DE2027613A1 - New ester amide salts and their use as antistatic preparations - Google Patents

Description

Our symbols: O.Z. 26 805 Rt / Fe 6700 Ludwigshafen, June 4th, 1970

New ester amide salts and their use as antistatic Spin finish

The present invention relates to new salts of long chain Esteramides and their use as antistatic preparation agents for textile fibers, especially for those which contains cellulose or regenerated cellulose.

It is known that many structures made of macromolecular substances in the processing or use of disturbing electrostatic Tend to charge. This tendency is particularly common in structures made of fully synthetic macromolecular structures Fabrics; however, it is not limited to these, but also occurs with fibers made from cellulose esters and even with such made of cellulose, regenerated cellulose, silk, wool and other plant and animal substances as soon as the in primarily dependent on the relative humidity The moisture content of these fibers falls below a certain limit. This limit value differs from fiber type to fiber type.

Antistatic to the on fully synthetic macromolecular fabrics Active compounds include cation-active, anion-active | and non-ionic compounds such as the tertiary ones or quaternary salts of long-chain alkyl compounds of nitrogen and sulfur, phosphoric acid partial ester salts of fatty alcohols or their oxethylates as well as oxethylated fatty acids, fatty alcohols, etc.

All of these antistatic agents are now found to be either no or minimal electrical improvement Cause conductivity in regenerated cellulose fibers, d. H. that their antistatic effectiveness on these fibers is markedly poor. Fibers or threads made of regenerated

179/69 '-2-

1 0986 1/1911

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In normal climates (65 $> rel. humidity, 20 to 25 ⁰ G), cellulose, ie rayon and rayon, has only a slight tendency to charge; the conductivity is 0.5. 10 i ο However, disruptive electrostatic charges occur when the relative humidity drops to values below 50 #; the conductivity decreases by a power of ten, as can be seen from the following values.

Material: unprepared rayon; Cotton type 40 / 1.5

relative humidity in <fo (25 °) electrical conductivity in 10 ¹⁰ 'i

27 500

47. 6.0

65 0.05

Although an optimum moisture eingehal _A can be ten in the rayon mills, which are equipped with air conditioning, yet electrostatic also charges occur when high-speed spinning devices are used "The emerging high distortion and frictional forces increase in temperature in a short-distance limited zone in the immediate vicinity of the fiber cylinder causes a local reduction in the relative humidity and thus leads to an increase in the electrical resistance.

It must therefore be made of an antistatic, which should also be useful for regenerated cellulose, that its presence on the textile material at low humidity increases the conductivity approximately to the value that Has regenerated cellulose in a normal climate, ie. so the

10 1
Conductivity of 500. 10 sr by 3 - 4 powers of ten

JL

increases. This condition is not met by the above-mentioned known antistatic agents.

New compounds have now been found which meet the requirement mentioned and which are therefore not only based on fully synthetic ones macromolecular substances, on cellulose esters and on non-cellulosic native dyes, but also have an antistatic effect on cellulose and regenerated cellulose.

10 9 8 5 1/19 11 -3-

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2 027613 The new compounds correspond to the general formula

0 0 0
JR-GXR ^ -YOR ^ -C-OJ ^{θ M} (i),

in which R is an aliphatic hydrocarbon radical with 11 to 21 carbon atoms, of the radicals X and Y one

4 2
-0-, the other RR is a radical of the formula -G _n H _2n - or

-Έ-,
3
-GoHz-OO ₉ H.-, R a divalent hydrocarbon radical with 2 to 6 carbon atoms, R a hydrogen atom or an alkyl radical with 1 to 4 carbon atoms, η an integer from 2 to 4 and M * a proton, an alkali metal ion or an unsubstituted one or substituted ammonium ion.

For commercial reasons, especially potassium and, in particular, sodium ions come into consideration as alkali metal ions M. Substances of the formula I in which M * are ammonium ions have proven to be particularly advantageous. A preferred group of ammonium ions Μ ^Φ corresponds to the general formula

R ⁶

R ⁵ -HR ⁷ (II) R ⁸

■ 5 ■
In this formula, R denotes an alkyl group with 1 to 3 carbon atoms or preferably a hydrogen atom, optionally substituted by -OH, R denotes a hydrogen atom or an aliphatic hydrocarbon group optionally substituted by -OH with 1 to 22 carbon atoms, preferably an alkyl or alkenyl group with 12 to 18 Carbon-

