DE2315298A1 - SYNTHETIC FIBERS AND FEDES CONTAINING EXTENDED CHAIN DIAMINOTETROLE AS ANTISTATIC ADDITIVES - Google Patents

Description

Synthetic fibers and threads that are chain-extended Contain diamino tetröle as antistatic additives

The present invention relates to antistatic fibers and threads made of polyamides, polyesters, polyurethanes, polyureas or polysulfonamides ^ the chain-lengthened antistatic agents Contains diamino tetra oils.

It has been found that fibers and filaments with excellent antistatic properties are obtained if - for Increase in molecular weight and viscosity of chain-extended diaminotetröle in fiber and thread-forming polymers incorporated. The chain-extended diaminotetrol is predominantly a branched chain-extended polymer Reaction product of a tetrol of the formula

CH _x CH _x

WoCHCH ₉ ) "(CH ₅ CH0) _Q (CH ₉ CH _o 0) H

y ^ c s c. a cc χ

CH _x NRN CH _x , 3. _χ , 3

) f

309845/1058

in which a, b, c, d, w, x, y and ζ are an integer and R is a divalent C ^ -C ₁ , -hydrocarbon radical, preferably a Cj-Cg-alkyl radical, with a diepoxide or a compound, what divalent radicals of the formulas

0 0

Il It

- C ■ - R ¹ - C - and

OHH O

It t S ti

-CNR ¹ -NC-

results, where R 'is a divalent aromatic, heterocyclic, cycloaliphatic or aliphatic radical or a combination of these radicals.

The ethylene oxide content in the antistatic agents according to the invention is preferably 10-90 % ₉ based on the molecular weight of the diamino tetrol,

The invention thus relates to antistatic fibers or threads made from polyamides, polyesters, polyureas, polyurethanes or polysulfonamides thereby characterized as being 1-12% by weight of a predominantly branched one chain-extended polymeric reaction product from a compound of the formula

CH, CH,

J t j

H (OCH ₂ CH ₂ ) (OCHCH ₂ ) _c (CH ₂ CHO )

CH _x ^ NRN CH,

^{3 3}

/
₂₂ ) _z (OCHCH ₂ ) _d

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where a, b, c, d, w, χ, y and ζ are an integer and R is a divalent C, .- C. ^ -Hydrocarbon residue, preferably a C.-Cg ~ alkyl radical, and is off a diepoxide or a compound containing divalent radicals of the formulas

0 0

Il Il

- C - R ¹ -C-

and

OHH O

Il t 1 Il

-CNR ¹ -NC-

results in which R ^{1 is} a divalent aromatic, heterocyclic, cycloaliphatic or aliphatic radical or a combination of these radicals.

The chain-extended compound is accordingly used in proportions of 1-12% by weight, but preferably in proportions of 2 × 10 % By weight, conventional, fiber-forming polymers were added.

The extended chain tetroi compound used as an antistatic additive in the present invention becomes comprehensive in U.S. Patent 2,979,528. Such Tetroid compounds are available as block copolymers with molecular weights between 1,650 and over 26,000 as "Tetronic series" available in the stores. These series differ in the length of the polyoxyethylene and polyoxypropylene chains. A 3 and 4 digit key number indicates the molecular composition. If 4 digits are used

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the first two explain the average molecular weight of the hydrophobic polyoxypropylene branches on the alkylenediamine compound. If only 3 digits are used, only the first digit is used for this purpose. The last digit of each key number represents the content of hydrophilic polyoxyethylene units in percent by weight with an accuracy of 10 %. The tetrol compounds in the examples are described in this way. The branched chain extended compounds of the present invention are soluble in common solvents such as water, benzene or ethyl alcohol and usually melt below 75 ° C.

As diamines, on which the tetrols are built, can in addition to ethylenediamine, aliphatic diamines with 1-13 carbon atoms, preferably having 1-6 carbon atoms can be used. The polyepoxylated compounds can according to the method of British Patent 793,915, Example 1, can be prepared. The other according to the invention Classes of compounds can be prepared in a manner similar to that described in Example 10 of U.S. Patent 3,009,884 will.

Typical of the acids and their esters, which turn out to be Use chain-lengthening bifunctional suppliers of radicals are dialkyl esters of phthalic acid, isophthalic acid or terephthalic acid, for example dimethyl terephthalate and also dimethyl esters of adipic acid, phthalic acid, sebacic acid, glutaric acid, pimelic acid or isocinchomeronic acid.

