DE2219557A1 - NEW ANTISTATICS - Google Patents

Description

FARBENFABRIKEN BAYER AG

LEVERK US EN-Bayerwerk 2 0 «, APR.

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New antistatic agents

The invention relates to antistatic agents for synthetic polymers which, by reacting the alcoholates, are more suitable Oxalkylation products with activated halogen carbonamides or sulfonamides with elimination of metal halides develop.

It is known oxalkylation products as the surface resistance to use lowering additives to polymers. The disadvantage of such antistatic agents is their solubility, in water and the resulting washability from formed structures, such as fibers, in aqueous post-treatment processes, such as dyeing or washing. It has now been found that Oxalkylation products become insoluble in water if they have tertiary carbonamide or sulfonamide groups in the molecule. The antistatic properties of these new products even exceed those of the unmodified oxyalkylation products.

The invention accordingly relates to compounds which are sparingly soluble in water and which are suitable as antistatic agents for synthetic polymers the general formula

LeA 14 332

309844/1177

where m means numbers from 1-150,

η stands for the numbers 1 and 2,? ? 1Q S S 7

R is hydrogen or a methyl radical, R is a straight-chain or branched alkyl radical with

1-20 carbon atoms or an aryl radical, X for the radicals 0

It

-C- or -SO ₂ -,

B is an alkylene radical with 1-2 carbon atoms or an arylene radical of the general formula

denotes in which R _{2 is} hydrogen, a lower alkyl radical with 1-6 carbon atoms or fluorine, chlorine or bromine, R, hydrogen, -NH ₂ , -NO ₂ , -CN, -CF ₃ , -Cl or

R R

t r

-SO

2 / ÖV40-CH-CH) ^ A, where

R.

R, R ₁ , X and m have the meaning given above,

0 dd

A stands for the radicals R ₄ -O-, R ₄ -N-, R ₄ -N <, R ₄ -CO-.

RR
0-CH-CH ^ _1n OR ₅ -O-,

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0984W1177

0-CH-CH ^ N- and

RR 0 0

O Ho-CH-CHJJ-OCR ₅ -CO-

where R, R- ,, Rp >> R *, X and m represent the abovementioned radicals, R ^ represents an alkyl radical with 1-30 carbon atoms, an aryl, alkylaryl or arylalkyl radical, R _{5 represents} a straight-chain or branched one Alkylene group with 1-30 carbon atoms and

a straight-chain or branched alkyl radical with 1-20 carbon atoms, an aryl radical or, in the case η ■ = 1, a radical of the general formula

R t

-R ₅ -NXB- (O-CH-CH) ^ - A, where R, R ₁ , R ₅ , A, B ^ X and m have the meanings given above.

These new compounds are produced by the alcoholates of polyether diols from ethylene oxide "or propylene oxide, or of oxyalkylation products, preferably with ethylene oxide, propylene oxide or mixtures of the two reacted alcohols, diols, primary or secondary amines, mono- or dicarboxylic acids of the general formula

"RR

LeA 14 332

3098 4 4/117

where m are numbers from 1-150, η is the numbers 1 and 2,

R is hydrogen or a methyl radical,

M means an alkali metal and

It

A for the radicals R ₄ -O-, R,, _{R 4} -N <, R _{4 -CO-}

R ₄ -N-

R.

R-,

1\

N-X

RR 0-CH-CH) ₅ OR ₅ -O-,

R,

RRR ₄ 0-CH-CH) ₅ N- and

RR OO

^K l R _x -TO V-40-CH-CH) -0-CR _c , -C-0- ^ Λ— / m ο

Ro I

stands in which R and m are the abovementioned radicals, X is the radicals 0

I!

-C- or -SO ₂ -

stands,

R-, a straight-chain or branched alkyl radical with 1-20 carbon atoms or is an aryl radical,

R _{2 is} hydrogen, a lower alkyl radical with 1-6 carbon atoms or a halogen radical such as fluorine, chlorine or bromine,

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S 2213557

Hydrogen, -NH ₂ , -NO ₂ , -CN ^ -CF ₃₁ -Cl or

is, where R, R ₁ , A, X and m have the meaning given above, R ^ is an alkyl radical with 1-30 carbon atoms, an aryl, alkylaryl or arylalkyl radical and R- is a straight-chain or branched alkylene radical with 1- 30 carbon atoms, with inert gas and exclusion of moisture in the temperature range from 0-150 C either in the melt or in an inert solvent with an activated halogen compound with tertiary carbonamide or sulfonamide groups of the general formula

