2-chloro-4,6-bis(nonaxisymmetric)-1,3,5-triazine as an intermediate in the synthesis of surfactants
(57) Abstract:The invention relates to organic chemistry, in particular to derivatives of 1,3,5-triazine and 2-chloro-4,6-bis(nonaxisymmetric)-1,3,5-triazine structureas an intermediate in the synthesis of cationic type surfactants.1 N. p. F.-ly, 1 table. The invention relates to organic chemistry and chemistry of surface-active substances (surfactants), specifically to new substituted 1,3,5-triazine-2-chloro-4,6-bis(nonaxisymmetric)-1,3,5-triazine (HNAT) structureas an intermediate in the synthesis of cationic type surfactant.As you know, the chemistry of surfactants is booming. This is due not only to the level of sanitary-hygienic preparation of the population, but also the need to develop new, effective, non-toxic and do not cause allergic reactions of compounds capable of lowering the surface tension of liquids and having good detergency even in hard water. The last condition is the best answer cationic type surfactant, a range which, unfortunately, is very limited. Development of new cationic surfactants of the type of task is most important.Its use as surface-active substances is unknown.Known also Tetramethylammonium chloride (TMAH) structureThe specified connection get known quaternization reaction of dimethylaminoacetyl chloride stands for Hoffman and used as cationic surfactants (cationic surfactant) [see Surfactants and compositions. The Handbook. /Ed. by M. Y. Pletnev. - M.: OOO “firma Clavel”. 2002. - 768 C.]. TMAH used as surfactants and conditioning supplements in conditioners and balms (prototype).The disadvantage of applying CMAH is relatively low ability to reduce the surface tension of aqueous solutions, as well as the high acidity of solutions.Technical solution to the problem is to increase the ability to reduce the surface tension of water which is achieved by to increase surface activity and reduce the acidity of the solutions proposed to use the newly synthesized intermediate in the synthesis of surfactant - 2-chloro-4,6-bis(nonaxisymmetric)-1,3,5-triazine (HNAT) structureThe novelty of the claimed proposal is seen that the proposed synthesis of a new compound HNAT, the use of which as an intermediate allows to synthesize a new cationic type surfactant (cationic surfactant), which reduces the surface tension and the acidity of aqueous solutions in comparison with known CMAH.At the same time declared 2-chloro-4,6-bis(nonaxisymmetric)-1,3,5-triazine (HNAT) get known method, the reaction of cyanuric chloride with p-toluensulfonate-methylamine (1:2 mole) in solution in acetone, in the presence of equimolar amount of sodium bicarbonate [see C. N. Zaplishny, I. A. Asaturyan, G. M. Poghosyan. Synthesis Djalilov esters of 2-piperidyl-4,6-diglycyl-s-triazine. - Arm.chem.J., 1976, T. 29, No. 12, S. 1065-1067].Source cyanuric chloride immediately before use purify by crystallization from CCL4and the solvent is subjected to fractionation and dried by known methods using known cationic surfactant Tetramethylammonium (TMAH) - the prototype application.Examples of specific performance of the alleged proposal (synthesis of intermediate HNAT and surfactants based on it) are presented below in examples 1-4.Example 1. 