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Typical polyepoxy compounds that can be used to extend the length of the chain the Diaminotetröle are such polyepoxy verb indungen as described in British Patent 793,915, on page 2, lines 48-121, such as can be described as follows:

"The organic polyepoxy compounds, which Suitable for the preparation of the polymeric products of this invention are organic compounds, the only groups reactive under the reaction conditions have at least two epoxy groups contain. Excludes those compounds that are carboxyl, hydroxyl, phenolic Contain hydroxyl, amino, amido, imido and mercapto groups. These groups are reactive under the conditions of this reaction with epoxy groups of the polyepoxy compound or with Hydroxyl groups and alkali metal alcoholate groups of the polyoxyalkylene glycol and therefore interfere with the desired condensation reaction. Polyepoxy compounds that are free from such interfering groups, can be aliphatic, cycloaliphatic and aromatic. You can use non-reactive substituent groups, such as alkyl, aryl, organic ester, phosphate ester, halogen and cyano groups. as well the polyepoxy compounds can have olefinic radicals Contain double bonds. The preferred organic polyepoxy compounds are aliphatic, cycloaliphatic and aryl-substituted aliphatic compounds, the only ones under the reaction conditions reactive groups contain at least two epoxy groups in which oxygen is only in oxirane,

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Ether and ester arrangement is not old. Particularly preferred are those diepoxy compounds which are formed only from carbon, hydrogen and oxygen, and in which the oxygen is only contained in an oxirane, ether and ester arrangement, and in which the Epox.y groups are end groups of an aliphatic or are aryl-substituted aliphatic compound or wherein the epoxy group or groups include interconnected carbon atoms of a cycloaliphatic ring system. Representative of these preferred compounds are: butadiene diepoxide, diglycidyl ether of _s diglycidyl ether of 2,2-bis- (4-hydroxyphenyl) propane, 4-vinyl-cyclohexene diepoxide, dicyclopentadiene diepoxide, bis (2,3-epoxycyclopentyl) ether ₉ Ethylene glycol bis (3,4-epoxy-methylcyclohex, an-carboxylate) and 3,4-epoxy-methylcyclohexylmethyl-3,4-epoxymethylcyclohexane-carboxylate _{, etc.}

The subject of the present invention is not limited to the compounds listed above. Rather, it can be a large number of other organic ones Polyepoxy compounds can be used. While it it is preferred that the epoxy groups are end groups, or carbon atoms connected to one another Include cycloaliphatic ring system, on the other hand, can also be aliphatic ^ and substituted aliphatic compounds ^ which contain epoxy groups in the linear carbon chain are used will. These compounds, which contain epoxy groups in the linear carbon chain, react somewhat slower compared to compounds with terminal epoxy groups.

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231529a

Mixtures of two or more polyepoxy compounds can also be used according to the invention or, if so desired, can Polyoxyalkylene glycol can be reacted successively with various polyepoxy compounds.

Such polyepoxy compounds serve both as chain extenders between polyalkylene glycol chains and as a chain linker. The primary hydroxyl groups of the polyoxyalkylene glycol react preferentially with den.Epoxygruppen with branching of the polyglycol chains, secondary hydroxyl groups are formed by opening the epoxy ring. "

Likewise useful as chain-extending, divalent radicals are those which differ from aromatic or aliphatic ones

Derive diisocyanates. These have the general formula

OCN - R ¹ - NCO where R ^{1 is} as defined above.

The antistatic fibers and filaments of the present invention can contain conventional additives such as antioxidants, stabilizers, Matting agents, dyeing auxiliaries and dyes contain.

The antistatic fibers and threads obtained according to the invention can be used where there is little electrostatic charge is required. For example, they can be in the form of fine denier continuous filaments for Underwear or with a coarser titer than

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■ 231529b ■■?

Carpet fibers either as continuous or as staple fibers can be used to reduce static electricity to prevent in carpets.

Another object of the invention is a method for producing antistatic fibers and threads from Polyamides, polyesters, polyureas, polyurethanes or polysulfonamides, characterized in that one 1-12 wt .-% of a predominantly branched chain-extended polymeric reaction product from a Compound of formula

^ CH,

D D

H (0CH ₂ CH ₂ ) ^ (0CHCH ₂ )

CH ₃

₃
H (OCH ₂ CH ₂ ) _z (OCHCH ₂ ) _d

where a, b, c, d, w, x, - y and ζ are an integer and R is a divalent C ^ -C ^, - hydrocarbon radical, is preferably a Cj-Cg-alkyl radical, and from a diepoxide or a compound containing divalent radicals of the formulas

0 0

II Il

-C-R '-C-

and

OHH O

Ii t! Il

C-N-R '-N-C

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3 0: ■ -.: = ■ / 10 5 8

results in which R ^{1 is} a divalent aromatic, heterocyclic, cycloaliphatic or aliphatic radical or a combination of these radicals,

in the fiber-forming starting materials before or during the polymerization or in the molten polymers dispersed prior to spinning and the polymer mixtures obtained are spun by conventional methods.

