WO1993015257A1

WO1993015257A1 - Use of block copolyesters containing poly(alkylene glycol) blocks as smoothing agents in spinning preparations

Info

Publication number: WO1993015257A1
Application number: PCT/EP1993/000124
Authority: WO
Inventors: Ulrich Eicken; Raymond Mathis; Norbert Bialas
Original assignee: Henkel Kommanditgesellschaft Auf Aktien
Priority date: 1992-01-25
Filing date: 1993-01-20
Publication date: 1993-08-05
Also published as: DE4202065A1

Abstract

This invention concerns the use, as smoothing agents in preparations for spinning synthetic filaments, of block copolyesters of the formula (A-COO)m-B in which A is a complex monocarboxylic-acid group and B an m-hydric poly(ether alcohol) group with a mean molecular weight of 400 to 6000 and m = 2 to 6 hydroxyl groups. The invention also concerns a method of producing the block copolyesters described, as well as spinning preparations containing such smoothing agents.

Description

"Use of block copolyesters with polyalkylene glycol blocks as smoothing agents in spin finishes"

The present invention relates to the use of block copolyesters based on polyether alcohols and hydroxycarboxylic acids as smoothing agents in spin finishes for synthetic filaments, a process for producing these block copolyesters and spin finishes containing such smoothing agents.

In the production of synthetic fibers, the first process that takes place immediately after the filaments are formed is the treatment of the fiber surface with preparation agents. It is generally known that man-made fibers can neither be manufactured nor processed without providing the filaments with such a preparation. These preparation agents, which are mostly referred to as "spin finishes" in the German-language literature, have to be applied to the filaments, among other things, since the original rough surface of the polymer filaments causes high frictional forces. When the filaments are in constant contact with one another or with the guide elements of the spinning machines, these frictional forces cause the filaments to rub off, which ultimately leads to fila breakage. In order to reduce these high frictional forces, spinning preparations contain smoothing agents. Typical smoothing agents for spin finishes are vegetable, animal and mineral oils or also synthetic esters, silicones, polyethers and ethoxylated fatty acids, esters and alcohols. In recent years, the texturing process has been increasingly used by the fiber manufacturers, since texturing enables smooth filament yarns to be converted into voluminous and / or elastic yarns that are produced

Give textiles a voluminous, air-enclosing character. In the texturing process, the smooth filament yarns are twisted, which can be fixed or even increased by thermal treatment under defined tension. This means special requirements for smoothing agents in the spin finishes which are to be applied to filaments to be textured. For example, the smoothing agents should significantly reduce the friction on the texturing elements and filament fibers, and should be very thermostable, so that no crack products are formed during the thermal treatment that resinify the texturing bar or filaments. Instead of thermostable smoothing agents, the common addition compounds of ethylene oxide and / or propylene oxide to alcohols can also be used, since these depolymerize almost completely without residue during the thermal treatment and are therefore removed from the texturing rail. However, fragments such as aldehydes escape into the atmosphere, which can be avoided for a variety of reasons. Another disadvantage is the relatively poor biodegradability of the addition compounds with propylene oxide units, since residues on the filaments can get into the waste water during washing, for example before dyeing.

The object of the present invention was to provide readily biodegradable smoothing agents which, on the one hand, reduce the high friction in spin finishes on filaments and, on the other hand, are temperature-stable up to about 250 ° C. under the conditions of the thermal treatment during texturing.

Surprisingly, it has been found that block copolyesters with blocks of polyether alcohols and hydroxycarboxylic acids or polyhydroxycarboxylic acids solve this task. Block copolyesters with blocks of polyalkylene glycols and polymerized hydroxycarboxylic acids are mentioned as suitable textile lubricants from German published patent application DE-A-24 30 342, but no more precise details can be found there. Now, however, common textile lubricants differ from smoothing agents for spin finishes in their requirements, especially with regard to thermal stability. Accordingly, it cannot be inferred from the reference in the German Offenlegungs¬ that these block copolyesters are also suitable smoothing agents for spin finishes.

