The method of obtaining succinate sodium salt of chitosan

 

(57) Abstract:

Usage: in veterinary medicine, medicine and cosmetics as foaming agent, hydrant or emulsifier. Describes how to obtain succinate sodium salt of chitosan, comprising preparing a homogeneous solution of chitosan, its secretion by treatment with an alkaline agent, the interaction of the resulting suspension of chitosan with succinic anhydride, neutralizing the mixture and isolation of the target product by the method of drying, characterized in that the processing of chitosan solution is carried out to obtain a pH of 6.9 and 7.5, are amorphization of chitosan in the form of the aqueous suspension in cavitation or mechanical fields with shear effect, conduct interaction with powdered succinic anhydride with a particle size of not more than 100 μm, the neutralization mixture is conducted aqueous alkaline solution, and the selection of the target product can be done without the use of organic solvents by using spray or freeze drying. The technical result - the increase of ecological purity and effectiveness of the method of producing succinate sodium salt of chitosan without using organic solvents. table 2.

The invention relates is ora can be used in veterinary medicine, medicine and cosmetics.

Known methods for producing acylated amino groups of chitosan anhydrides of dicarboxylic acids [Author's certificate N 508212, class C 08 B 37/08. Bull. N 11. 25.03.76,; RF Patent N 2100373, class C 08 B 37/08. Bull. N 36. 27.12.97,].

The closest known by the decision of similar problems is a method for carboxyl-containing derivatives of chitosan by conducting the reaction in a homogeneous conditions in two stages, different pH environment [Author's certificate N 802290, class C 08 B 37/08. Bull. N 5 07.02.81]. In the first stage is formed sodium salt of polyampholyte with 48 - 52% profilirovannyh free amino groups of chitosan, after the second stage of quantitative acylation of all amino groups of chitosan, which is confirmed by conductometric titration. It is essential that the principle of carrying out the reaction in a homogeneous environment will require dissolution anhydrides of dicarboxylic acids in an organic solvent, in addition there is the need to use organic solvents in the allocation sodium salt of polyampholyte or the target product.

It is known that polar organic compounds can be firmly adsorbed on chitin, chitosan and their derivatives [Kosarev A., Lazarus is the breaking of these biopolymers. Production and application of chitin and chitosan. Abstracts of the 4th all-Russian conference. M: VNIRO, 25.04.1995. S. 77; R. Chen and Huei Hwa Horng-Dar. Effect of chain flexibilities of chitosans on the physical and permeability properties of the ultrafiltration membranes prepared. 1stInternational conference of the european chitin society. Abstracts book. Brest-France. September 11-13 1995. P. 38; M. Weltrowski, J. Patry, M. Bourget Reactive filter for textile dyes adsorption. 1stInternational conference of the european chitin society. Abstracts book. Brest-France. September 11-13 1995. P. 39.], moreover identified polyextremophiles the nature of the dependence of adsorption from the ionization potential of the organic molecules. Selective adsorption on these biopolymers due to the formation of stronger links between the groups-OH, -NH2and-NHCOCH3macromolecules chitosan and organic molecules than their hydrogen bonds with water molecules [Kosarev A., Lazareva, E. C., Kryvtsov,, Study of adsorption of organic substances on chitin, chitosan and some chemical derivatives of these biopolymers. Production and application of chitin and chitosan. Abstracts of the 4th all-Russian conference. M: VNIRO, 25.04.1995. S. 77; Arnett, E. M. Quantitative comparison of weak organic bases. Modern problems of physical organic chemistry. A collection of reviews. M.: Mir, 1967. S. 195] . Complete removal of the polar organic the temperatures [Manson J., Sperling L. Polymer blends and composites. M. : Mir, 1979]. Therefore, the removal of organic molecules from the macrovolume of chitosan and its derivatives in vacuum and especially when air drying is almost impossible. Consequently, succinate sodium salt of chitosan, obtained by the method of [Author's certificate N 802290, class C 08 B 37/08, bull. N 5 07.02.81] or [Bulls B. N., Bykova C. M., Krivosheina L. I., Alekseev, S. M., Zakharova, E. I., Golubeva O. A. Development of technology for water-soluble forms of chitosan. Production and application of chitin and chitosan. Abstracts of the 4th all-Russian conference. M: VNIRO, 25.04.1995. C. 26], when all stages is carried out in organic medium, is detected in the analysis of these products and the presence of organic solvents.