The following Examples 1 through 21 describe preferred antistatic additives, which are detailed in the following Examples 1-21 can be used.

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CD

Example Type of additive Chain extender Chain melt additive

No. Type (a) extended viscosity in %

Polyether molar ratio

1 Lactam DMT * 3 Lactam Il 4th Lactam Il VJl during the
Polymerization Il 6th during the
Polymerization ! I 7th during the
Polymerization It 1 8th Lactam ft .A
O
I. ? during the
Polymerization ■ II 10 during the
Extrusion ■ II. 11 during the
Extrusion Il 12th Lactam Methv

Lactam

(4-cyclohexyl isocyanate)

Methyl n-b Is- (4-cyclohexyl = isocyanate)

1 600 4th 7th 500 4th 17th 500 4th 1 600 4th 7th 500 4th 17th 500 4th 7th 500 δ 7th 500 6th 7th 500 6th 7th 500 8th 7th 500 4th

7th

ί>

OO

Example type of additive chain extender chain 'melting additive no. Type (a) extended viscosity in %

Polyether molar ratio

14th during the
Extrusion Methylene bis
(4-cyclohexyl-
isocyanate) 0.9 15th Lactam Diglycidyl ether
des 2.2-to-
(4-hydroxyphenyl) -
propane 0.9 16 Lactam Diglycidyl ether des
2,2-bis-ν 4-hydroxy-
phenyl) propane 0.9 17th during the
Extrusion Diglycidyl ether des
2,2-bis- (, 4-hydroxy
phenyl) f-propane 0.9 18th Lactam DMT *
(60 % EO in poly
ether) 0.9 19th during the '
Extrusion DMT *
(20% EO in the molecule) 0.9 20th during the
Extrusion DMT *
(80 % EO in the molecule) 0.9 21 during the
Extrusion
(in polyamide-6,6) DMT * 0.9

.7 500 6 000

6,000 6,000 8,000

(a) The polyether of Examples 1 to 17 contains 40 % ethylene oxide in the molecule.

* Dimethyl terephthalate

The following are the properties of such tetrol compounds indicated, which are identified in the examples by the "Tetronic" numbers.

Tetronic number molecular Brookfield stock melting point weight viscosity point ° c at 25 ⁰ C ⁰ C (cps)

908
1 302 26th
7th 100
800 fixed
1,300 13th 58
liquid at
Room temperature 1 504
1 506 12th
20th 500
000 1 570
fixed 18th • bVV VVV4O4% r ^ r «iUhV ^ r ^ B * ^ * * ^ ^ *» ^ β
liquid at
Room temperature
50 example 1

A reaction vessel equipped with a heater and stirrer was charged an antistatic agent with a mixture of 1 520 g £ -caprolactam, aminocaproic acid, 80 g and 60 g, by reaction of a tetrol with is "Tetronic" count 1 504 with dimethyl terephthalate in a molar ratio 1 ι 0, 7 was obtained. This additive is soluble and has in.Toluol at 100 ⁰ C a melt viscosity of 1600 cp. The reaction vessel was then flushed with nitrogen and the mixture was stirred at 255 ^° C. and under atmospheric pressure during

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polymerized for an hour. The polymerization was then followed for 2.3 hours at atmospheric Heated under pressure and while flushing with nitrogen and stirring at the same time.

A low pressure was then maintained in the reaction vessel with a further supply of nitrogen and the polymer was extruded from the reaction vessel in the form of a tape. The polymer tape was cooled, pelletized, washed and then dried. It was a white, solid polymer with a rel. Viscosity of about 55 to 60 obtained. The viscosity was measured at a concentration of 11 g in 100 ml of 90 #iger formic acid at 25 ⁰ C. (ASTMD-789-62T).