An object of the present invention is accordingly the use of block copolyesters of the general structure (A-C00) _m -B, where an integer from 2 to 6 means and

A the monovalent residue of a complex monocarboxylic acid of the general structure (A)

R-CO (R ² ), (A)

means what

R = H, or an optionally substituted alkyl and / or

Alkenyl radical with 1 to 24 carbon atoms R * = H, or an optionally substituted alkyl and / or

Alkenyl radical with 1 to 24 carbon atoms p = 0 or 1 n = zero or a number from 1 to 200 and R ² = a divalent optionally substituted alkyl and / or Alkenyl radical with 1 to 24 carbon atoms and

B an m-valent radical of a polyether alcohol with an average molecular weight of 400 to 6000 and with 2 to 6 hydroxyl groups selected from the group of polyalkylene glycols, adducts of ethylene, propylene and / or butylene oxide with aliphatic diols with 2 to 36 C atoms and / or on aliphatic polyols with 3 to 6 hydroxyl groups and with 4 to 10 C atoms, as a smoothing agent in spin finishes for synthetic filaments.

The block copolyesters of the general structure used for the purposes of the invention are known compounds which are described in German Offenlegungsschrift DE-A-2430342 or in European Patent EP-B-424. Theoretically, the block copolyesters used according to the invention are derived from the complex monocarboxylic acids of the general structure A-C00H and / or their derivatives such as lower esters of alkanols with 1 to 6 C atoms and also from polyether alcohols with an average molecular weight of 400 to 6000 and with 2 to 6 hydroxyl groups. The complex monocarboxylic acids correspond to those in German Offenlegungsschrift DE-A-2430342 and European patent EP-B-424 and are in turn derived from monohydroxymonocarboxylic acids of the general structure (A2) ^'

where R1, R2 and p have the meaning given for the general structure (A). Examples of suitable monohydroxymonocarboxylic acids are, in particular, 12-hydroxystearic acid and / or 9 c-octadecen-12-ol acid (ricinoleic acid). 12-hydroxystearic acid is accessible by hydrogenating ricinoleic acid. Ricinoleic acid itself, in the form of its triglycerides, is the main constituent of castor oil, which still contains triglycerides of palmitic, stearic, oleic and linoleic acid - to name the most important. The technical ricinoleic acid obtained from castor oil therefore always contains the monocarboxylic acid palmitic, stearic, oleic and linoleic acid in quantities depending on the area of cultivation and crop failure. As a rule, the monocarboxylic acids listed are contained in amounts of about 5 to 20% by weight. From this it can be deduced that the technical 12-hydroxystearic acid obtained by hydrogenation of technical ricinoleic acid also contains monocarboxylic acids as an impurity, especially stearic acid.

The complex monocarboxylic acid of the general structure A-COOH can be prepared according to German published patent application DE-A-2430342 by intermolecular esterification of the monohydroxymonocarboxylic acids (A2) in the presence of a conventional monocarboxylic acid which contains no hydroxyl groups and accordingly acts as a chain terminator . The carboxylic acid acting as a chain terminator is provided by the RCO group in the general structure (A). Since the 12-hydroxystearic acid and ricinoleic acid preferred in the context of the invention always contain, as mentioned, the impurities palmitic, stearic, oleic and linoleic acid, the RCO group of the general structure (A) preferred for the alkyl and / or alkenyl radical derived from these acids. In principle, the amount of chain terminating monocarboxylic acid present determines the number of condensed monohydroxy monocarboxylic acids, ie the index n. The amount of chain terminating monocarboxylic acid can be determined by simple experiments and calculations. For example, a mixture of 15% by weight of stearic acid and 85% by weight of 12-hydroxystearic acid gives a complex monocarboxylic acid with an average value of 4 for the index n, which corresponds to an average molecular weight of 1500 to 1600. Preferred in terms of the inventions fertilizer A is derived from technical 12-hydroxystearic acid and / or technical ricinoleic acid. A is very particularly preferably derived from technical 12-hydroxystearic and / or technical ricinoleic acid and has a degree of polymerization n in the range from 1.5 to 10.

In the block copolyesters of the general structure used according to the invention, B represents an m-valent radical of a polyether alcohol having 2 to 6 hydroxyl groups and an average molecular weight of 400 to 6000. For the purposes of the invention, the term polyether alcohol is used for those compounds which have at least two ether groups and have at least two free hydroxyl groups. Accordingly, the polyether alcohols are selected from the group already described. The adducts are preferably those of ethylene oxide and / or propylene oxide with aliphatic saturated diols having 2 to 22 carbon atoms, such as ethylene glycol, neopentyl glycol, 1,4-butanediol, 1,8-octanediol, 1,12-dodecanediol and 1,18-octadecanediol and / or those of ethylene oxide and / or propylene oxide on glycerol, trimethylolpropane _for pentaerythritol and / or dipentaerythritol. The polyalkylene glycols can be homopolymers and copolymers and the latter can be block and random polymers of ethylene, propylene and butylene oxide. B particularly preferably represents a divalent radical of a polyether alcohol, ie m denotes the number 2. Of these, in turn, polyethylene glycols are particularly suitable, preferably with a molecular weight of 600 to 3000 and in particular of 800 to 1500.