The aim of the invention is to eliminate the above drawbacks, the increase in the purity of the target product, environmental cleanliness and efficiency of the method of its production.

The objective is achieved by obtaining succinate sodium salt of chitosan in the interaction of activated chitosan at a pH of 6.9-7.5 C powdered succinic anhydride with a particle size of not more than 100 μm and selection of the target product from its aqueous solutions without Primea progestacare [Gilbert R. D., Patton P. A. Liquid crystal formation in cellulose and cellulos derivatives. Progress in Polymer Science. 1983. V. 9. P. 115 - 131]. This is evidenced by the exponent in the equation Mark-Houwink-Sakurada equal to chitosan - 0,85 [Gamzazade A. I. Shlimak V. M., Sklar A. M., Shtikova E. V., Pavlova S. A., S. V. Rogojin // Acta Polymerica 1985. V. 36. N 8. P. 420]. Projectcost chitosan and its derivatives is a result of intramolecular hydrogen bonds and steric effects, complicating the possibility of rotation around the glycosidic linkages connecting links in the chain. With increasing concentration of these polymers can form liquid crystalline solutions [Gilbert R. D., Patton, P. A. Liquid crystal formation in cellulose and cellulos derivatives. Progress in Polymer Science. 1983. V. 9. P. 115 - 131; Revol, J. F., L. Godbout, Orts B., R. H. Marchessault Chitin crystallite suspensions in water: phase separation and chiral nematic ordering. 1stInternational conference of the european chitin society. Abstracts book. Brest-France September 11-13 1995. P. 38.; E. Belamie, Giraud-Guille, M. , Domard A. Microscopic studies of chitosan in condensed phases. 1stInternational conference of the european chitin society. Abstracts book. Brest-France. September 11-13 1995. P. 11]. Microscopic examination of chitin [Revol J. F., L. Godbout, Orts B., R. H. Marchessault Chitin crystallite suspensions in water: phase separation and chiral nematic ordering. 1stInternational conference of the european chitin society. Abstracts book. Brest-France September 11-13 1995. P. 38] and chitosan [E. Belamie, Giraud-Guille, M. , Domard A. Microscopic studies of chitosan in condensed phases. 1stInternational conference of the european chitin society. Abstra what's "fingerprint pattern" [Gilbert R. D., Patton, P. A. Liquid crystal formation in cellulose and cellulos derivatives. Progress in Polymer Science. 1983. V. 9. P. 115 - 131] . It is essential that the supramolecular organization of chitosan is saved and after the processes of hydrolysis, and with the increase in the solution concentration of the macromolecule are ordered with the formation of liquid-crystalline chiral-nematic state [E. Belamie , Giraud-Guille, M., Domard A. Microscopic studies of chitosan in condensed phases. 1stInternational conference of the european chitin society. Abstracts book. Brest-France. September 11-13 1995. P. 11]. Obviously, such processes macromolecular organization occur in the process of planting chitosan.

