1,5-bis-(2-hydroxyethyl)-biuret as a component polymer compositions and method thereof


(57) Abstract:

Usage: in the chemistry of polymers as a component of the polymer compositions. The inventive product 1,5 bis (2 hydroxyethyl) biuret as a component of the polymer compositions and the method of its production. Reagent 1: 1 (2 hydroxyethyl) urea. Reaction conditions: reagent 1 is heated at 170 - 190C to stop shedding ammonia. The output is close to quantitative. 2 S. p. f-crystals, 1 table.

The invention relates to new chemical compound 1,5-bis-(2-hydroxyethyl)-biuret, or diethanolamine, and how to obtain it.

There are various polyfunctional of hydroxycobalamin simple matter oligoesters used for the synthesis of polyesters, polyurethanes and other polymers [1]

Known methods for producing hydroxyl-containing substances simple oligoesters interaction of glycerol, trimethylolpropane, Ethylenediamine, hexanetriol and other compounds containing more than one active hydrogen atoms, with propylene oxide or a mixture of ethylene oxide [2]

The closest to the proposed substance on the structure is well-known compound 1,3-bis-(2-hydroabietyl)-urea, used as an inhibitor netref is a rule well-known way to obtain 1-(2-hydroabietyl)-urea (-acetylacetone) the interaction of equimolar amounts of urea and monoethanolamine [4] the Use of this substance as a component of the polymer compositions is not known.

Closest to the proposed method is a method of obtaining biureta by heating urea reaction


when 130-205aboutWith a residual pressure of not more than 200 mm RT.article before the formation of mixtures containing urea and biuret, followed by the separation of biureta of a mixture of [5]

To create different polymer compositions proposed new compound 1,5-bis-(2-hydroxyethyl)-biuret as a component of the polymer compositions.

Also we propose a way to obtain 1,5-bis-(2-hydroxyethyl)-biureta, wherein 1-(2-hydroxyethyl)-urea (-acetylacetone) heated at 170-190aboutTo stop shedding ammonia.

1,5-bis-(2-Hydroxyethyl)-biuret (diethanolamine) has the formula

HO(CH2)2NHCONHCONH(CH2)2OH and represents under normal conditions viscous colorless transparent liquid, not crystallized when cooled to -20aboutAnd not prehoneymoon when heated to 170aboutWith both at atmospheric pressure and in vacuum (residual pressure of 20 mm RT.cent.).

The composition and structure of the obtained compounds proved by elemental analysis, determination of content CLASS="ptx2">


Calculated C Of 37.7; H 6,8; N 22,0.

The content of Oh-groups found 18,0 calculated 17,8.

Molecular weight (cryoscopy in phenol): found 194, calculated 191.

Diethanolamine infinitely miscible with water, soluble in dimethylformamide, in little methanol and isopropanol, insoluble in heptane, benzene, toluene, xylene, carbon tetrachloride, dioxane, butyl acetate, chlorobenzene, cyclohexanone, acetone, diisopropyl ether. The viscosity of detonability at 20aboutWith equal 1634 SDR, 30aboutWith 715 SDRs, at 40aboutWith 330 centipoise at 50aboutWith SDR 166, at 60aboutWith 93 SDR.

In the IR spectrum of the molecule of the compound has a biuret structure, which is confirmed by the characteristic frequencies 1680 and 1720 cm-1. In the field of high frequencies very broad intense band with a maximum 3390 cm-1is involved in a hydrogen bond with hydroxyl groups, and strips 2880 and 2935 cm-1belong to the ethylene groups-CH2-CH2-.

The simultaneous presence in the molecule of detonability reactive OH - and NH-groups in combination with the linear structure of the molecule allows it to note is I get detonability-acetylacetone (pure or crude), heated up to 170-190aboutC and maintained at this temperature and with stirring until completion of the reaction, which is celebrated on the termination of the allocation of ammonia. Diethanolamine get to the exit, close to quantitative. The prior art reaction (1), in which the urea is converted into biuret. However, this reaction cannot be completely turned urea in biuret [5] in Addition, the unknown ways of getting whatever symmetrically disubstituted biletov by heating monosubstituted ureas. Therefore, the ability to implement the proposed method does not follow from the prior art.

