NL8104516A - ANIMAL PREPARATION AND TEXTILE PROCESSING PROCESSES OBTAINED THEREFROM - Google Patents

Description

'* * · * · * *

Diester preparation and. textile processing compositions obtained therewith.

The invention relates to a combination of cycloaliphatic diesters and high-boiling aromatic esters and their use in fiber treatment and textile processing preparations.

U.S. Pat. No. 3,925,589 relates to the use of emulsions of esters derived from polyoxyalkylene glycols of molecular weight 300-4000 and a dibasic acid mixture of a dimer acid of 32-54 carbon atoms and a short chain dibasic acid of 2-12 carbon atoms to lubrication of polyamide fibers.

US Pat. No. 3,694,257 relates to the use of polyesters prepared by reacting polyols with a dibasic or tribasic acid as textile auxiliaries for softening textile fabrics.

U.S. Patent 3,329,633 relates to improving the lubricity of polyhexamethylene-20 adipamide fibers by adding 0.1-5.0 wt% oleic acid dimer to the polymer during the final polymerization step.

US Patent 4,135,878 relates to the incorporation of up to 10 wt% dimer acid in an emulsifier-solvent degreasing composition for treating textile goods under alkaline conditions.

The preparation of addition products from conjugated octadecadienoic acid and unsaturated acids and / their hydrogenation is described by Teeter et al, J. Org. Chem., Vol. 22 (1957) pp. 512-514 and in U.S. Pat. Nos. 3,899,476 and 3,981,682.

The preparation of esters from the Cl diacid adduct has been described by Ward et al, J. Amer. Oil Chemists * Soc., Vol.

57 (1975) pp. 219-224. Ethoxylated esters with 4-119 ethylene oxide units are said to be particularly effective lime soap dispersants. The alkyl esters are used as special 8104516 ...... 2 ..

* Suitable for use as a lubricant, especially for use as a textile lubricant and plasticizers for PVC.

The use of lower aromatic esters in the treatment of textiles, especially as dyeing auxiliaries, is well known and is described in U.S. Pat. Nos. 2,880,050, 2,881,045, 3,036,876, 3,124,412, 3,929,407 and 3,932,128.

Literature references pertaining to the use of phthalic esters in dyeing processes are U.S. Pat. Nos. 2,833,613, 2,934,397, 2,982,597, 3,667,899, 3,973,907, and 4,032,291.

Phthalic esters have been used as components of textile lubricants, for example, according to U.S. Pat. Nos. 2,212,369, 2,241,246, 2,882,231, and 3,853,607.

The use of hydroxyalkyl or alkoxyalkyl benzoates as paint aids or fixatives is described in U.S. Pat. Nos. 3,532,454, 3,950,419 and 3,917.

447.

Higher trialkyl trimellitates have been listed as components of a soil release agent in U.S. Pat. No. 3,824,125.

The invention now relates to a new combination of cycloaliphatic and high boiling aromatic esters, which, when used as constituents of textile processing agents, in particular for polyester fibers, make superfluous one or more process steps, which are otherwise customary, without the final properties of the damage treated fiber.

According to one aspect of the present invention, cycloaliphatic diesters of the formula 1, wherein R is already 30 or unsubstituted, straight or branched chain alkyl of 4-20 carbon atoms, polyoxyalkylene of the formula Η0 (0χΗ ^ 0) ^ 0χΗ ^ - or phosphated polyoxyalkylene of the formula 2 or a salt thereof, wherein (CHO) is a group (CH_CH-O), (CH-O)

Jxynor 22 n * 3 6 n or (CH „CH„ 0) (CH ^ O) and n is 2-22, while the sum of p + q 2 2 p.> Oq 35 equals n, combined with a high-boiling aromatic 8104516 * *

V

3 ester of the formula ArGOO-R ^ -OOGAr or ArCOOR ^, wherein Ar represents unsubstituted or substituted monocyclic aryl, alkylene of up to 8 carbon atoms or polyoxyalkylene of the formula -CH "(0-CH"), wherein r 2 or 3 and is s to 15, r 2 r r 2 r s * 5 and R 1 represents alkyl or alkenyl of 8-30 carbon atoms to form a base for a fiber and fabric treatment composition for many purposes.

In another aspect, the invention relates to novel cycloaliphatic diester compounds, which may also be referred to as formula 1, wherein R Ar * COO (CH-CHoO) CH "CEL-, Ar'C00 (CoH, O) C „H, -, z / η Ζ Ζ J onjo

Ar'COOiC ^ .O) (CH.0) GH, - or Ar'C00 (CoH, 0) (Ο ,, Η, Ο) C0H.- represents zopdoqdo jopz4qz4, Ar * substituted or unsubstituted monocyclic aryl and n, p and q have the above meaning, yet are other compounds than the aforementioned compounds of the formula 1, so that they will be distinguished as compounds of the formula 1a, while the aforementioned compounds will be designated as compounds with the formula 1.

The invention further relates to synthetic fibers or fabrics coated with a treating agent containing any of the above compositions.

The invention further relates to the processing of synthetic fibers into goods, which are then dyed, using a composition of the invention as the sole fiber treatment agent.

The invention also relates to a method for manufacturing fabrics or articles from synthetic fibers or fabrics, wherein the fibers or fabric are coated with 1-2 wt% knitting or weaving lubricant, containing 5-1.5 wt% cycloaliphatic diester of the formula 1, contains 30-50 wt% high boiling aromatic ester, 5-15 wt parts dye dispersant and 10-30 wt emulsifier, dispersant and / or antistatic agent, knits or weaves the fibers into a fabric or a knitted or woven article and the fabric or 8104516%. * - 4 knitted or woven article dyes, if one uses cycloaliphatic diesters of the formula. 1a, these form 5-65 wt.% Of the treatment composition.

The invention further relates to a process for the treatment of a synthetic fiber, wherein a spinning equipment comprising (1) a cycloaliphatic diester, is applied to the fiber up to a pick-up of 0.4-0.75 wt. (2) contains a high-boiling aromatic diester and (3) contains a colorant dispersant, twists the thus-coated synthetic fiber at 180-1030 ° C, knits or weaves the resulting twisted fiber into fabric or knits the twisted twill into a knitted article and fabric or knit the knit.

According to another aspect, the invention relates to a method for reducing the heat and historical properties and the degree of crystallinity of a synthetic fiber, while decreasing the temperature, whereby the fiber can be woven, and while decreasing the temperature, wherein the fiber absorbs dye, applying to the fiber a composition of 0.4-0.75 wt.% containing a cycloaliphatic diester of the formula 1 and a high-boiling aromatic ester at a ratio of cycloaliphatic diester to high-boiling aromatic ester from 0.1: 1 to 10: 1 and wherein the combination of cycloaliphatic diester and high-boiling aromatic ester forms 10-90 wt.% of the composition and twists the fiber thus coated at 180-230 * 0. In addition, the above preparation may contain a colorant spreading agent of the formula R ^ COOR ^. Cycloaliphatic diesters of the formula 1a form 10-90% by weight of the preparation.

Figures 1-4 depict micrographs of polyester yarn treated with the preparation of Example XV and with a known spinning equipment preparation.

The dibasic acid used in the preparation of the compositions of the invention is a Diels-Alder adduct of acrylic acid and linoleic acid and can be prepared as described in U.S. Pat. No. 3,753,968.

8104516 i »\ \ 5 $

This diacid has the formula 3 and is therefore a mixture of 5- and 6-carboxy-4-hexyl-2-cyclohexene-1-octanoic acid.

The diacid is commercially available from Westvaco and is referred to as "Diacid 1500".