7th
atoms, R is a hydrogen atom, an optionally substituted with -OH or -NH «alkyl radical with 1 to 3 carbon atoms or a radical of the formula - ( ^G _m ^H 2m ~ °) ~ ^H ' ^{in äer m} an integer from 2 to 4 and ρ is an integer from 2 to 20

8th
represents, and R represents a hydrogen atom, an optionally substituted by -OH alkyl radical having 1 to 3 carbon atoms or a radical of the formula - (C _1n H ₂ -O) -H, in which m is an integer from 2 to 4 and q is an integer Represents number from 2 to 20,

-4-109851 / 1911

-4- O.Z. 26 805

Another group of ammonium ions M *, which may be contained in the substances of the formula I, derives from alkylene or polyalkylenepolyamines from the fact that their basic Nitrogen atoms are acylated except for at least one with longer-chain carboxylic acid residues.

The new compounds of formula 1 can be obtained by processes known per se, for example by adding a natural or synthetic, saturated or unsaturated fatty acid with 12 to 22 carbon atoms, such as lauric, myristic, Palmitic, stearic, behenic, oleic, erucic, linoleic or linolenic acid, with an oxyalkylamine such as xthanolamine, N-methylethanolamine, N-propylethanolamine, propanolamine, butanolamine or aminodiglycol in a molar ratio of 1: 1 »around Aaid and / or ester, the intermediate product of no free hydroxyl or amino group in a molar ratio of 1: 1 with a dioarboxylic acid anhydride, such as succinic acid, glutaric acid, maleic acid, 1,2,5,6-TetrahydiOphthalic acid or phthalic anhydride and, if desired, the remaining free carboxyl group of the product formed wholly or partially neutralized with a base. Suitable bases for this are, for example, sodium or potassium hydroxide, ammonia, mono-, di-, trimethyl- or -äthyl-, -propyl- or -butylamine, ethyl-propylamine or the corresponding aminoalkyl or oxalkylamine compounds; also stearyl, oleyl, coconut oil, palm kernel oil or their N-substituted derivatives such as dimethylstearylamine, dimethylpalrakernfettamine and oxethylation products of oleyl, Stearyl and palm kernel fatty amine, furthermore basic reacting Uraa ions products of C ₁₂ "" ^C 22 ~ ^ ^e ** ^{98luren m1} "* polyamines, such as ethylene, propylene, butylenediamine, diethylene, dipropylene, dibutylenetriaroin, triethylene or tripropylenetetramine in such molar ratios that another baaiiob.ee N-equivalent is present, and finally quaternary ammonium hydroxides from these amino compounds.

At the first stage of the process, Je arises. according to the working conditions, especially the reaction temperature, and depending after the starting components either predominantly the amide egg predominantly the prayer or an oeminch of both.

109851/1911

COPY. "° -" BAD ORiGiNAL

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Because of their properties described above, the compounds of the formula I can be subjected to any desired antistatic treatment Surfaces, for example those of plates, foils and other shaped bodies, and in particular used as antistatic preparations for textile fiber material of any type will. Examples of textile fiber material include: threads, fibers, yarns, woven fabrics, knitted fabrics, tufts and wadding. she The structures mentioned can, for example, be made from polyamides or acrylonitrile polymers. Vinyl chloride or vinylidene chloride polymers, polyurethanes, linear polyesters, cellulose esters, consist of silk, wool or other vegetable or animal materials; particularly emphasized are structures from Cellulose or Regeratoellulose.

Since the compounds of formula 1 are very or less easily dispersible in water, they can, for example, directly be applied in the form of their aqueous preparations to the surfaces to be treated, for example by spraying on, dipping, brushing on or pouring on. In some Cases is the use of a suitable commercially available one Emulsifiers are required to obtain stable aqueous preparations, but the substances of the formula I can often be used Distribute in water without using auxiliary materials.

The compounds of formula I react in aqueous solution, if the cation contains a long-chain Al Icy Ire at, amphoteric, d. H. in acidic medium predominates the catlonia, in an alkaline medium the anionic effect. BE optimal and a reaction tailored to the respective purpose can be set by the degree of neutralization. So it did when treating textile fibers that contain or consist of cellulose or regenerated cellulose, goose Especially proven to use mixtures au, dit at least contain a free acid of the formula I and at least one salt of the formula I, especially those mixtures which contain at least a Sals of the formula I with a long-chain cation, in particular with a cation carrying 12 to 16 carbon atoms in a chain. In general, in order to avoid mixtures in which acid and salt

_copY 109851/1911 - «- ■

BATH ORIGINAL

-6- 'O.Z. 26 805

Formula I have the same AmIn, dool * iat daa no condition for effectiveness. The free acids can also through the general formula

0 0 0

r'-c-x-r-T- (Mr-G-OH (in)

are reproduced, in which the variables have the same meaning as in formula I. The mixtures are obtained, for example, in a simple manner by the in the preparation Only some of the acids of the formula III that are formed are shown below the salsen of formula I neutralized. Such mixtures have a particularly strong antistatic effect on cellulose and regenerated cellulose.

