<?xml version="1.0" encoding="UTF-8"?>
<!DOCTYPE article PUBLIC "-//NLM//DTD JATS (Z39.96) Journal Publishing DTD v1.3 20210610//EN" "JATS-journalpublishing1-3.dtd">
<article article-type="research-article" dtd-version="1.3" xmlns:mml="http://www.w3.org/1998/Math/MathML" xmlns:xlink="http://www.w3.org/1999/xlink" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xml:lang="en"><front><journal-meta><journal-id journal-id-type="publisher-id">chemicallytech</journal-id><journal-title-group><journal-title xml:lang="en">Fine Chemical Technologies</journal-title><trans-title-group xml:lang="ru"><trans-title>Тонкие химические технологии</trans-title></trans-title-group></journal-title-group><issn pub-type="ppub">2410-6593</issn><issn pub-type="epub">2686-7575</issn><publisher><publisher-name>MIREA – Russian Technological University (RTU MIREA).</publisher-name></publisher></journal-meta><article-meta><article-id pub-id-type="doi">10.32362/2410-6593-2019-14-5-61-70</article-id><article-id custom-type="elpub" pub-id-type="custom">chemicallytech-1550</article-id><article-categories><subj-group subj-group-type="heading"><subject>Research Article</subject></subj-group><subj-group subj-group-type="section-heading" xml:lang="en"><subject>SYNTHESIS AND PROCESSING OF POLYMERS AND POLYMERIC COMPOSITES</subject></subj-group><subj-group subj-group-type="section-heading" xml:lang="ru"><subject>СИНТЕЗ И ПЕРЕРАБОТКА ПОЛИМЕРОВ И КОМПОЗИТОВ НА ИХ ОСНОВЕ</subject></subj-group></article-categories><title-group><article-title>Novel polymer surfactants based on the branched silatrane-containing polyesters and polyethers</article-title><trans-title-group xml:lang="ru"><trans-title>Новые полимерные ПАВ на основе разветвленных силатрансодержащих полиэфиров</trans-title></trans-title-group></title-group><contrib-group><contrib contrib-type="author" corresp="yes"><name-alternatives><name name-style="eastern" xml:lang="ru"><surname>Истратов</surname><given-names>В. В.</given-names></name><name name-style="western" xml:lang="en"><surname>Istratov</surname><given-names>V. V.</given-names></name></name-alternatives><bio xml:lang="ru"><p>Истратов Владислав Викторович, кандидат химических наук, старший научный сотрудник лаборатории гетероцепных полимеров</p><p>Scopus Author ID 17136964600, Researсher ID J-7017-2014</p><p>119991, Москва, ул. Вавилова, д. 28</p></bio><bio xml:lang="en"><p>Vladislav V. Istratov, Cand. of Sci. (Chemistry), Senior Researcher of the Laboratory of Heterochain Polymers</p><p>Scopus Author ID 17136964600, Researcher ID J-7017-2014</p><p>28, Vavilova ul., Moscow, 119991, Russia</p></bio><email xlink:type="simple">slav@ineos.ac.ru</email><xref ref-type="aff" rid="aff-1"/></contrib><contrib contrib-type="author" corresp="yes"><name-alternatives><name name-style="eastern" xml:lang="ru"><surname>Гомзяк</surname><given-names>В. И.</given-names></name><name name-style="western" xml:lang="en"><surname>Gomzyak</surname><given-names>V. I.</given-names></name></name-alternatives><bio xml:lang="ru"><p>Гомзяк Виталий Иванович, кандидат химических наук, старший преподаватель кафедры химии и технологии высокомолекулярных соединений им. С.С. Медведева</p><p>Scopus Author ID 55841680300, Researсher ID E-4518-2017</p><p>119571, Москва, пр-т Вернадского, д. 86</p></bio><bio xml:lang="en"><p>Vitaly I. Gomzyak, Cand. of Sci. (Chemistry), Senior Lecturer of the Medvedev Chair of Chemistry and Technology of Macromolecular Compounds</p><p>Scopus Author ID 55841680300, Researcher ID E-4518-2017</p><p>86, Vernadskogo pr., Moscow, 119571, Russia</p></bio><email xlink:type="simple">vgomzyak@gmail.com</email><xref ref-type="aff" rid="aff-2"/></contrib><contrib contrib-type="author" corresp="yes"><name-alternatives><name name-style="eastern" xml:lang="ru"><surname>Ямскова</surname><given-names>О. В.</given-names></name><name name-style="western" xml:lang="en"><surname>Yamskova</surname><given-names>O. V.