The diacid can be esterified with alcohols, for example using acidic catalysts such as p-toluenesulfonic acid, methanesulfonic acid or sulfuric acid. During the esterification, the reaction mixture is preferably also treated with a decolorizing agent, for example coal or clay.

After the esterification, the diacid is reduced to the corresponding compound of the formula 1, ie a compound which differs from the compound of the formula 3 in that it does not have the double bond. For this, use can be made of a nickel catalyst such as Raney nickel, nickel on kieselguhr or nickel on aluminum oxide. The amount required ranges from 5 to 10% by weight of the ester.

The hydrogenation takes place after the esterification in order to prevent complex formation between nickel and the free acid. Other catalysts, for example platinum or rhodium, do not cause this problem, but are too expensive.

The catalyst can be filtered through a plate and window filter press. The product is the resulting filtrate.

Polyoxyalkylene diesters are prepared by reacting the diacid with ethylene or propylene oxide in the presence of an alkaline catalyst. The reaction occurs at both acidic sites and the ethylene oxide addition is allowed to continue until the product becomes at least dispersible or preferably water soluble. This corresponds to the addition of a total of 5-25 ethylene oxide units. The product obtained using ethylene oxide has a structure for hydrogenation, which can be represented by the formula 4, wherein x + y = 5 to 25.

The phosphorelated product is easily obtained by reaction with phosphorus pentoxide. The saturated diester 35 can be obtained by nickel catalyzed hydrogenation 8104516 V <6 • Φ {> ring.

. In the phosphorilated derivative, the hydrogenation must precede the phosphorilation. The phosphorilated derivatives can be converted into their salts by reaction with a metal hydroxide. Sodium and potassium salts are preferred.

Compounds of formula 1a are obtained by treating polyoxyalkylene intermediates with an aromatic acid, for example, benzoic acid, toluic acid or mellitic acid, usually with an acidic catalyst. Hydrogenation of the double bond in the cycloaliphatic ring can take place before or after esterification with the aromatic acid.

The diesters used in the compositions of the invention have slightly varying properties. However, I can determine the following general correlation between the structure and the properties of representative preferred diesters (in hydrogenated form): dilauryl ester liquid, good heat resistance, good lubricant.

20 bis (2-ethylhexyl) ester liquid, good heat resistance, good lubricant.

solid distearyl ester, good heat resistance, good lubricant.

bis (ethoxylated) ester (15 solid, heat resistant, 25 moles ethylene oxide) cohesive.

bis (phosphated, ethoxylated) solid, heat resistant, ester (15 moles ethylene oxide) cohesive, antistatic.

Examples of R when it represents substituted alkyl in the products of the invention are butoxy-30-butyl, 10-hydroxystearyl, 10-hydroxydecyl, 10-halo stearyl, uhalkanoyloxyalkyl, etc.

Diesters, which one. Preferred according to the invention are those of formula 1, wherein R is a. straight or branched chain alkyl of 4-20 carbon atoms, b. 2-ethylhexyl, lauryl or stearyl, 8104516 \ c. H0 (CH2CH2O) nCH2CH2-, d. HOCCHHgO) - e. H0 (C2H40) p (C3H60) qCaH6-, f. (HO) 2 ^ 0 (^ 2 ^ 20 ^ 112012- or a 2 out thereof, 5 g. C6H5C0 (C2H40) nC2H4-, h. CH3C6H4C0 (C2H4O) nC2H4-, i. C, H_C0 (C, H, 0 ) and j. CH3C6H4CO (C3H10) nC3H6

The fabric treatment compositions of the invention 10 may of course contain more than 1 diester, for example a mixture of bis (alkyl) esters or a mixture containing a bis alkyl ester in combination with a bis (polyoxyalkylene) or bis (phosphate polyoxyalkylene) ester of a corresponding salt.

Esters of the types described in U.S. Pat. Nos. 3,694,257, 3,925,589 and 4,135,878 may be used in place of the cycloaliphatic diesters of formula 1 or to replace or partially replace the diesters of formula 1 replacement of about 45% of the diesters of formula 1a are used.

The term "high-boiling aromatic ester" is here understood to mean an ester of the formula ArCOO-R-OOCAr or ArC00R2 wherein Ar represents monocyclic aryl with up to 10 carbon atoms, R 1 alkylene with 2-8 carbon atoms or polyoxyalkylene of the formula -CH "(O-CH"), wherein r is 2 or 3, r 2 r r 2 r s 9 25 and s to 15 and R 2 represents unsubstituted or substituted alkyl or alkenyl of 8 to 30 carbon atoms.

Thus, aromatic esters used in the present invention are, for example, esters of benzoic acid, tolue acid, dimethyl benzoic acid, trimethyl benzoic acid, butyl benzoic acid, and the like acids.

In the case of aromatic esters, alkylene (R) ethylene, propylene, hexylene, 2,2-dimethyltrimethylene, butylene, heptamethylene and octylene including the various isomers thereof.

Polyoxyalkylene diesters include those which are 8104516

** V

\ * w .....

8 derived from polyethylene glycol or polypropylene glycol,

In the case of monoaromatic esters, alkyl may be octyl, nonyl, decyl, dodecyl, tridecyl, hexadecyl, stearyl, and alkenyl may be any corresponding monounsaturated function, eg oleyl.

Preferred aromatic diesters are those in which: a. Ar is phenyl, b. Ar is tolyl, 10 c. R. j is ethylene or propylene, including a.

and B. each, d. R. j is ethyleneoxyethylene or propyleneoxypropylene, including a. And b. each. polyoxypropylene of molecular weight is 200-500, including a. and b. each and f. decyl, dodecyl, hexadecyl, tridecyl, octadecyl or oleyl, including a. and b. each.

Examples of equivalents of the above-described high-boiling aromatic esters are esters of benzyl alcohol and substituted or unsubstituted aromatic acids of 6 or more carbon atoms, or substituted or unsubstituted aliphatic acids of 8 or more carbon atoms, including, for example, benzyl laurate, benzyl pelargonate, benzyloctate, benzyl palmitate, benzyl stearate, benzyl oleate, benzyl hydroxyl stearate and benzyl benzoate. The esters of substituted benzyl alcohols can of course also be used.

It has been found that aromatic esters which fall outside the above definition, in particular methyl, ethyl, propyl, butyl, pentyl and hexyl benzoate, lack the heat resistance, low odor and good lubricating properties required for the plurality of functions performed by the compositions of the invention.

Ethoxylated castor oil used in the compositions contains 15-100 oxyethylene units, preferably 40-80.

The hydrogenated castor oil derivatives contain 5-200 oxyethylene units, preferably 20-30. These substances can be purchased from ICI America and Whitestone Chemical.

Ethoxylated alkyl phenols used in the compositions of the invention contain up to 20 carbon atoms in the alkyl function and 1-25 ethylene oxide units. Preferred examples are ethoxylated nonylphenol with 10-15 ethylene oxide units.

Ethoxylated alkanols include those derived from alkanols of 12-15 carbon atoms, including mixtures thereof, or secondary alcohols of 11-15 carbon atoms, also including mixtures containing 6-15 ethylene oxide units.

Phosphated ethoxylated alkanols or phenols used in the compositions of the invention generally contain less ethylene oxide units than unphosphated compounds. Examples of materials to be used are the potassium salts of POE (10) nonylphenol phosphate, POE (3,5) lauryl alcohol phosphate, POE (7) lauryl alcohol phosphate, POE (9) lauryl alcohol phosphate, POE (6) decyl alcohol phosphate and POE (9) decyl alcohol phosphate. The formula given for the phosphated ethoxylated derivatives includes various products, including phosphated mono- and diesters, which have been obtained by reaction between the ethoxylated diacids and 5%.