In accordance with one embodiment of the present invention, block copolyesters of the general structure are used in which B is the divalent radical of a polyethylene glycol with a molecular weight of 800 to 1500, in particular up to 1200, and A is derived from a complex monocarboxylic acid based on technical 12- Hydroxystearic acid and / or technical ricinoleic acid and the degree of polymerization n a Number from 1 to 10 means. These block copolyesters practically consist of a hydrophilic polyethylene glycol block and a hydrophobic polyhydroxycarboxylic acid block, both of which are biodegradable.

In accordance with European Patent EP-B-424, the block copolyesters used according to the invention can be produced either by a one-pot process or by a step process. After the step process, the monohydroxymonocarboxylic acids are first partially or completely esterified with one another (precondensed) in the presence of chain-terminating monocarboxylic acids. These precondensed complex monocarboxylic acids, which correspond to the general structure A-C00H, are then esterified with the polyether alcohols until almost all of the hydroxyl and carboxyl groups have reacted. After the one-pot process, the monohydroxymonocarboxylic acids (A2), monocarboxylic acids and polyether alcohols are esterified with one another from the start in a reaction vessel. According to the European patent specification, the block copolyesters obtained by both processes are very similar in composition and in properties.

According to a further object of the invention, the block copolyesters used according to the invention can be produced by a new process which is characterized in that esters of the complex monocarboxylic acid of the general structure A-C00H with lower alkanols having 1 to 6 carbon atoms with polyether alcohols the average molecular weight of 400 to 6000 with 2 to 6 hydroxyl groups selected from the group of polyalkylene glycols, adducts of ethylene, propylene and / or

Butylene oxide can be esterified on aliphatic diols with 2 to 36 C atoms and / or on aliphatic polyols with 3 to 6 hydroxyl groups and with 4 to 10 C atoms with simultaneous removal of the resulting alcohols with 1 to 6 C atoms. In the process according to the invention, instead of the monomeric or polymeric (precondensed) monohydroxycarboxylic acid, its esters with alkanols having 1 to 6 carbon atoms are used. As in the esterification process, the ester of the precondensed monohydroxycarboxylic acid can also be used. However, the ester and the polyether alcohol are in any case transesterified in a one-pot process in the customary manner with simultaneous removal of the alkanol having 1 to 6 carbon atoms which is formed.

For the purposes of the invention, it is preferred if the esterification known per se or the esterification according to the invention is carried out in weight ratios of polyether alcohol to, optionally precondensed, hydroxycarboxylic acid of 1: 9 to 9: 1. After the transesterification process according to the invention, block copolyesters are surprisingly obtained, in particular when the same proportions by weight are used, which give finely divided and more stable aqueous dispersions than those obtained by the normal esterification processes according to German Offenlegungsschrift DE-A-2430342 and European Patent EP-B- 424 block copolyesters produced.

The esterification or transesterification is generally carried out in the presence of the known catalysts such as titanium tetrabutylate, tin octoate or sodium methylate.

