It was launched in 1930 in Germany. Today, non-ionic surfactants in terms of production take the second place after anionic. In the US, they account for 25% of the total surfactant production. This is primarily due to their valuable properties:

• high detergency and ability to keep pollution in the solution even without additional additives;
• chemical resistance in hard water;
• good compatibility with auxiliary components of the detergent mixture;
• high rate of biodegradability in wastewater.

Among other things, the wide distribution of non-ionic surfactants is due to the fact that the raw material for their production can serve a variety of organic compounds with long-chain alkyl or alkylaryl radicals and functional groups with a mobile hydrogen atom. The variation of the properties of nonionic surfactants is carried out by changing the length of the hydrophobic or hydrophilic part of the molecule without significant changes in technology.

Recently, due to the low bactericidal ability, in particular in the ethoxylated alkylphenols, the production of non-ionic surfactants is somewhat reduced. However, in the coming years we can expect a sharp increase in their output due to the expansion of their application in the field of enhanced oil recovery processes.

Classification

Getting

Nonionic surfactants are compounds containing a hydrophobic hydrocarbon radical, on the one hand, and a hydrophilic part of the molecule, which is usually a polyethoxylated chain. Therefore, non-ionic surfactants are obtained on the basis of substances containing a fatty and fatty-aromatic radical associated with a functional group, and ethylene oxide. The following methods are known for producing nonionic surfactants:

1. Fatty acids RCOOH + nC 2 H 4 O → RCOO n H

2. The amino alcohols HOC 2 H 4 NH 2 + nC 2 H 4 O → HOC 2 H 4 NHn H

3. Fatty alcohols ROH + nC 2 H 4 O → RO n H

4. Fatty mercaptans RSH + nC 2 H 4 O → RS n H

5. Poly (ethyethylated alkylphenols) RC 6 H 4 OH + nC 2 H 4 O → RC 6 H 4 On H

In industry, the most common method is the periodic method of ethoxylation, although there are installations operating under a continuous scheme. Production of nonionic surfactants in a batch process is carried out at 130-180 ° C and 0.15-0.5 MPa in the presence of alkaline catalysts. The catalysts used are powdered caustic soda, sodium methylate metallic potassium, or solid caustic potassium. In a continuous process, acid catalysts BF 3 are used.

Properties

Nonionic surfactants do not dissociate into water into ions, but dissolve in it. The solubility in water is due to the formation of hydrogen bonds between the hydrogen atoms of the water molecules and the oxygen atoms of the polyoxyethylene chain:

With increasing temperature, the solubility of non-ionic surfactants decreases due to the weakening of hydrogen bonds and the dehydration of molecules. This causes turbidity of the solution, and the temperature at which turbidity is observed depends on the number of ethylene oxide groups. If a non-ionic surfactant contains more than 15 ethylene oxide groups, its ability to hydrate is so great that its aqueous solutions do not grow turbid even when boiled. With a decrease in temperature, nonionic surfactants are able to rehydrate and dissolve in water. Non-ionic surfactants with 3-4 ethylene oxide groups practically do not dissolve in water, but are well soluble in non-polar media, for example, in oils.

Application

Nonionic surfactants are most widely used as good

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First MGMU them. THEM. Sechenov

Ministry of Social Development of Russia

Faculty of Pharmacy

Department of Analytical, Physical and Colloid Chemistry

NEONOGENOUS SURFACE - TWINE

Completed: Gorbatkina D.V.

Student 2 courses 19 groups

Faculty of Pharmacy

Moscow 2011

Surfactants

whatsuch aSurfactant?

Surface active substances (Surfactant) - chemical compounds that, while concentrating on the interface, cause a decrease in surface tension.

Surface active substances - this is a group of compounds used in pharmaceutical practice to improve the technological or therapeutic properties of various drugs. The use of surfactants in the manufacture of drugs and medicine is constantly increasing, which is associated with a number of very valuable properties - stabilizing and emulsifying ability, a significant effect on the membrane permeability of the skin and mucous membranes, etc.

Main quantitative characteristic Surfactant is an superficial activity  - the ability of a substance to reduce the surface tension at the phase boundary is a derivative of the surface tension with respect to the surfactant concentration when C tends to zero. However, surfactant has a limit of solubility (the so-called critical micelle concentration or CMC), with which when the surfactant is added to the solution, the concentration at the interface remains constant, but at the same time the self-organization of the surfactant molecules in the bulk solution (micelle formation or aggregation) occurs. As a result of this aggregation, so-called micelles are formed. A distinctive feature of micelle formation is the clouding of the surfactant solution. Aqueous solutions of surfactants, when micelle formation also acquire a bluish tint (gelatinous tint) due to the refraction of light by micelles.