In many instances, the composition of the invention is left on the fiber during dyeing and therefore acts as a dye auxiliary, in which case 10-25 wt% dye dispersant is included. By "colorant dispersant" here is meant a compound of the formula RgCOOR ^, wherein R ^ represents an ethoxylated alkyl phenol radical of the formula 5, wherein a is 0-12 and b is 1-24, or an ethoxylated alkanol radical with the formula 6, wherein c is 7-12 and d is 1-24 and wherein R 1 represents straight or branched chain alkyl or alkenyl of 1 to 21 carbon atoms, phenyl or tolyl.

Examples of dye dispersants are therefore esters of laurylic acid, myristic acid, palmitic acid, coconut acid, oleic acid, stearic acid, isostearic acid, 8104516. benzoic acid and tolic acid and ethoxylated nonyl phenol, octyl phenol, dodecyl phenol, n-decanol, n-dodecanol. n-tetradecanol or n-hexadecanol. The degree of ethoxylation is 1-25 ethylene oxide units per 5 alkyl phenol or alkanol, preferably 6-15 ethylene oxide units.

Preferred colorant dispersants are those in which a. 11-17 contains carbon atoms, including mixtures thereof, b. Rg is n-C ^ H ^, c. n-C ^ H ^ is, d. R3 is iso-C ^ H ^, e. R ^ is phenyl, f. R3 is 15 g. a is 9, including any of a.-f., h. c 11-14, including mixture thereof and each of a. - f., i. b is about 9.5, including each of a.f., 20 j. d is 6-10, including each of a.-f., k. b is 6-15, including any of a.-f. and l. a is 9, b is 8-10 and R ^ n-C ^ E ^.

The preparations are particularly suitable for the treatment of synthetic fibers such as polyester, polyamide and polyacrylic. The polyester may be spun or twisted polyester or elemental fiber or warp yarn and may be woven, knitted, tufted, punctured or nonwoven. The polyester can be a polyalkylene terephthalate, for example polyethylene terephthalate or a polyester prepared from cyclohexane dimethanol. The polyamide can be of types 6, 6,6 or 6,10. The acrylic can be straight acrylic (acrylic nitrile) or moda-cryl (modified with vinyl chloride or vinylidene chloride). The compositions are also suitable for use or mixtures of the above fibers with each other and with cellulose products (cotton, rayon, etc.) or wool.

8104516 11

The compositions can be applied at any stage of fiber processing. Examples of application to polyester fiber now follow: 5 A. Application as a spin finish:

The formulation is applied to yarn from a 10-20% emulsion to obtain 0.25-10% yarn finish. The treated yarn can be collected into yarns which can be used in high speed twisting machines.

Preparations used as spin finishes preferably have the following composition:

Parts by weight

Cycloaliphatic diester with the formula 1. 20-40

High-boiling aromatic ester 20-40

Dye dispersant 10-20

Emulsifiers, dispersants and / or antistatic agents 20-30. The compositions preferably contain 25-35 parts by weight of cycloaliphatic diester and 25-35 parts by weight of high-boiling aromatic ester.

Spin-pruning compositions preferably contain a cycloaliphatic diester, wherein R represents alkyl of 4-20 carbon atoms, most preferably 6-12 carbon atoms.

The high-boiling aromatic ester is preferably derived from a glycol, the most preferred diesters being derived from ethylene, propylene or butylene glycol and benzoic or toluic acid.

The colorant dispersant is preferably an ethoxylated nonyl phenol ester, especially nonyl phenol.

The emulsifiers, etc., preferably consist of ethoxylated castor oil, ethoxylated hydrogenated castor oil, and phosphated ethoxylated alkyl phenol in weight ratios from 1: 2: 2 to 1: 3: 3.

A most preferred spin preparation composition consists essentially of: Weight parts: 5 Cycloaliphatic bis (2-ethylhexyl) ester 25-35

Propylene glycol dibenzoate 25-35

Ethoxylated Nonylphenolurate 10-20

Ethoxylated Castor Oil 4-6

Ethoxylated Hydrogenated Castor Oil 8-12 10 Ethoxylated Nonylphenol Phosphate, K Salt 8-12 • The spin finishes can be diluted with water to form a stable emulsion or dispersion before use. The spin finish is preferably applied to include 0.4-0.75 wt%.

A representative polyester which has been treated with the spin finish composition of the invention up to 0.5-0.6% inclusion has lower heat history properties than a known spin finish treated yarn. Yarns thus treated can therefore be twined at a lower temperature than hitherto possible and dyed at lower temperatures than previously used. Moreover, the spider equipment does not vaporize or smoke during twisting at 200-24ÖeC. With spun yarns, the finish increases the cohesive properties of the yarn and provides the desired lubrication during stocking, carding, drawing, spinning and spinning.

Once applied, the spin finish compositions of the invention deserve not to use known lubricants to prevent maturation of the finish. Maximum benefits are achieved by exclusive use of the formulations of the. invention during the processing of the treated yarn into goods and during dyeing.

Spin preparation compositions using the cycloaliphatic diesters of the formula 1a, e.g. 8104516

J

13 approve within the following limits:

Parts by weight

Cycloaliphatic diester of the formula 1a 40-80

Colorant dispersant 5-25 5 Emulsifiers, dispersants and / or antistatic agents 20-30

Most preferably, the spin finish compositions contain 50-70 wt% cycloaliphatic diester of formula 1a and 10-25 parts by weight of colorant dispersant.

10 B. Application for knitting:

The formulation is used as a knitting lubricant and is left on the yarn during subsequent yarn processing. That is, the lubricant need not be removed by degreasing like conventional lubricants. Being able to omit a previously required processing step is an important advantage of the present invention. While weaving or knitting, high temperatures are reached due to friction and speeds, but the lubricants of the invention remain functional and do not gum or collect on the device. At the dyeing stage, the lubricant / dyeing aid is not degraded during dyeing (120-130 ° C) and / or does not cause smoke during drying and heat-setting of the fiber. The non-occurrence of foggy blue smoke during drying and heat-curing is important because of the increasingly stringent standard requirements for air pollution.

The lubricants of the invention preferably have the following composition: 30 parts by weight

Cycloaliphatic diester of the formula 1 10-30

High-boiling aromatic ester 25-60

Dye Diffuser 10-30

Emulsifiers, etc. 10-30 35 Most preferably, the composition contains 15-30 parts by weight of 8104516 to 14-cycloaliphatic diester, 25-45 parts by weight of high-boiling aromatic ester and 15-25. parts by weight of colorant dispersant.

Preference is given to the same cycloaliphatic diester and the same colorant dispersing agent as in the spin preparation composition. However, the high boiling aromatic ester is preferably a dibenzoate or ditoluate of di- or triethylene glycol or di- or tripropylene glycol.

The known emulsifiers and antistatic agents 10 are preferably ethoxylated alkyl phenols and the corresponding phosphoric acid esters, most preferably ethoxylated nonyl phenol.

Other materials in the lubricating composition are, for example, an antioxidant such as butylated hydroxytoluene in an amount of up to 0.5 wt%, an alkanolamine such as triethanol-15 amine in an amount of up to 5.0 wt% and up to 5.0 wt% of water.

The most preferred lubricating composition includes:

Parts by weight

Cycloaliphatic bis (2-ethylhexyl) ester 25-35 20 Dipropylene glycol dibenzoate 25-45

Ethoxylated Nonyl Laurate 15-25

Ethoxylated Nonylphenol 5-15

Butylated hydroxytoluene 0.05-0.2

Ethoxylated Nonyl Phosphate 5-10 25 Triethanolamine 1-5

Water 1-2

For satisfactory behavior, the intake, expressed as a minimum percent extractable when the treated fabric or fiber is introduced into the dyeing machine, must be at least:

Minimum% extractable

Cycloaliphatic diester of the formula 1 0.075

High-boiling aromatic ester 0.075

Dye Diffuser 0.050 35 The amount attached varies with the point 810451615 in the fiber processing to which the lubricant is applied, but is from about 0.25 to about 5.0% by weight of the fiber. During knitting, the adhesion is preferably 0.1 to 1.5 wt%.