</given-names></name></name-alternatives><bio xml:lang="ru"><p>Ямскова Ольга Васильевна, кандидат химических наук, научный сотрудник лаборатории гетероцепных полимеров</p><p>Scopus Author ID 56816874700</p><p>119991, Москва, ул. Вавилова, д. 28</p></bio><bio xml:lang="en"><p>Olga V. Yamskova, Cand. of Sci. (Chemistry), Researcher of the Laboratory of Heterochain Polymers</p><p>Scopus Author ID 56816874700</p><p>28, Vavilova ul., Moscow, 119991, Russia</p></bio><email xlink:type="simple">olga_yamskova@mail.ru</email><xref ref-type="aff" rid="aff-1"/></contrib><contrib contrib-type="author" corresp="yes"><name-alternatives><name name-style="eastern" xml:lang="ru"><surname>Маркова</surname><given-names>Г. Д.</given-names></name><name name-style="western" xml:lang="en"><surname>Markova</surname><given-names>G. D.</given-names></name></name-alternatives><bio xml:lang="ru"><p>Маркова Гали Дмитриевна, кандидат химических наук, старший научный сотрудник лаборатории гетероцепных полимеров</p><p>Scopus Author ID 7003815520</p><p>119991, Москва, ул. Вавилова, д. 28</p></bio><bio xml:lang="en"><p>Gali D. Markova, Cand. of Sci. (Chemistry), Senior Researcher of the Laboratory of Heterochain Polymers</p><p>Scopus Author ID 7003815520</p><p>28, Vavilov ul., Moscow, 119991, Russia</p></bio><email xlink:type="simple">mgaly@yandex.ru</email><xref ref-type="aff" rid="aff-1"/></contrib><contrib contrib-type="author" corresp="yes"><name-alternatives><name name-style="eastern" xml:lang="ru"><surname>Комарова</surname><given-names>Л. Г.</given-names></name><name name-style="western" xml:lang="en"><surname>Komarova</surname><given-names>L. G.</given-names></name></name-alternatives><bio xml:lang="ru"><p>Комарова Людмила Григорьевна, кандидат химических наук, старший научный сотрудник лаборатории гетероцепных полимеров</p><p>Scopus Author ID 7102405938</p><p>119991, Москва, ул. Вавилова, д. 28</p></bio><bio xml:lang="en"><p>Lyudmila G. Komarova, Cand. of Sci. (Chemistry), Senior Researcher of the Laboratory of Heterochain Polymers, A.N. Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences</p><p>Scopus Author ID 7102405938</p><p>28, Vavilova ul., Moscow, 119991, Russia</p></bio><xref ref-type="aff" rid="aff-1"/></contrib><contrib contrib-type="author" corresp="yes"><name-alternatives><name name-style="eastern" xml:lang="ru"><surname>Измайлов</surname><given-names>Б. А.</given-names></name><name name-style="western" xml:lang="en"><surname>Izmaylov</surname><given-names>B. A.</given-names></name></name-alternatives><bio xml:lang="ru"><p>Измайлов Борис Александрович, доктор химических наук, профессор, ведущий научный сотрудник лаборатории гетероцепных полимеров</p><p>Scopus Author ID 24610651200</p><p>119991, Москва, ул. Вавилова, д. 28</p></bio><bio xml:lang="en"><p>Boris A. Izmaylov, Dr. of Sci. (Chemistry), Professor, Leading Researcher of the Laboratory of Heterochain Polymers</p><p>Scopus Author ID 24610651200</p><p>28, Vavilova ul., Moscow, 119991, Russia</p></bio><email xlink:type="simple">izmaylov38@yandex.ru</email><xref ref-type="aff" rid="aff-1"/></contrib><contrib contrib-type="author" corresp="yes"><name-alternatives><name name-style="eastern" xml:lang="ru"><surname>Васнёв</surname><given-names>В. А.</given-names></name><name name-style="western" xml:lang="en"><surname>Vasnev</surname><given-names>V. A.</given-names></name></name-alternatives><bio xml:lang="ru"><p>Васнев Валерий Александрович, доктор химических наук, профессор, заведующий лабораторией гетероцепных полимеров</p><p>Scopus Author ID 7004556739</p><p>119991, Москва, ул. Вавилова, д. 28</p></bio><bio xml:lang="en"><p>Valerii A. Vasnev, Dr. of Sci. (Chemistry), Professor, Head of the Laboratory of Heterochain Polymers</p><p>Scopus Author ID 7004556739</p><p>28, Vavilova ul., Moscow, 119991, Russia</p></bio><email xlink:type="simple">vasnev@ineos.ac.ru</email><xref ref-type="aff" rid="aff-1"/></contrib></contrib-group><aff-alternatives id="aff-1"><aff xml:lang="ru"><institution>Институт элементоорганических соединений имени А.Н. Несмеянова РАН</institution><country>Россия</country></aff><aff xml:lang="en"><institution>A.N. Nesmeyanov Institute of Organoelement Сompounds, Russian Academy of Sciences</institution><country>Russian Federation</country></aff></aff-alternatives><aff-alternatives id="aff-2"><aff xml:lang="ru"><institution>МИРЭА – Российский технологический университет (Институт тонких химических технологий имени М.