CS254911B1 - Addition salts of oxyethylated fatty amines with fatty acids - Google Patents

Abstract

The solution describes addition salts suitable as lubricants for surface treatment of glass fibers of general formula I, where R1, R2 is an alkyl or alkenyl residue with 12 to 18 carbon atoms and x + y is 5 to 25, with both x and y being different from zero.

Description

The invention relates to addition salts of oxyethylated fatty amines with fatty acids.

Oxyethylated fatty amines are known and are prepared by the addition of ethylene oxide to fatty amines to form nonionic adducts with surface-active properties (Blažej A. et al.: Tenzidy, Alfa Bratislava 1977). The application properties of these compounds are most often extended either by quaternization, mainly using dimethyl sulfate, epichlorohydrin, or by esterification of the hydroxyl groups of the derivative.

Various lubricants are used to treat glass and mineral fibers, whether intended for the reinforcement of plastics and rubbers, or for various technical purposes, which contain lubricants in their composition to improve the textile properties of the fibers. Compounds used as lubricants in lubricating compositions must meet several conditions, which in particular must be soluble or emulsifiable in water and stable at a pH of less than 7. For these reasons, it is not possible to use various soaps as lubricants, whether sodium, potassium, ammonium or triethanolamine with fatty acids.

Mainly for these reasons, various non-ionic compounds based on alkylene oxides, such as alkyl polyglycol ethers, acyl polyglycol ethers, etc., are used as lubricants. Although the use of these compounds is sufficient for a number of fiber applications, they have proven to be ineffective in formulating compositions that must provide good fiber cuttability. When analyzing this problem, we found that the main reason for the poor effectiveness of conventional lubricants is that the polymer film of the lubricant has enclosed them in its structure, which at the same time has a negative effect on the reduction of fiber stiffness as a result of plasticization of the polymer coating by the lubricant.

We have found that these problems can be effectively addressed by using the compounds of the invention as lubricants in lubricating compositions.

The invention describes fatty acid addition salts of oxyethylated fatty amines of the general formula I (C2H1O3H2O3)

R1—COOH. N—Rz \ (CzH4Oj _y H

- (Π where represents

R1 is an alkyl or alkenyl radical with 12 to 18 carbon atoms,

R2 is an alkyl or alkenyl radical having 12 to 18 carbon atoms, x and y are 5 to 25 and x and y are different from zero.

The preparation of these salts can be carried out by the action of fatty acids of general formula II

Rl—COOH (II) to oxyethylated fatty amines of general formula III (CzHiO) _x H /

Rz—N \

(CzHiOjyH (III) where Ri, R2, x and y have the same meaning as in the general formula of the salt, at a temperature of 30 to 90 °C in the melt or in the presence of a diluent, preferably water. Fatty acids are used either individually, but most often in mixtures as fatty acids isolated from various oils and fats. Of these, the most important are the fatty acids of coconut, cottonseed, soybean, sunflower, hemp and flax oil.

The invention is further explained by way of examples.

Example 1

300 g of oxyethylated sterylamine with 7 moles of ethylene oxide and 146 g of a technical mixture of fatty acids based on oleic acid with the composition given in Table 1 were introduced into the flask.

Table 1 acid (%) by weight oleic 83.4 linoleic 10.4 linolenic 3.6 stearic 1.2 behenic 0.5 unidentified 0.9

The batch was homogenized by stirring at 60 °C for 0.5 h. The prepared salt mixture has a viscosity at 20 °C of 382 mPa.s, a density of 0.9644 g.cm'' and _D ²⁰ = 1.4683.

Example 2

300 g of oxyethylated stearylamine with 7 moles of ethylene oxide and 146 g of oleic acid were introduced into the flask. The batch was homogenized by stirring at 60 °C for 0.5 h. The prepared salt has a viscosity at 20 °C of 316 mPa s, a density of 0.9672 g . cm ^-3 and _{a D} ²⁰ of 1.4714. Example 3

300 g of oxyethylated cocosamine (a mixture of fatty amines

C12 to C11 with an average molecular weight of 220) with 25 moles of ethylene oxide and 63 g of stearic acid. The batch was homogenized at 60 °C for 0.5 h to form salts with a melting point of 30 to 31 °C. By dissolving in ethyl alcohol, a solution containing 50% by weight of salt with a viscosity at 20 °C of 9.6 mPa.s, a density of 0.9060 g cm ^-3 and _{a D} ²⁰ = 1.4313 was prepared.

Example 4

300 g of oxyethylated stearylamine with 7 moles of ethylene oxide and 142 g of a technical mixture of fatty acids with the concentration given in Table 2 were introduced into the flask.

Table 2

The batch was homogenized by stirring at 60 °C for 0.5 h. The prepared salt mixture has the appearance of a waxy mass at 20 degrees Celsius with a melting point of 32 to 33 °C and a 50% by weight solution in ethyl alcohol has a viscosity of 16 mPa.s at 20 °C, a density of 0.8842 g.cm ^-3 and _{a D} ²⁰ of 1.4142.

Example 5

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40 g of oxyethylated stearylamine with 20 moles of ethylene oxide were introduced into the flask. Salt preparation procedure as in example 1. Addition of fatty acids, melting point of salts and their properties 50% by mass. solutions in e-

acid (%) by weight ethyl alcohol is listed in table 3, state- -------------------- — measured at 20 °C. stearic 52 4 palmitic 42.3 laurel 1.9 arachnoid 0.7 caprylic 0.1 pentadecanoic acid 0.3 heptadecanoic acid 1.7 caprine 0.3 unidentified 0.3 Table 3 acid weight (g) melting point viscosity n,D ²⁰ density (°C) (mPa . s) (g . cm- ³ ) stearic 9.9 45—46 11.4 0.9041 1.4115 palmitic 8.9 37—38 10.8 0.9054 1.4126 laurel 6.9 33—34 10.2 0.9059 1.4130 Example 6 a large amount of salt was used in the oilseed. Its influence on the properties is stated- Go to the bank submitted by 40 g oxyethyl alcohol given in table 4. of stearylamine as in example 5. For example- Table 4 acid 4.9 7.8 9.8 11.8 14.7 oil (g) melting point 34—35 35—36 35—36 36—37 30—31

(°C)

Equimolar salt, i.e. using 9.8 g of oleic acid, reduces the surface tension of water at 20 °C at a concentration of Ig . Γ' to 39.1 raN . m ^-1 , oxyethylated stearylamine alone to 42.6 mN . m ^-1 . The foaming capacity of these aqueous solutions is 52.8 % when using oxyethylated stearylamine and 3.8 % when using its salt with oleic acid. By dissolving the salt in ethyl alcohol to a content of 50 % by weight, a solution is prepared with a viscosity at 20 degrees Celsius of 10.1 mPa . s, a density of 0.9048 gram . cm ^-3 and _D ²⁰ = 1.4127.

Claims (2)

Acid addition salts of oxyethylated fatty amines with fat acids of formula I (C ₂ H4O) _x H R 1 —COOH. N - R 2 - (C 2 H 10 O 5 H) (I) wherein represents R1 is an alkyl or alkenyl radical of 12 to 18 carbon atoms, R2 is an alkyl or alkenyl radical having 12 to 18 carbon atoms, x-f- y being 5 to 25 and x and y being different from zero.