In preparing knitting lubricants using aliphatic diesters of formula la, the composition is preferably:

Parts by weight

Cycloaliphatic diester of the formula 1a 10-60 10 Colorant dispersant 10-30

Emulsifiers, dispersants and / or anti-static agents. 10—60

Most preferably, the lubricating compositions contain 20-40 parts by weight of diester of the formula 1a and 15-25 parts by weight of colorant dispersant.

For satisfactory behavior, the intake, expressed as a minimum% extractable, when the treated fiber or fabric is placed in the dyeing machine, must be:: 20 Minimum% extractable

Cycloaliphatic diester of the formula 1a 0.45

Clay dust dispersant 0.05

The amount added is generally adjusted to the same as for the lubricant containing the di-ester of the formula 1.

Another type of knitting lubricant prepared according to the invention has the composition:

Parts by weight

Cycloaliphatic diester of the formula 1 5-15 30 High-boiling aromatic ester 30-50

Colorant dispersant 5-15

Emulsifiers, etc. 10-20

Ethylene oxide-propylene oxide copolymer 10-30

The knitting lubricants may also contain up to 0.25 wt% antioxidant and up to 5 wt% alkanolamine, for example dibutyl-8104516-ethanolamine.

It is preferred that the knitting lubricants contain a cycloaliphatic diester, wherein R represents alkyl of 4-20 carbon atoms, more preferably 6-12 carbon atoms.

The high-boiling aromatic ester is preferably a dibenzoate or ditoluate of ethylene or propylene glycol. Particular preference is given to propylene glycol dibenzoate.

The color dispersant used in the knitting lubricant is preferably an ester of a ethoxylated alkanol, more preferably the decanate, laurate, myristate or palmitate of ethoxylated decyl, lauryl, myristyl or hexadecyl alcohol.

The emulsifiers in the knitting lubricant are preferably ethoxylated alkanols and corresponding phosphates. Preference is given to ethylene oxide-propylene oxide copolymer of molecular weight 2000-5000.

A most preferred knitting lubricant is:

Parts by weight 20 Cycloaliphatic bis (2-ethylhexyl) ester 8-12

Propylene glycol dibenzoate 35-45

Ethoxylated lauryl laurate 8-12

Ethoxylated lauryl alcohol 8-12

Butylated hydroxytoluene 0.5-2 25 Ethylene oxide-propylene oxide copolymer 20-25

Ethoxylated Lauryl Alcohol Phosphate 3-6

Dibutylethanolamine 1-3

The lubricant is applied by dripping or spraying on the needles to 1-2% uptake on the yarn. The preparation thus applied gives fiber-metal and metal-metal lubrication at temperatures of 38-66 ° C. The preparation shows no degradation or gumming on the knitting machine.

The aforementioned lubricants promote even dye pick-up when left on the fabric or yarn during dyeing. Their presence 8104516 17 actually contributes to color exhaustion at 115-130 ° C. The lubricants do not cause excessive foaming and do not adversely affect the color fastness of the dyed fabric.

5 Lubricant containing a diester of formula 1a contains 20-50 parts by weight of this substance. The other properties of the components are as above.

The use of these preparations reduces or prevents the occurrence of odor and smoke inside and outside the processing plants. In addition to reducing air pollution, the lubricating compositions of the invention also reduce water pollution. In general, tax on high B0D / C0D or separable oils is no longer necessary.

15 C. Use as a cone oil;

For use as a cone oil intended for use after weaving or during yarn winding, the compositions of the invention also contain a predominant amount, up to 70% by weight, of ethylene oxide-propylene oxide copolymer 20 of molecular weight 2000-5000. Examples of suitable materials

* (fö dO

All are Ucon ^ LB and HB (Union Carbide Corp.), the Pluronics ^ (BASF) or Jeffox fluids (Texaco, Ine.).

Cone oil preparations according to the invention contain: 25 parts by weight

Cycloaliphatic diester of the formula 1 5-10

High-boiling aromatic ester 5-10

Dye dispersant 2-5

Emulsifiers, dispersants and / or anti-static agents 10-20

Ethylene oxide-propylene oxide copolymer 6 0-7 0

Preferred cycloaliphatic diesters for cone oil formulations include those wherein R is alkyl of 4 to 20 carbon atoms. most preferably 6-12 carbon atoms.

The high boiling aromatic ester is preferably 81045 1 6 - * - 4 * * 18 derived from an alkanol of 8-30 carbon atoms. most preferably decyl, lauryl or myristyl benzoate or toluate.

The colorant dispersant is preferably an ester of ethoxylated alkylphenol, most preferably nonylphenol.

The emulsifiers are preferably ethoxylated alcohols, the corresponding phosphates and ethoxylated hydrogenated castor oil.

Other ingredients in the cone oil formulation are, for example, about 0.5 wt% antioxidant as butylated hydroxytoluene, up to about 2.5 wt% alkanolamine as triethanolamine, and up to 2.5 wt% water.

The most preferred cone oil formulation is:

Parts by weight 15 Cycloaliphatic bis (2-ethylhexyl) ester 6-8

Lauryl benzoate 6-8

Ethoxylated Nonylphenol Cocosester 2-4

Ethoxylated lauryl alcohol 8-12

Ethoxylated Hydrogenated Castor Oil 2-4 20 Ethoxylated Nonylphenol Phosphate 2-4

Ethylene oxide-propylene oxide copolymer 60-70

Butylated hydroxyl toluene 0.05-0.2

Triethanolamine 0.5-2

Water 0.5-2 25 Gonus oil according to the invention penetrates the fiber quickly, but is not thrown off the fiber or the feed roller during the addition. The treated yarn is sufficiently lubricated for easy winding, knitting or weaving of the yarn. The preparation is stable and shows no smoke, yellowing or discoloration at temperatures up to about 66 ° G.

D. Paints:

Paint aids according to the invention consist of: 8104516 19

Weight part

Cycloaliphatic diester of the formula 1 15-40

High-boiling aromatic ester 20-55

Paint dispersant 10-25 5 Emulsifiers, and so on. 10-30

The cycloaliphatic diesters used for this aspect of the invention are preferably those wherein R represents alkyl of 4-20 carbon atoms, most preferably 6-12 carbon atoms.

Preferred high boiling aromatic esters for this use are dibenzoates and ditoluates of mono- and diethylene or propylene glycols.

Preferred paint dispersants for this aspect of the invention are esters of ethoxylated alkylphenols, especially ethoxylated no-phenylphenol.

It is preferred that the paint auxiliaries also contain ethoxylated castor oil, ethoxylated hydrogenated castor oil, as well as the phosphate (potassium salt) of an ethoxylated cycloaliphatic ester, i.e., wherein R 20 is phosphated polyoxyethylene.

Preferably, the paint aid compositions contain 15-35 parts by weight of cycloaliphatic diester of the formula 1, 35-55 parts by weight of high-boiling aromatic ester and 10-20 parts by weight of colorant dispersant.