The antistatic agent containing the polycapronamide pellets were melted at about 285 ⁰ C and it psig extruded under a pressure of 1500 by a 16-hole nozzle. The die holes were 0.036 cm (0.014 inch) in diameter to produce 250 denier fiber. The fiber was taken up at a speed of 300 m / min and drawn to about 3 »5 times the extruded length, so that a yarn with a linear density of 70 denier was produced. A control yarn with no antistatic addition was made using the same procedure.

Example 2

The antistatic 70 denier polycapronamide yarn and the control yarn, both prepared according to Example 1 became one processed simple, conventional tissue. The yarn

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held a half Z turn. The tissue became a subjected to the usual washing process and then in an aqueous dye bath, the Nylomin Acid Scarlet C3GS- and Nylomine Acid Yellow contained C3GS dyes, according to, dyed in scarlet tones using a conventional dyeing process. The anti-static fabric could be used in dyed the same shade as the control fabric and also had the same feel. Neither was it the light resistance of the fabric is changed by the presence of the antistatic agent.

The tissues were tested in test specimens measuring 7.6 * 12.8 cm cut up. These fabric samples were tested for their antistatic properties according to the general method in TECHNICAL MANUAL OF THE AMERICAN ASSOCIATION OF TEXTILE CHEMISTS AND COLORISTS, (1969 Edition), 4j>, 206-207 Method determined. This test method is called "Electrostatic Clinging of Fabrics: Fabric-to-Metal Test "and is registered under the number A.A.T.CC. 115-1969, registered. This test method is referred to below as the tissue / metal adhesion test.

The time it takes each tissue sample to peel off was registered. Fresh test samples and fresh rubbing fabrics were used for each determination. The samples were made in triplicate in warp and weft direction checked with polyamide-6,6 and polyester rubbing fabrics. The average values are in the table contain.

Fabric samples were also subjected to repeated washes for verification the durability of the antistatic properties

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subject. They were washed in commercially available washing machines with standard washing and rinsing cycles at a temperature of about 70 ⁰ C using conventional detergents. The fabrics were then dried in a commercially available dryer at temperatures of about 80 ^° C. for about 30 minutes. Before testing, wrinkles were ironed out with a clean, dry iron. The samples were then conditioned at 20 % relative humidity and a temperature of 24 ^° C. for at least 24 hours. (Technical Manual of the AATCC page B-124, Paragraph 4.3 _f s.9.4).

The average times it took for the fabric samples to peel off after 0 and 25 wash cycles are shown in Table 1. The antistatic measurements were carried out at 20 % relative humidity and at a temperature of 24 ^° C. Accordingly, the relative humidity was 20 % and not 40 %, as described in the AATCC procedure.

Example 3

The process of Example 1 was repeated with a material of similar structure, with the exception that the DMT / polyether molar ratio was 0.9 and the melt viscosity at 100 ^° C. was 7,500 cp. The results of the fabric / metal adhesion test are shown in Table 1.

Example 4

The procedure of Example 1 was repeated with a material of similar structure, except that the DMT /

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309 84 5710 58

Polyether molar ratio 1.0 «nd which contain 17 500 cp at ^{100 ° C. in Table 1,}

17 500 cp.betrug at 100 ⁰ C. The results are in

Example 5

A glass reaction vessel equipped with a heater and a stirrer was charged with a mixture of 1,520 g of 6-caprolactam and 80 g of aminocaproic acid. The mixture was then flushed with nitrogen and ^{heating and stirring, heated to 255 °} C. for one hour under atmospheric pressure and simultaneous stirring, were continued for a further 4 hours to complete the polymerization reaction under a nitrogen blanket. During the last 30 minutes of the polymerization, 60 g of the antistatic additive of Example 1 was added to the polycaproamide and stirring was continued for thorough mixing. Under a low Stickstoffdruck'wurde'das polymer then extruded _s was then cooled, pelletized in a Wiley mill, washed, and dried thereon the tape in the form of a Polymerisatbandes. A white, solid polymer with a relative viscosity of about 55-60 was obtained «. The viscosity was determined as in Example 1. "The Polycap'ronamid pellets were melted at 285 G ^0. The melt was then spun under a pressure of 1500 psig through a 16-hole spinneret. The diameter of the spinning nozzle holes was 0.036 em and it was a multifilament with a! Titers of 250 to get "The fiber was withdrawn at a rate of about 300 m / min and to the 3 'of the extrude Läng © 5 times stretched. To this

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A 70 denier yarn was obtained. A control yarn with no antistatic additive was also made.

Example 6

The procedure of Example 5 was repeated with the antistatic additive of Example 3. The test results are included in Table 1.