В. Ломоносова)</institution><country>Россия</country></aff><aff xml:lang="en"><institution>MIREA – Russian Technological University (M.V. Lomonosov Institute of Fine Chemical Technologies)</institution><country>Russian Federation</country></aff></aff-alternatives><pub-date pub-type="collection"><year>2019</year></pub-date><pub-date pub-type="epub"><day>14</day><month>11</month><year>2019</year></pub-date><volume>14</volume><issue>5</issue><fpage>61</fpage><lpage>70</lpage><permissions><copyright-statement>Copyright &amp;#x00A9; Istratov V.V., Gomzyak V.I., Yamskova O.V., Markova G.D., Komarova L.G., Izmaylov B.A., Vasnev V.A., 2019</copyright-statement><copyright-year>2019</copyright-year><copyright-holder xml:lang="ru">Истратов В.В., Гомзяк В.И., Ямскова О.В., Маркова Г.Д., Комарова Л.Г., Измайлов Б.А., Васнёв В.А.</copyright-holder><copyright-holder xml:lang="en">Istratov V.V., Gomzyak V.I., Yamskova O.V., Markova G.D., Komarova L.G., Izmaylov B.A., Vasnev V.A.</copyright-holder><license xml:lang="ru" license-type="creative-commons-attribution" xlink:href="https://creativecommons.org/licenses/by/4.0/" xlink:type="simple"><license-p>Данная работа распространяется под лицензией Creative Commons Attribution 4.0.</license-p></license><license xml:lang="en" license-type="creative-commons-attribution" xlink:href="https://creativecommons.org/licenses/by/4.0/" xlink:type="simple"><license-p>This work is licensed under a Creative Commons Attribution 4.0 License.</license-p></license></permissions><self-uri xlink:href="https://www.finechem-mirea.ru/jour/article/view/1550">https://www.finechem-mirea.ru/jour/article/view/1550</self-uri><abstract><sec><title>Objectives</title><p>Objectives. Biologically active polymeric surfactants are a new promising class of macromolecules that can find application in medicine, cosmetology, and agriculture. In this study, a number of new biologically active amphiphilic polymers based on branched silatrane-containing polyesters and polyethers were obtained, and their surface-active properties were investigated.</p></sec><sec><title>Methods</title><p>Methods. The branched polymers were represented by polyethers and polyesters, obtained respectively via the anionic polymerization of 1,2-epoxypropanol or a combination of equilibrium polycondensation and ring opening polymerization. The polymers were modified with 3-isocyanopropylsilatrane and trimethylethoxysilane to obtain the amphiphilic compounds containing silatrane groups bonded to the polymer backbone by the urethane bond. The structure of the synthesized polymer silatranes was confirmed via nuclear magnetic resonance spectroscopy and gel permeation chromatography. The surface active properties of all the copolymers obtained were investigated in connection with their obvious amphiphilicity. In particular, the formation of micelles in aqueous solutions is such a property. The critical micelle concentrations were determined by a method of quenching the fluorescence of the polymers.</p></sec><sec><title>Results</title><p>Results. It was shown that the values of the critical micelle concentrations and the hydrophilic-lipophilic balance values of polymers determined by the Griffin equation correlate well with each other. A linear relationship between the hydrophilic-lipophilic balance and the critical micelle concentrations was established. At the same time, polyether-based polymers generally showed higher critical micelle concentrations than polyester-based polymers, although the hydrophilic-lipophilic balance values for polymers of different series, but with close degrees of substitution, were close. It was found that the use of all synthesized polymers as stabilizers of direct and reverse emulsions leads to an increase in the aggregative stability of both types of emulsions. The stability of emulsions depended both on the degree of substitution of peripheral hydroxyl groups of polymers by silatranes and on the molecular weight and structure of the branched block of polymers. The stability of direct emulsions increased for all polymers, while that of inverse emulsions decreased with an increasing degree of substitution of hydroxyl groups by silatranes. The increase of the branched block molecular weight led to an increase of droplet sizes for both direct and inverse emulsions. The smallest droplet size for direct and inverse emulsions was obtained using polymers with low molecular weight branched polyester blocks as surfactants.