The block copolyesters can be used alone or in a mixture with lubricants known from the prior art. Some of the block copolyesters, in particular those with polyethylene glycol blocks with molecular weights above 800, are present at room temperature (20 to 25 ° C.) as pasty masses. These pasty masses can be liquefied by heating and then converted into a dispersion with water. In most cases, however, it is desirable to use products which are liquid at room temperature, since one would like to save the melting process. This object can advantageously be achieved if known from the prior art te smoothing agents that are liquid at room temperature are added. Suitable smoothing agents are to be selected from the group of mineral oils, fatty acid esters of alkanols with 8 to 22 carbon atoms in the fatty acid residue and 1 to 22 carbon atoms in the alcohol residue, for example methyl palmitate, isobutyl stearate and / or 2-ethylhexyl tallow fatty acid, fatty acid esters of polyols with 2 to 6 hydroxyl groups, for example coconut fatty acid esters of glycerol, alkoxylated alcohols, for example adducts of ethylene oxide (EO) and propylene oxide (PO) with tallow alcohol, tri ethylol propane and / or pentaerythritol, polyalkylene glycols, for example ethylene oxide / propylene oxide mixed polymers , Guerbet alcohols such as 2-butylhexanol, 2-hexyloctanol and / or silicones. Very particularly preferred as further lubricants are fatty acid esters of alkanols with 1 to 12 carbon atoms in the alcohol residue, ethylene oxide / propylene oxide copolymers of alkanols with 2 to 22 carbon atoms, such as propanol, butanol, capron alcohol, pelargon alcohol, lauryl alcohol, myristyl alcohol, palmityl alcohol, Stearyl alcohol and / or behenyl alcohol, aliphatic diols with 6 to 25 C atoms and / or polyols such as trimethylolpropane, pentaerythritol, neopentyl glycol and / or glycerol as well as Guerbet alcohols with a total of 6 to 38 C atoms. The block copolyesters are particularly preferably used in the sense of the invention in a mixture with the known known smoothing agents, 15 to 95% by weight of block copolyesters and 5 to 85% by weight of the smoothing agents described being able to make up. The block copolyesters are particularly preferably used in amounts of 50 to 90, preferably 60 to 85% by weight with the known smoothing agents in amounts of 10 to 50, preferably 15 to 40% by weight, based on the mixture of smoothing agents.

It is surprising that smoothing agents as diverse as fatty acid esters and ethylene oxide / propylene oxide copolymers can be incorporated into the block copolyesters without phase separation occurring. For example, ethylhexyl stearate and an ethylene oxide / propylene oxide copolymer (Breox ^ from BP Chemicals) are not compatible (phase separation), but each that in itself with the block copolyesters. Mixtures of the block copolyesters with the known smoothing agents of the type described are single-phase and can be easily emulsified in water.

The block copolyesters are applied alone or in a mixture with other smoothing agents, preferably from an aqueous dispersion in the form of a suspension or emulsion. For the purposes of the invention, preference is given to applying aqueous dispersions of block copolyesters, optionally in a mixture with further smoothing agents, to the synthetic filaments immediately after they have emerged from the spinneret. To prepare the aqueous dispersions, the block copolyesters are generally emulsified in water before application. It has proven particularly advantageous in the present invention that the block copolyesters are self-emulsifying in water, so that emulsifiers can be dispensed with. The use of emulsifiers known from the prior art, such as mono- and / or diglycerides, for example glyceryl mono- and / or glycerol dioleate, alkoxylated, preferably ethoxylated and / or propoxylated fats, oils, fatty alcohols with 8 to 24 carbon atoms and / or CQ- to Cig-alkylphenols, for example castor oil with 25 moles of ethylene oxide and / or CQ- to Ci8 ~ fatty alcohol with 8 moles of propylene oxide and 6 moles of ethylene oxide, if desired alkoxylated ZQ- to C24 ~ fatty acid mono- and / or diethanola ide, for example ethoxylated oleic acid mono- and / or diethanolamide, tallow fatty acid mono- and / or diethanolamide and / or coconut fatty acid mono- and / or diethanolamide is possible in customary amounts, if desired.

If particularly pronounced antistatics are required, commercially available antistatics such as alkali and / or ammonium salts of alkoxylated, preferably ethoxylated and / or propoxylated, optionally end-capped Cg to C22 ~ al yl and / or CQ to C22 ^_A alkylene alcohol sulfonates, Reaction products from optionally alkoxylated CQ to C22 ^_A 1'yl alcohols with phosphorus pentoxide or phosphorus oxychloride in the form of their alkali Li, ammonium and / or amine salts, for example phosphoric acid esters of ethoxylated Ci2-Ci4 ~ fatty alcohols, neutralized with alkanolamine, alkali and / or ammonium salts of Cg- to C22 ~ alkyl sulfosuccinates and / or amine oxides.

If desired, the block copolyesters used according to the invention can also be mixed with customary auxiliaries from the group of thread closing agents, pH regulators, bactericides and / or corrosion inhibitors. The thread-closing agents which are known from the prior art are polyacrylates, fatty acid sarcosides and / or copolymers with maleic anhydride (Melliand Textile Reports (1977), page 197) and / or polyurethanes in accordance with German Offenlegungsschrift DE-A-3839468. pH regulators are, for example, Ci to C4 carboxylic acids and / or Ci to C4 hydroxycarboxylic acids, alkali metal hydroxides and / or amines.