Typical Surfactant  - organic compounds of a diphilic structure, i.e. containing atomic groups in the molecule, which differ greatly in the intensity of interaction with the environment (in the most practically important case, water). So, in the surfactant molecules there is one or several hydrocarbon radicals that make up the oleo or lipophilic part (it’s also the hydrophobic part of the molecule), and one or more polar groups, the hydrophilic part. Oleophilic (hydrophobic) groups weakly interacting with water determine the tendency of a molecule to transition from an aqueous (polar) medium to a hydrocarbon (nonpolar) medium. Hydrophilic groups, on the contrary, keep the molecule in a polar medium or, if the surfactant molecule is in a hydrocarbon fluid, determine its desire to transition to a polar medium. Thus, the surface activity of surfactants dissolved in non-polar liquids is caused by hydrophilic groups, and dissolved in water by hydrophobic radicals.

Surfactant classification

1. Ionogenic

o Cationic

o Anionic

o Ampholytic

2. Non-ionic

By the type of hydrophilic groups, surfactants are divided into ionic, or ionic, and non-ionic, or nonionic. Ionic surfactants dissociate in water into ions, some of which have adsorption (surface) activity, while others (counter-ions) are adsorption-inactive. If anions are adsorption active, surfactants are called anionic, or anionic, in the opposite case - cationic, or cation-active.

Non-ionic  will be considered later.

TO anion-active  include chemical compounds with an anion in the form of a radical with a long alkyl chain determining the surface activity of the compound — these are organic acids and their salts.

A typical example of anionic surfactants are soaps, which are a mixture of sodium salts of higher fatty acids - stearic, oleic, etc. The most common sodium salts, which under normal conditions have the character of a solid mass.

TO cationic  surfactants include salts of quaternary ammonium bases, alkylamines, cyclic amines, etc. The surface activity of the compounds of this subgroup is due to the presence of cations. Usually these substances have bactericidal properties. The polar nature of cationic surfactants implies their ability to various kinds of chemical interactions with many medicinal substances, which requires careful use and mandatory verification of compatibility with individual medicinal substances.

Of the four groups of surfactants, the most biologically unfavorable are cation-active.

Ampholytic surfactants are represented mainly by derivatives of amino acids and aminophenols. The surface activity of a substance of this group depends on the pH in which they are located: in acidic - they are cationic, in an alkaline medium - anionic.

The most important representatives of the surfactants of the ampholytic group are phosphatides of plant and animal origin, which have been widely used in the pharmaceutical and food industries.

The most widely used in pharmaceutical technology, in particular in the manufacture of drugs by the pharmacy method, are non-ionic surfactants.

Non-ionic surfactants

This is the most promising and fast-growing class of surfactants.

Nonionic surfactants are compounds that dissolve in water without being ionized. The solubility of nonionic surfactants in water is due to the presence of functional groups in them. As a rule, they form hydrates in aqueous solution due to the occurrence of hydrogen bonds between water molecules and oxygen atoms of the polyethylene glycol part of the surfactant molecule. Their group is represented by polyglycolic and polyglycolic esters of fatty alcohols (for example, disubstituted - Disodium Laurethsulfosuccinate - a flowable liquid consisting of citric acid and fatty alcohols).

Nonionic surfactants are condensation products of glycosides with fatty alcohols, carboxylic acids and ethylene oxide.

Classification:

Nonionic surfactants are divided into groups that differ in the structure of the hydrophobic part of the molecule, depending on which substances formed the basis for the preparation of polyglycol ethers. On the basis of alcohols get ethoxylated alcohols RO (C 2 H 4 O) n H; based on carboxylic acids - ethoxylated fatty acids RCOO (C 2 H 4 O) n H; on the basis of alkyl phenols and alkyl naphthols, ethoxylated alkyl phenols RC 6 H 4 O (C 2 H 4 O) n H and compounds RC 10 H 6 O - (C 2 H 4 O) n H; on the basis of amines, amides, imidazolines - ethoxylated alkylamines RN [(C 2 H 4 O) n H] 2, compounds RCONH (C 2 H 4 O) n H, compounds of formula III; on the basis of sulfamides and mercaptans - surfactants of the type RSO 2 NC (C 2 H 4 O) n H] 2 ​​and RS (C 2 H 4 O) n H. A separate group consists of proxanols (p lyu r o and n) - ethylene - and propylenoxy-doped copolymers BUT (C 2 H 4 O) x (C 3 H 6 O) y (C 2 H 4 O) z H, where x, y and z range from a few to a few dozen, and proxamines (tetronics; formula IV) - ethylene - block copolymers and propylene oxides, obtained in the presence of ethylene diamine. Alkylacetylene glycols serve as the basis for the preparation of surfactants of the type H (OC 2 H 4) n -OCR "R: C CCR" R "" O (C 2 H 4 O) n H; phosphoric acid esters of the type (RO) 2 P (O) O (C 2 H 4 O) n H; pentaerythritol-type V esters

Getting

Most non-ionic surfactants are obtained by condensation of fatty acids, fatty alcohols (C = 8-18), fatty amines with ethylene oxide:

where n is the number of ethylene oxide molecules.

The condensation products are called hydroxyethylamine compounds.

The condensation of fatty acids with glycols get esters with non-ionic properties:

Of the fatty acids used lauric, stearic, oleic, palmitic and FFA of various fractions. Condensation is carried out in the presence of acidic or alkaline catalysts at a temperature of 185С.

Non-ionic surfactants include alkylolamides derived from alkylolamines and fatty acids or their methyl esters. From alkylolamines use primary ethanolamines or isopropanolamines, diethanolamines. For example, alkylolamide nonionic surfactants are obtained by synthesis of fatty acids and primary alkylolamine:

They are also obtained by condensation of alkylolamides with ethylene oxide:

In addition to these, there are many other methods for the synthesis of nonionic surfactants. The chemical industry produces for CMC a number of non-ionic surfactants.

Sintanol  DS-10 - is a mixture of polyglycolic esters of synthetic primary alcohols of the Xu-Cjg fraction obtained by catalytic reduction of methyl esters of synthetic fatty acids. The empirical formula is C n H2 „+ i (CH2 - CH 2 0) m H, where l = 10 - 18; tp = 8 - 9.

Sintanol  AJIM - 10 - is a mixture of polyglycolic esters of synthetic primary higher fatty alcohols of the C12 - C14 fraction obtained by organo-aluminum synthesis.

Sintanol  ACSE-12 - is a mixture of polyglycol ethers of primary alcohols of the C16 - C2o fraction obtained by organo-aluminum synthesis; CMC based on it have increased flowability. Sintamide-5 - is a mixture of alkylolamides of synthetic fatty acids. Empirical formula p. - CONH-CH2O (CH2 ~ CH2O) n H, where R is C 10 - C 16; n = 5 - 6. CMC on its basis has a lower pricing.

OC-20 (ethoxylated high molecular weight alcohols; the average number of attached ethylene oxide molecules is 20) has a waxy consistency and color from yellow to light brown.

In the production of non-ionic surfactants, the purity of the initial synthesis products is important. Ethylene oxide, for example, may contain impurities of not more than 0.2% (mass.). Ethylene oxide is toxic, flammable, forms explosive mixtures with air, therefore, when carrying out the process it is necessary to observe special safety measures: to protect ethylene oxide from fire, air and pollution; store it in tanks in an inert gas atmosphere, usually nitrogen.

Hydrophobic components (fatty acids, amides, alcohols, etc.) and caustic soda are loaded into the reactor, after which air is removed from the reactor by blowing it twice with nitrogen. The mixture is heated with stirring to 150 ° C, then the gas-air mixture is pumped out, lowering the pressure to 20 mm Hg. Art., and fed into the reactor in a stream of nitrogen liquid ethylene oxide. The nitrogen pressure in the reactor is maintained at 0.7 atm. Next stop the flow of ethylene oxide to the pressure decreased. During the reaction, the pressure in the apparatus decreases and the temperature rises. The reaction mixture is cooled, ethylene oxide is added, after which the temperature rises to 170 - 180 ° C and the pressure to 0.25 - 0.28 MPa. At the end of the reaction, the pressure in the reactor drops to atmospheric.

The oxyethylation reactor is an autoclave designed for operation at overpressure (0.35 MPa). The autoclave is equipped with a heat exchanger (the reaction is exothermic) and a stirrer.