Most of the compounds of formula I have a pronounced one Avivage effect, d. H. the textile material treated with these compounds is soft and smooth, so that in addition to the antistatic Equipment is accompanied by a significant upgrade. These This fact is of particular importance when using the compounds according to the invention as a cellulose fiber paratlons agent. Sine Spun rayon treated with the compounds can be broken down without the use of large amounts of known preparations the basis of fat bodies even at low relative humidity on high-speed spinning and mixing units process without electrostatic «charging phenomena see below «Own.

The compounds according to the invention are not a further important property which is necessary for a preparation agent of is of eminent importance, namely the corrosion-inhibiting Effect.

They also have the advantage that they are clearly soluble in mineral oils such as those used for the production of spin finishes and winding oils, if necessary with use of waste from to BU £ 10, calculated on the amount of connections of the Formula I, on solubilizers, such as fatty alcohols, fatty acids or their Oxäthyllerunßsprodukte.

109851/191 1 ~ ⁷ ~

COPY:. .ί, BAD ORIGINAt-

- O.Z. 26 805

The compounds of the formula I have an excellent emulsifying power for the production of spinning finishes commonly used white and paraffin oils, so that these oils represent self-emulsifying formulations by adding those compounds in amounts of 20 to 30 *, based on the weight of the oil component Able to form extremely stable aqueous emulsions, the application of which on textile materials leads to excellent antistatic effects.

example 1

1 mol of a technical, saturated fatty acid (essentially C ₁₂ to C ₁₈ , average chain length C 16) is reacted with 1 mol of N-methylethanolamine at 150 to 155 C under nitrogen. After θ to 9 hours, the reaction water is distilled off and a titer of 0.7 Ue 1.0 ml ^ sodium hydroxide solution per gram in alcohol (phenolphthalein) is reached.

In the resulting fatty acid-N-methyläthanolamid the equimolar amount of powdered succinic anhydride is added in portions under nitrogen at 60 to 70 ⁰ C. After 3 stUndigem Hachrtthren at 60 bia 70 ⁰ C the succinic anhydride is dissolved and reacted. Titer in alcohol (phenolphthalein) 2.7 to 2.8 ml j sodium hydroxide solution per gram.

From the Bernsteinsäurehalbester the salt is prepared by stirring at 40 to 50 ⁰ C with the amount äqulraolaren Dimethylpalmkernfettamin. Yellowish *, oily liquid that dissolves in water with a pH of 5-6.

The reaction product is Sheet 10 $ oleic acid to improve stability to the aqueous treatment liquors.

With 2 g of this mixture per liter of aqueous solution containing sit a pH of 6 is treated rayon old • Ines titer of 1.7 dtex and 40 mm Sohnittlänge 10 minutes at 45 ⁰ C, it is squeezed to a 100 i * Restfeuohte, and dry them at 80 to 100 ⁰ O. lfaoh conditioning in an atmosphere τοπ 27 to 29 i » rel. Humidity and a temperature of 22 to 24 ⁰ C, the treated material has the electro-conductive

10 9 8 51/1911 ■ -β-

'f rjDOPY BAD ORIGINAL

-8- O.Z. 2β 805

10 1
speed 0.26. 10 q , an untreated Paser sample in the Ve: '

about this 280. 10 ¹⁰ A.

The linear rate of corrosion "when exposed to the aqueous solution of the reaction product described above on test steel boiler plate H 1, material no. 10 081, DIN 17 007- is 0.0047 mm / year; the approach to the solution the water used caused a rate of 0.07 mm / year.

Example 2

30 parts by weight of the reaction product described in example ¹ 1, including the added 10% oleic acid with 70 parts by weight of a mineral oil having the following characteristics (Somentor S 28)

Density at 20 ⁰ O: 0.825

Flash point: 135 ⁰ O Pour point: -20 ⁰ O viscosity
at 20 C: ⁰ E: 1.4

mixed and this mixture converted into a 10 fi ige emulsion with cold water. The emulsion is still completely homogeneous at room temperature after 14 days in the standing test, ie there is no creaming or change in appearance.