X-ray diffraction analysis showed a significant dependence of the degree of crystallinity of chitosan from the method of its production [Rogovin E.V, Akopova T. A., Zelenetsky S. N. The study of extrusion grinding chitosan. Production and application of chitin and chitosan. Abstracts of the 4th all-Russian conference. M : VNIRO, 25.04.1995. C. 27]. Unlike suspension extrusion chitosan [Akopova T. A., Rogovin, S. H., Vikhoreva, A., Zelenetsky S. N., Golbreich HP, N., Et Al.With. Polymer sciense ser. Conn. B.-M. 1991. So 33. N 10. S. 735] has a lower degree of crystallinity [Rogovin E.V, Akopova T. A., Zelenetsky S. N. The study of extrusion grinding chitosan. Production T. A., Rogovin, S. H., Vikhoreva, A., Zelenetsky S. N., Golbreich HP, N., Et Al.With. Vysokomolecul. Conn. B. - M. 1991. So 33. N 10. S. 738]. It is essential that the hillshade from alkali after planting increases the degree of crystallinity and, consequently, to reduce its reactivity. It is important to note that when you activate the chitosan by dry extrusion grinding crystalline structure is almost completely disappears, while the molecular weight is reduced by 50% [Rogovin E.V, Akopova T. A., Zelenetsky S. N. The study of extrusion grinding chitosan. Production and application of chitin and chitosan. Abstracts of the 4th all-Russian conference. M: VNIRO, 25.04.1995. C. 27.].

Almost complete amorphization of chitosan occurs in the processing of aqueous suspensions in cavitation or mechanical fields with shear strain, especially if this treatment is subjected to a freshly prepared suspension of chitosan. It should be noted that the suspension of chitosan obtained by the neutralization of a weak acid (e.g. acetic acid) in an aqueous solution of chitosan is slightly alkaline (pH 8.5 - 9.0 in). When conducting a neutralization to a pH of 6.9 - 7.5 part of the amino groups of chitosan deposited in the sediment, náchod the polymer (table 1).

Symbols in the table: MM - srednevozrastnoe molecular weight chitosan, [HAc] - residual concentration of acetic acid in the chitosan, ADC - concentration quaternionic of amino groups in chitosan.

*By dissolving chitosan used hydrochloric acid [Vikhoreva, A., Rogovin, S. H., Akopova T. A., Zelenetsky S. N., Golbreich HP, the Study of fractional composition of chitosan solid and suspension methods. Polymer sciense ser. Conn. S. B. 1996. So 38. N 10. C. 1781].

As can be seen from table 1, the decrease of molecular weight of chitosan causes a sharp decrease in output during its deposition and simultaneous increase in the concentration quaternionic of amino groups in chitosan residual amount of acetic acid. Thus, an 80% yield of chitosan at his deposition from acidic aqueous solutions by neutralization of the environment can be achieved by using polymers with MM 40 000.

For chemical modification used samples of chitosan with a degree of dezazetilirovanie acetamide groups 74 - 82% and srednevozrastnoe molecular weight of 26000 - 650000. The degree of dezazetilirovanie original chitosan and the degree of substitution of the amine groups on acetamide was determined by the method of potentiometer hydrochloric acid 0,03 N aqueous solution of NaOH by well-known methods [Vikhoreva, A., Rogovin, S. H., Akopova T. A. , Zelenetsky S. N., Golbreich HP, the Study of fractional composition of chitosan solid and suspension methods. Polymer sciense ser. Conn. S. B. 1996. So 38. N 10. C. 1781]. Srednevozrastnoe the molecular weight of chitosan in the 25oC was determined by the method of [Gamzazade A. I. Shlimak V. M., Sklar A. M. , Shtikova E. V., Pavlova S. A., S. V. Rogojin // Acta Polymerica. 1985. V. 36. N 8. P. 420].

Synthesis of chitosan succinate was carried out at equimolecular ratio of succinic anhydride and NH2groups of chitosan. For additional activation of chitosan in the form of viewsrasmodeus fine suspension used magnetic and propeller stirrer (600 rpm), the homogenizer brand MPW 302 (Poland) and mixer with high-speed (1400 rpm) disk stirrer special design that allows you to create cavitation and mechanical fields with shear effect on the working volume.