The block copolyesters are preferably used in the form of their aqueous dispersion. The aqueous dispersions of the block copolyesters have a water content of 99.8 to 60% by weight and an active substance content of block copolyesters of between 0.2 to 40% by weight. Aqueous dispersions with an active substance content of block copolyesters between 0.2 to 10% by weight are recommended for laboratory tests, in particular for filament free of preparation. For practical applications, the active substance content is preferably between 3 to 40 and in particular between 5 to 30% by weight. The application amount of the aqueous dispersion is in the range customary for the textile industry between 0.1 and 30% by weight, preferably between 1 and 10% by weight, based on the weight of the filaments. The use of the block copolyesters according to the invention enables synthetic filaments to be imparted the required smoothness properties, in particular the synthetic filaments made of polypropylene, polyester and / or polyamide and in particular polyester. Another object of the invention are spin finishes for synthetic filaments containing a mixture of smoothing agents, characterized in that the mixture of smoothing agents consists of

15 to 95 wt .-% block copolyester of the general structure (A-C00) _m B with the meanings given in claim 1 for A, B and m and 5 to 85 wt .-% smoothing agents liquid at room temperature selected from the group mineral oils, fatty acid esters with 8 to 22 carbon atoms in the fatty acid residue and 1 to 22 carbon atoms in the alkanol, fatty acid esters of polyols with 2 to 6 hydroxyl groups, alkoxylated alcohols, Guerbet alcohols, polyalkylene glycols and silicones.

Preference is given to spin finishes whose mixture of smoothing agents consists of block copolyesters of the general structure, where A is derived from the complex monocarboxylic acid based on technical 12-hydroxystearic acid and / or technical ricinoleic acid and B is a divalent polyethylene glycol radical and fatty acid esters with 8 to 22 C- Atoms in the fat residue and 1 to 22 carbon atoms in the alkanol residue.

If desired, the spin finishes can additionally contain the emulsifiers already described in amounts of 0.1 to 5, the anti-static agents described in amounts of 0.1 to 5, customary auxiliaries from the group of thread-closing agents described, pH value regulators, Contain bactericides and / or anti-corrosion agents in amounts of 0.1 to 5% by weight, based on the spin finish, the 100% by weight missing amounts being water. The spin finishes preferably contain water in amounts of 99.8 to 60% by weight and a total active substance content of 0.2 to 40% by weight. The total active substance content is the content of all components of the spin finish except water, whereby for laboratory applications the total Active substance content is preferably in the range from 0.2 to 10% by weight and for practical applications is between 3 to 40% by weight.

B e i s p i e l e

A) Preparation of the copoly ere

example 1

690 g of ricinoleic acid with an acid number (DIN 53402) of 93 were added with 295 g of polyethylene glycol with an average molecular weight of 1000 in the presence of 1.0 g of a tin-based esterification catalyst (Swedcat ^R 3, from Swedstab) and 100 ml of xylene Temperatures between 180 to 200 ° C esterified until no more water could be distilled off azeotropically. Then xylene was distilled off in vacuo. A paste-like copolyester with an acid number of 18 was obtained. The block copolyester forms a finely divided emulsion with water (active substance content 10% by weight).

Example 2

350 g of commercial ricinoleic acid (composition in percent by weight: palmitic acid 1.3; stearic acid 1.1; oleic acid 4.4; ricinoleic acid 87; linoleic acid 6.2) with an acid number of 173 were mixed with 0.5 g of tin octoate and 100 ml of xylene esterified at 180 to 200 ° C until 9 ml of water had separated. Then 150 g of polyethylene glycol with an average molecular weight of 1000 were added and esterified with the precondensed ricinoleic acid at 180 to 200 ° C. until the block copolyester obtained had an acid number of 16. To isolate the copolyester, xylene was previously distilled off in vacuo.

The average particle diameter in an aqueous dispersion (10% by weight of active substance) is 260 nm.

Example 3

500 g of ricinoleic acid with an acid number of 173 were analogous to Example 1 with 500 g of polyethylene glycol with an average molecular weight of 1000 esterified with xylene as entrainer (12 hours) until a paste-like copolyester with the acid number 4.7 was obtained after azeotropic distillation of water and removal of xylene.