Treating polyamide strands with a 1 'follow emulsion which are prepared by simple dilution of the above 10 Taigen emulsion with cold water, by dipping, spin-coated onto 70 $ Restfeuohte and dried at 80 to 100 ⁰ O. If the electrical conductivity of the sample at $ 28> rel. humidity and 23 ⁰ O 9. 10 ¹⁰ ^, while the untreated starting material has a value of more than 1,000. 10 ¹⁰ X (measuring limit).

The threads treated in the manner described above are characterized by high surface smoothness and a soft, pliable one Handle off; the running properties during further processing, such as rewinding, twisting and knitting are considerably improved compared to unprepared threads; electrical charging occurs not on. 10 9851/1911 -9-

-9- O.Z. 26 805

20276 7

The linear rate of corrosion when exposed to the aqueous Solution of the reaction product described above on test steel boiler plate H 1, material no. 10 081, DIN 17 007 is 0.00032 mm / year; the water used to make up the "" solution produced a rate of 0.07 mm / year.

Example 5

Polyacrylonitrile fibers of the wool type with a sonitt length of 60 mm and a fineness of 3.3 dtex are prepared with 3 g / l of the compounds described in Example 1 in the manner described there. After centrifuging at 50 i> residual moisture and drying at 80 ⁰ O results in a fiber material whose electrical conductivity fi rel at 28th Humidity and 23 ⁰ O

10 1

0.4. 10 = k compared to the unprepared material

400 10 ¹⁰ - is ο

Example 4

1 mole of tech. Oleic acid is reacted with 1 mol of N-methylethanolamine at 145 to 150 ^{0 O under nitrogen.} After about 1.5 hours, the reaction water is distilled off and reached a titer of from 0.9 to 1.0 ml per gram j _Q hydroxide solution in alcohol (Phenolphthaiein).

In the resulting oleic acid-N-methyläthanolamid (crude product), the equimolar amount of powdered succinic anhydride is added in portions under nitrogen at 50 to 60 ⁰ O. After 10 hours of stirring at 60 to 70 ⁰ O, the reaction is complete. Titer in alcohol (phenolphthalein) 2.3-2.4 ml j sodium hydroxide solution per gram.

The succinic acid half-ester is made by stirring with the equimolar amount
salt made.

equimolar amount of stearylamine at 50 to 70 ⁰ O the stearylamine

Spun rayon of the cotton type (40 mm, 1.7 dtex) is treated in a known manner with an aqueous solution containing 2 g of the aforementioned compound per liter; results after centrifuging at 100 i> residual moisture and drying at 80 to 100 ⁰ O

-10-10 9851/1911

-10- O.Z. 26 805

a flake whose electrical conductivity is 27 # rel. humidity and 23 ⁰ G 0.44. Is 10 ° ^; the unprepared comparison sample, on the other hand, shows a value of 400. 10 ¹⁰ ^.

The linear rate of corrosion upon exposure to the aqueous solution of the reaction product described above Test steel boiler plate H 1, material No. 10 081, DIN 17 007 is 0.023 mm / year; the water used to make up the solution produced a rate of 0.07 mm / year.

Example 5

1 mol of oleic acid with 1 mole of N-methylethanolamine, and then with the amide content ($ 86>) amount of maleic anhydride (0.86 mol) to calculated. To neutralize the acidic ester formed, oleylamine + 4 ÄO is used and so much of this base is used until the aqueous solution of the reaction product has a value of 4. Otherwise one works according to the information in Example 4. A cellulose flake which was prepared under the conditions described in Example 4 with the above-described compound has an electrical conductivity of 27 $> rel. Humidity and 23 ⁰ O of 0.055. 10 ^ r on, the untreated comparative sample 400. 10 ¹⁰ 1.

The linear rate of corrosion when exposed to the aqueous Solution of the reaction product described above on test steel boiler plate H 1, material no. * 10 081, DIN 17 007 is 0.004 mm / year; the water used to make up the solution produced a rate of 0.07 mm / year.

Examples 6 to 20

According to the following general rule, those in the table 1 with "A" to "N" designated compounds or mixtures of compounds of the formula I are prepared.

1 . Level (method c *)

1 mol of fatty acid (a) is reacted with 1 mol of amino alcohol (b) ^{at 145 to 150 ° C. under nitrogen.} After 10 to 15 hours

109851/1911 " ¹¹ "

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all the water of reaction is distilled off and a pus of 0.9 - 1.0 ml of n / 10 NaOH per g of product, in ethanol against Phenolphthalein titrated, achieved.