</p></sec><sec><title>Conclusions</title><p>Conclusions. The results obtained prove the possibility of creating polymer surfactants containing silatrane groups. By varying the structure of the polymer, its molecular weight and the degree of substitution of peripheral functional groups, it is possible to obtain surfactants with desired surface properties.</p></sec></abstract><trans-abstract xml:lang="ru"><sec><title>Цели</title><p>Цели. Биологически активные полимерные ПАВ являются новым многообещающим классом макромолекул, которые могут найти применение в медицине, косметологии, сельском хозяйстве. В данном исследовании был получен ряд новых амфифильных полимеров на основе разветвленных силатран-содержащих полиэфиров и исследованы их поверхностно-активные свойства.</p></sec><sec><title>Методы</title><p>Методы. Разветвленные полимеры были представлены простыми и сложными полиэфирами, которые получали соответственно способом анионной полимеризации 1,2-эпоксипропанола либо комбинацией равновесной поликонденсации и полимеризации с раскрытием цикла. Для получения амфифильных соединений, содержащих силатрановые группы, связанные с полимерным каркасом уретановой связью, полимеры были модифицированы 3-изоцианопропилсилатраном и триметилэтоксисиланом. Структура синтезированных полимерных силатранов была подтверждена методами ЯМР-спектроскопии и гель-проникающей хроматографии. Поверхностно-активные свойства всех полученных сополимеров были исследованы в связи с их очевидной амфифильностью, в частности, таким свойством является образование мицелл в водных растворах. Методом гашения флуоресценции полимеров были определены величины критических концентраций мицеллообразования (ККМ).</p></sec><sec><title>Результаты</title><p>Результаты. Показано, что величины ККМ и определенные в соответствие с уравнением Гриффина величины гидрофильно-липофильного баланса (ГЛБ) для полимеров коррелируют, при этом была установлена линейная зависимость между указанными величинами. Полимеры на основе простых полиэфиров в целом показывали более высокие значения ККМ, чем полимеры на основе сложных полиэфиров, хотя величины ГЛБ для полимеров разных серий, но с близкими степенями замещения были близки. Было обнаружено, что использование всех синтезированных полимеров в качестве стабилизаторов прямых и обратных эмульсий приводит к увеличению агрегативной устойчивости эмульсий обоих типов. Устойчивость эмульсий зависела как от степени замещения периферийных гидроксильных групп полимеров силатранами, так и от молекулярной массы и строения разветвленного блока полимеров. Для всех полимеров устойчивость прямых эмульсий возрастала, а обратных эмульсий – снижалась с увеличением степени замещения гидроксильных групп силатранами. С увеличением молекулярной массы разветвленного блока размеры капель как прямых, так и обратных эмульсий увеличивались. Наименьший размер капель прямой и обратной эмульсии был получен при использовании в качестве ПАВ полимеров с низкомолекулярными разветвленными блоками на основе сложных эфиров.</p></sec><sec><title>Заключение</title><p>Заключение. Полученные результаты показывают возможность создания полимерных ПАВ, содержащих силатрановые группы. Варьируя строение полимера, его молекулярную массу и степень замещения периферийных функциональных групп, возможно получение ПАВ с заданными поверхностными свойствами.