Synthesis and research of polyurethane urea with 2-(2-aminoethoxy)ethan-1-amine and 3-{2-[2-(3-aminopropoxy)ethoxy]ethoxy}propane-1-amine as macrochain extenders, and compositions with ifosphamide based on them

Q4 Chemistry

Voprosy Khimii i Khimicheskoi Tekhnologii Pub Date : 2024-02-01 DOI:10.32434/0321-4095-2024-152-1-70-80

S. Prymushko, N. Galatenko, R. Rozhnova, G. Kozlova, I. Gladyr, N.O. Danko

{"title":"Synthesis and research of polyurethane urea with 2-(2-aminoethoxy)ethan-1-amine and 3-{2-[2-(3-aminopropoxy)ethoxy]ethoxy}propane-1-amine as macrochain extenders, and compositions with ifosphamide based on them","authors":"S. Prymushko, N. Galatenko, R. Rozhnova, G. Kozlova, I. Gladyr, N.O. Danko","doi":"10.32434/0321-4095-2024-152-1-70-80","DOIUrl":null,"url":null,"abstract":"Polyurethane urea (PUU) was synthesized using macrochain extenders of 2-(2-aminoethoxy)ethan-1-amine (DA1) and 3-{2-[2-(3-aminopropoxy)ethoxy]ethoxy}propan-1-amine (DA3) at a molar ratio of 4,4'-diaminodiphenylmethane (DADP) to DA1 and DA3 as 30:70; 50:50; and 70:30. The tensile strength () of PUU is in the range of 0.74–2.21 MPa, and the relative elongation at break () is 27.4–1003%. According to the DSC method, the studied PUUs are single-phase systems. The glass transition temperature (Tg) of the PUU DA1 series is from 21.920C to –39.480C, and the glass transition temperature for the PUU DA3 is from –20.040C to –33.960C. Based on the synthesized PUUs, composite materials were prepared containing 1 wt.% of ifosfamide (IFO) (=0.74–2.21 MPa, and =31.8–276.3%). According to the results of thermophysical studies, the compositions with IFO are single-phase systems with Tg of –24.80C to –36.220C. Thus, the introduction of IFO into the composition leads to an increase in the packing density of the macrochain, a decrease in the size of the free volume and, consequently, a decrease in the mobility of the blocks in space and a decrease in Сp. Compositions with IFO are resistant to temperatures of ~2500C, which allows thermal sterilization before use. Using the HPLC-UV method, the dynamics of IFO release from samples of PUU compositions synthesized at a molar ratio of DADP:DA1 as 0.5:0.5 and DADP:DA3 as 0.7:0.3 was investigated. It was established that IFO is released within 60 days from compositions based on PUU DA3 in the amount of 29.6%, and from compositions based on PUU DA1 in the amount of 42% with respect to the total amount of IFO introduced. The resulting composites are promising materials for medicine as means of local prolonged therapeutic action.","PeriodicalId":23684,"journal":{"name":"Voprosy Khimii i Khimicheskoi Tekhnologii","volume":"527 1","pages":""},"PeriodicalIF":0.0000,"publicationDate":"2024-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Voprosy Khimii i Khimicheskoi Tekhnologii","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.32434/0321-4095-2024-152-1-70-80","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"Chemistry","Score":null,"Total":0}

引用次数: 0

Abstract

Polyurethane urea (PUU) was synthesized using macrochain extenders of 2-(2-aminoethoxy)ethan-1-amine (DA1) and 3-{2-[2-(3-aminopropoxy)ethoxy]ethoxy}propan-1-amine (DA3) at a molar ratio of 4,4'-diaminodiphenylmethane (DADP) to DA1 and DA3 as 30:70; 50:50; and 70:30. The tensile strength () of PUU is in the range of 0.74–2.21 MPa, and the relative elongation at break () is 27.4–1003%. According to the DSC method, the studied PUUs are single-phase systems. The glass transition temperature (Tg) of the PUU DA1 series is from 21.920C to –39.480C, and the glass transition temperature for the PUU DA3 is from –20.040C to –33.960C. Based on the synthesized PUUs, composite materials were prepared containing 1 wt.% of ifosfamide (IFO) (=0.74–2.21 MPa, and =31.8–276.3%). According to the results of thermophysical studies, the compositions with IFO are single-phase systems with Tg of –24.80C to –36.220C. Thus, the introduction of IFO into the composition leads to an increase in the packing density of the macrochain, a decrease in the size of the free volume and, consequently, a decrease in the mobility of the blocks in space and a decrease in Сp. Compositions with IFO are resistant to temperatures of ~2500C, which allows thermal sterilization before use. Using the HPLC-UV method, the dynamics of IFO release from samples of PUU compositions synthesized at a molar ratio of DADP:DA1 as 0.5:0.5 and DADP:DA3 as 0.7:0.3 was investigated. It was established that IFO is released within 60 days from compositions based on PUU DA3 in the amount of 29.6%, and from compositions based on PUU DA1 in the amount of 42% with respect to the total amount of IFO introduced. The resulting composites are promising materials for medicine as means of local prolonged therapeutic action.