25 A most preferred paint aid composition contains:

Parts by weight

Cycloaliphatic bis (2-ethylhexyl) ester 15-25

Dipropylene glycol dibenzoate 35-55 30 POE nonylphenol laurate 10-20 POE castor oil 4-6 POE hydrogenated castor oil 8-12 POE cycloaliphatic diester phosphate, potassium salt 8-12

Cycloaliphatic diesters of the formula 1a are used in paint auxiliaries, which contain: 8104516 20

Parts by weight

Cycloaliphatic diester of the formula IA. 40-90

Color dispersant 10-25

Emulsifiers, etc. 10-30 Preferably, these preparations contain 5-85 parts by weight of cycloaliphatic diester of the formula 1a.

A most preferred paint aid composition contains:

Parts by weight 10 Cycloaliphatic diester of the formula 1a, where RC, H_C0 (CoH £ 0) CH, - is 55-65 6 5 3 6 n 3 6 POE (9.5) nonylphenolurate 15—25 POE (80) castor oil 5-15 POE (25) hydrogenated castor oil 5-15 The compositions are applied in the dye bath in an amount of 0.25-1.0%, based on the weight of the goods. The dye bath is acidic (pH = 5 ± 0.5) and contains dye as the only additional ingredient. This is in contrast to known methods, where 2-4% paint aid and other dispersing agents are required. In addition, the paint flow is less sensitive to the degree of temperature change than with the known systems. The paint temperature in both systems is usually 130 ° C in a spray paint device.

Dyed yarn obtained using the compositions of the invention compares favorably with known dyed yarn in properties such as lightfastness, wrinkle, depth of color and uniform coloring.

Thus, the compositions of the invention, when applied to a synthetic fiber in manufacture or used as a weaving processing aid in place of the known lubricants, not only promote the dye affinity of the fiber, but also generally make the there is no need for follow-up operations and the associated chemical consumption.

35 Good examples of unnecessary handling and 8104516 * 21 treatments are: 1. Lubrication during knitting or weaving.

2. Degreasing and removal of lubricant.

3. Paint carrier during painting.

5 4. Paint dispersant during dyeing.

5. Color dispersant during dyeing.

6. Fiber lubricant during dyeing.

7. Defoaming agent during painting.

8. Post-cleaning and degreasing after dyeing.

10 9. Wind lubricant for dyed yarn.

A most preferred general purpose textile treatment composition consists of: 15 parts by weight

Bis (2-ethylhexyl) cycloaliphatic ester 15-25

Propylene glycol dibenzoate 30-50

Polyoxyethylene nonylphenolurate 15-20

Polyoxyethylene castor oil hydrogenated 5-15 20 Polyoxyethylene castor oil 5-15

The following examples illustrate the invention. In these examples, the temperatures are given uncorrected in ° C. Unless otherwise indicated, all parts and percentages are by weight.

25

Example I

Preparation of dialkyl ester of the formula 1, wherein R is 2-ethylhexyl.

352 g or 1 mol of diacid 1550, 273 or 2.1 mol of 2-ethylhexanol, 1.5 g of p-toluenesulfonic acid and 2 g were charged into a three-necked flask equipped with stirrer, thermometer, nitrogen purge, condenser, side arm receiver and heating mantle. decolorized cabbage. The air was purged from the flask with nitrogen and the reaction mixture was heated at 160-170 ° C for 4-6 hours with stirring. The water formed during the reaction was collected in the side arm receiver 8104516 V * * * 22 ". The reaction was continued until the acid value was below 5 mg KOH / g. Catalyst and carbon were filtered off. The ester product and 25 g of nickel on kieselguhr were placed in a stirred heated pressure vessel The mixture was heated to 160-170 and pressurized with hydrogen at 400 psig. After 6-8 hours, a sample was taken and the iodine value was The reaction was continued until the iodine value was below 0.5 g iodine / 100 g mixture.

The product was cooled to 50 ° C and the catalyst was filtered off.

Esters are similarly prepared from: 1. Diacid 1550 and decyl alcohol, mol ratio 1: 2.

2. Diacid 1550 and tridecyl alcohol, mol ratio 15 1: 2.

3. Diacid 1550 and Neodol 25, a mixture of linear C 2 -C 2 alcohols, 1: 2 molar ratio.

4. Diacid 1550 and butanol, mol ratio 1: 2.

Example II

A. Preparation of polyoxyethylene diester of formula 1, wherein R represents HO (C 1 -GH-O) CH, .CH-).

i l η l δ

352 g or 1 mole of Diacid 1550 was introduced into a stirred autoclave fitted with a heating coil and a cooling coil. 1.0 g of potassium hydroxide was added to the reactor as a catalyst. The temperature was brought to 100 ° C and the reactor was stripped under vacuum for 30-60 minutes to remove any residual water from previous washings of the reactor or from one or more reagents introduced onto the catalyst.

The reactor was purged with nitrogen to remove air, again vacuum and purged with nitrogen again. The reactor was heated to 140 ° C with stirring and 100 g or 2.3 mol of ethylene oxide was added. The pressure within the reactor immediately rose to 30-50 psig. After an induction time of 35. An exothermic polymerization reaction was started for 30-60 minutes (up to 150-160 ° C) with a concomitant pressure drop to 0 psig since ethylene oxide was consumed. Ethylene oxide was added to the reactor to a total of 660 g or 15 moles. The temperature was kept at 150-160 ° C by cooling.

The addition of ethylene oxide was stopped and the reaction was allowed to continue for an additional 30 minutes. The reactor was cooled to 90-100 ° C and purged twice with nitrogen.

A sample of the product had a hydroxyl number of 110 mg KOH / g (15 moles ethylene oxide added to the diacid. The diester was acidified with acetic acid to neutralize the potassium hydroxide catalyst and 3 g hydrogen peroxide was added to change the color of the bleaching and clarifying the product The reactor was cooled to 30 ° C and the product was filtered through filter paper using a porcelain filter.

B. Reduction to the polyoxyethylene diester.

The product of Example IIA and 25 g of nickel on kieselguhr were added to a stirred heated pressure vessel.

The mixture was heated to 160-170 ° C and pressurized to 400 psig with hydrogen. After 6-8 hours, samples were taken intermittently to determine the iodine value. The reaction was continued until the iodine value was less than 0.5 / 100 g mixture.

Example III

Preparation of phosphated polyoxyethylene diester of the formula 1, wherein R (HO) oP (O) O (CHoCH 2 O) CH 2 CH 2 - z z z z z z.

Mill polyethoxylated diacid obtained as in Example IIB were heated to 50-60 ° G, stirred and thoroughly purged with nitrogen to remove air. About 1015 or 1.0 mole of this material was added 24 g or 0.17 mole. An exothermic reaction immediately occurred (exothermic to 85-95 ° C). The reaction mixture was kept at this temperature by cooling and an additional 24 g or 0.17 mole of 8104516 1 * was added. - 24 P205. The reaction was continued for 3 hours until all ^ 2 ^ 5 was added. The reaction was cooled to 50 ° C before a sample was taken. The product had an acid number of 32 mg KOH / g (indicates that the reaction is complete). The batch was bleached with 5 g hydrogen peroxide at 85-95 ° C, cooled to 30 ° C and filtered.

Example IV

Preparation of propylene glycol dibenzoate.

84 g or 1.1 moles of propylene glycol, 244 g or 2 moles of benzoic acid and 0.8 g of p-toluesulfonic acid were placed in a three-necked flask equipped with stirrer, cooler, receiver, thermometer, nitrogen purge and heating mantle. The air from the flask was purged with nitrogen and the flask contents heated to 160-170 ° C.

The water formed in the reaction was continuously removed.

The reaction was continued until the product had an acid number of less than 5 mg KOH / g. The mixture was cooled and filtered.

Other esters are prepared using the following reagents.

1. Dipropylene glycol and benzoic acid, mole ratio 1: 2.

2. PPG 200 and benzoic acid, molar ratio 1: 2.

3. PPG 500 and benzoic acid, molar ratio 1: 2.

25

Example V

Preparation of polyoxyethylene nonylphenyl laurate.