BXN ^
Ύ

0
dd
wherein X is the radicals -C- or -SOp-,

R ₁ denotes a straight-chain or branched alkyl radical with 1-20 carbon atoms or _1% aryl radical, Hal stands for fluorine, chlorine or bromine,

B is an alkylene radical with 1-2 carbon atoms or an arylene radical of the general formula

means where R _{2 is} hydrogen, a lower alkyl

LeA 14 332 - 5 -

309844/1 177

radical with 1-6 carbon atoms or a halogen radical such as fluorine, chlorine or bromine, R, hydrogen, -NH ₂ , -NO ₂ , -CN, -CF ₃ , -Cl or

means, where

R ₁ and X stand for the radicals mentioned above, R is hydrogen or a methyl radical, m is numbers from 1-150 and A. for the radicals R ₄ -O-,

* 4 2 ^X ) NX

R ₄ -N-, R ₄ -NC, R ₄ -CO-, R / _R.

3 R ₂

R-i

R R

T!

(0-CH-CH) -OR ₅ -O-,

R,

^R ]
R-,

- (O-CH-CH) -N- and

R,

RR 0 0
0-CH-CH) -OCR ₅ -CO-, wherein

LeA 14 332

3098 44/1 177

R, Rj, Rp, R ₅ , X and m denote the radicals mentioned above, R. is an alkyl radical with 1-30 carbon atoms, an aryl-j-alkylaryl or arylalkyl radical and R is a straight-chain or branched alkylene radical with 1-30 Carbon atoms and Y is a straight-chain or branched alkyl radical with 1-20 carbon atoms, an aryl radical or a radical of the general formula

R ₁ RR
-R ₅ -NXB- ^ O-CH-CH) -A, where R, 'R ₁ , R ₅ , A, B,

X and m have the meaning given above,

reacted with elimination of alkali halide. The method described above is another subject matter of the present invention.

Examples of polyether diols or oxyalkylation products for the preparation of the new antistatic agents according to the invention are called:

CH ₃

CH

? ■

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3Ö98U / 1 177

H- (O-CH ₂ -CH ₂ - ^ OC-

These polyethers are suitable starting compounds with ethylene or propylene oxide according to known processes by Alkoxylie tion accessible.

As activated halogen compounds with tertiary carbonamide or sulfonamide groups according to the invention, for example the following compounds that can be produced by known processes are in question:

H ²⁵

NO

Cl Cl

Cl Cl

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2213557

O CH, tr τ ·>

Cl- (σ> -CN- (CH ₂ ) ₂ -Ν

N y \

CH, CH, CH, CH,

The types of antistatic where R-, for. -NHp stands, be through catalytic hydrogenation with Raney nickel obtained from the corresponding nitro compounds.

As inert solvents, for example, benzene, toluene, Dioxane, DMF, DMA or N-methylpyrrolidone are used.

Hydrogen, helium or nitrogen can be used as inert gases.

For the preparation of the new compounds according to the invention You can proceed as follows, for example:

In an inert gas atmosphere with exclusion of moisture from a polyether diol or oxyalkylation product corresponding alcoholate produced. That can be done by adding either the equimolecular amount of an alkali metal to the reaction is brought, or the stoichiometrically calculated amount of the alcoholate of a low-boiling alcohol, such as e.g. of the methanol or ethanol, is added and the methanol or the ethanol is removed by vacuum distillation. in the

Le A 14 332 - 9 -

309844/1177

Following this, the alcoholate produced is either in the melt or in an inert solvent such as DMF the activated halogen compound is reacted at temperatures in the range from 0-150 C with elimination of the alkali metal halide. It is advisable to cool the reaction mixture in the event of an exothermic reaction. As soon as the reaction mixture is neutral reacts, the quantitative implementation is finished. The resulting alkali halide is then filtered - ·. severed.

Of course, the compounds of the process according to the invention can also be prepared by adding alcoholates of polyether diols or oxyalkylation products with activated halogen compounds, which have a carbon ester or Have sulfonic ester grouping in the molecule, and then reacts with a secondary amine.

The new compounds are in most cases at room temperature waxy and not crystalline. Their raw tone is colorless to slightly yellow. They are suitable because of their property as an admixture to polymers, in particular to acrylonitrile polymers, considerably reduce their surface resistance, furthermore because of their good compatibility with polymers and finally excellent as antistatic additives because of their poor water solubility.

