CS216442B1 - N, N'-bis (alkylethyl) -1,2-propanediamine dioxides and their method of preparation - Google Patents
N, N'-bis (alkylethyl) -1,2-propanediamine dioxides and their method of preparation Download PDFInfo
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- CS216442B1 CS216442B1 CS106381A CS106381A CS216442B1 CS 216442 B1 CS216442 B1 CS 216442B1 CS 106381 A CS106381 A CS 106381A CS 106381 A CS106381 A CS 106381A CS 216442 B1 CS216442 B1 CS 216442B1
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Abstract
Vynález sa týká N,N'-bis(alkylmetyl)-l,2-pro- pándiamíndioxidov všeobecného vzorca R — B-CHj — CH — H-R CH, CH, CH, kde R značí 8 až 14 atomov uhlíka v lineárnom ^lkylovom reťazci a sposobu ich přípravy z N,N'- bis(alkylmetyl)- 1 ,2-propándiamínov oxidáciou vodným roztokom peroxidu vodíka. Einálne zlúčeniny majú výrazný antimikrobiálny účinok* á vykazujú aj povrchovoaktívne vlastnosti.The invention relates to N,N'-bis(alkylmethyl)-1,2-propanediamine dioxides of the general formula R — B-CHj — CH — H-R CH, CH, CH, where R denotes 8 to 14 carbon atoms in a linear alkyl chain and the method of their preparation from N,N'-bis(alkylmethyl)-1,2-propanediamines by oxidation with an aqueous solution of hydrogen peroxide. Einal compounds have a significant antimicrobial effect* and also exhibit surface-active properties.
Description
Vynález sa týká N,N'-bis(álkylmetyl)-l,2-propándiamíndioxidov všeobecného vzorcaThe invention relates to N, N'-bis (alkylmethyl) -1,2-propanediamine dioxides of the general formula
kde R značí 8 až 14 atómov uhlíka v alkylovom reťazci a spósobu přípravy týchto diamíndioxidov.’where R represents 8 to 14 carbon atoms in the alkyl chain and a process for the preparation of these diamine dioxides.
Nearomatické amínoxidy sú známe ako zmáčadlá, čistiace a dispergačné prostriedky, používajú sa nielen v priemysle textilnom, papierenskom, kožiarskom ale aj vo fotografii, pri príprave syntetic- , kých vláken, aj ako súčasť protipožiamych pien, kvapalných otěrových detergentov, našli použitie a,j v laserovéj technologii, ďalej ako insekticidy, používajú sa vo farmácii ale aj v organickéj syntéze.Non-aromatic amine oxides are known as wetting, cleaning and dispersing agents and are used not only in the textile, paper, leather, but also in photography industries, in the preparation of synthetic fibers, as well as in fire retardant foams, liquid abrasive detergents laser technology, as well as insecticides, are used in pharmacy but also in organic synthesis.
Amínoxidy, ktoré obsahujú vo svojej molekule najmenej jeden dlhý alkylový reťazec, patria medzi účinné povrchůvóaktívne a detergenčné zlúčeniny a okrem toho vykazujú napr. výrazný antimikrobi! álny efekt.Amine oxides which contain at least one long alkyl chain in their molecule are active surfactant and detergent compounds and additionally exhibit e.g. distinctive antimicrobes! effect.
' Z diamíndioxidov je doteraz známých len poměrně málo zlúčenín. Z derivátov vyššie uvedeného typu nie je známa ani jedna látka. Všetky zlúčeniny, ktoré sú predmetom vynálezu sú látky nové, doteraz v chemickej literatúre neopísané, u ktorých sa zistili doteraz neznáme účinky naí mikroorganizmy. >Of the diamine dioxides, only a few compounds are known so far. None of the above-mentioned derivatives is known. All of the compounds of the invention are novel substances not previously described in the chemical literature, which have so far been found to have unknown effects on our microorganisms. >
V príkladoch sú uvedené vybrané zlúčeniny,1' ktoré sú predmetom vynálezu ako aj ich sposob přípravy spolu s ich charakterizáciou a uvedením •ich antimikrobiálnej účinnosti vyjadrenej ako minimálna inhibičná koncentrácia — MIC —v (Xg/ml na kmene: Staphylococcus aureus, Escherichia coli a Candida albicans.The examples show selected compounds 1 'of the invention as well as their method of preparation together with their characterization and indication of their antimicrobial activity expressed as the minimum inhibitory concentration - MIC - v (Xg / ml on Staphylococcus aureus, Escherichia coli and Candida albicans.