After the heterogeneous interaction of activated chitosan in the form of the aqueous suspension with powdered succinic anhydride with a particle size of not more than 100 μm working the mixture was incubated for 30 min and neutralized alkaline aqueous solution to pH environment of 8.5, which corresponds to equimolecular translation H-forms of chitosan succinate in him who Fazana in the resulting product contains 5 - 7 mol.% disodium salt of succinic acid, the presence of which can be seen as a positive aspect due to its biological activity [Luzbel K. C., Kobzeva C. K. Influence of dietary applications of succinic acid on some of the indicators of metabolism of broiler chickens. Actual problems of veterinary medicine. Proceedings of the international conference. Barnaul. 1995 S. 136]. It is known that succinic acid in its pure form is used as an active biostimulator with loss of strength, loss of health, mental and physical fatigue. Developed and implemented at the drugstores drug on the basis of succinic acid on THE 2634-001-35492597-96.

All stages of the synthesis of succinate sodium salt of chitosan without the use of organic solvents and isolation of the target product by the method of freeze or spray drying leads to a number of distinctive advantages obtained product: there are no impurities of organic nature and the oxidation products, high degree of dispersion increases the solubility, which expands the field of use and direct use (in the manufacture of ointments, cream scrubs and other beauty products).

Testing structurales the basics of 18% at pH 4 to 0.1 in terms of microemulsion installation RCM - 7 are stable within the applicable GOST 29188.3-91 retention. The rheological properties of the emulsion increases with increasing concentration of sodium salt of succinate chitosan and molecular weight of the original chitosan.

These circumstances demonstrate compliance of the proposed technical solution the criterion of "novelty".

The proposed method of producing succinate sodium salt of chitosan fully tested in laboratory and industrial conditions. Currently produced commercially by order of the various organizations for use in cosmetics.

The invention is demonstrated by the following examples.

Example 1. 750 g of chitosan with a characteristic viscosity of 6.9 (srednevozrastnoe molecular weight equal to 330 000 [Gamzazade A. I. Shlimak V. M., Sklar A. M., Shtikova E. V., Pavlova S. A., S. V. Rogojin // Acta Polymerica. 1985. V. 36. N 8. P. 420]) and the degree of dezazetilirovanie 76,0% dissolved under stirring for 3 hours at 15oC in 25 l of 1% aqueous solution of acetic acid. The solution is filtered through a nylon mesh to remove insoluble impurities, the content of which is 3 wt.%. To the resulting solution while stirring, slowly add about 6.5 to the of litre of belting fabric diagonal weave, washed with distilled water and wring out. The result is a finely dispersed suspension of chitosan with solids 14,44 wt.%. Then 693 g of the resulting suspension was diluted with 1.8 l of distilled water and stirred for 1.5 min homogenizer brand MPW-302, then when running the homogenizer for 3 min batch add equimolar amount of succinic anhydride in the form of powder with particle size less than 100 microns. The reaction mixture was incubated for 30 min at 10-15oC and neutralized with 2.5 wt.% aqueous solution of NaOH to pH 8.5 by adding to the mix consistency. Target product produce by lyophilization and obtain 142 g of a white powder, odourless. The characteristics of the target product are shown in table 2.

Example 2. Planting chitosan conduct of its solution, 3 wt.%, in aqueous acetic acid, 1 wt.%, after pre-filtering to remove insoluble impurities by neutralizing environment water NaOH, 2.5 wt.%, to a pH of 6.9 with a yield of 96%. Additional activation of chitosan in the form of the aqueous suspension is carried out using the high-speed mixer with a disk stirrer. A portion of succinic anhydride and make a batch for 3 minutes at a temperature of suspen CLASS="ptx2">

Example 3. Planting of chitosan from his solution is carried out at a pH of 7.2 with the release of 98%. Additional activation of chitosan in aqueous suspensions of 1.6 wt.% carried out in a reactor with a propeller stirrer at 20oC for 30 minutes Target product produce by vacuum spray drying. Other stages analogous to example 1. Properties of the target product are shown in table 2.