Example 4

400 g of commercial ricinoleic acid of the composition analogous to Example 2 were esterified together analogously to Example 2 in the presence of 0.5 g tin octoate and 100 ml xylene until 9 ml water had separated. 100 g of polyethylene glycol with an average molecular weight of 1000 were then added to this precondensed ricinus acid and esterified with one another analogously to Example 2 until after the azeotropic distillation of water and the removal of xylene, a pasty copolyester with an acid number of 6.0 was incurred.

Example 5

700 g of methyl ester of commercial ricinoleic acid (hydroxyl number = 153) were mixed with 300 g of polyethylene glycol with an average molecular weight of 1000 in the presence of 1.0 g of a tin-based esterification catalyst (Swedcat ^R 5 from Swedstab) at temperatures between 200 and 220 ° C transesterified. The methanol formed was continuously distilled off. After 12 hours, 55 g of methanol had been separated off. A vacuum was then applied and another 3 g of methanol were distilled off. A paste-like block copolyester with the characteristic numbers acid number = 1.0, hydroxyl number (DIN 53240) = 30.0, saponification number (DIN 53401) = 136 was obtained. By emulsifying the block copolyester in water, an opaque emulsion with an average particle diameter of 76nm.

Compatibility of the block copolyesters

A block copolyester composed of 70 parts by weight of ricinoleic acid and 30 parts by weight of polyethylene glycol (MW 1000) was mixed with 20 parts by weight of the following smoothing agents:

A comparison test showed that different textile smoothing agents are not always compatible.

80 parts by weight of esters from pre-fatty acid and pentaerythritol and 20 parts by weight of Breox ^R 50 A 380; BP Chemicals: cloudy, 2 phases

80 parts by weight of ester from hydr. Tallow fatty acid and 2-ethylhexanol and 20 parts by weight of Breox ^R 50 A 30; BP Chemicals: cloudy, 2 phases Thermal resistance

To make statements about the temperature resistance and volatility of the pure

Obtaining copolyester was carried out using the dish test: 3 g of copolyester according to Example 2 were weighed into an aluminum dish and stored in a drying cabinet at 180 to 200 ° C. for 3 to 18 hours, cooled and weighed. The mass loss in% was recorded. Table 3 shows the results for thermal resistance.

Examples of use

On preparation-free polyester filaments (yarn type: pre-oriented yarn-PES; fineness 143 dtex, number of filaments 34; spinning speed 3300 m / min), in a laboratory facility, spin finishes with an oil layer (ie total active substance content of the components of the spin finish; except water) of a) 0.2 or b) 0.4 wt .-% applied. Aqueous 0.4 or 0.8% by weight spin finishes of the composition were used

Spin preparation 1

Block copolyester according to Example 2 was converted into a 0.4 or 0.8% by weight dispersion with water.

Spin preparation 2

Block copolyester according to Example 5 was converted into a 0.4 or 0.8% by weight dispersion with water.

Spin preparation 3

80 parts by weight of spin preparation 1 were with

20 parts by weight of a spin finish VI

26% by weight of n-butyl stearate

31% by weight of i-butyl stearate 8% by weight adduct pelargonic acid ^• 9 mol ethylene oxide (EO) 10% by weight cetylstearyl ether ^• 3 mol EO

5% by weight tridecyl phosphate

5 wt .-% Na salt of Dinonylsulfosucciπate 15 wt .-% castor oil ^• 25 mol EO mixed. It goes without saying that a 0.4% by weight spin preparation 1 was mixed with a 0.4% by weight spin preparation VI (analogously for 0.8% by weight).

Spin preparation 4

80 parts by weight of spin preparation 1 (0.4 or 0.8% by weight) were mixed with 20 parts by weight of spin preparation VI (0.4 or 0.8% by weight) as in spin preparation 3 mixed.

Spin preparation 5

70 parts by weight of spin preparation 1 (0.4 or 0.8% by weight) were mixed with 30 parts by weight of spin preparation V2 (0.4 or 0.8% by weight) from butanol • 50 % By weight of E0 ^■ 50% by weight of propylene oxide (PO) (MW approximately 1200) is added analogously to spin preparation 3.

In order to test the properties of the copolyesters as smoothing agents, the following parameters of the spin finishes on polyester filament were determined:

- dynamic coefficients of friction against ceramics at a speed of 2 to 200 m per minute, measured on the Rothschild F-meter (climate 20 ° C, 65% relative humidity)

- Electrostatic charging on ceramics at a speed of 2 to 200 m per minute, measured on Eltex inductive voltmeters (climate: 20 ° C, 65% relative humidity) Table 1 summarizes the dynamic coefficients of friction and table 2 summarizes the electrostatic charge which was observed in the spin finishes with an oil coating of 0.2 and 0.4% by weight.

