CS257372B1 - N-oxides 1-alkoxy-2-dimethylaminoethanes and method of their production - Google Patents
N-oxides 1-alkoxy-2-dimethylaminoethanes and method of their production Download PDFInfo
- Publication number
- CS257372B1 CS257372B1 CS868067A CS806786A CS257372B1 CS 257372 B1 CS257372 B1 CS 257372B1 CS 868067 A CS868067 A CS 868067A CS 806786 A CS806786 A CS 806786A CS 257372 B1 CS257372 B1 CS 257372B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- alkoxy
- dimethylaminoethane
- dimethylaminoethanes
- oxides
- dodecyl
- Prior art date
Links
- 150000001204 N-oxides Chemical class 0.000 title claims abstract description 11
- 238000000034 method Methods 0.000 title claims description 10
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims abstract description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 7
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 6
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 6
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 6
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 6
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 5
- 230000000845 anti-microbial effect Effects 0.000 abstract description 4
- 239000004094 surface-active agent Substances 0.000 abstract description 2
- 239000000645 desinfectant Substances 0.000 abstract 1
- -1 1-heptyloxy-2-dimethylaminoethane N-oxide Chemical class 0.000 description 8
- 241000191967 Staphylococcus aureus Species 0.000 description 6
- 241000191963 Staphylococcus epidermidis Species 0.000 description 6
- 230000003385 bacteriostatic effect Effects 0.000 description 6
- RUOIDUVXLQMCLH-UHFFFAOYSA-N 2-heptoxy-N,N-dimethylethanamine Chemical compound CCCCCCCOCCN(C)C RUOIDUVXLQMCLH-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 244000063299 Bacillus subtilis Species 0.000 description 4
- 241000194032 Enterococcus faecalis Species 0.000 description 4
- 241000222122 Candida albicans Species 0.000 description 3
- 229940095731 candida albicans Drugs 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 230000001408 fungistatic effect Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 235000014469 Bacillus subtilis Nutrition 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
- 229910003446 platinum oxide Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- ZMJBAJXDOXQVME-UHFFFAOYSA-N 2-decoxy-n,n-dimethylethanamine Chemical compound CCCCCCCCCCOCCN(C)C ZMJBAJXDOXQVME-UHFFFAOYSA-N 0.000 description 1
- DSNJGFLHEVDMHH-UHFFFAOYSA-N 2-dodecoxy-n,n-dimethylethanamine Chemical compound CCCCCCCCCCCCOCCN(C)C DSNJGFLHEVDMHH-UHFFFAOYSA-N 0.000 description 1
- 241000193830 Bacillus <bacterium> Species 0.000 description 1
- ZFECSGZKBXLMMU-UHFFFAOYSA-N CCCCCCCCCCCOCCN(C)C Chemical compound CCCCCCCCCCCOCCN(C)C ZFECSGZKBXLMMU-UHFFFAOYSA-N 0.000 description 1
- 241001480037 Microsporum Species 0.000 description 1
- 241001609978 Trichophyton terrestre Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000004851 dishwashing Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000004872 foam stabilizing agent Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- YZFHBUXXJLCVQH-UHFFFAOYSA-N n,n-dimethyl-2-octoxyethanamine Chemical compound CCCCCCCCOCCN(C)C YZFHBUXXJLCVQH-UHFFFAOYSA-N 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Učelom N-oxidov l-alkoxy-2-dlmethylamínoetánov je zlepšenie rozpustnosti vo vodě a antimikrobiálnych vlastností l-alkoxy-2- -dimetylamínoetánov. Uvedeného účelu sa dosiahne použitím N-oxidov-l-alkoxy-2-dimetylamínoetánov obecného vzorca I kde R představuje heptyl, oktyl, nonyl, decyl, undecyl, alebo dodecyl a sposobu ich přípravy tak, že sa l-alkoxy-2-dimetylamínoetány obecného vzorca II R—OCH2CH2—N— (CH2)3 (II), kde R představuje heptyl, oktyl, nonyl, dodecyl, undecyl, alebo dodecyl, oxidujú 25 až 30 °/o hmot. vodným roztokom peroxidu vodíka pri teplote 50 až 60 °C. N-Oxidy 1-alkoxy-2-dimetylamínoetánov majú ipoužitie v chémii tenzidov a dezinfekčných látok.The purpose of N-oxides of 1-alkoxy-2-dimethylaminoethane is to improve water solubility and antimicrobial properties of 1-alkoxy-2- -dimethylaminoethane. That purpose is achieved by using N-oxide-1-alkoxy-2-dimethylaminoethanes of formula (I) wherein R represents heptyl, octyl, nonyl, decyl, undecyl, or dodecyl and cause them by preparing 1-alkoxy-2-dimethylaminoethane of formula II R-OCH 2 CH 2 —N— (CH 2) 3 (II), wherein R is heptyl, octyl, nonyl, dodecyl, undecyl, or dodecyl, oxidize 25 to 30% by weight. aqueous hydrogen peroxide solution at 50-60 ° C. N-oxides of 1-alkoxy-2-dimethylaminoethanes they have in use surfactant and disinfectant chemistry.