The industry uses periodic and continuous technological schemes of the process of ethoxylation.

Properties

The colloid-chemical properties of surfactants of this class vary widely depending on the length of the hydrophilic polyglycol chain and the chain length of the hydrophobic part in such a way that different representatives of one homologous series can be good wetting agents and emulsifiers. The surface tension of homologues of ethoxylated alkylphenols and primary alcohols with a constant content of ethylene oxide groups decreases in accordance with the Traube rule, that is, with each additional CH 2 group, the surface tension decreases. In the best case scenario, it can reach (28-30) 10 -3 N / m with a critical micelle concentration. The micellar mass is very large; for tweens, for example, it reaches 1,800. Non-ionic surfactants are less sensitive to salts, causing water hardness, than anion-active and cation-active surfactants. The wetting ability of non-ionic surfactants depends on the structure; optimum wetting ability has surfactant branched structure:

Ethoxylated C 10 -C 18 alcohols with n from 4 to 9 and pluronic form spontaneous oil / water and water / oil microemulsions. Nonionic surfactants are well combined with other surfactants and are often included in the formulation of detergents.

Non-ionic surfactants exist only in liquid or pasty form, and therefore cannot be contained in solid detergents (soap, powders).

Application. Pharmaceutical industry

Starch. Starch in the form of paste turned out to be a good stabilizer of pharmaceutical emulsions.

Starch paste (Mucilago Amyli). For the preparation of pharmaceutical emulsions proposed N.G. Goykhman (1939). To emulsify 10 g of oil, 5 g of starch in the form of paste is required. Most of the dry weight of starch (97.3-98.9%) are starch polysaccharides, the rest is impurities: protein substances (0.28 - 1.5%), fiber (0.2-0.69%) and ash substances (0.30-0.62%). Small amounts of higher fatty acids and 2-glycerol phosphoric acid are found in starches obtained from cereals. Kleysterization is externally expressed in a strong swelling of starch grains, their rupture and the formation of a viscous hydrosol.

Cellulose and her derivatives . Like starch, the molecular chains of cellulose are built from glucose residues, but differ in the spatial arrangement of these units. Due to the presence of hydroxyl groups, cellulose is able to esterify, forming derivatives with high stabilizing ability.

Methylcellulose is a methyl cellulose ethers of varying degrees of esterification; soluble in water.

Carboxylmethylcellulose is an ester of cellulose and glycolic acid. It is used in the form of sodium salt (sodium carboxymethylcellulose), since carboxymethylcellulose itself is insoluble in water.

Methylcellulose and sodium carboxymethylcellulose for the preparation of pharmaceutical emulsions are used in the form of 1-2% solutions.

Table 1

Production of technical detergents

Fiber production

Agricultural industry

Production of household detergents

This type of surfactant adds to the detergent softness, safety, environmental friendliness (biodegradability of non-ionic detergents is 100%). They stabilize soap suds, have soft thickener properties, have a bradykinase and polishing effect, restoring the outer layers of the epidermis and hair, and contribute to enhancing the effect of therapeutic additives of the cleansing drug.

Another type of detergent is non-ionic detergents. The fat soluble group in detergent (V) is a kind of fat soluble group in alkyl benzene sulfonates and soaps, and the residue is a long chain containing many oxygen atoms and a OH group at the end that are hydrophilic. Typically, non-ionic synthetic detergents exhibit high detergency, but weakly form foam.

Mining industry

Paint industry

Twins

TO non-ionic surfactants include the condensation products of ethylene oxide with various high molecular weight fatty acids and alcohols, as well as sorbitan esters, fatty acid esters and sucrose, etc.

In pharmaceutical practice, the most frequently used surfactants of this particular group and among them especially such as spins are esters of fatty acids and non-polyoxyethylated sorbitan, tweens are esters of polyoxyethylene sorbitan and fatty acids, sucrose monopalmitate, sucrose monostearate, sucrose distearate, emulsifier T -1, T-2 emulsifier, etc.

Ofstories

In the USSR, tweens were first synthesized in 1958 at the All-Union Scientific Research Institute of Organic Semiconductors and Dyes.

whatsuch atweens?

Twins  - it is slightly colored fluids of varying degrees of viscosity, soluble in water.

Getting

Tweens are obtained by treating spans (spans are partial esters of fatty acids and hexatomic hexatomic alcohol derived from sorbitol. The number in the name of the span (for example, span-20) corresponds to the percentage of acid) with ethylene oxide in the presence of caustic soda as a catalyst. Esterification occurs at the site of free hydroxyls.