</p></sec></trans-abstract><kwd-group xml:lang="ru"><kwd>разветвленные полимеры</kwd><kwd>силатраны</kwd><kwd>мицеллообразование</kwd><kwd>эмульсии</kwd></kwd-group><kwd-group xml:lang="en"><kwd>branched polymers</kwd><kwd>silatranes</kwd><kwd>micellization</kwd><kwd>emulsions</kwd></kwd-group><funding-group><funding-statement xml:lang="ru">Работа выполнена при финансовой поддержке РФФИ (грант № 17-03-01089). Исследования полимеров проведены при поддержке Министерства науки и высшего образования Российской Федерации с использованием научного оборудования Центра исследования строения молекул ИНЭОС РАН.</funding-statement><funding-statement xml:lang="en">This work was supported by the Russian Foundation for Basic Research (Grant No. 17-03-01089). Polymer research was carried out with the support of the Ministry of Science and Higher Education of the Russian Federation using scientific equipment from the Center for Molecule Composition Studies of the INEOS RAS.</funding-statement></funding-group></article-meta></front><back><ref-list><title>References</title><ref id="cit1"><label>1</label><citation-alternatives><mixed-citation xml:lang="ru">Tamariz Е., Rios-Ramírez А. Biodegradation of Medical Purpose Polymeric Materials and Their Impact on Biocompatibility. In: Biodegradation – Life of Science. Ed. by Rolando Chamy. IntechOpen Ltd., London, 2013; pp. 3-29. [Electronic resource]. URL: https://www.intechopen.com/books/biodegradation-life-of-science/biodegradation-of-medical-purpose-polymeric-materials-and-their-impact-on-biocompatibility</mixed-citation><mixed-citation xml:lang="en">Tamariz Е., Rios-Ramírez А. Biodegradation of Medical Purpose Polymeric Materials and Their Impact on Biocompatibility. In: Biodegradation – Life of Science. Ed. by Rolando Chamy. IntechOpen Ltd., London, 2013; pp. 3-29. [Electronic resource]. URL: https://www.intechopen.com/books/biodegradation-life-of-science/biodegradation-of-medical-purpose-polymeric-materials-and-their-impact-on-biocompatibility</mixed-citation></citation-alternatives></ref><ref id="cit2"><label>2</label><citation-alternatives><mixed-citation xml:lang="ru">Kumar N., Ravikumar M.N.V., Domb A.J. Biodegradable block copolymers. Adv. Drug Deliv. Rev. 2001;53(1):23-44. http://dx.doi.org/10.1016/S0169-409X(01)00219-8</mixed-citation><mixed-citation xml:lang="en">Kumar N., Ravikumar M.N.V., Domb A.J. Biodegradable block copolymers. Adv. Drug Deliv. Rev. 2001;53(1):23-44. http://dx.doi.org/10.1016/S0169-409X(01)00219-8</mixed-citation></citation-alternatives></ref><ref id="cit3"><label>3</label><citation-alternatives><mixed-citation xml:lang="ru">Tian H., Tang Z., Zhuang X., Chen X., Jing X. Biodegradable synthetic polymers: Preparation, functionalization and biomedical application. Prog. Polym. Sci. 2012;37(2):237-280. http://dx.doi.org/10.1016/j.progpolymsci.2011.06.004</mixed-citation><mixed-citation xml:lang="en">Tian H., Tang Z., Zhuang X., Chen X., Jing X. Biodegradable synthetic polymers: Preparation, functionalization and biomedical application. Prog. Polym. Sci. 2012;37(2):237-280. http://dx.doi.org/10.1016/j.progpolymsci.2011.06.004</mixed-citation></citation-alternatives></ref><ref id="cit4"><label>4</label><citation-alternatives><mixed-citation xml:lang="ru">Junginger H.E. Drug Targeting and Delivery: Concepts in Dosage Form Design. CRC Press, 1992. 300 p.</mixed-citation><mixed-citation xml:lang="en">Junginger H.E. Drug Targeting and Delivery: Concepts in Dosage Form Design. CRC Press, 1992. 300 p.</mixed-citation></citation-alternatives></ref><ref id="cit5"><label>5</label><citation-alternatives><mixed-citation xml:lang="ru">Ostroumov S.A. Biological Effects of Surfactants. CRC Press, 2005. 304 p.</mixed-citation><mixed-citation xml:lang="en">Ostroumov S.A. Biological Effects of Surfactants. CRC Press, 2005. 304 p.</mixed-citation></citation-alternatives></ref><ref id="cit6"><label>6</label><citation-alternatives><mixed-citation xml:lang="ru">El-Shahawi M.M., Shalaby A.A.S., Gabre A.M.E., Ghonim A.E.M. Surface active properties and biological activities of novel anionic surfactant based on oxapyridazinone derivatives. J. Surfact. Deterg. 2016:19(1):137-144. https://doi.org/10.1007/s11743-015-1756-9</mixed-citation><mixed-citation xml:lang="en">El-Shahawi M.M., Shalaby A.A.S., Gabre A.M.E., Ghonim A.E.M. Surface active properties and biological activities of novel anionic surfactant based on oxapyridazinone derivatives. J. Surfact. Deterg. 