查看原文本刊更多论文

以 2-(2-氨基乙氧基)乙烷-1-胺和 3-{2-[2-(3-氨基丙氧基)乙氧基]乙氧基}丙烷-1-胺为大链延伸剂的聚氨酯脲的合成与研究，以及以它们为基础的含 ifosphamide 的组合物

使用 2-(2-氨基乙氧基)乙烷-1-胺（DA1）和 3-{2-[2-(3-氨基丙氧基)乙氧基]乙氧基}丙-1-胺（DA3）的大链延伸剂合成了聚氨酯脲（PUU），4,4'-二氨基二苯基甲烷（DADP）与 DA1 和 DA3 的摩尔比分别为 30:70、50:50 和 70:30。PUU 的拉伸强度（）范围为 0.74-2.21 MPa，相对断裂伸长率（）为 27.4-1003%。根据 DSC 方法，所研究的 PUU 均为单相体系。PUU DA1 系列的玻璃化转变温度（Tg）为 21.920C 至 -39.480C，PUU DA3 的玻璃化转变温度为 -20.040C 至 -33.960C。根据合成的 PUU，制备了含有 1 wt.% 的 ifosfamide (IFO) 的复合材料（=0.74-2.21 MPa，=31.8-276.3%）。根据热物理研究结果，含有 IFO 的组合物是单相体系，其 Tg 为 -24.80C 至 -36.220C。因此，在组合物中引入 IFO 会导致大链的堆积密度增加，自由体积减小，从而降低嵌段在空间的流动性，降低 Сp。含有 IFO 的合成物可耐受 ~2500C 的温度，因此可在使用前进行热消毒。使用 HPLC-UV 方法，研究了 DADP:DA1 的摩尔比为 0.5:0.5 和 DADP:DA3 的摩尔比为 0.7:0.3 时合成的 PUU 组合物样品中 IFO 的释放动态。结果表明，以 PUU DA3 为基础的复合材料在 60 天内释放出的 IFO 占总 IFO 量的 29.6%，而以 PUU DA1 为基础的复合材料在 60 天内释放出的 IFO 占总 IFO 量的 42%。由此产生的复合材料是一种很有前景的医药材料，可作为局部延长治疗作用的手段。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

来源期刊

Voprosy Khimii i Khimicheskoi Tekhnologii Chemical Engineering-Chemical Engineering (all)

CiteScore

0.90

自引率

0.00%

发文量

期刊介绍： Voprosy Khimii i Khimicheskoi Tekhnologii (Issues of Chemistry and Chemical Technology) is published bimonthly by the Ukrainian State University of Chemical Technology and accepts Ukrainian- or English language high-quality original articles and reviews concerning various fields of research in chemistry and chemical engineering. Our unusual title “Voprosy khimii i khimicheskoi tekhnologii” originates from the transliterated initial Russian title “Issues of Chemistry and Chemical Technology“. The fact of the matter is that Voprosy khimii i khimicheskoi tekhnologii was founded in 1965 as a scientific journal mainly for Russian-reading and Russian-speaking readership when «the Iron Curtain» existed. Since 1991, after Ukraine declared its independence, our Journal began to publish the articles in Ukrainian and English. Multilingualism is our established tradition. We remember and cherish our traditions, but we follow the latest trends in modern science. Papers that are multidisciplinary or address new or emerging areas of chemistry and chemical engineering are particularly encouraged. Thus, the scope is dynamic. It includes but is not limited to the traditional areas of general, inorganic, organic, analytical, physical chemistry and electrochemistry, as well as all conventional areas of chemical engineering (chemistry of high molecular compounds, technology of inorganic and organic substances, processing of combustible minerals, chemical technology of silicates, processes and apparatus of chemical productions, etc.). The Journal publishes papers dealing with newer interdisciplinary areas such as materials science, nano-science, catalysis, computational and theoretical chemistry, surface phenomenon and colloidal systems, environmental chemistry, green chemistry.