In a three-necked flask equipped as in Example IV, 750 g or 1.1 moles of polyoxyethylated nonylphenol (9.5 moles of oxyethylene, NP 9.5), 208 or 1 mole of lauric acid and 2.4 g of p-toluenesulfonic acid were introduced. The air was purged from the flask with nitrogen and the mixture was heated to 160-170 ° C until an acid number of less than 10 mg KOH / g was obtained. The product was cooled and filtered.

Other polyoxyethylene nonyl phenol esters are similarly prepared from: 8104516 * * 25.

1. NP 9.5 and coconut fatty acid, molar ratio 1: 1.

2. NP 9.5 and oleic acid, molar ratio 1: 1.

3. NP 9.5 and stearic acid, 1: 1 molar ratio.

5 4. NP 9.5 and benzoic acid, molar ratio 1: 1.

Example VI

Ethoxylated castor oil and hydrogenated castor oil were prepared as in Example 2. The ethylene oxide is added to the hydroxyl group of castor oil.

Example VII

A fabric treatment composition was prepared by combining fabrics prepared as above in the following weight amounts:

Wt%

Bis-2-ethylhexyl diester (Example I) 20

Propylene glycol dibenzoate 40

Polyethoxyethylene nonyphenolurate 20 (9.5 moles ethylene oxide) 20

Polyethoxyethylene hydrogenated castor oil (25 moles ethylene oxide) 10

Polyethoxyethylene castor oil (80 moles ethylene oxide) 10 25

Example VIII

The fabric treatment composition of Example VII was applied to a test sheet of 10 g of T56 polyester fiber during the dyeing process in the following manner: The test sheet was placed in a stainless steel beaker containing 150 ml of water, 0.067 g of disperse yellow 67, 0.091 g of disperse red 91, 0.026 g of disperse blue 56, 0.1 g of acetic acid (56%) and 0.03 g of fabric conditioner. The beaker was sealed and placed in a launderometer at 38 ° C. The temperature was brought to 130 ° C at 4-5 ° C per minute and held thereon for 30 minutes. The beaker was cooled to 52 ° C at 4-500 rpm and taken from the launderometer. The polyester rag was taken out of the cup. The rag was evenly colored in a medium brown shade. The aqueous solution used was nearly dye exhausted. The rag was washed with cold water and dried in an oven at 121 ° C.

Example IX

Polyester puff weave (1500 pounds) was loaded into a 6 port Gaston County jet machine. The machine was filled with water and the goods were steam-washed. The machine was refilled and brought to 60 ° C. 15 Pounds of acetic acid (56%) and 4.5 pounds of the preparation of Example VII were dropped into the jet from the chemical chamber.

After 5 minutes, 18 pounds of Samaron Yellow 6 GSL (disperse yellow 114), 15 pounds of Bucron Rubine 2BNS (disperse red) and 13 pounds of Foron Blue SBGL (disperse blue 73) were added to the sprayer from the chemical chamber. The syringe was sealed and brought to 130 ° C. The temperature was held at 130 ° C for 30 minutes and returned to 66 ° C. The fabric was tint tested and the shade conformed to the standard. The temperature was lowered to 38 ° C. The spent paint liquid was discharged and the machine was again filled with water. The goods were rinsed thoroughly and removed from the syringe. The goods were cut into strips, dried and inspected. The final inspection gave high quality goods.

During the paint job using the preparation of Example VII, the odor in the paint house was much less than with known systems. During the drying and heat-curing at the end of the paint job, little smoke came out of the ovens. The comfort of the employee was therefore significantly improved.

The paint aid easily undergoes degradation when added to the factory drain. The following 35 values were obtained: 8104516 27. Known . Paint aid as 'system above' COD mg / kg 2.-640,000 2,210,000 BOD mg / kg <2,000 750,000 5 Ratio, COD: BOD> 1300: 1 2.95: 1

Since little dye adjuvant remains on the fabric after dyeing, use of the product of Example VII does not adversely affect the fastness properties of dyed goods.

The above is a good example of an application of the preparation to production scale.

Example X.

The procedure of Example IX was repeated, but no preparation of Example VII was used. When checked at the end of the paint job, the shade is slightly less due to incomplete dye exhaustion. The charge temperature was brought back to 132 ° C and held for an additional 30 minutes. The next check showed that the shade was up to the standard of 20, on which the goods were rinsed, removed, cut into strips and dried. On inspection, the goods were found to have paint streaks, prints, poor coverage, and a generally uneven paint distribution from one end to the other and from piece to piece. The goods had to be reprocessed by putting them back into a dyeing machine and treating with additional dye and color dispersant, the goods were kept in the machine for 3-4 hours until an even dyeing was achieved, but the fabric had a poor appearance due to the long processing.

This comparative example shows that omission of the composition of the invention produces an unacceptable dyeing.

Example XI

35 A textile treatment composition is prepared from 8104516 ........ 28 .....

the following components: 'GèW%

Bislavury diester (Example I) 20

Dipropylene glycol dibenzoate 40 5 POE (9.5) nonylphenol coconut fatty acid ester 20 POE (80) castor oil 10 POE (25) hydrogenated castor oil 10

This preparation is comparable in properties to the preparation of example VII.

10

Example XII

A fabric treatment composition as in Example 7 was prepared, except that 22 wt% polyoxyethylene diester (Example IIB) and 28 wt% propylene glycol dibenzoate were used. The formulation improves polyester fabric processing as described in Example IX.

Example XIII

A textile fabrication preparation as 20 in Example 7 was prepared, except that 18 wt% phosphated polyoxyethylene diester (Example III) and 42 wt% dipropylene dibenzoate were used. The preparation improves the processing of polyester fabric and acts as an anti-static agent.

Example XIV

a. A textile treatment composition as in Example VII was prepared from the following ingredients:

Wt%

Cycloaliphatic bis (2-ethylhexyl) ester 30.0 30 Dipropylene glycol dibenzoate 30.0 POE (9.5) nonylphenol laurate 15.0 POE (80) castor oil 5.0 POE (25) hydrogenated castor oil 10.0 POE (15) diester phosphate potassium salt (example III) 10.0 35 b. The preparation thus obtained was applied to a 150-denier polyester fiber from a 10104516 29% 20% aqueous solution as a spin-finish, which was then spun and twisted. The finish of the yarn before twisting was 0.29% and after twisting 0.25%. The twisted yarn formed a good ball.

Spin-mounted fittings did not cause smoke, dripping, or collection on heater plates, and did not cause any other runout difficulties.

The twisted yarn was knitted into a double stitch fabric on an Invoit 18 Gauge 10 machine. The yarn was easy to knit with minimal heat build-up on the knitting machine. No mist of mist or odor occurred in the workspace during knitting.

The fabric was brought to the dyeing room and introduced into a 6-port Gaston County jet machine. The. goods were not washed or degreased by flooding. Foaming during tissue insertion was significantly less than in fabrics treated with known lubricants. The fabric was dyed as in Example IX into a product which was judged to be a superior quality product. Both the paint yield and the barre coverage were improved and the fabric had a better overall appearance than untreated fabric.

