CS245884B1 - Surface-active polyamine esters - Google Patents

Abstract

The invention describes novel surface-active polyaminoesters based on diethylenetriamine and triethylenetetramine. They can be prepared by reacting C4—C8 alkyl acrylates with an amine followed by neutralization with water-soluble acids such as acetic acid. The compounds are suitable for the processing of glass fibers.

Description

The invention describes novel surface-active polyamine esters based on diethylenetriamine and triethylenetetramine. They can be prepared by treating the amine with C ₄ -C ₈ alkyl acrylates followed by neutralization with water-soluble acids such as acetic.

The compounds are suitable for processing glass fibers.

The present invention relates to surface-active polyamine esters suitable for the processing and treatment of glass fibers.

Aliphatic polyamine based surfactants are known. Usually, Sia are prepared by condensation, amidation of fatty acids with polyamines such as diethylenetriamine, triethylenetetramine followed by solubilization of the water-soluble acids, of which acetic acid is of industrial importance. In order to obtain the light products, the reaction is carried out in an inert gas atmosphere, optionally by azeotropic processes at temperatures above 150 ° C, usually in the presence of catalysts. Substantially more preferred is a process using glycidyl esters of fatty acids in the synthesis. The main disadvantage of this process is that glycidyl esters of fatty acids are not commercially available and, last but not least, lack of essential fatty acids.

The disadvantages associated with the energy consumption, equipment, and availability of raw materials are eliminated in the manufacture of the surfactant compounds of the invention. The invention provides surfactant polyamine esters of the formula k [R 1 NH (CH 2 CH 2 NH) _y CH ₂ CH ₂ NH 2] wherein k represents an integer, 1 to 4, n an integer of 1, 2 or 3, y an integer of 1 or 2,

R ₍ radical of the structure · —CH ₂ CH ₂ COOR 3,

R, is H or R · _T,

_{R: t} alkyl of 4-8 carbon atoms and x an anion of a strong organic or inorganic acid ·.

The preparation of these compounds can be carried out by reacting diethylenetriamine or triethylene amine to the corresponding linear or branched alkyl alkyl acrylates such as, n-butyl, isobutyl, pentyl, n-octyl, 2-ethylhexyl in a molar ratio of 1: 1 to 2 followed by ineutralization , phosphoric, acetic and the like.

The advantage of this procedure is the ease of availability

- x n

the use of 2-ethylhexyl acrylate is of utmost importance not only for its easy availability but also for health reasons. For the eyes it is without danger and its toxicity is just right, it dies with glycerin, for the skin its action is comparable with sodium. Due to the fact that the addition proceeds at a sufficient rate up to 100 ° C and no by-products are released during the reaction, their production is also feasible in enterprises not directly involved in chemical production.

The invention is further illustrated by way of example.

Example 1

Preparation of polyaminoesters of formula

C _and H ₅ © Θ

GH3 (CH 2] ₃ C H CH ₂ NH ₂ OOCCH9CH (CH9CH NH ₂ j _{s CH2 CH2} NH2. OOCCH3

100 g of 2-ethylhexyl acrylate and the corresponding polyamine were charged to a flask equipped with heating, stirrer and thermometer. The batch was kept at 80 ° C for 2 h. When the temperature dropped to 30 ° C, it was neutralized with acetic acid. The amounts of amine and acid are given in Table 1.

Table, 1 amine batch (g) acetic acid (g) diethylenetriamine triethylenetetramine

56.0 32.6

63.5 29.7

The properties of the prepared polyamine esters are shown in Table 2 and were determined at 20 ° C.

Table 2 y mol. weight viscosity (g.mol ^{-1 13} ) (mPa.s)

347.49

390.53

Ud ²⁰

1018

1021 density (kg. M ^-3 )

1.4741

1.4808

7196

292

The effect of diethylene-water-based polyamine ester at 20 ° C is shown in Table 3 of triamine on the reduction of surface tension

Table 3

gl ^_1 0.5 2 4 6 mN.m ^-1 31.3

28.3

28.3

28.3

Example 2

Preparation of the polyamine ester of formula

CH ₃ (CH ₂ j ₃ OOCC2H4NHC ₂ H ₄ NHC ₂ H ₄ H4NHC ₃ NHC ₂ HiCo (CH _{2) 3} CH _third H ₃ PO ₄

To the flask was charged 60 g of butyl acrylate and 34.2 g of triethylenetetramine. The batch was held at 90 ° C for 1.5 h. After the temperature dropped to 30 ° C, 27 g of 85% phosphoric acid were neutralized and diluted with water to 50% salt solution. Prepared polyamime ester having a molecular weight of 500.53 g. . m ^{-1 -1} has a density of 1124 kg at 20 ° C. nv ^{: 1} and a viscosity of 58.2 mPa. with.

Example 3 Θ R3 [R 3 OOCCH 2 CH 2 NHH 2 CH 2] 2NH. OOCCH3

100 g of the appropriate alkyl acrylate and diethylenetriamine were charged to the flask. The batch was held at 90 ° C for 1.5 h. After the temperature dropped to 3.0 ° C, it was neutralized with acetic acid. Amine amounts, acids and properties are shown in Table 4.

Preparation of polyamine ester of formula:

Table 4 Moleic acid. mass n _D ²⁰ (g) (g.mol ^-1 ) amine (g)

n-butyl 40.2 23.4 419.55 1.4276 n-pentyl 36.3 21.2 447.55 1,4700 2-ethylhexyl 28.0 16.3 531.77 1.4682

The effect of the 2-ethylhexyl acrylate-based polyamine ester on the reduction of the surface water saver at 20 ° C is shown in Table 5.

Table 5

gl ^-1 0.2 0.5 14 niN.nr ¹ 32.3 30.3

Example 4

The polyamine ester of 2-ethylhexyl acrylate, diethylenetriamine and acetic acid base prepared by the procedure of Example 3 was used to treat the slanted fibers. his

29,3 28,2 The additive reduced the flood dust content of glass fibers, as measured by the weight of the drift, from 15 to 20 mg / kg to 5 to 10 mg / kg, thus improving the working environment in the processing of the fibers.

Claims (2)

245884 SUBJECT MATTER 1. Surfactant polyamino esters of the general formula k © [R1NH (CH2CH2NH) yCH2CH2NHR2] kn © - x where k is an integer of 1 to 4, n all is 1, 2 or 3, y is an integer * 1 or 2, Rj is a structure residue -CH 2 CH 2 COOR 3, R 2 is hydrogen or R b R 3 is an alkyl of 4 to 8 carbon atoms and an anton of an organic or inorganic acid. 2. A surfactant polyamine ester of the formula-C8-R10-OOCCH3CH2NHCH2CH2NHCH2CH2NHCH2CH2COOR3. OOCCH 2 wherein R 1 is 2-ethylhexyl. Severografia, n. P., Závod 7, Most Price 2,40 Kcs