2-chloro-4,6-bis(nonaxisymmetric)-1,3,5-triazine (HNAT). A mixture of 1.5 g (0.02 mol) aminouksusnoy acid, 3,47 g (0.02 mol) of nonanol-1 and 3.8 g (0.02 mol) of p-toluenesulfonic acid in 25 ml of benzene is boiled with a nozzle Dean-stark and reflux to the visual termination of water in the nozzle. The mixture is boiled for a further 3 h, distilled benzene to half volume, and the residue is distilled to dryness in a water jet vacuum on a water bath. Get 3.5 g (91%) p-toluensulfonate danilovogo ester of glycine (TSG) as a white, amorphous and highly hygroscopic substance with so pl. 25-27°C.Found, %: C 58,11; N 8,58; N 3,52; C18H31NSO5. Calculated, %: C 57,88; N. Of 8.37; N 3,75.X , cm-1: 3430-3300 ush.with. (-NH+3); 1720 cf. (C=0); 1630, 1595, 1500 cf. (C=C, C=N - t. and cyanurates cycle.); 1140, 1100, 1015 cf. (C-O-C).DMR , M. D. (group): 7,55-the 7.65 (2H D., N.2+N6hair dryers) J=8,3; 6,83-7,01 (2N D., N.3+N6hair dryers) J=8,3; of 5.05 (3H, S., NH+3); 4,04-4,29 (N m, -(CH2)6-); 3,96-4,01 (2N so, och2); 3,88-to 3.92 (2H m, NH+3To a solution of 0,86 g (0,0047 mol) of cyanuric chloride in 15 ml of acetone was added 3.5 g (0,0094 mol) obtained TSG and under stirring and the temperature of 5-7°C in small portions was added 1.56 g (0,0186 mol) of sodium bicarbonate. The reaction mixture was stirred for another 1 h at the same temperature, 2 hours at 20 and 12 h at 40°C. the Mixture is evaporated in a water jet vacuum to dryness, the residue is thoroughly washed with water and purified by crystallization from alcohol with activated carbon. After drying obtain 2.0 g (83%) of 2-chloro-4,6-bis(nonaxisymmetric)-1,3,5-triazine (HNAT) as a white crystalline substance with so pl. 121-123°C.Found, %: C 58,70; N 8,81; N 13,48. C25H44N5O4Cl. Calculated, %: 58,39; N To 8.62; N 13,62.X , cm-1(group): 3230, 3070 cf. (N-H); 1735 S. (C=0); 1570, 1550 cf. (C=C, C=N - t. and cyanurates cycle.); 1120, 1065 cf. (C-O-C).DMR , M. D. (group): 7,54-to 7.99 (2H, ush.S., NH); 3,99-4,00 (m, 4H, OCH2); 3,82-of 3.96 (m, 4H, NCH2); 1,55-of 1.64 (4H square, CH2CH3) J=6,0; 1,16-1,40 (24N m, CH2CH2CH2); or 0.83 to 0.92 ( 6N so, CH3) J=6,0.Mol. ion (mass by a spectroscope) 514.Example 2. 2-chloro-4,6-bis(nonaxisymmetric)-1,3,5-triazine (HNAT). Under conditions analogous to example 1, from the same quantities cyanuramide obtain 2.1 g (87%) of 2-chloro-4,6-bis(nonaxisymmetric)-1,3,5-triazine (HNAT) as a white crystalline substance with so pl. 121-123°C.Found, %: C 58,70; N 8,81; N 13,48. C25H44N5O4Cl. Calculated, %: 58,39; N To 8.62; N 13,62.X , cm-1(group): 3230, 3070 cf. (N-H); 1735 S. (C=0); 1570, 1550 cf. (C=C, C=N - t. and cyanurates cycle.); 1120, 1065 cf. (C-O-C).DMR , M. D. (group): 7,54-to 7.99 (2H, ush.S., NH); 3,99-4,00 (m, 4H, och2); 3,82-of 3.96 (m, 4H, NCH2); 1,55-of 1.64 (4H square, CH2CH3) J=6,0; 1,16-1,40 (24N m, CH2CH2CH2); or 0.83 to 0.92 (6N so, CH3) J=6,0.Mol. ion (mass by a spectroscope) 514.Thus obtained HNAT then used for obtaining surfactants in examples 3 and 4.Example 3. 