Examples 1-3 illustrate the method according to the invention. Examples 4, 5 are comparative examples 6, 7 illustrate the possibilities of using a diet - nabirat in polymer compositions.

P R I m e R 1. 208 g-acetylacetone heated under stirring at 185aboutTo stop shedding ammonia 1 teaspoon Released ammonia absorb 0,5 N. HCl solution. Obtain 195 g of a viscous colorless liquid, not crystallized when cooled to -20aboutC, and 13 g of ammonia. After that, when the 120aboutThe product was incubated for 0.5 h in vacuum (residual pressure of 20 mm RT. Art. ), skipping the thief HCl. Remove from the refrigerator 2 g of solid by-product, melting at 84aboutWith and containing 37,9 With, 15,3 N 6.2 N, and 1.0 OH and HCl are 4 g of ammonia.

After soaking in the vacuum get 185 g of diethanolamine (exit 97), the composition and characteristics described above.

P R I m m e R 2. 280 g of distilled H2O dissolve 120 g of urea and 122 g of monoethanolamine. The resulting solution was heated at 103aboutC for 30 h under reflux until the termination of allocation of ammonia. Then clean the fridge and distilled water. Obtain 205 g of molten crude-acetylacetone, crystallized when cooled to temperatures below 93aboutWith containing 26,4 total nitrogen. Raise the temperature to 170aboutC and maintained at this temperature was obtained, acetylacetone for 2 h, absorbing the released gaseous ammonia (29 g) of 0.5 N. the HCl solution. The obtained viscous liquid is kept in a vacuum (residual pressure of 30 mm RT. Art. ) at 120aboutC for 0.5 hours Get 180 grams of diethanolamine (exit 95) in the form of a viscous slightly yellow liquid, in the IR spectrum does not differ from the ones described in example 1. The elemental composition of the product: From 38.9; H 7,8; N 22,1. The content of Oh-groups of 18.5

P R is (3 h). Get a product similar to example 1. Yield 95

P R I m e R 4 (comparative). Repeat the experiences of example 1, heat-acetylacetone at 160aboutC. for 6 h heating the evolution of ammonia ceases. Of the liquid product obtained after 6 h of heating, cooling crystallizes unreacted-acetylacetone.

P R I m e R 5 (comparative). Repeat the experiences of example 1, heating-acetylacetone at 200aboutTo stop shedding ammonia (40 min). Get a product similar to example 1, however, painted a light brown color.

P R I m e R 6. 100 wt.h. epoxy resin ED-20 or its mixture with the resin deg-1 was mixed with 15-20 wt.h. detonability, utverjdali the mixture at 90-100aboutC for 4 h and then at 150aboutC for 14 h, and investigated the physico-chemical and physico-mechanical characteristics of the obtained epoxypropanol. The research results shown in the table indicate the applicability of detonability for curing epoxy resins in compositions that can be used as a binder for fiberglass, caulking compounds and adhesives.

P R I m e R 7. To 30.8 g of dimethylformamide are dissolved in permisiveness acid with ethylene glycol and glycerin, and 0.08 g of diethanolamine. The resulting solution was mixed with 3.4 g of diphenylmethanediisocyanate (MDI) containing 53,3 4,4'-MDI, 38.7% of 2,4'-MDI and 8 2,2'-MDI, heated to 70-80aboutC and stirred at this temperature for about an hour, until the content of NCO-groups reaches to 0.8 and then added 0.11 g of benzoyl chloride and 54.8 g of toluene. Get solution of polyurethane. 16.5 g of the resulting solution of polyurethane mixed with 16,35 g nitrocellulose lacquer SC-573, in which pre-add 0.5 g of castor oil and 0.5 g of dibutyl phthalate. The resulting mixture was diluted with 49,0 g of ethyl acetate and used as a varnish to fix the coating on the leather. Lacquer stable for more than 3 months, the stickiness of the coating is missing, it thermomechanical stability 130aboutWith, resistance to wet friction over 1,000 revolutions of the disk, resistance to repeated bending over 50,000.

1. 1,5-Bis-(2 hydroxyethyl)-biuret as a component of the polymer compositions.

2. The way to obtain 1,5-Bis-(2-hydroxyethyl) biureta, wherein 1-(2-hydroxyethyl) urea is heated at 170 190oTo stop shedding ammonia.


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