1st stage (method ß)

1 mol of fatty acid (a) is ^{reacted with 1.2 to 1.5 mol of amino alcohol (b) at 145 "to 150 °} C. under nitrogen. The titer is 0.9-1.0 ml of n / 10 NaOH each g of product is already reached after 7 to 12 hours The excess amino alcohol is distilled off under reduced pressure, finally at 125 0/5 torr.

2nd stage

The product from stage 1 is mixed with the equimolar amount of dicarboxylic acid anhydride (c) at 50 to 80 ° C. with stirring in a nitrogen atmosphere; after stirring the mixture for 6 to 10 hours at 70 to 90 ^° C., the reaction to form the compound of the formula III has ended. The free acids obtained have the titre indicated in column (d) of table 1. It is determined in alcoholic solution with In-NaOH against phenolphthalein and expressed in ml Tn-NaOH per g substance.

3rd stage

1 mole of compound of formula III is melted and under The molar amount of base (f) indicated in column (e) is gradually added to stirring. It occurs depending on the molar ratio complete or partial neutralization of substance of formula III to base (f).

The products A to N produced in this way were partly alone, partly mixed with additives in distilled water to form emulsions with a content of 10% by weight of non-aqueous Components emulsified. The emulsions were then application technology checked. The results are summarized in the table. The following is explained in detail:

Column g: Here are the products of formula I used denoted by the symbols used in Table 1. "T" means Parts by weight in cases where the products are

109851/1 9t 1 ~ ¹² ~

-12- O.Z. 26 805

were used together with additives.

Columns h and i: The symbols given in these columns have the following meanings?

"T." = X parts by weight "0" = oleic acid

"R" = adduct of 1 mole of castor oil and 40 moles of ethylene oxide

(ipti _ mineral oil with the key figures given in example 2

"S" = mineral oil with the following key figures (ondina oil 1): density at 20 ⁰ G 0.845 flash point 185 ⁰ G

otockpunkt -37 ⁰ G · ·

Viscosity at 20 ⁰ G [ ⁰ EJ 5.0

n _D 1.466

Column k; Resistances of the 10% emulsions mentioned above of the products of the formula I or the mixtures of these and the additives. Mean:

"very good" = ^{none after standing at 20 '0} G for 14 days

Creaming After 14 days of creaming.

"good" = after 14 days of stelae at 20 ⁰ G only low

Column 1: Here are values for the linear corrosion rate specified in mm / year according to DIN 17 007, which is the result of the action of dilute aqueous emulsions of the products or Mixtures on test steel boiler plate H 1, material no. 10 081 were found. The concentration of the emulsions tested is added in brackets. The water used to make up the emulsions causes a linear corrosion rate of 0.07 mm / year.

"n.b." = not determined.

Columns m, η and o: Here 3 are values for the electrical conductivity of cellulose polyacrylonitrile and polyamide fibers before and after their treatment with aqueous emulsions of the products

109851/1911 ~ ¹³ ~

-13- O.Z. 26 805 '

or mixtures according to columns g, h and i. The values were obtained after conditioning the untreated fibers or the fibers treated as indicated below in an atmosphere of 27 to 28 % relative humidity and 23 to 24 ^° C.

10 1

certainly. You are in 10. ^ l expressed.

• Si.

The fibers were treated as follows: rayon; Rayon floc of fibers of 1.7 dtex and 40 mm cut length is treated for 10 minutes at 45 ⁰ O with an aqueous emulsion containing 0.2 $ active ingredient content, has squeezed to 100% residual moisture content and dried at 80 to 100 ⁰ G.

Polyacrylonitrile; Fibers of the wool type of 3.3 dtex and 60 mm cut length will be treated for 10 minutes at ^"0 45 G with an aqueous emulsion containing 0.3 # active ingredient content, has spun down to 50 fi residual moisture content and dried at 80 G.

Polyamide: filament in a strand form is treated at 20 ⁰ G continuously by dipping with a 5 i ° agents containing aqueous emulsion such that a 20 $ strength by weight wet pickup results. The impregnated material is dried at 80 to 100 ⁰ G.