2-Trimethylammoniumchloride-4,6-bis(nonlexical-ylmethylamino)-1,3,5-triazine (TCT). Through a solution of 2.0 g (to 0.0039 mol) HAT in 20 ml of a mixture of absolute benzene and ether (1:1 by volume), with stirring and at a temperature of 20°C, in a weak stream of nitrogen bubbled dry trimethylamine within 4 h Formed abundant precipitate is filtered off, washed with dry benzene (210 ml) and dried. Obtain 1.8 g (89,6%) target TNCT in the form of a white crystalline powder with so pl. 133-145°NFound, %: C 58,49; N 9,11; N 14,78. C28H53N6O4Cl. Calculated, %: C 58,66; N 9,31; N 14,66.X , cm-1(group): 3090, 3060 cf. (N-H); 1739 S. (=O5-8,99 (2H, ush.S., NH); 4,00-4,10 (m, 4H, och2); 3,85-of 3.97 (m, 4H, NCH2); 3,25 (N S., NMe3); 1,57-of 1.65 (4H square, CH2CH3) J=6,0; 1,20-1,40 (24N m, CH2CH2CH2); 0,85-0,93 (6N so, CH3) J=6,0.Mol. ion (mass by a spectroscope) 573.Example 4. 2-Trimethylammoniumchloride-4,6-bis(nonyloxy-carbonylmethyl)-1,3,5-triazine (TCT). Under conditions analogous to example 3, 2.0 g (to 0.0039 mol) HNAT and dry trimethylamine with the only difference that the bubbling continued for 3.5 h at 15°C, gain of 1.87 g (93%) TNCT in the form of a white crystalline powder with so pl. 133-145°NFound, %: C 58,49; N 9,11; N 14,78. WITH28H53N6O4CL. Calculated, %: C 58,66; N 9,31; N 14,66.X , cm-1(group): 3090, 3060 cf. (N-H); 1739 C. (C=O); 1595, 1530 cf. (C=C, C=N - t. and cyanurates cycle.); 1220 cf. (NMe3); 1065, 1030 cf. (C-O-C).DMR , M. D. (group): 7,55-8,99 (2H, ush.S., NH); 4,00-4,10 (m, 4H, och2); 3,85-of 3.97 (m, 4H, NCH2); 3,25 (N S., NMe3); 1,57-of 1.65 (4H square, CH2CH3) J=6,0; 1,20-1,40 (24N m, CH2CH2CH2); 0,85-0,93 (6N so, CH3) J=6,0.Mol. ion (mass by a spectroscope) 573.Synthesized TNTC used as cationic type surfactants.While preparing their water naibolshee pressure of the bubbles on the device Rehbinder [see A. Schwartz and J. Perry. Surfactants. - M.: Publishing House. IL, 1953, S. 263]. For comparison, using an aqueous solution of Tetramethylammonium chloride (TMAH) the appropriate concentration. As a control, use the variant with the water that does not contain any additives. Received data (the results of three measurements) were averaged, and the average values were used for further calculations. Surface activity in % of control was determined by the formula=a-bi/ini·100%,where a and bi- the value of the control sample and experimental, respectively. The results are summarized in table.As can be seen from this table that the application of the proposed TND as a cationic surfactant leads to the following results.If TNTC use it as a cationic type surfactant at a concentration of 0.01 to 10.0 wt.% reduces the value in comparison with control by 40.7-261,5% (19,6-50,5 instead 71,0 n/m), while the use of known Tetramethylammonium chloride reduced this indicator in comparison with control only 28.1-213% (22,6-55,4 instead 71,0 n/m).In addition, it was found that the acid properties of the proposed SAS compared to the known decreased by 1 is so the application stated TNTC as cationic type surfactants significantly reduce the magnitude of the surface tension of their aqueous solutions, and also to reduce the acidity of the solutions, which is very important from the point of view of subsequent practical application, since the solutions have a high surface activity even at high (1·10-1wt.%) the dilutions and low acidity, which reduces consumption by DV and improves the environment.2-Chloro-4,6-bis(nonaxisymmetric)-1,3,5-triazine structureas an intermediate in the synthesis of cationic type surfactants.
FIELD: organic chemistry, medicine.