Example XV

a. A spin preparation preparation was prepared:

Wt%

Cycloaliphatic bis (2-ethylhexyl) ester 30

Propylene glycol dibenzoate 30 30 POE (9) nonylphenol laurate 15 POE (81) castor oil 5 POE (25) hydrogenated castor oil 10 POE (10) nonylphenol phosphate, potassium salt 10 b. The preparation of part a. Was applied as a 20% emulsion to polyester yarn (505 denier / 34 filamentary fiber) by a single dip in a dry incorporation of 0. 5-0.6%. The treated yarn and the yarn that was treated with a known lubricant (Diamond Shamrock FT 504, which contains a fatty acid ester as lubricant 5 and nonionic ethoxylate as an emulsifier and antistate at 0.2-0.6% inclusion) were 205-22Q ° C twisted on a sample Scragg X-2 twisting machine. After twisting, the treated yarns were tested for thermal and other properties. The following results were obtained: 10 8104516 31 c o S ~ o C O co ° g T- o co> o <t

CO

μ cd CÖ «3>> O o ω o 3 bd (U o rd oi— 4J -Tj r- <tvO WM UI OCM <J- ajT) c vo co en Αί μ sr h xi Jl T — J CÖ · < - 00 0) 0) <- -u * - o

O, <u M CO Φ 4J B

& <u o «Μ m o

cd rD r- w O

CM 'm • μ o 2 ft o μ co>

PJ

μ i I o * ^

c <u O

• rl 0)> “£ *

Cu M o

ra 4J c O O

ra cö »o το μ a)> oo oo o μ 3 oo o \ oot— töc <t <f to ra bm ^ οι π cd μ c co oo Ai μνο ^ * τι <uo eo o ® ï- ui i- oe μ o co α> μ * - <tö ft μ «μ ra p μ ft öo T- s- 'μ

W Ö N -M

W g q) o

Η P

O M

• S «* o * CJ o ^ o

ÖO

«V Λ / * \ X-. 0) Q) Η Ό 5-i

O M

_C <U

μ g 0) <u · μ · η g μ μ ra α ο ο • Η ο Η Ö 3 / "·« Ο Μ J0 (U Α! -Μ μ w Μ Μ

^ C Pb 00 C

α) α) «-) C μ

> 3 · Η CÖ Ή (U

ο -β S w d yes cd cd w μ μ μ CÖ Pi

<D oo <U μ O

gra J3 μ OT

tj cj cd α) η co μ

Μα) · 0) <U

c Ai C Hi S μ cd <u μ T) A3 Ai Μ w o CJ μ '~ /

<u r-l · μ 5J C

μ cd Tl 0 P * m μ + j o μ <u o <u g dl fl μ Ai ω Ό M w 3 O μ · η (U m * rt

<u C cu Ai * m S

i— (μ cu, c η P μ

m g μ '(U

ra -μ cd a5, <u • HC IH CJ ü ë 3 <u · μ · μ s co co p P ft P Η P & · «8104516 - 32 TMA .is a measure of the tendency to soften or melt a yarn heated under constant tension. The decrease in TMA. An upper case DSC of the test yarn indicates that the degree of crystallinity is less than that of yarn, that is. 5 has been treated with a known spin apparatus. Accordingly, treated fibers could be twisted at a lower temperature than usual and also absorb dye at lower temperatures than usual, leading to lower energy costs.

10 8104516 ♦ »- 33 - c. sdcrofotografiseh examination of thread sections showed that both threads retained their configurations. Thus, it is believed that the observed changes in heat history were caused by changes in crystallinity generated by the applied spin equipment. The paint penetration of both yarn samples was essentially equivalent, but the paint absorption of the fibers treated with the compositions of this example is greater. The micrographs (Figures 1-4) also show that the crystallinity of the test samples has changed.

d. The lubricating properties of the yarns were evaluated on the Scragg X-2 machine under various conditions. The yarn was twisted at 340 m / min at 205-220 ° C. The following results were obtained: 15 8104516 <· • 34 Λ g ir> on r »v £> ο, 5 Aft A Λ *» ·

μ co COCOCOODftCON ^^ NN

^ τ— τ— τ— * —τ— τ— ν— · τ — τ ~ V- <τ— "d uo ιίϊ®'ί (0« ιΟ · 'ί'ί, · | ΑΝ qj * s! cn T- <Ncscncscncno \ Ocscn μα) ld unmcnuntnunun-tfunioun Μ Μ

6> S

60 Λ · 2 ö ΰ ft.μ ιτ> so <on <ininstN «i <nin 0 ^ 2 τ— ▼ - τ— * ~ τ— τ— τ— τ— τ— τ— • μ μ μ D Μ> d co ooO'ieoOeomtn'Dojio α) νο r ^ Ovovovovovovovovovo τ— r— τ— <- τ— ·> ρ— τ- τ- * τ * - τ— cs r ~ - r ^ ovi-noocnmor ^ r ^ vo Η ο · ^ ιηιηιη'ί'ίΌοοιη'ί'ί τ- <· <· ιηι ^. »- Γ ^ · ίήοοοιΝΐηνο Η <) ί'Ο '^ ιη'ΐ'ί-ίη'ί'ί' # Ρ ! Μ

0) 4) Ο OOOCLOOLOOOOO

Ρ η «λλλλαλλλλλ

O + J VO vOvOvDtriunvOvor> »vOvO'vO

• μ to on nnncinnnnflncη 5 cd Μ -60 ^ 0) d T)> · μ rHin vftin ^ Dmm κι ui m- ui in

Cjrd cuun ounounm m m to un m

4) d Tics <N CS on cs CS Μ Μ N N N

μ Ο T3 "el ·> ·> ·> * · * η λ r. n ft

Hi · μοη t> eo-cnononcn_cnoncncnco a m s <a> v & s t3 a I H _

d ·· 4) O

0) U 4) O

m 3 ϋ cn cd ds) μ 00 4) μ * - ο * - r— <v “r— .— τ— τ— un vo σι 'v.'ö 4) σ \ o cn σ \ σ \ σ> ο σ \ σ \ σ> σ \ ιμα) Μ λ >> ·> - «·> ·> *« «« »• rj ft ν τ— ι— τ— τ— τ— τ— ▼ - τ— Ί—

• μ ι-ι ft U

χ 4) cd d odd a

w w μ + J

A a ca μ a a a.

d tj cd 4) d h _ 6 0) 4) Οι- d '"nt — οΜοη'ΐίΛνοΓ ^ .αο' ^ '-'- τμ 0 a a fc * 5 a PQ> 8104516" ~, t 4 - 35 -

The frictional properties, breaking strength, elongation and shrinkage during heating were evaluated equivalent.

e. The effect of the twisting temperature on the dye pick-up of yarn knitted and dyed was examined at 180-230 ° C. The paint absorption by the fiber was measured with a Macbeth Color Eye instrument.

The test sample was twisted using the preparation of Example XV (a) and contained no other additives.

The control sample contained Hipochem TA-3 a commercially available paint carrier containing chlorinated solvents, methyl naphthalene and emulsifiers.

The K / S values (Kubelk-Munk / Scattering) were calculated as follows: _ / (1 reflection; 2X reflection 15 The K / S value is directly proportional to the amount of dye on the fabric.

The following results were obtained: Temperature K / S with K / S with appr.% Color permeability carrier of target 20 _ Image XV (a) _ 180 5.999 6.580 9.7 185 5.907 6.510 10.1 190 5.814 6.556 12.8 195 5,814 6,432. 10.6 25 200 5.721 6.426 12.3 205 5.719 6.484 13.4 210 5.715 6.490 13.6 215 5.816 6.542 12.5 220 5.879 6.614 12.5 30 225 5.993 6.734 12.4 230 6.151 6.888 12.0

These results show that the test fabrics had K / S values that were about 10% higher than with a fabric dyed using a known support. In addition, the paint pick-up was relatively uniform over a wide temperature range before twisting. These data further indicate that the application of the spin finish is relatively more uniform than before.

f. Large amounts of polyester which had dissipated after using the spin finish of Example XV (a) were fabric woven and dyed in Gaston County Jet Machines without the addition of lubricant, color dispersant, paint aid or paint carrier. The treated polyester always gave 7-12% higher color yields than usual. The heat history of barseconds dropped 3 - 30 depending on style and hue.