As examples of the antistatic additives to be used according to the invention are mentioned:

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HCH,

O CH. (CH ₂ -CH ₂ -OJ ₁ J = CH ₂ -CN-

_T / ^C 2

CH ₃ -

CjH

NO,

_T / ^CH 3

CH ₃ - (CH ₂ ) ₁₇

N- | (CH

NO,

Cl Cl

, o> -o- (ch ₂ -ch ₂ -ow (o> -so ₂ -n

. .CH

Cl Cl

/ ^CH 3

, J ₆ -O- (CH ₂ -CH ₂ -O) ^ o] ^XCH 3

TTOo

NO

H ₁₉ C ₉

CH ₃ • CH ₃ O

₃ O- ^ CH ₂ -CH ₂ -O> ϊο {0 ^> -CN-CH ₂ -CH ₂ -N - C-

L (0-

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-H-

98E4 / 1177

it

^Ν0

CH ₃

If

O ti

-0- (CH ₂ -CH ₂ -O) ₅ CH ₂

'CH _x

^H 13 ^C 6

^C 6 ^H 13

In the following examples the parts by weight are related to! the parts by volume such as kilograms to liters.

example 1

71.9 parts by weight of a dry ethoxylated stearyl alcohol (Mn = 719, determined via the OH number) are mixed with 5.4 parts by weight of sodium methylate dissolved in 50 parts by volume of methanol. After removal of the methanol at 70 ⁰ C in vacuum is cooled to 20 C. Then slowly 12.2 parts by weight of N, N-dimethyl-chloroacetamide with cooling and passing over stick

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3098U / 1 1 77

substance is added dropwise so that the temperature does not exceed ^{25 0 C.} After the dropwise addition, the mixture is stirred for a further 30 minutes. One . The sample dispersed in water then shows a pH = 7.1. To remove the common salt, the reaction product is taken up in 250 parts by volume of dry benzene, filtered after the addition of activated charcoal and the benzene is removed again by vacuum distillation. An almost colorless product of the constitution which is liquid at room temperature remains

Pi CH - (CH ₂ ) fi < ³

Yield: 77.2 parts by weight (= 96 % of theory)

Example 2

4.6 parts by weight of sodium are dissolved in 170.6 parts by weight of an anhydrous ethoxylated dodecyl alcohol (Mn = 853, determined via the OH number) while passing nitrogen over it. The alcoholate is dissolved in 350 parts by volume of dry DMF and then 71.9 parts by weight of N-methyl-N-stearyl-chloroacetamide are added in portions, while stirring and passing nitrogen over it, so that the temperature does not exceed 50.degree. After the reaction has ended - a sample dispersed in water has a pH = 7 - the precipitated sodium chloride is filtered off after the addition of Α carbon and the DMF is removed in vacuo. A slightly yellow colored, waxy product of the composition remains. _% .

OCH ₃ . ·

) ₁₇ -CH

Yield: 231 parts by weight (= 98 % of theory)

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309844/1 177

Example 3

146.8 parts by weight of anhydrous oxethylated N-methylstearylamine (Mn = 734, determined via the OH number) are mixed with 10.8 parts by weight of sodium methylate in 50 parts by volume of methanol. After removing the methanol in vacuo at 70 ° C., the alcoholate is dissolved in 300 parts by volume of dry DMF. Under a stream of nitrogen, 52.9 parts by weight of N, N-dimethyl 3-nitro - 4-chloro-benzenesulfonamide was added portionwise such that the temperature does not exceed 50 ⁰ C. The mixture is subsequently stirred at 50 ° C. for 1 hour. Then the neutral solution is freed from the precipitated common salt by filtration after adding Α-charcoal. After removing the DMF by vacuum distillation, 187.6 parts by weight (= 97.5% of theory) of a yellow-colored product of the composition which is liquid at room temperature remain

Example 4

134.2 parts by weight of dehydrated oxethylated isononylphenol (Mn = 671, determined by the OH number) are mixed with 10.8 parts by weight of sodium methylate in 50 parts by volume of methanol while passing nitrogen over it. The methanol is then DMF in vacuo at 60 ⁰ C quantitatively removed and the remaining alcoholate in 250 parts by volume of anhydrous dissolved. 71.5 parts by weight of N, N-dimethyl-penta-chloro-benzene-sulfonamide are added in portions to this solution, while stirring and bubbling over nitrogen, so that a temperature of 70 ° C. is not exceeded. After the exothermic reaction has ended, the mixture is stirred at 70 ^° C. for a further 2 hours. The neutral reacting solution is then excreted after the addition of Α-charcoal