SUBSTANCE: invention describes novel derivatives if 1,3,5-triazine of the general formula (1): wherein R1 means halogen atom, (C1-C3)-alkyl, (C1-C3)-alkoxy-group, N-(di)-(C1-C3)-alkyl, NH-(C2-C3)-alkynyl, N,N-(C1-C3)-alkyl, (C2-C3)-alkynyl or 1-pyrrolidinyl, 1-piperidinyl or 1-morpholinyl group; R2 means hydrogen atom (H), (C1-C3)-alkyl possibly substituted with hydroxy-, (C1-C3)-alkoxy- or phenoxy-group; R3 means H, -CF3, (C1-C3)-alkyl possibly substituted with hydroxy-, (C1-C3)-alkoxy-, phenoxy-group or 1-morpholinyl group; or R2 and R3 in common with phenyl group to which they are bound form benzodioxolane or naphthalene cyclic system; R4 means H, -CF3 or (C1-C3)-alkoxy-group; X means -NH, N-(C1-C3)-alkyl, -CH2, oxygen atom (O) or a bond carbon-carbon; Y means group of the general formula (A) , (B) or (C) wherein R5 means -OH or -CH2OH; R6 means H or phenyl; n = 0 or 1; R7 means (C1-C3)-alkyl; R8 means H, -OH or (C1-C3)-alkoxy-group; R9 means H or (C1-C3)-alkoxy-group; R10 and R11 mean independently H or (C1-C3)-alkyl; Z means -NOH or O, or their pharmacologically acceptable salts, pharmaceutical composition possessing (ant)agonistic activity to adenosine-A3 receptors and using novel compounds in treatment of such diseases as chronic pains, arthritis, cerebrospinal sclerosis, asthma, psoriasis and others.
EFFECT: valuable medicinal properties of compounds and pharmaceutical composition.
15 cl, 4 tbl, 2 ex
SUBSTANCE: detergent applicable for washing and watering of all types of textiles both under domestic conditions and in industrial contains, wt %: surfactants 1-14, sodium tripolyphosphate 20-30, sodium liquid glass 3, carboxymethylcellulose 0.5-0.8, polycarboxylate "Akremon" 0.1-1.5, soda ash 5-10, optical bleacher 0.2-0.3, odorant 0.05-0.1, sodium chloride 0.5-4.0, oxyethylated isononylphenol/triethanolamine/sodium hydroxide interaction product 1-14, water and sodium sulfate to 100%. Detergent may further contain of nonionic surfactants 0-3, sodium bicarbonate 0-5, polyvinylpyrrolidone 0-0.3, and foam suppressor 0-0.2.
EFFECT: enhanced detergent effect and acquired softening effect.
8 cl, 2 tbl, 8 ex
FIELD: cleaning apparatus.
SUBSTANCE: method comprises setting the filters and equipment in a contact with the cyclic nitroxyl and repeated oxidizer made of per acid or its salt or cyclic nitroxyl and repeated oxidizer made of hydroperoxide, or compound free of brome.
EFFECT: improved quality of cleaning.
9 cl, 4 tbl, 5 ex
SUBSTANCE: detergent composition has pH ranging from neutral to alkaline and contains an aqueous solution. The solution contains 0.005-10% surfactant with low foaming capacity; 0.005-10% corrosion inhibiting compound selected from C4-C16 alkylpyrrolidones and C1-C18 alkylamines and 0.01-15% modifying additive for preventing precipitation when metal ions react with the said surfactant. The cleaning solution contains a corrosion inhibitor and leaves a small amount of residue. The compositions are used not only at the washing stage of the cleaning cycle, but at one of the subsequent stages of the rinsing cycle in order to optimise cleaning and prevent rusting.
EFFECT: improved anti-corrosion and cleaning properties.
14 cl, 3 tbl
SUBSTANCE: described is a sanitary-hygienic cleaning agent containing the following components, wt %: hydrogen chloride (with respect to 36% hydrochloric acid 15.5-22) 5.58-7.92, nonionic surfactant 0.5-1.6, polyelectrolyte 2.0-6.0, hexamethylenetetramine 0-4.0, acid corrosion inhibitor 0.03-0.1, water - the balance. The acid corrosion inhibitor used is a reaction product of polyethylene polyamines with benzyl chloride in molar ratio 1:3, respectively, or a reaction product of polyethylene polyamines with oleic acid and benzyl chloride in molar ratio 1:1:3, respectively.