Description
Vynález sa týká N-oxidov l-alkoxy-2-dimetylamínoetánov a sposobu ich přípravy.The present invention relates to N-oxides of 1-alkoxy-2-dimethylaminoethanes and to a process for their preparation.
l-Alkoxy-2-dimetylamínoetány sú známe ako antimikrobiálne posobiace zlúčeniny už veta rokov. Bolí připravené kondenzáciou alkoholátu sodného s N-dimetylamínoetylchloridom, alebo reakciou N-dimetylamínoetanolátu sodného s alkylbromidom, alebo alkyljodidom [G. F. Grail, L. E. Tenenbaum, A. V. Tolstouchov: J. Amer. Chem. Soc. 1313 (1952); Η. T. Clarke: J. Chem. Soc. 1808 (1912); L. Binet, D. Kohler: Compt. rend. soc. biol. 345 (1941)]. Praktickému využitiu antimikrobiálnych vlastností týchto zlúčenín však bráni ich slabá rozpustnost vo vodě. Nepodařilo sa ich rozpustit ani v zmesi s různými detergentmi. Rozpustné vo vodě sú hydrochloridy týchto zlúčenín, ktoré však nie sú kompaktibilné s běžnými aniónaktívnymi tenzidmi a detergentami, pretože tvoria katiónaktívne tenzidy.1-Alkoxy-2-dimethylaminoethanes have been known as antimicrobial depressants for many years. It was prepared by condensing sodium alcoholate with N-dimethylaminoethyl ethyl chloride, or by reacting sodium N-dimethylaminoethanolate with an alkyl bromide or an alkyl iodide [G. Grail F., Tenenbaum L.E. Tolstouchov, A.V. J. Amer. Chem. Soc. 1313 (1952); Η. T. Clarke, J. Chem. Soc. 1808 (1912); L. Binet, D. Kohler, Compt. rend. Soc. Biol. 345 (1941)]. However, their poor solubility in water prevents the practical use of the antimicrobial properties of these compounds. They could not be dissolved even when mixed with various detergents. Water-soluble are the hydrochlorides of these compounds, but they are not compatible with conventional anionic surfactants and detergents because they form cationic surfactants.
Uvedené nevýhody odstráňuje tento vynález. Podstatou vynálezu sú N-oxidy 1-alkoxy-2-dimetylamínoetánov obecného vzorca IThese disadvantages are overcome by the present invention. The present invention provides N-oxides of 1-alkoxy-2-dimethylaminoethanes of formula (I)
R~ OCH?CH5-N-(CH^? R ~ OCH ? CH 5 -N- (CH 2 -);
O (I) kde R představuje heptyl, oktyl, nonyl, decyl, undecyl, alebo dodecyl. Ďalej je podstatou vynálezu sposob přípravy zlúčenín obecného vzorca I, ktorý spočívá v tom, že na l-alkoxy-2-dimetylamínoetán obecného vzorca IIO (I) wherein R represents heptyl, octyl, nonyl, decyl, undecyl, or dodecyl. The present invention further provides a process for the preparation of compounds of the formula (I) which comprises: for 1-alkoxy-2-dimethylaminoethane of the formula (II)
R—OCH2CH2—N— (CH2)3 (II), kde R představuje heptyl, oktyl, nonyl, decyl, undecyl, alebo dodecyl, sa působí 30 % hmot. vodným roztokom peroxidu vodíka pri teplote 50 až 60 °C.R-OCH 2 CH 2 -N- (CH 2) 3 (II), wherein R represents heptyl, octyl, nonyl, decyl, undecyl, or dodecyl, is treated with 30 wt. aqueous hydrogen peroxide solution at 50-60 ° C.