Depending on which of the spans reacts to the esterification reaction and what degree of polymerization of ethylene oxide, the following twins are distinguished (Table 2).

Table 2. Tweens used in pharmacy

Trading			Consistency
title	Chemical composition
	Polyoxyethylene - (20) - sorbi-tanmonolaurat
	Polyoxyethylene - (20) - sorbi-tanmonopalmitat
	Polyoxyethylene - (20) - sorbic-takmonostearate
	Polyoxyethylene - (4) - sorbic-tanmontselerat
	Polyoxyethylene - (20) - sorbic tantristearate
	Polyoxyethylene - (20) - sorbi-tano-monooleate
	Polyoxyethylene - (5) - sorbi-tano-oleate
	Polyoxyethylene - (20) - sorbic tantrioleate

The table shows that there are several types of polysorbates: monolaurate is indicated by the number 20 (TWEEN-20), monopalmitate - 40 (TWEEN-40), monostearate - 60 (TWIN-60) and monooleate - 80 (TWIN-80). They are of natural origin, because based on sorbitol (otherwise - sorbitol, glucitol - a substance with a sweet taste and often used as a sugar substitute in dietary products, it is obtained from fruits, often from fruit seeds) and fatty acids from base oils: coconut - TWIN-20, palm - TVINY - 40 and - 60, olive - TWIN-80. The higher the number of polysorbate, the value of its HLB (hydrophilic-lipophilic balance) becomes smaller, i.e. the ability to create stable emulsions decreases, especially in combination with other emulsifiers having a lower HLB.

Physical and chemical properties

Colorless, viscous, waxy substances. Density<1. Плохо растворяются в воде, растворимы в спирте. Твины размягчаются при 15-18° и разлагаются при нагревании выше 160-180°, температура разложения падает с увеличением номера твина. Гидролизуются в присутствии щелочей. Спаны неионогенные поверхностно-активные вещества (Шварц).Т. затвердевания 10-15°

Toxic act. Relatively low toxicity.

Animals When administered through the mouth to laboratory animals for the 6 studied spans, LD50 = 16h40 g / kg, and for 8 tweens LD50 = 3.75h5.45 g / kg (Marszall). However, when tweens and spans were added to the feed, growth was delayed, changes in the kidneys, a decrease in the number of surviving newborn rats (Oser, Oser), lowering blood pressure (Marszall), thirst, incomplete feed intake, diarrhea, anemia, bleeding from urinary organs, increased mortality (Jetter; Poling et al.), but Gracham and Grice did not observe this. Tweens at a concentration of 0.5-1 mg / ml have a pronounced biological activity, inhibiting the growth of cell cultures and inhibiting the incorporation into the cells of the precursors of the synthesis of DNA, RNA and proteins (Surkov and others).

A number of tweens and, to a lesser extent, spans, are cocancinogens. Twins, containing in their molecule a long-chain fatty acid (for example, stearic, palmitic) and relatively soluble in water, are the strongest coccarcinogens in experiments on mice. At low concentrations, some tweens (for example, tween-60) have anticarcinogenic properties (Setala et al.).

Person. A study of blood and urine in healthy and sick people who received 6 g Spana-60 or Tween-60 every day did not reveal any abnormalities (Woldstein et al.). However, it has been established that a dose of 5 g of tween-20 can cause hemolysis of blood in humans. All 14 investigated spans and tweens did not irritate the eye mucosa and skin (Marszall).

Application

o feed additives

o emulsifiers in the food industry

o as stationary phases in chromatography

o In microbiological practice, tween-80 (polyoxyethylene derivative of sorbitan-monooleate) is more often used to determine the lipolytic activity of bacteria (eg, mycobacteria

o stabilization of microbial suspensions, processing of fat-containing materials for research.

o Often used in industrial and home cosmetics for the introduction of a product with a predominant aqueous phase of fatty or essential oils, as well as fragrances and fragrances.

Will considerspecificexamples:

TWIN-80

Polysorbate-80 / Polysorbate-80

Chemicalname: glycol, tween 80, polyoxy-ethylene (20) sorbitan monooleate

Description: The surfactant TWEEN-80 is polyoxyethylene (20) sorbitan monoaleate with a molar mass of 1226 g / mol. The structure of its molecule, as well as the molecule of nonionic surfactants TWEEN-20, includes a six-membered ring, to which two polar chains (C 2 H 4 O) n and (C 2 H 4 O) m are attached, where n + m = 20 . The non-polar hydrocarbon radical is also part of the TWEEN-80 nonionic surfactant molecule; however, unlike the TWEEN-20 molecule, it contains 11 carbon atoms.