LeA 14 332 - 14 -

309844/1 177

The sodium chloride is separated off by filtration and freed from DMF by vacuum distillation. 195.8 parts by weight remain (= 98.7% theory) of an only slightly yellow colored material of the composition which is not solid at room temperature

pt π

^H 19 ^C 9 ^ ΓΊ

Cl Cl

Example 5

To 113.0 parts by weight of anhydrous ethoxylated 1,6-hexanediol (Mn = 565, determined by the OH number) are added 21.6 parts by weight of sodium methylate in 60 parts by volume of methanol, the methanol is distilled in vacuum quantitatively at 70 C. and added with stirring and passing nitrogen over the 117.0 parts by weight of N, N-diethyl-3-nitro-6-chloro-benzenesulfonamide was added portionwise to that the temperature of 70 ⁰ C is not exceeded. To complete the reaction, stirring is continued for a further 2 hours at 70 ° C. until the reaction mixture reacts neutrally. It is then dissolved in 250 parts by volume of DMF, filtered after adding Α carbon and the DMF removed again in vacuo. The residue is yellow in color, partly solid at room temperature and has the constitution

SO ₀ -N 2

^ (CH ₂ ) ₆ yield: 206.4 parts by weight (= 95.8 % of theory)

LeA 14 332 - 15 -

309844/1 177

Λ *

? 9 1

Example 6

In 105.9 parts by weight of an anhydrous segment polyaddition product from ethylene oxide and propylene oxide (Mn = 1059, determined by the OH number)

flit ΠΤΤ

CH ₃ CH ₃

HO- (CH-CH ₀ -OW (CH ₀ -CH ₀ -O) - (CH ₀ -CH-O) ^ h

4.6 parts by weight of sodium are dissolved at 70 ° C. with exclusion of moisture and oxygen. 45.7 parts by weight of N, N-dimethyl-3-nitro-4-chlorobenzamide are added in portions to the alcoholate while passing nitrogen over it and stirring. The temperature is kept at 70 ⁰ C. To complete the reaction, stirring is continued for 3 hours at 70 ^° C. until the reaction is neutral. The reaction mixture is then dissolved in 300 vol. Parts of DMF, Α carbon is added, the mixture is filtered and the DMF is removed again in vacuo. The yellow colored reaction product

^CH 3

3 y

CH ₀ -Ch-Oh (oVc-N

C. λ / 3 \ / "

is obtained in quantitative yield and is at room temperature not fixed.

For conversion of the nitro groups into the corresponding amino functions of 72.0 parts by weight of the above product Raney nickel atm in 200 parts by volume of DMF with 10 parts by weight under a hydrogen pressure of 40 at 75 ⁰ C for 1 hour hydrogenated. After removing the hydrogenation catalyst by filtration and stripping off the DMF in vacuo, 67.9 parts by weight (= 98.3% of theory) are obtained

an almost colorless reduction product of the constitution: NH _{0 Π} ττ _ru NH ₀

_Π ττ _ru NH _{0 n}

- (O-CH-CH ₀ WO- (CH ₀ -CH ₀ -OWp ₇ (CH ₉ -CH-OWo) CN;

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3 0984W1177

Example 7

A 27 # strength dimethylformamide solution of a polyacrylonitrile copolymer from 94 parts by weight of acrylonitrile, 5 parts by weight of methyl acrylate and 1 part by weight of Methallylsulfonsaurem-Na-Salz with a K value of 87 (according to Fikentscher) the following Antistatic agents added in various amounts:

H ₁₉ C ₉

I!

CH 2 5

As is known, the solutions are dry spun into threads. After air conditioning at 23 ° C and 50% relative humidity the surface resistance of the drawn threads is measured. Then the threads are treated with a 0.5% solution of a Haldels usual detergent washed at 40 ° C. The subsequent measurement of the surface resistance involves drying, and air conditioning ahead.