Výhodou N-oxidov l-alkoxy-2-dimetylamínoetánov oproti l-alkoxy-2-dimetýlamínoetánom a ich hydrochloridom je dobrá rozpustnost vo vodě, antimikrobiálna účinnost a stabilita vo vodných roztokoch, alebo v suchom stave. Ďalšou výhodou N-oxidov 1-alkoxy-2-dimetylamínoetánov ich kompaktibilita s běžnými aniónaktívnymi tenzidmi. Příklad 1Advantages of N-oxides of 1-alkoxy-2-dimethylaminoethanes over 1-alkoxy-2-dimethylaminoethanes and their hydrochlorides are good water solubility, antimicrobial activity and stability in aqueous solutions or in the dry state. Another advantage of the N-oxides of 1-alkoxy-2-dimethylaminoethanes is their compatibility with conventional anionic surfactants. Example 1
18,7 g (0,1 mólu] l-heptyioxy-2-dimetylaminoetánu sa rozpustí v 30 ml 96 % hmot. etanolu a k tomuto roztoku sa přidá po kvapkách 30 ml 30 % hmot. vodného roztoku peroxidu vodíka počas 30 minút. Teplota sa počas prikvapkávania a potom ešte hodiny udržuje v rozmedzí 50 až 60 °C. Po přidaní celého množstvo peroxidu vodíka sa reakčná zmes zakalí, ale počas zahrievania sa vyčíri, pretože vznikajúci N-oxid je v zmesi vody a alkoholu rozpustnější. Po vychladnutí sa přidá do zmesi 0,1 g oxidu platičitého a nechá sa stát 2 dni, pokial' sa nerozloží prebytočný peroxid vodíka. Oxid platičitý sa odfiltruje a z filtrátu sa oddestiluje voda s etanolom pri tlaku 3 kPa. N-oxid sa potom suší v exikátore nad oxidom fosforečným. Výťažok bol 94 %, t. j. 19,1 g N-oxidu l-heptyloxy-2-dimetylamínoetánu. Na infračervenom spektre bolí tieto určujúce absorpčně pásy: 2 955, 2 920, 2 850, 2 760, 1 462, 966 a 720 cm'1. V hmotnostnom spektre boli tieto určujúce píky: 187, 173, 102, 88 a 72.18.7 g (0.1 mol) of 1-heptyioxy-2-dimethylaminoethane are dissolved in 30 ml of 96% by weight ethanol, and 30 ml of a 30% by weight aqueous hydrogen peroxide solution are added dropwise over 30 minutes. the reaction mixture becomes cloudy after heating, but becomes clear during heating because the N-oxide formed is more soluble in the water / alcohol mixture. of 0.1 g of platinum oxide and allowed to stand for 2 days until excess hydrogen peroxide decomposes, platinum oxide is filtered off and water and ethanol are distilled off at a pressure of 3 kPa from the filtrate, and the N-oxide is dried in a desiccator over phosphorus pentoxide. The yield was 94%, i.e. 19.1 g of 1-heptyloxy-2-dimethylaminoethane N-oxide, and on the infrared spectrum, the following determining absorption bands were: 2 955, 2 920, 2 850, 2 760, 1 462, 966 and 720 cm -1. first in the mass spectrum were those in peaks: 187, 173, 102, 88 and 72.
Elementárna analýza pre C11H213NO2, molekulová hmotnostf 203,3 vypočítané:Elemental analysis for C 11 H 21 NO 2, MW 203.3 calculated:
64,93 % hmot. uhlíka,64.93% wt. alkyl,
12,30 % hmot. vodíka,12.30 wt. H,
6,89 % hmot. dusíka. zistené:6.89% wt. nitrogen. found:
64,78 % hmot. uhlíka,64.78% wt. alkyl,
12,41 % hmot. vodíka,12.41% wt. H,
6,79 % hmot. dusíka.6.79% wt. nitrogen.
N-Oxid l-heptyloxy-2-dimetylamínoetánu má bakteriostatickú účinnost na druhy mikroorganizmov Staphylococcus aureus, Staphylococcus epidermidis a Bacillus subtilis 100 mg . i-1.1-Heptyloxy-2-dimethylamino-ethane N-oxide has bacteriostatic activity on Staphylococcus aureus, Staphylococcus epidermidis and Bacillus subtilis species of 100 mg. i -1 .
Příklad 2Example 2
Postupuje sa ako v příklade 1 s tým rozdielom, že sa namiesto l-heptyloxy-2-dimetylamínoetánu použije 20,1 g (0,1 mólu) 1-oktyloxy-2-dimethylamínoetánu. Výťažok bol 95%, t. j. 20,6 g N-oxidu l-oktyloxy-2-dimethylamínoetánu. Baáteriostatická a fungistatická účinnost na mikroorganizmy Staphylococcus aureus a Staphylococcus epidermidis je 10 mg. i-1, na druhy Bacillus subtilis, Streptococcus faecalis a Candida albicans je účinná koncentrácia 100 mg. i-4.The procedure was as in Example 1 except that 20.1 g (0.1 mol) of 1-octyloxy-2-dimethylaminoethane was used instead of 1-heptyloxy-2-dimethylaminoethane. The yield was 95%, i.e. 20.6 g of 1-octyloxy-2-dimethylamino-ethane N-oxide. The bacteriostatic and fungistatic efficacy for Staphylococcus aureus and Staphylococcus epidermidis is 10 mg. i -1, to the species Bacillus subtilis, Streptococcus faecalis and Candida albicans are effective concentration of 100 mg. i -4 .