Example 4. Additional activation of chitosan in aqueous suspensions 3.77 wt. % conducted on laboratory magnetic stirrer at 16.5oC for 30 minutes Target product produce by vacuum spray drying. Other stages analogous to example 1. Properties of the target product are shown in table 2.

Example 5. After the resultant deposition rates of high molecular weight chitosan at pH environment of 7.5 (yield 98%) and washing from chitosan of low molecular weight products in the form of an aqueous suspension of 3 wt.% treated with hydrogen peroxide, 0.1 wt.%, at 85oC for 32 minutes After filtration and triple leaching of low molecular weight chitosan activate in the form of an aqueous suspension, 4 wt.%, in the reactor with a disk stirrer. Other stages carried out analogously to example 1. Properties of the target product are shown in table 2.

Example 6. Chitosan with size CNU dezazetilirovanie 74% in the form of an aqueous suspension is treated with hydrogen peroxide, subjected to filtration, washing and interact with polutorakratnomu excess succinic anhydride analogously to example 5. Properties of H-forms of chitosan succinate are shown in table 2.

Example 6 activation absence of chitosan proposed method leads to a significant reduction of the degree of substitution of the amino groups. Although this example was taken polutorakratnomu excess of succinic anhydride with respect to the concentration of amine groups in the original chitosan, concentration succinamide groups in the obtained chitosan succinate equal to 60 mol.%, 22 - 27% less than the concentration of these groups in the target product, obtained in examples 1 to 5 (table. 2). This indicates limited availability of functional amino groups of chitosan in the reaction with succinic anhydride in heterogeneous conditions.

It is important to note that the concentration succinamide groups in chitosan succinate obtained in example 6, after storage for 9 months at room temperature increased to 66%. This means that when stored in dry form there is a partial conversion quaternionic forms of the amino groups of chitosan in succinamide. As succinic acid is a dibasic carboxylic cycloeucalenol chitosan, the transformation which succinamide group will lead to the formation of chemical cross-link, and partial loss of solubility of chitosan succinate. It is found experimentally that such a sample after storage for 9 months really is not completely soluble in environments with a pH of 1.6 11.4 in. The phenomenon is important to determine the stable storage conditions for the H-forms of chitosan succinate.

During the synthesis of succinate chitosan with molecular weight of less than 40 000 in order to avoid losses, the destruction process is carried out after the resultant deposition rates of high molecular weight chitosan, when possible thorough washing from low molecular weight organic products. If necessary there is a possibility of regulating the ratio of free and quaternionic form of amino groups in succinate sodium salt of chitosan by changing the pH of the environment by neutralizing the H-forms of chitosan succinate diluted aqueous solutions of bicarbonate of soda or sodium hydroxide. In addition, the proposed method allows to obtain the target product with a specified concentration of succinic acid or the disodium salt of succinic acid (5 - 10%) by introducing into the reaction of succinic anhydride in the amount more than you want the process to obtain the composite chitosan succinate and succinic acid in various ratios as in the form of an H-shape, and in the form of sodium salt with a specified degree of neutralization with a high degree of purity and with almost no loss (output when the freeze-drying process 98%).

The method of obtaining succinate sodium salt of chitosan, comprising preparing a homogeneous solution of chitosan, its secretion by treatment with an alkaline agent, the interaction of the resulting suspension of chitosan with succinic anhydride, neutralizing the mixture and isolation of the target product by the method of drying, characterized in that the processing of chitosan solution is carried out to obtain a pH of 6.9 and 7.5, are amorphization of chitosan in the form of the aqueous suspension in cavitation or mechanical fields with shear effect, then spend interaction with powdered succinic anhydride with a particle size of not more than 100 μm, the neutralization mixture is conducted aqueous alkaline solution, and the selection of the target product can be done without the use of organic solvents by using spray or freeze drying.

 

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