Example 7

The procedure of Example 5 was repeated with the antistatic additive of Example 4. The test results are included in Table 1.

Example 8

The procedure of Example 1 was repeated with the exception that 90 g instead of 60 g of the additive was described in Example 3 »were used. The corresponding test results are included in Table 1.

Example 9

The procedure is the same as that of Example 5 except that 90 g of the additive described in Example 3 is used will. The results are shown in Table 1.

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Example 10 ■

A glass reaction vessel equipped with a heater and a stirrer was filled with a mixture of 1520 g of 5-caprolactam and 80 g of aminocaproic acid are charged. The mixture was purged with nitrogen and heated to 255 ° C. over an hour with stirring at atmospheric pressure heated. Heating and stirring were continued for another 4 hours to complete the polymerization reaction. At a low nitrogen pressure, the polymer from the glass reaction vessel was in the form of a polymer tape extruded. At this point in time, 90 g of the antistatic additive according to Example 3 were poured over a static Mixer mixed into the polymer. It became a uniform Dispersion of the antistatic JLm extrudate obtained. The polymer tape was then cooled in a Wiley mill pelletized, washed and then dried. In this way a white, solid polymer with a relative viscosity of about 50-60 was obtained. the relative viscosity was determined as in example 1.

The polycapronamide pellets were melted ^{at about 285 ° C.} This melt was spun through a 15-hole spinneret under 1500 psig pressure. The other conditions correspond to those of Example 1. A 70 denier yarn was obtained which was compared with a control yarn without the addition of antistatic agents.

Example 11 ■.

The procedure is the same as in Example 10 except that 112 grams of the antistatic additive was used. The test results are shown in Table 1.

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Example 12

The process corresponds to that of Example 1. 60 g of an antistatic additive were obtained by reacting the tetrol "Tetronic" 1504 and methylene bis (4-cyclohexyl isocyanate). This substance had an ethylene oxide content of about 40 % and the diisocyanate / polyether Molar ratio was 0.9 The antistatic test results are shown in Table 1.

Example 13

The procedure corresponds to that of example 1. It is the antistatic supplement of Example 12 is used except that 90 g is used. The test results are included in Table 1.

Example 14

The procedure corresponds to that of Example 10. 90 g of the compound of Example 12 are used. the Test results are given in Table 1.

Example 15

The procedure corresponds to that of Example 1. 60 g of the antistatic additive were used, which is obtained by reacting the tetrol "Tetronic" 1504 with the diglycidyl ether of 2 _f 2-bis (4-hydroxyphenyl) propane. This compound has an ethylene oxide content of about 40 % and the ratio of diglycidyl ether to polyether is 0.9. The test results are shown in Table 1.

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Example 16 JO

The procedure corresponds to that of example 15 with the Exception that 90 g of the additive are used. The test results are shown in Table 1.

Example 17

The procedure is the same as in Example 10 and the additive has the structure of that used in Example 15 Compound with the exception that 90 g are used. The test results are shown in Table 1.

Example 18

The additive corresponds to that of Example 1 with the exception that the compound contains 60 % ethylene oxide ("Tetronic" 1506). As in Example 1, 90 g of the additive are added to the lactam mixture. The test results are shown in Table 1.

Example 19

The procedure corresponds to that of Example 10 with 90 g a compound obtained from "Tetronic" 1302 and DMT became. The test results are shown in Table 1.

Example 20

The procedure corresponds to that of Example 10 with 90 g of a compound obtained from "Tetronic" 908 and DMT became. The test results are shown in Table 1.

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Example 21 94

94 parts of polyhexamethylene adipamide and 6 parts of the additive from Example 10 are mixed in the melt at 285 ⁰ C. The melt is spun off using a spinneret and the fibers are drawn and tested (see Table 1).

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Table 1

Electrostatic adhesion of fabrics (fabric-to-metal test)

Average time required for the tissue samples to detach themselves from the metal (in seconds)

Antistatic 1 unwashed Washing cycles in the tissue 3. no 4th 600 + 600 + - example 5 0 . 53 Il 6th 0 105 Il 7th 0 83 Il 8th 0 39 Il 9 0 88 Il 10 0 52 Il 11 0 48 Il 12th Ό 44 Il 13th 0 55 Il 14th 0 38 Il 15th 0 *. ' 90 Il 16 0 68 Il 17th 0 52 Il 18th 0 110 Il 19th 0 80 Il 20th 0 71 Il 21 0 93 It 0 75 Il 0 95 Il 0 97

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Example 22 f *

The procedure of Example 9 was repeated to prepare a polymer which is described below with the Letter A. The procedure of Example 10 was repeated to produce a polymer which is denoted by B.