Consumerpropertiesandadvantages:

· Non-ionic surfactant / emulsifier for oil-in-water emulsions;

· Can be used in combination with various low-HLB hydrophobic emulsifiers to create a wide range of stable oil-in-water and water-in-oil emulsion systems. (especially good to use in combination with fatty alcohols, such as Cetearyl alcohol. The classic combination is Polysorbate-80 and Sorbitan Oleate);

· Excellent solubilizer and stabilizer for essential oils;

· Moisturizing agent;

· Excellent lubricant;

· It has a calming effect on the skin;

· The soft antistatic and conditioning properties;

· Viscosity modifier;

· Dispersing agent;

· May improve hair growth.

Application:

· Air fresheners;

nonionic ionization surface activity

· Body sprays and other products in which oils need to be solubilized in water;

· Means for washing the body;

· Shampoos and hair conditioners (especially those that prevent hair loss);

· Lotions, tonics;

· Bath and shower oils;

· Bath bombs (adding 2 teaspoons of polysorbate-80 to 2 cups of the bomb mixture will improve and make the hiss of the final product longer);

· Self emulsifying body scrubs with salt and sugar.

Recommendedpercentinputatrecipes: 1-5% to 50%. To solubilize essential oils and fragrances, it is recommended to take the ratio of Polysorbate-80 and oils / fragrances from 1: 0.5 to 1: 1.

Externalview: A viscous, amber-colored, odorless liquid.

Solubility: soluble in water, oils and alcohol (isopropyl alcohol).

pH: 5-7 (5 - 10% aqueous solution) HLB: 15 (to create oil-in-water emulsions) Conditionsstorage: Very stable when stored in a closed container in a cool dry place.

Termshelf life: With proper storage at least 18 months from the date of manufacture.

EmulsifierT-2. Diester triglycerol. Wax-like, hard (at 20%) yellow or light brown color. It is obtained by esterification of glycerol trimer with saturated fatty acids with 16-18 carbon atoms (or only stearic acid) at a temperature of 200 ° C.

As a general provision, it should be pointed out that the emulsifying action of non-ionic surfactants is the more effective, the better the polar and non-polar portions of the emulsifier molecule are balanced between the two phases of the emulsion. This means that the diphilic molecule (if the emulsifier is good) must have affinity for both polar and non-polar media. Only under the condition of a balanced emulsifier molecules will be located on the interfacial surface, and will not dissolve predominantly in any one of the phases.

The emulsifier T-2 molecules can be considered as well balanced, since it takes only 1.5 g to obtain 100 ml of a stable 10% emulsion. The balance rule also applies to ionic emulsifiers. In this case, the balance is determined, on the one hand, by the length of the hydrocarbon chain, and on the other, by the affinity of the ionic group in water.

Conclusion

Due to its exceptional properties, nonionic surfactants are widely used in almost all industries. It is important to note that nonionic surfactants are most widely used in pharmaceutical technology, in particular in the manufacture of drugs by the pharmacy method.

Bibliography

1. Van Krevelen DV, Properties and chemical structure of polymers, trans. With English, M., 1976;

2. http: // ru. wikipedia.org/

3. http: // wiki. laser.ru

4. http://www.propartners.ru/pid243.html

5. http://www.chemport.ru/chemical_encyclopedia_article_6226.html

6. http://www.referat.ru/referats/view/29646

7. http://techlekform.ru/index2. php? option = com_content & task = view & id = 426 & pop = 1 & page = 0

8. http://www.sintez-oka.ru/glavnaya/

9. http://studentbank.ru/view. php? id = 56779 & p = 1

10. http://soap-formula.ru/index. php? option = com_content & task = view & id = 704 & Itemid = 75

11. http://www.xumuk.ru/vvp/2/276.html

12. http: // dic. academic.ru/dic. nsf / dic_microbiology / 2864 /% D0% A2% D0% B2% D0% B8% D0% BD% D1% 8B # sel

13. http: //www.hfp. spb.ru/production/Tween-80

14. http://www.bibliofond.ru/view. aspx? id = 21453

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