-14- 10985 Wl 9 1 1

product
the For
mel I

D.
E.

1st stage

Stearic acid

Oleic acid

' Il ti

technical fatty acid C ₁₉ -C ₁₈ (avg.
Chain length

⁰ )

Table 1

2nd stage

1-amino-2- (2-hydroxyethoxy) ethane

3-aminopropanol

Ethanolamine

N-methylethanolamine

2-amino-2-methyl-propa-

Isopropanolamine

2- (tert-butylamino) ethanol

N-methylethanolamine

2-aminobuta-

Succinic anhydride

Maleic acid app.

Succinic anhydride

1,2,5,6-tetrahydrophthalic acid anhydride

Bernsteins.-anh.

Phthalic acid app.

G-Iu tar sau reanh.
Maleic acid app.

Succinic anhydride

Il
Ii

Maleic acid app.

2.2-2.4

2.0-2.3 2.3-2.4

2.1

2.3-2.4 2.3-2.4

2.2-2.4

2.1-2.4 2.5-2.7

2.7-2.9

• I

2.8

2.7-2.8

3rd stage

Dirnethyl palm kernel fatty amine

NaOH

Adduct of 1 mole of oleylamine and 4 moles of ethylene oxide, dimethyl palm kernel fatty amine, and stearyl amine

Whore thylpalmkern fe ttamin

NH_ 3-Amino-1-ethylaminopropane

Dirnethyl palm kernel fatty amine

NaOH

Adduct of 1 mole of stearyl- ¹ ^?

amine and 9 moles of ethylene oxide ⁰ ^

NJ triethanolamine ^ nro

Table 2

example 100 Product dei
Formula I.
G - 10 H additions
i - P. Persistence in
emulsion
k Lin. Corrosion
speed
1 Electr.
Rayon
m Conductivity 10
Polyacrylonitrile
η 1_
polyamide
O 100 A. 20th - - - - 280-400 400 1000 untreated A. - 257 T. very good 0.0093 (0.26) 0.12 n.b. 1 * 5 6th 100 T. B. T. 0 - P. Well , 0.0012 (l, 0 #) n.b. n.b. 12th . 7th T. C. T. R. - Well n.b. 0.02 0.15 n.b. 8th D. - 233 d. very good 0.035 (0.2 #) 0.07 n.b. n.b. 9 100 T. E. 10 - - Well n.b. n.b. n.b. 0.5 O
CO 10 100 P. 10 - - Well 0.0074 (0.2 #) 0.95 0.38 n.b. 00
CJi 11 G - - good to very good 0.015 (0.2 #) 0.14 n.b. n.b. 12th 100 T, H T. - S. Well n.b. 0.07 n.b. n.b. 13th T. I. T. R. - Well n.b. n.b. 0.7 n.b. co
—Λ 14th K - 233 d. Well 0.0027 (0.2 #) 0.06 0.25 n.b. _i 15th 100 T. L. 10 - - 0 Well 0.005 (1.05g) n.b. n.b. 0.2 16 M. - very good n.b. 0.27 n.b. n.b. ! 7 M. - 10 d. Well n.b. n.b. 0.09 n.b. 18th T. N T. - Well n.b. n.b. n.b. 2.4 19th - very good 0.0087 (0.2 #) 0.36 0.47 n.b. 20th

-16- O.Z. 2β 805

The threads treated as specified were characterized by high surface smoothness and a soft, pliable G-riff the end; the running properties during further processing by rewinding, twisting and knitting were considerably improved compared to those of the untreated materials and also under Under unfavorable conditions, no disruptive electrical charges could be detected.

-17- 1098 51/1911

Claims (4)

Claims in which R is an aliphatic hydrocarbon radical with 11 to 21 carbon atoms, of the radicals X and Ύ one -0-, the other RR a radical of the formula - ⁰ ^ p _n - or-Gg ^ -O-OpH.-, R a divalent hydrocarbon- remainder with 2 to 6 carbon atoms, R ^ a hydrogen atom or an Al, kyl radical with 1 to 4 carbon atoms, η an integer from 2 to 4 and M * a proton, an alkali metal ion or mean an unsubstituted or substituted ammonium ion. 2. Use of a compound according to claim 1 or a mixture of several such compounds for the antistatic treatment of surfaces. ■ 3. Use of a compound according to claim 1 or one Mixture of several such compounds as an antistatic preparation agent for textiles: lasergu%. 4. Use of a mixture of compounds according to spoke 1, the at least one free acid of formula 1 and at least a salt of the formula I contains * as an antistatic preparation agent for textile fibers, the gelulose or Contains or consists of regenerated cellulose * Bardic aniline & soda labrife AS