Příklad 3Example 3
Postupuje sa ako v příklade 1 s tým rozdielom, že sa namiesto l-heptyloxy-2-dimetylamínoetánu použije 21,5 g (0,1 mólu) 1-nonyloxy-2-di'metylamínoetánu. Výťažok bol 90%, t. j. 20,8 g N-oxidu l-nonyloxy-2-dimetylamínoetánu. Bakteriostatická a fungistatická účinnost na druhy mikroorganizmov Staphylococcus aureus, Staphylococcus epidermidis, Bacillus subtilis a Streptococcus faecalis je 10 mg . i-1, na‘Trychophyton terrestre a Candida albicans je účinná koncentrácia 100 mg. i-1.The procedure is as in Example 1 except that 21.5 g (0.1 mole) of 1-nonyloxy-2-dimethylaminoethanol is used instead of 1-heptyloxy-2-dimethylaminoethane. The yield was 90%, i.e. 20.8 g of 1-nonyloxy-2-dimethylaminoethane N-oxide. The bacteriostatic and fungistatic efficacy of Staphylococcus aureus, Staphylococcus epidermidis, Bacillus subtilis and Streptococcus faecalis is 10 mg. i -1 , on Trychophyton terrestre and Candida albicans, the effective concentration is 100 mg. i -1 .
Příklad 4Example 4
Postupuje sa ako v příklade 1 s tým rozdielom, že namiesto l-heptyloxy-2-dimetylamínoetánu sa použije 22,9 g (0,1 molu) 1-decyloxy-2-dimetylamínoetánu. Výfažok bol 87%, t. j. 21,3 g N-oxidu l-decyloxy-2-dimetylamínoetánu. Bakteriostatická a fungistatická účinnost je na druhy mikroorganiz mov Staphylococcus aureus, Staphylococcus epidermidis, Bacillus subtilis a Streptococcus faecalis 10 mg . 1_1, na Candida albicans, Trichophyton terrestre a Microsporum gypsaeum 100 mg .i-1.The procedure was as in Example 1 except that 22.9 g (0.1 mol) of 1-decyloxy-2-dimethylaminoethane was used instead of 1-heptyloxy-2-dimethylaminoethane. The yield was 87%, i.e. 21.3 g of 1-decyloxy-2-dimethylaminoethane N-oxide. Bacteriostatic and fungistatic efficacy is 10 mg for Staphylococcus aureus, Staphylococcus epidermidis, Bacillus subtilis and Streptococcus faecalis species. 1 _1 , Candida albicans, Trichophyton terrestre and Microsporum gypsaeum 100 mg .i -1 .
Příklad 5Example 5
Postupuje sa ako v příklade 1 s tým rozdielom, ze namiesto l-heptyloxy-2-dimetylamínoetánu sa použije 24,3 g (0,1 molu) 1-undecyloxy-2-dimetylamínoetánu. Výfažok bol 83 %, t. j. 21,5 g N-oxidu 1-undecyloxy-2-dimetylamínoetánu. Bakteriostatická účinnosť je na druhy mikroorganizmov Staphylococcus aureus a Staphylococcus epidermidis 10 mg.l-1, na Bacillus substilis a Streptococcus faecalis 100 mg . I-1.The procedure was as in Example 1 except that 24.3 g (0.1 mol) of 1-undecyloxy-2-dimethylaminoethane was used instead of 1-heptyloxy-2-dimethylaminoethane. The yield was 83%, i.e. 21.5 g of 1-undecyloxy-2-dimethylaminoethane N-oxide. Bacteriostatic activity is 10 mg.l -1 for Staphylococcus aureus and Staphylococcus epidermidis species, 100 mg for Bacillus substilis and Streptococcus faecalis. I -1 .