2016:19(1):137-144. https://doi.org/10.1007/s11743-015-1756-9</mixed-citation></citation-alternatives></ref><ref id="cit7"><label>7</label><citation-alternatives><mixed-citation xml:lang="ru">Schreier S., Malheiros S.V.P., de Paula E. Surface active drugs: Self-association and interaction with membranes and surfactants. Physicochemical and biological aspects. Biochim. et Biophys. Acta. 2000;1508:210-234. http://dx.doi.org/10.1016/S0304-4157(00)00012-5</mixed-citation><mixed-citation xml:lang="en">Schreier S., Malheiros S.V.P., de Paula E. Surface active drugs: Self-association and interaction with membranes and surfactants. Physicochemical and biological aspects. Biochim. et Biophys. Acta. 2000;1508:210-234. http://dx.doi.org/10.1016/S0304-4157(00)00012-5</mixed-citation></citation-alternatives></ref><ref id="cit8"><label>8</label><citation-alternatives><mixed-citation xml:lang="ru">Pegiadou S.P. Synthesis, characterization and surface properties of 1-N-L-tryptophan glycerol ether surfactants. J. Surfact. Deterg. 2000;3(4):517-525. http://dx.doi.org/10.1007/s11743-000-0151-y</mixed-citation><mixed-citation xml:lang="en">Pegiadou S.P. Synthesis, characterization and surface properties of 1-N-L-tryptophan glycerol ether surfactants. J. Surfact. Deterg. 2000;3(4):517-525. http://dx.doi.org/10.1007/s11743-000-0151-y</mixed-citation></citation-alternatives></ref><ref id="cit9"><label>9</label><citation-alternatives><mixed-citation xml:lang="ru">Amin M.S., Eissa A.M.F., Shaaban A.F., El-Sawy A.A., El-Sayed R. New heterocycles having double characters as antimicrobial and surface active agents. Part 2: Anionic compounds from fatty acid isothiocyanate. Ind. J. Chem. 2003;1:313-319.</mixed-citation><mixed-citation xml:lang="en">Amin M.S., Eissa A.M.F., Shaaban A.F., El-Sawy A.A., El-Sayed R. New heterocycles having double characters as antimicrobial and surface active agents. Part 2: Anionic compounds from fatty acid isothiocyanate. Ind. J. Chem. 2003;1:313-319.</mixed-citation></citation-alternatives></ref><ref id="cit10"><label>10</label><citation-alternatives><mixed-citation xml:lang="ru">Logine R.B. Pyrrolidone-based surfactants (a literature review). J. Am. Oil. Chem. Soc. 2003;72(7):759-771. https://doi.org/10.1007/BF02541023</mixed-citation><mixed-citation xml:lang="en">Logine R.B. Pyrrolidone-based surfactants (a literature review). J. Am. Oil. Chem. Soc. 2003;72(7):759-771. https://doi.org/10.1007/BF02541023</mixed-citation></citation-alternatives></ref><ref id="cit11"><label>11</label><citation-alternatives><mixed-citation xml:lang="ru">Amin M.S., Eissa A.M.F., Shaaban A.F., El-Sawy A.A., El-Sayed R. New heterocycles having double characters as antimicrobial and surface active agents. Part 1: Nonionic compounds from fatty acid isothiocyanate. Grasas y Aceites [Fats and oils]. 2004;55(4):370-377. https://doi.org/10.3989/gya.2004.v55.i4.203</mixed-citation><mixed-citation xml:lang="en">Amin M.S., Eissa A.M.F., Shaaban A.F., El-Sawy A.A., El-Sayed R. New heterocycles having double characters as antimicrobial and surface active agents. Part 1: Nonionic compounds from fatty acid isothiocyanate. Grasas y Aceites [Fats and oils]. 2004;55(4):370-377. https://doi.org/10.3989/gya.2004.v55.i4.203</mixed-citation></citation-alternatives></ref><ref id="cit12"><label>12</label><citation-alternatives><mixed-citation xml:lang="ru">El-Sayed R., Wasfy A.A.F., Aly A.A. Synthesis of novel heterocycles with antimicrobial and surface activity. J. Heterocycl. Chem. 2005;42:125-130. https://doi.org/10.1002/jhet.5570420119</mixed-citation><mixed-citation xml:lang="en">El-Sayed R., Wasfy A.A.F., Aly A.A. Synthesis of novel heterocycles with antimicrobial and surface activity. J. Heterocycl. Chem. 2005;42:125-130. https://doi.org/10.1002/jhet.5570420119</mixed-citation></citation-alternatives></ref><ref id="cit13"><label>13</label><citation-alternatives><mixed-citation xml:lang="ru">Mahfud R., Agag T., Ishida H., Shaikh S., Qutubuddin S. Synthesis