265.
[10]	Cao Y, Gu J, Wang S, et al. Guanidine-functionalized cotton fabrics for achieving permanent antibacterial activity without compromising their physicochemical properties and cytocompatibility[J]. Cellulose, 2020, 27: 6027-6036.
[11]	Stec A, Sikora M, Maciejewska M, et al. Bacterial metabolites: a link between gut microbiota and dermatological diseases[J]. International Journal of Molecular Sciences, 2023, 24 (4) : 3494.
[12]	Qin R, Du L, Li H, et al. Reasonable multi-functionality of cotton fabric with superior flame retardancy and antibacterial ability using ammonium diphosphate as cross-linker[J]. Chemical Engineering Journal, 2024, 485: 149848.
[13]	康高炜. 一种新型磷氮系多功能阻燃剂的制备及其在棉织物中的应用[D]. 上海: 东华大学, 2024.
[14]	Yang J, Ma W, Hu D, et al. Facile preparation and flame retardancy mechanism of cyclophosphazene derivatives for highly flame‐retardant silicone rubber composites[J]. Journal of Applied Polymer Science, 2021, 138 (17) : 50297.
[15]	Usri S N K, Jamain Z, Makmud M Z H. A review on synthesis, structural, flame retardancy and dielectric properties of hexasubstituted cyclotriphosphazene[J]. Polymers, 2021, 13 (17) : 2916.
[16]	于永建, 李玲, 段宪法. 环三磷腈衍生物在环氧树脂阻燃方面的应用[J]. 化工新型材料, 2019, 47 (4) : 230-234.
[17]	Zarybnicka L, Machotova J, Kopecka R, et al. Effect of cyclotriphosphazene-based curing agents on the flame resistance of epoxy resins[J]. Polymers, 2020, 13 (1) : 8.
[18]	Zhou L, Zhang G, Yang S, et al. The synthesis, curing kinetics, thermal properties and flame rertardancy of cyclotriphosphazene-containing multifunctional epoxy resin[J]. Thermochimica Acta, 2019, 680: 178348.
[19]	余建华, 杨振. 弱阳离子软片CS的应用[J]. 天津纺织科技, 2018(2) : 56-58.
[20]	Jamain Z, Khairuddean M, Saidin S A. Synthesis and characterization of 1, 4-phenylenediamine derivatives containing hydroxyl and cyclotriphosphazene as terminal group[J]. Journal of Molecular Structure, 2019, 1186: 293-302.
[21]	周江明. 新型环三磷腈衍生物阻燃剂的合成及其在环氧树脂中的应用[J]. 热固性树脂, 2025, 40 (2) : 46-50.
[22]	Zhao B, Kolibaba T J, Lazar S, et al. Facile two-step phosphazine-based network coating for flame retardant cotton[J]. Cellulose, 2020, 27: 4123-4132.
[23]	Sharma I, Sinha R K, Singh T, et al. Synthesis, characterization and antibacterial activity of hexasubstituted Coumarin-based Schiff base derivative of cyclophosphazene[J]. Journal of Macromolecular Science: Part A, 2024, 61 (12) : 986-992.
[24]	黄小彬, 尹林, 唐小真. 一种新型有机无机杂化聚磷腈高分子的制备及表征[J]. 中国科学(B辑: 化学), 2008 (1) : 43-47.
[25]	Pan X, Liu J, Guo X, et al. Synthesis and analysis of a novel phospho-nitrile flame retardant for cotton fabric[J]. Materials Today Communications, 2024, 40: 109350.
[26]	Ngamsurach P, Praipipat P. Antibacterial activities against Staphylococcus aureus and Escherichia coli of extracted piper betle leaf materials by disc diffusion assay and batch experiments[J]. RSC Advances, 2022, 12 (40) : 26435-26454.