Přiklad 6Example 6
Postupuje sa ako v případe 1 s tým rozdielom, že namiesto l-heptyloxy-2-dimetylamínoetánu sa použije 25,7 g (0,1 móluj 1-dodecyloxy-2-dimetylamínoetánu. Výfažok bol 80 %, t. j. 21,8 g N-oxidu 1-dodecyloxy-2-dimetylamínoetánu. Bakteriostatická účinnosť je na mikroorganizmy Staphylococcus aureus a Staphylococcus epidermidis 100 mg . I-1.The procedure is the same as in case 1 except that 25.7 g (0.1 mol of 1-dodecyloxy-2-dimethylaminoethane) is used instead of 1-heptyloxy-2-dimethylaminoethane, the yield being 80%, i.e. 21.8 g of N- 1-oxide-2-dodecyloxy dimetylamínoetánu. the bacteriostatic activity is on the microorganisms Staphylococcus aureus and Staphylococcus epidermidis of 100 mg. I-1.
Příklad 7Example 7
Postupuje sa ako v příklade 1 s tým rozdielom, že sa použije 25 % hmot. vodný roztok peroxidu vodíka. Výfažok bol 80 %, t. j.The procedure was as in Example 1 except that 25 wt. aqueous hydrogen peroxide solution. The yield was 80%, m.p. j.
16,3 g N-oxidu l-heptyloxy-2-dimetylamínoetánu.16.3 g of 1-heptyloxy-2-dimethylamino-ethane N-oxide.
Vynález móže nájsť použitie pri príprave detergentných a tenzidných kompozícií, prípravkov na umýváme riadov a stabilizátorov pěny.The invention may find use in the preparation of detergent and surfactant compositions, dishwashing compositions and foam stabilizers.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS868067A CS257372B1 (en) | 1986-11-07 | 1986-11-07 | N-oxides 1-alkoxy-2-dimethylaminoethanes and method of their production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS868067A CS257372B1 (en) | 1986-11-07 | 1986-11-07 | N-oxides 1-alkoxy-2-dimethylaminoethanes and method of their production |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS806786A1 CS806786A1 (en) | 1987-09-17 |
| CS257372B1 true CS257372B1 (en) | 1988-04-15 |
Family
ID=5430784
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS868067A CS257372B1 (en) | 1986-11-07 | 1986-11-07 | N-oxides 1-alkoxy-2-dimethylaminoethanes and method of their production |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS257372B1 (en) |
-
1986
- 1986-11-07 CS CS868067A patent/CS257372B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS806786A1 (en) | 1987-09-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4113857A (en) | Process for the preparation of iodophor compounds and methods for stabilizing iodophor pharmaceutical compositions containing the same | |
| DE69014865T2 (en) | PEROXYCARBOXYLIC ACID. | |
| KR100222017B1 (en) | Dyeing composition containing 5,6-dihydroxyindolines and keratinous fibres dyeing process | |
| EP1102538B1 (en) | Plant growth regulator compositions | |
| CS257372B1 (en) | N-oxides 1-alkoxy-2-dimethylaminoethanes and method of their production | |
| JP3457028B2 (en) | Quaternary ammonium salt compound having antibacterial activity and method for producing the same | |
| US3979382A (en) | Dichlorocyanurate silver complexes | |
| US3953605A (en) | Antimicrobial quaternary ammonium compounds compositions | |
| JP3525523B2 (en) | Antibacterial agent and method for producing the same | |
| EP0373613B1 (en) | Pyridine-3-percarboxylic acid monopersulfate | |
| AU2720301A (en) | Novel process for the preparation of alpha-(2-4-disulfophenyl)-n-tert-butylnitrone and pharmaceutically acceptable salts thereof | |
| US4059687A (en) | Ester substituted dibiguanides and non-toxic antimicrobial compositions thereof | |
| RU2071477C1 (en) | Hydroxyquinolinium dicitrate-borate exhibiting antimicrobial property | |
| US5002763A (en) | Water soluble complexes of polyvinylpyrrolidone, hydrogen chloride and iodine and process for making the same | |
| FI58917B (en) | PROCEDURE FOR FRAMSTAELLNING AV BIS- (2-PYRIDYL-1-OXID) DISULFID | |
| US4082756A (en) | Quaternary quinuclidinium carbamates and thiocarbamates | |
| US6046344A (en) | Process for the preparation of hydroxypropylated quaternary ammonium compounds containing an ester functional group | |
| CN1138759C (en) | Novel process | |
| US7357881B2 (en) | Cycloamide-transition metal complexes and bleach catalysts | |
| KR960007164B1 (en) | Dichloro-substituted imidazole derivatives as anti-agents | |
| US4421749A (en) | Aluminum pyridinethiols as antimicrobials | |
| US3961075A (en) | Ether-linked quaternary ammonium compositions | |
| CA2013743A1 (en) | Preparation of glutaric acid derivatives | |
| US4038303A (en) | Quaternary ammonium carbamide compounds | |
| US3400144A (en) | Basic copper-(ii)-salts of alkylsulfuric acids |