and evaluation of novel anionic polymeric surfactants based on polybenzoxazines. J. Colloid Interface Sci. 2013; 407:339-347. http://dx.doi.org/10.1016/j.jcis.2013.06.042</mixed-citation><mixed-citation xml:lang="en">Mahfud R., Agag T., Ishida H., Shaikh S., Qutubuddin S. Synthesis and evaluation of novel anionic polymeric surfactants based on polybenzoxazines. J. Colloid Interface Sci. 2013; 407:339-347. http://dx.doi.org/10.1016/j.jcis.2013.06.042</mixed-citation></citation-alternatives></ref><ref id="cit14"><label>14</label><citation-alternatives><mixed-citation xml:lang="ru">Voronkov M.G., Zelcans G., Mazeika I. Silatranes: Intra-complex heterocyclic compounds of pentacoordinated silicon. Pure Appl. Chem. 1966;13(1-2):35-59. https://doi.org/10.1351/pac196613010035</mixed-citation><mixed-citation xml:lang="en">Voronkov M.G., Zelcans G., Mazeika I. Silatranes: Intra-complex heterocyclic compounds of pentacoordinated silicon. Pure Appl. Chem. 1966;13(1-2):35-59. https://doi.org/10.1351/pac196613010035</mixed-citation></citation-alternatives></ref><ref id="cit15"><label>15</label><citation-alternatives><mixed-citation xml:lang="ru">Voronkov M.G., Baryshok V.P. Atranes as a new generation of biologically active substances. Her. Russ. Acad. Sci. 2010;80:514-521. https://doi.org/10.1134/S1019331610060079</mixed-citation><mixed-citation xml:lang="en">Voronkov M.G., Baryshok V.P. Atranes as a new generation of biologically active substances. Her. Russ. Acad. Sci. 2010;80:514-521. https://doi.org/10.1134/S1019331610060079</mixed-citation></citation-alternatives></ref><ref id="cit16"><label>16</label><citation-alternatives><mixed-citation xml:lang="ru">Puri J. K., Singh R. Chahal V. K. Silatranes: A review on their synthesis, structure, reactivity and applications. Chem. Soc. Rev. 2011;40:1791-1840. https://doi.org/10.1039/B925899J</mixed-citation><mixed-citation xml:lang="en">Puri J. K., Singh R. Chahal V. K. Silatranes: A review on their synthesis, structure, reactivity and applications. Chem. Soc. Rev. 2011;40:1791-1840. https://doi.org/10.1039/B925899J</mixed-citation></citation-alternatives></ref><ref id="cit17"><label>17</label><citation-alternatives><mixed-citation xml:lang="ru">Lin Y., Song B., Han A., Hu S., Ye F., Xie Z. 2011. Synthesis of γ-arylmethylene-aminopropyl-3,7,10-trimethyl-silatrane derivatives and their activities of regulating plant growth. Phosphor Sulfur Silicon Relat. Elem. 2011;186(2):298-303. http://dx.doi.org/10.1080/10426507.2010.496747</mixed-citation><mixed-citation xml:lang="en">Lin Y., Song B., Han A., Hu S., Ye F., Xie Z. 2011. Synthesis of γ-arylmethylene-aminopropyl-3,7,10-trimethyl-silatrane derivatives and their activities of regulating plant growth. Phosphor Sulfur Silicon Relat. Elem. 2011;186(2):298-303. http://dx.doi.org/10.1080/10426507.2010.496747</mixed-citation></citation-alternatives></ref><ref id="cit18"><label>18</label><citation-alternatives><mixed-citation xml:lang="ru">Khankhodzhaeva D.A., Voronkov M.G. Effect of cresacin on the growth, development, and productivity of cotton plants. Doklady Akademii nauk SSSR = Dokl. Akad. Nauk. 1993;333:124-126.</mixed-citation><mixed-citation xml:lang="en">Khankhodzhaeva D.A., Voronkov M.G. Effect of cresacin on the growth, development, and productivity of cotton plants. Doklady Akademii nauk SSSR = Dokl. Akad. Nauk. 1993;333:124-126.</mixed-citation></citation-alternatives></ref><ref id="cit19"><label>19</label><citation-alternatives><mixed-citation xml:lang="ru">Voronkov M.G., Dolmaa G., Tserenpil S., Ugtakhbayar O., Chimidtsogzol A. Stimulation of barley seed germination by micromolar aqueous solutions of silatrane and cresacin. Dokl. Biol. Sci. 2005;404(1):367-369. http://dx.doi.org/10.1007/s10630-005-0138-2</mixed-citation><mixed-citation xml:lang="en">Voronkov M.G., Dolmaa G., Tserenpil S., Ugtakhbayar O., Chimidtsogzol A. Stimulation of barley seed germination by micromolar aqueous solutions of silatrane and cresacin. Dokl. Biol. Sci. 2005;404(1):367-369. http://dx.doi.org/10.1007/s10630-005-0138-2</mixed-citation></citation-alternatives></ref><ref id="cit20"><label>20</label><citation-alternatives><mixed-citation xml:lang="ru">Burlakova E.B., Baikov P.Y., Papina R.I., Kartsev V.G. Bimodal effect of the picolinic acid derivatives on the rate of wheat and pea germination. Izvestia Akademii nauk SSSR. Seria biologiceskaa = Izv. Ross. Akad. Nauk. Ser. Biol. 1996;1:39-45.