LeA 14 332 - 17 -

309844/117 7

The results are compiled in Table 1 below. A thread sample without the addition of antistatic serves as a comparison. '

Table 1

Weight -% A. Surface resistance at 23 C and ₁₀ 13 after 5 washes 50 % rel. ₁₀ 13 Weight -% B. . ίο ¹⁰ > 10 ¹³ 10 ¹⁰ Weight -% C. Humidity [IQ 10 ¹⁰ 9. 10 ¹⁰ after 10 washers 10 ¹¹ Weight -% D. after the ver
stretch 10 ¹⁰ 8th . 10 ¹⁰ 10 ¹⁰ Antistatic additive Weight -% E. ίο ¹⁰ 1 . 10 ¹⁰ 8th . 10 ¹⁰ Example 8 *
9 10 ¹¹ 7th 10 ¹⁰ 1.. 10 ¹¹ 6th 1 . 10 ¹¹ 4th 1 . 7th 5. 2. without 2. 10 8th 15th 10 5

Exactly as described in Example 7, the antistatic agents mentioned there are a 27% strength diethylformamide solution of a polyacrylonitrile copolymer from 61.3 parts by weight of acrylonitrile, 37 parts by weight of vinylidene chloride and 1.7 parts by weight of sodium methallyl sulfonic acid with a K value of 80 (according to Fikentscher) added in different amounts. As in example 1 will be the threads are produced using the dry spinning process, the surface resistance is determined and the washing processes are carried out.

The measurement results for the surface resistance as a function of the antistatic additive and the number of washes are shown in Table 2.

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Table 2

Antistatic additive Surface resistance at 23 ⁰ C and 50 % rel.
Humidity ΓΡ3 \
nadh 5 washing after 10 washes after the ver
stretch > 10 ¹³
8th . 10 ¹⁰
6th 10 ¹⁰
3. 10 ¹¹
6th 10 ¹⁰
2. -10 ¹⁰ 1 1 io ¹¹
8th . 10 ^ °
3. 10 ¹¹
• 6. 10 ¹⁰
1 . 10 ¹⁰ without
10 wt -. ° / o A
10 wt% B
5 wt% C
8 wt% D.
15 wt% E. > 10 ¹³
8th . 10 ¹⁰
5. 10 ¹⁰
1 . 10 ¹¹
4th 10 ¹⁰
1 . 10 ¹⁰

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Claims (3)