EFFECT: high efficiency of removing rust and hardness salt deposits from toilet bowls, faience sinks and ceramic tile surfaces, faster treatment and longer shelf life of the cleaning agent.
3 cl, 4 ex
SUBSTANCE: invention relates to product for washing with standard dose of detergent, which contains: a) surface active substance, selected from anionic, non-ionic surface active substance and their mixtures; and b) bleaching system, which contains: (i) organic bleaching catalyst, consisting of aryliminium ion, selected from the group, consisting of zwitter ions; and (ii) source of activated peroxygen, selected from the group, consisting of: preliminarily formed peracid; source of hydrogen peroxide; and their mixtures, enclosed into water-soluble or dispersible film; and, at least, approximately 50 wt % of anionic and/or non-ionic surface active substance and, at least, approximately 50 wt % of aryliminium ions are contained in, at least, one liquid composition, with aryliminium ion being zwitter ion, which has structure, selected from the group, consisting of a) where: in (1) (i) R1 is selected from the group, consisting of: 2-propylheptyl, 2-butyloctyl, 2-pentylnonyl, 2-hexyldecyl, n-hexyl, n-octyl, n-decyl, n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, iso-nonyl, iso-decyl, iso-tridecyl and iso-pentadecyl; (ii) R2 is independently selected from the group, consisting of #: H, branched alkyl group, containing from 3 to 12 carbon atoms, and linear alkyl group, containing from 1 to 12 carbon atoms, preferably R2 is independently selected from H and methyl groups; (iii) n stands for integer number from 0 to 1, b) 3-(3,4-dihydroisoquiinolinium)propanesulphonate; c) and their mixtures.
EFFECT: claimed product is convenient for application, stable and acceptable for use in wide range of washing temperatures.
19 cl, 3 tbl, 7 ex
SUBSTANCE: invention relates to composition for bleaching stains or soiling on textile materials. Composition contains H2O2 or H2O2 precursor and from 0.00001 to 1 wt %, counted per the total weight of composition, formula (1) compound. In formula (1) R1, R2, R3, R4 are hydrogen; or R1, R2, R3, R4 independently on each other are OR11 or NO2; or R1 and R2 are bound together with formation of phenyl; R5 stands for hydrogen; R6 stands for hydrogen; R7 is group with anion A-; k represents 1; A- is anion of inorganic acid, selected from Cl- or Br-; R10 stands for C1-C28alkyl; R11 is C1-C18alkyl. The invention also relates to granule, to method for bleaching stains on textile materials and to application of formula (1) compound as catalyst of oxidation reaction in context of bleaching stains or soiling on textile materials.
EFFECT: obtaining composition with high bleaching activity, which does not cause considerable damage to fibres.
SUBSTANCE: combinations of 1-aza-3,7-dioxabicircle [3.3.0] octane compounds with silicic acid esters and their use as precursors of the odoriferous substances, containing their detergents and cleaning products, emollient conditioners and cosmetics, as well as the method of prolonging the flavour perception of such means and the method of attenuation of bad odors through the use of the claimed combination, are proposed.
EFFECT: proposed combinations of the precursors may firmly block the unpleasant odors and provide a sustained impression of flavour.
15 cl, 2 tbl, 2 ex
SUBSTANCE: cleaner concentrate is described for a vehicle heat transfer system comprising an aluminum component, manufactured by brazing in a protective atmosphere containing more than 15 wt % of freezing temperature reduction means, 8 to 35 wt % of oxalic acid and an azole compound wherein the wt % is based on the total weight of the cleaner concentrate.
EFFECT: concentrate is a homogeneous solution.
17 cl, 6 tbl, 32 ex