</mixed-citation><mixed-citation xml:lang="en">Burlakova E.B., Baikov P.Y., Papina R.I., Kartsev V.G. Bimodal effect of the picolinic acid derivatives on the rate of wheat and pea germination. Izvestia Akademii nauk SSSR. Seria biologiceskaa = Izv. Ross. Akad. Nauk. Ser. Biol. 1996;1:39-45.</mixed-citation></citation-alternatives></ref><ref id="cit21"><label>21</label><citation-alternatives><mixed-citation xml:lang="ru">Purification of Laboratory Chemicals. Ed. by Armarego W.L.E., Perrin D.D. Berlin: Buttleworth-Heinemann, 1998. 480 p.</mixed-citation><mixed-citation xml:lang="en">Purification of Laboratory Chemicals. Ed. by Armarego W.L.E., Perrin D.D. Berlin: Buttleworth-Heinemann, 1998. 480 p.</mixed-citation></citation-alternatives></ref><ref id="cit22"><label>22</label><citation-alternatives><mixed-citation xml:lang="ru">Sunder A., Hanselmann R., Frey H., Mülhaupt R. Controlled synthesis of hyperbranched polyglycerols by ring-opening multibranching polymerization. Macromolecules. 1999;32(13):4240-4246. http://dx.doi.org/10.1021/ma990090w</mixed-citation><mixed-citation xml:lang="en">Sunder A., Hanselmann R., Frey H., Mülhaupt R. Controlled synthesis of hyperbranched polyglycerols by ring-opening multibranching polymerization. Macromolecules. 1999;32(13):4240-4246. http://dx.doi.org/10.1021/ma990090w</mixed-citation></citation-alternatives></ref><ref id="cit23"><label>23</label><citation-alternatives><mixed-citation xml:lang="ru">Istratov V.V., Gomzyak V.I., Krupina T.V., Vasnev V.A., Chvalun S.N. Amphiphilic linear-branched copolylactides and disperse systems on their basis. Polym. Sci. B. 2017;59(6):730-736. http://dx.doi.org/10.1134/S156009041706001X</mixed-citation><mixed-citation xml:lang="en">Istratov V.V., Gomzyak V.I., Krupina T.V., Vasnev V.A., Chvalun S.N. Amphiphilic linear-branched copolylactides and disperse systems on their basis. Polym. Sci. B. 2017;59(6):730-736. http://dx.doi.org/10.1134/S156009041706001X</mixed-citation></citation-alternatives></ref><ref id="cit24"><label>24</label><citation-alternatives><mixed-citation xml:lang="ru">Dumitriu A.-M.-C., Cazacu M., Shova S., Turta C., Simionescu B.C. Synthesis and structural characterization of 1-(3-aminopropyl)silatrane and some new derivatives. Polyhedron. 2012;33(1):119. http://dx.doi.org/10.1016/j.poly.2011.11.014</mixed-citation><mixed-citation xml:lang="en">Dumitriu A.-M.-C., Cazacu M., Shova S., Turta C., Simionescu B.C. Synthesis and structural characterization of 1-(3-aminopropyl)silatrane and some new derivatives. Polyhedron. 2012;33(1):119. http://dx.doi.org/10.1016/j.poly.2011.11.014</mixed-citation></citation-alternatives></ref><ref id="cit25"><label>25</label><citation-alternatives><mixed-citation xml:lang="ru">Griffin W.C. Calculation of HLB values of non-ionic surfactants. J. Soc. Cosmet. Chem. 1954;5(4):249-256.</mixed-citation><mixed-citation xml:lang="en">Griffin W.C. Calculation of HLB values of non-ionic surfactants. J. Soc. Cosmet. Chem. 1954;5(4):249-256.</mixed-citation></citation-alternatives></ref><ref id="cit26"><label>26</label><citation-alternatives><mixed-citation xml:lang="ru">Istratov V.V., Kautz H., Kim Y.-K., Schubert R. Linear-dendritic nonionic poly(propylene oxide)–polyglycerol surfactants. Tetrahedron. 2003:59(22):4017-4024. http://dx.doi.org/10.1016/S0040-4020(03)00470-8</mixed-citation><mixed-citation xml:lang="en">Istratov V.V., Kautz H., Kim Y.-K., Schubert R. Linear-dendritic nonionic poly(propylene oxide)–polyglycerol surfactants. Tetrahedron. 2003:59(22):4017-4024. http://dx.doi.org/10.1016/S0040-4020(03)00470-8</mixed-citation></citation-alternatives></ref></ref-list><fn-group><fn fn-type="conflict"><p>The authors declare that there are no conflicts of interest present.</p></fn></fn-group></back></article>