Claims 1. Containing tertiary carbonamide or sulfonamide groups, for synthetic polymers antistatic compounds of the general formula where m means numbers from 1-150, η stands for the numbers 1 and 2,
R is hydrogen or a methyl radical, R _{1 is} a straight-chain or branched alkyl radical with 1-20 carbon atoms or an aryl radical, 0
dd X stands for the radicals -C- or -SO ₂ -, B an alkylene radical with 1-2 carbon atoms or an arylene radical of the general formula means in which R _{2 is} hydrogen, a lower alkyl radical with 1-6 carbon atoms or a halogen radical such as fluorine, chlorine, bromine or iodine, R, hydrogen, -NH ₂ , -NO ₂ I-CN, -CF ^, -Cl or RR
-S0 ₂ - <^ 0 _) - (0-CH-CH) -A, where LeA 14 332 - 20 - 309844/1177 / i R, R ₁ , X and m have the meaning given above, Ry ₁ 0 A for the radicals R ₄ -O-, R ₄ -N-, R ₄ -NC, R ₄ -CO-, ₄ D-CH-CH) -N and. ^Ln NX Marg RR 0 0 (0-CH-CHj _n -OCR ₅ -CO- where R, R ₁ , R ₂ , R- *, X and m are the abovementioned radicals, R _{4 is} an alkyl radical having 1-30 carbon atoms, an aryl, alkylaryl or arylalkyl radical, R _{5 is} a straight-chain or branched alkylene radical having 1-30 carbon atoms and Y is a straight-chain or branched alkyl radical with 1-20 carbon atoms, an aryl radical or in the case η = 1 is a radical of the general formula LeA 14 332 - 21 - 309844/1 177 R R -R ₅ -NXB- (O-GH-GH) -A is where R, R ₁ , R ₅ , A, B, X and m are as defined above 2. Process for the production of tertiary carbonamide or sulfonamide groups for synthetic polymers Antistatic "active compounds, characterized in that polyether diols or oxyalkylation products are used general formula "R R where m are numbers from 1-150, η stands for the numbers 1 and 2, R is hydrogen or a methyl radical, M means an alkali metal and A for the radicals R - 0-, R ^ -N, R, -Ny R ^ · I! RR
ι t / - <0-CH-CH) _1n OR ₅ -O-, R. R R; ! I I 4 0-CH-CH) -N- and R R- 0 0 -CH-CH) -OCR ₅ -CO- LeA 14 332 - 22 - 30 98 4 Λ / 117? stands, in which R and m denote the radicals mentioned above, X stands for the radicals O, R _{1 is} a straight chain -C- or -SO ₀ - ger C. or a branched alkyl radical with 1-20 carbon atoms or an aryl radical, Rp is hydrogen, a lower alkyl radical with 1-6 carbon atoms or a halogen radical such as fluorine, chlorine or bromine, R-, hydrogen, -MH ₂ , -NO ₂ , -CN , -CF ,, -Cl or RR - ^S0 2 ~ {oV ~ t ° - ^ ^H "^ ^H ) _m ^{A is} »
X where R, R-,, A, X and m have the meaning given above, R ^ is an alkyl radical with 1-30 carbon atoms, an aryl, alkylaryl or _{arylalkyl radical and R 1} - for a straight-chain or branched alkylene radical with 1- Represents 30 carbon atoms; under inert gas and with exclusion of moisture in the temperature range of 0-150 ⁰ C, either in the melt or in an inert solvent with an activated halogen compound having a tertiary carbonamide or sulfonamide group of the general formula HaI-BX-Nf ^x
Y 1! wherein X is the radicals -C-, or -SO ₂ -, R, a straight-chain or branched alkyl radical with 1-20 carbon atoms or an aryl radical, LeA 14 332 - 23 - 309844 / 1-177 Hal stands for fluorine, chlorine or bromine, B is an alkylene radical with 1-2 carbon atoms or an arylene radical of the general formula ^R 3 means where Rp is hydrogen, a lower alkyl radical with 1 ~ 6 carbon atoms or a halogen radical such as fluorine, chlorine or bromine, R, hydrogen, -CN, -CF ₃ , -Cl RR
or -SO ₂ -ZO) - ^ O-CH-CH) ₅ A, where R, and X stands for the radicals mentioned above, R was is hydrogen or a methyl radical, m is numbers from 1-150 and A for the radicals R ^ -O-, R ^ -N-, R ^ -C-O-, R, LeA 14 332 3098U / 1177 and RR 0 0 '-CH-CH) ^ OCR ₅ -CO- stands, where R, R ^, R ₂ , R ,, X and m are the above-mentioned radicals, Rr is an alkyl radical with 1-30 carbon atoms, an aryl, alkylaryl or arylalkyl radical and Rc is a straight-chain or branched alkylene radical with 1- 30 carbon atoms and Y is a straight-chain or branched alkyl radical with 1-. 20 carbon atoms, an aryl radical or a radical of general formula R R f I -R ₅ -NXBK) -CH-CH) ₅ A, wherein R, R-,, R ₅ , A, B, X and m have the meaning given above, be reacted with elimination of alkyl halide. 3. Use of compounds of the general formula RR - LeA 14 332 - 25 - 3098U / 1177 where m means numbers from 1-150, η stands for the numbers 1 and 2, R is hydrogen or a methyl radical, R, a straight-chain or branched alkyl radical with 1-20 carbon atoms or an aryl radical, X for the remainders 0 tf -C- or -SO ₂ -, B is an alkylene radical with 1-2 carbon atoms or an arylene radical of the general formula where Rp is hydrogen, a lower alkyl radical with 1-6 carbon atoms or a halogen radical such as fluorine, chlorine, bromine or iodine, R-, hydrogen, - RR is -NO ₂ , -CN, -CF ^, -Cl or -SO ₂ -ZqV- (O-CH-CH ^ A, where R-, R, R ₁ , X and m are those mentioned above Have meaning 0 ff A for the radicals R ^ -O-, R ^ -N, R ^ -Νς, R ^ -C-O-, i \ N-X. ? 2 r R. / I. 1 ifl R ₂ R, LeA 14 332 - 26 - 309844/1177 RRR /,
«·» Τ ^{1 and} R-, Rp _D ) NX _T RR OO R3- ^ O) - (0-CH-CH ^ OCR ₅ -CO- where R, R ₁ , Rp, R ^, X and m are the abovementioned radicals, R ^ is an alkyl radical having 1-30 carbon atoms, an aryl, alkylaryl or arylalkyl radical and Rc is a straight-chain or branched alkylene radical with 1-30 carbon atoms and Y is a straight-chain or branched alkyl radical with 1-20 carbon atoms, an aryl radical or, if η = 1, a radical of the general formula R ₁ RR -R ₅ -NXB-fO-CH-CH -) ^ A, wherein R, R ^, R ₅ , A, B, X and m have the meaning given above, in amounts of 1-20 wt .-%, based on the total mixture as Antistatic agents for acrylonitrile polymers with a minimum content of 60% by weight acrylonitrile. LeA 14 332 - 27 - 309844/1177