Pellets were produced from both polymers.

, The pellets were melted at 285 ° C and under a Pressure of 1,500 psig from the melt through a 70 hole spinneret spun off. The single hole diameter of the spinneret was 0.045 cm, and it became a multifilament obtained with a titer of 4,500 den. The multifilament was drawn off at a speed of 300 m / min and stretched to about 4 times the extruded length. The linear density of the yarn obtained in this way was 1,050. A control yarn Without the addition of antistatic agents, it was produced in the same way.

The yarns were textured using a steam nozzle. Two yarn ends were twisted around one another with 1 1/2 S turns. The yarns were made into a carpet with a smooth loop fabric with a weight per square meter of 676 g. The number of stitches was 6.5 / inch and the pile height 23/32 to 25/32 cm (9/32 to 10/32 inch). The carpet has been dyed and given a latex backing provided * The static charge on the carpet was tested by measuring the build-up of electrostatic voltage on a person who walked the carpet. The measurement method is described in CRI Walk Test for carpets, registered under

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AATCC 134-1969. The carpet was conditioned at 21.6% and 20 % relative humidity.

The results can be found in the following table will: .

Polymer Static Bepeh test

Polymer A 4.8 KV

Polymer B 5.8 KV

Control carpet 14.1 KV

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Claims (5)

Claims 1. Antistatic fibers and threads made from polyamides, polyesters, polyureas, polyurethanes or polysulfonamides ^ characterized in that they contain 1-12 wt .-% of a predominantly branched chain-extended polymeric reaction product from a compound of the formula ι 3 t 3 H (OCH ₂ CH ₂ ) _y (OCHCH ₂ ) _c ί ^Η 3 NRN, j H (OCh ₀ CH ₀ WEEK ₀ ) S ^ \ (CH ₀ CHO) ₁ where a, b, c, d, w, x, y and ζ are an integer and R is a Cj-C ^ divalent hydrocarbon radical is, and from a diepoxide or a compound which divalent radicals of the formulas 0 0 U If - C - R ¹ -C- and OH HO Il I I Il -CNR ¹ -NC-results,
Al 38 - 25 - 3 0 8 8 4 b / 10 5 8 '■■ ■■ J6 - ■ ..' ■ ·. ■ '■■' in which R ^{1 is} a divalent, aromatic, hetero- ". cyclic, cycloaliphatic or aliphatic radical or a combination of these radicals, 2. Antistatic fibers and threads "according to -Anspruch ^ Iv; characterized in that R is a C ^ -Cg -alkyl radical is. 3. Antistatic fibers and threads according to claim 1, characterized in that the ethylene oxide content in the diamino-tetrol is 10-90 %, based on the molecular weight of the diamino-tei; rols. 4. Antistatic fibers and threads according to claim 1, characterized in that they contain 2 to 10 wt .-% of the chain-extended polymeric reaction product. - · ,. · ...- - ^ -, _.,; ,. ·· :. ■;, -....; - '. . , _r 5. Process for the production of antistatic polyamides,. Polyester, polyurea, polyurethane or polysulf onamid fiber rn pde r threads, dadurcli ge mark t, that 1 12 wt .-? o. a predominantly branched one chain-extended polymeric reaction products, s from ...... a compound of the formula: /. . . :?.; ■? ■. CH, CH, H (OCH ₂ CH ₂ ) (OCHGH ₂ ) _c (CH ₂ CHO) CH, N-R-N CH ^ (OCHCH Al 38 - 26 - 3 0 9 8 4 S / 1 0 5 8 where a, b, c, d, w, χ, y and ζ are an integer and R is a divalent C 1 -C 4 hydrocarbon radical is, lind of a diepoxide or a compound which divalent radicals of the formulas 0 0 Il Il C - R »- C - and OH H Ό * It 1 1 Il CNR ¹ -NC results, wherein R ^{1 is} a divalent, aromatic, heterocyclic, cycloaliphatic or aliphatic radical or a combination of these radicals, evenly in the fiber or thread-forming starting materials before or during the polymerization or in the dispersed molten polymers before spinning and the polymers are spun into fibers and threads by conventional methods. Al 38 - 27 - 309845/1058 3 '(J ^3: r ■' · / 10 5 8