Příklad 1Example 1
0,04 mol N, N'-bis(metylnonyl)-l, 2-propándiamínu sa rozpustí v metanole, zahřeje na teplotu 40 až 50 °C a pomaly sa přidá 20 až 30 % vodný roztok peroxidu vodíka v trojnásobnom molárnom přebytku. Zmes sa nechá reagovat pri teplote 60 až 70 °C 4 hodiny. Po ochladení a rozložení nadbytečného peroxidu vodíka sa rozpúšťadlo a voda oddestiluje, produkt sa vysuší. Vzniká N,N'-bis(metylnonyl)-l,2-propándiamíndioxid ako olej s η2θ = 1,4662; Rf = 0,76 (Silufol; sústava aceton) : 1 N HCI (1 : 1); detekcia Dragendorfovým činidlom); výťažok 62 % teorie; IČ-spektrálne charakteristiky γΝΟ959 a 915 cm’1; MIC 800;. 1200; 800.N, N'-bis (methylnonyl) -1,2-propanediamine (0.04 mol) was dissolved in methanol, heated to 40-50 ° C and a 20-30% aqueous hydrogen peroxide solution was added slowly in triple molar excess. The mixture was allowed to react at 60-70 ° C for 4 hours. After cooling and decomposition of excess hydrogen peroxide, the solvent and water were distilled off, and the product was dried. N, N'-bis (methylnonyl) -1,2-propanediamine dioxide is formed as an oil with η 2 θ = 1.4662; Rf = 0.76 (Silufol, acetone system): 1 N HCl (1: 1); detection by Dragendorf reagent); yield 62% of theory; IR spectral characteristics γ ΝΟ 959 and 915 cm -1 ; MIC 800 ;. 1200; 800th
Příklad 2Example 2
Pracovný postup je zhodný s postupom uvedeným v příklade 1 s tým rozdielom, že do reakcie sa použil N,N'-bis(metyltridecyl)-l,2-propándiamín a suchý zvyšok sa prekryštalizoval zo suchého acetonu do konštantnej teploty tópenia. Vzniká N,N'-bis(metyltridecyl)-1,2-propándiamíndioxid s 1.1. 55 až 59 °C; Rf 0,56; výťažok 60 % teorie; IČ-spektrálne charakteristiky γ No 944 a 920 cm’1; MIC 100; 700; 70.The procedure is identical to that of Example 1 except that N, N'-bis (methyltridecyl) -1,2-propanediamine is used in the reaction and the dry residue is recrystallized from dry acetone to a constant melting point. N, N'-bis (methyltridecyl) -1,2-propanediamine dioxide is formed with 1.1. Mp 55-59 ° C; Rf 0.56; yield 60% of theory; IR spectral characteristics γ No 944 and 920 cm -1 ; MIC 100; 700; 70th
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS106381A CS216442B1 (en) | 1981-02-16 | 1981-02-16 | N, N'-bis (alkylethyl) -1,2-propanediamine dioxides and their method of preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS106381A CS216442B1 (en) | 1981-02-16 | 1981-02-16 | N, N'-bis (alkylethyl) -1,2-propanediamine dioxides and their method of preparation |
Publications (1)
| Publication Number | Publication Date |
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| CS216442B1 true CS216442B1 (en) | 1982-10-29 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS106381A CS216442B1 (en) | 1981-02-16 | 1981-02-16 | N, N'-bis (alkylethyl) -1,2-propanediamine dioxides and their method of preparation |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS216442B1 (en) |
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1981
- 1981-02-16 CS CS106381A patent/CS216442B1/en unknown
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