Table I dynamic coefficient of friction (ue) at m / min

Oil pad

0.4% (..— - 0.2% by weight (0.8% by weight of spin finish) (0.4% by weight of spin finish)

Spin finish 20 100 200 20 100 200

1 0.584 0.541 2 0.433 0.435 3 0.409 0.413

4 0.379 0.389 5 0.436 0.442

VI 0.314 0.337 V2

0.429 0.447

*

Table II electrical charging in kV / min at m / min

Oil coating 0.2% by weight 0.4% by weight

(0.4% by weight spin finish) (0.8% by weight spin finish)

Spin finish 20 100 200 20 100 200

It can be seen from Table I that initially the block copolyesters are good smoothing agents, the properties of which are further improved even by adding small amounts of smoothing agents known from the prior art (spin finish 3 to 5), with in individual cases (spin finish 5) lower oil layer better smoothing effect can be achieved than with the very good from the prior art (spinning preparation V2).

It can be seen from Table II that the pure block copolyesters have satisfactory antistatic properties, which are greatly improved by adding small amounts of known smoothing agents (spin finishes 3 and 4).

Table III: Thermal resistance

Weight loss in% dish test

180 ° C 200 ° C 230 ° C

Substance 3 h 18 h 3 h 18 h 3 h 18 h

Ex. 2 19 12 23 19 29

Claims

Patent claims

1. Use of block copolyesters of the general structure (A-C00) _m -B, where an integer from 2 to 6 means and

R-CO (-0- (R ² ) p- (A)

means what

R = H, or an optionally substituted alkyl and / or

Alkenyl radical with 1 to 24 carbon atoms Rl = H, or an optionally substituted alkyl and / or

B an m-valent radical of a polyether alcohol with an average molecular weight of 400 to 6000 and with 2 to 6 hydroxyl groups selected from the group of polyalkylene glycols, adducts of ethylene, propylene and / or butylene oxide with aliphatic diols with 2 to 36 C atoms and / or aliphatic polyols with 3 to 6 hydroxyl groups and with 4 to 10 C atoms, as a smoothing agent in spin finishes for synthetic filaments.

2. Use according to claim 1, characterized in that A is derived from the complex monocarboxylic acid based on technical 12-hydroxystearic acid and / or technical ricinoleic acid.

3. Use according to claim 1 or 2, characterized in that the integer means 2.

4. Use according to one of claims 1 to 3, characterized in that B is a divalent polyethylene glycol residue, preferably with a molecular weight of 600 to 3000, in particular 800 to 1500.

5. spin finishes for synthetic filaments containing a smoothing agent mixture, characterized in that the smoothing agent mixture consists of

15 to 95 wt .-% block copolyester of the general structure (A-C00) _m B with the meanings given in claim 1 for A, B and m and 5 to 85 wt .-% smoothing agents liquid at room temperature selected from the group mineral oils, fatty acid esters with 8 to 22 carbon atoms in the fatty acid residue and 1 to 22 carbon atoms in the alkanol residue, fatty acid esters of polyols with 2 to 6 hydroxyl groups, alkoxylated alcohols, Guerbet alcohols, polyalkylene glycols and silicones.

6. Spin finishes according to claim 5, characterized in that the smoothing agent mixture consists of block copolyesters of the general structure (A-C00) _m -B, where A is derived from the complex monocarboxylic acid based on technical 12-hydroxystearic acid and / or technical ricinoleic acid and B represents a divalent polyethylene glycol residue and fatty acid esters with 8 to 22 carbon atoms in the fat residue and 1 to 22 carbon atoms in the alkanol residue.

7. Process for the preparation of block copolyesters of the general structure (A-C00) _m B with the meaning given in claim 1, characterized in that esters of the complex monocarboxylic acid of the general structure A-COOH with lower alkanols having 1 to 6 C atoms with polyether alcohols of average molecular weight from 400 to 6000 with 2 to 6 hydroxyl groups selected from the group of polyalkylene glycols, addition products of ethylene, propylene and / or butylene oxide onto aliphatic diols with 2 to 36 C atoms and / or transesterified on aliphatic polyols with 3 to 6 primary hydroxyl groups and with 4 to 10 C atoms with simultaneous removal of the resulting alcohols with 1 to 6 C atoms.