Example XVI

Lubricant of the following composition.

prepared: 15 parts by weight of cycloaliphatic bis (2-ethylhexyl) ester 20.0 dipropylene glycol dibenzoate 39 »3 POE (9.5) nonylphenolurate 20.0 20 POU (10) nonylphenol 10.0 butylated hydroxytoluene 0.1 POE (9 5) nonylphenol phosphate 6.3 triethanolamine, 98% 2.5 water 1.8

Example XVII

Cone oil for use in an amount of 2 - k% after twisting was prepared from:

Parts by weight of cycloaliphatic bis (2-ethyl-hexyl) ester 7.50 lauryl benzoate 7.50 POE (9.5) nonylphenolconocarbon fatty acid ester 3.75 POE (3.5) lauryl alcohol 10.00 POE (25) hydrogenated castor oil 2.50 35 POE (10) nonylphenol phosphate 2.50 8104516 * - 37 -

Parts by weight

Ucon LB-65 61; 15 butylated hydroxytoluene 0.10 triethanolamine 1.00 5 water 1.00

This cone oil provided the necessary lubrication to easily wind, knit or weave the yarn. The oil did not cause any smoke, yellowing or discoloration during processing temperatures up to 65 ° C.

Example XVIII

Knitting lubricant according to the invention was prepared from:

Wt. % cycloaliphatic bis (2-ethylhexyl) ester 10.0 15 propylene glycol dibenzoate Ui, 0 lauryl (POE 9) laurate 10.0 POE (9) lauryl alcohol 10.0 butylated hydroxytoluene 0.1

Ucon LB-65 21.9 20 POE (9) lauric acid phosphate 5.0 dibutyl ethanolamine 2.0

The lubricant was applied to knitting needles in an amount of 1 - 2% by drip or spray and was an effective lubricant at 38 - 65 ° C.

25 Example XIX

Into a three-necked 1000 ml glass flask equipped with a stirrer, thermometer, nitrogen purge and Dean-Stark trap was charged: 122.0 g of benzoic acid 30 19 130 g of di-n-butylaminoethanol 1.3 g of methanesulfonic acid (70%) 0.3 g of subphosphoric acid ( 50%) 200.0 ml toluene

The resulting mixture was heated to 70 - 85 ° C and refluxed until the theoretical ...........- 1 8104516 t

V O

---------------------------------------- "I

38 g of 18 g of water had been removed. The sample was cooled and washed in a separatory funnel. Toluene was removed in a rotary evaporator. About 20 g of di-n-butylaminoethylb etc were recovered.

5 Amino-substituted alkyl esters of aromatic acids as prepared above may be used in the compositions of the invention to replace, in whole or in part, the unsubstituted aromatic esters which one would otherwise use.

10 Example XX

The representative benzyl ester as in Example XIX is prepared from: 227.0 g benzyl alcohol 1 * 00.0 g lauric acid 15 * 2.1 * g methanesulfonic acid (70%) 0.6 g hypophosphorous acid (50%)

The resulting mixture was heated and kept at 165-175 ° C until the theoretical amount of 37 S of water was removed. About 580 g of benzyl laurate 20 was collected.

The benzyl esters of pelargonic, octanoic, palmitic, stearic, oleic and hydroxystearic acids were prepared in a similar manner.

Example XXI

A diester of formula 1a was synthesized in a 2 L autoclave fitted with nitrogen purge, cooler and receiver to remove water. The amounts supplied were: 510.0 g of Diacid 1550, 2.0 g of alkali flakes, 636.0 g of ethylene oxide.

After purging with nitrogen, Diacid 1550 and lye were heated to 130 ° C. Ethylene oxide was fed over a 1 hour period, keeping the temperature at 150-165 ° 0 ... 35. The resulting ethoxylate was cooled to 8104516 * - 39 - ♦ 90 ° C and the molecular weight was determined with the hydroxyl number. A value of 139 was found. The following substances were added: 3.5 g glacial acetic acid 5 T, 5 g methanesulfonic acid (70%) 3 ^ 0.0 g benzoic acid.

After thorough purging with nitrogen, the temperature was brought and held at 165-170 ° C until the acid value was less than 5 mg KOI per gram. The theoretical amount of water was removed during the reaction and collected in the receiver. The sample was cooled and filtered.

The above preparation was hydrogenated in the 2 L autoclave: 1000.0 g above example 15 50.0 g Raney nickel QS hydrogen

The reduction was carried out at 100-125 ° C and 200-250 psig until the hydrogen consumption ceased. The product was cooled and filtered.

Similarly, a propoxylated dibenzoic acid ester was prepared.

Example XXII

A textile treatment composition was prepared: 25 wt. % dibenzoic acid ester of bispropoxylated cycloaliphatic ester (sample above) 60.0 POE (955) nonylphenol laurate 20.0 POE (8θ) castor oil 10.0 30 POE (25) hydrogenated castor oil 10.0

The preparation was used to treat woven polyester in a launderometer at 130 ° C.

Sodyecron Navy AR (disperse blue 281) and acetic acid were used in appropriate amounts. A 10 g polyester patch was treated with 0.05 g fabric treatment composition.

8104516 t «? r - 40 - ..........- .-. ........— - - - - 1 '1' - 1

Color yield, migration and uniformity were excellent.

The fabric also had a pleasant grip.

Example XXIII

Into a three-necked flask equipped as above was placed 5: 750.0 g polyoxyethylated nonylphenol (NP 9.5) 317.0 g hydroxystearic acid 4.0 g methanesulfonic acid (J0%) 10 1.0 g hypophosphorous acid (50

The mixture was heated to 160-170 ° C while purging nitrogen until the acid number was less than 10 mg KOH / gram. The product was cooled and filtered. About 1035 g of polyoxyethylene nonyl phenyl hydroxy stearate was collected. This substance can be used in place of the color dispersant of the previous example, i.e. POE (9.5) nonylphenol laurate.

8104516

Claims (34)

1. Textile treatment agent containing one or more emulsifiers, dispersants and / or antistatic agents "in the form of ethoxylated castor oil, ethoxylated hydrogenated castor oil, ethoxylated alkyl phenol, ethoxylated primary and / or secondary alkanol and / or a salt of a phosphated, ethoxylated primary alkanol and / or alkyl phenol, characterized in that the composition contains: a. a cycloaliphatic diester of the formula L, wherein R is substituted or unsubstituted straight or branched chain alkyl of k-20 carbon atoms, polyalkylene of the formula H0 (CH2CH20) nCH2CH2-, HO ^ HgO ^ Hg-, H0 (CH ^ O) (C ^ gO or HO () p (Cg ^ ii.0) represents phosphated polyoxyalkylene, where n is 2 - 22 and the sum of p + q equals n and 15 is a high-boiling aromatic ester of the formula ArC00-R ^ -00CAr or ArCOORg, wherein Ar represents a monocyclic aryl of up to 10 carbon atoms, R ^ alkylene of 2-8 carbon atoms or polyoxyalkylene of the formula -CrH2r ^ ^ -Cr ^ 2r ^ s 20 waa rbij, r is 2 or 3 and s is up to 15, and Rg represents alkyl or alkenyl of 8-30 carbon atoms, the ratio of cycloaliphatic diester to high boiling aromatic ester being 0.1: 1 to 10: 1 and the combination of cycloaliphatic diester and high boiling aromatic ester makes up 10-90% by weight of the fabric treatment agent. 2. Preparation according to claim 1, characterized in that it is a dyeing auxiliary containing 10-25% by weight of colorant dispersant of the formula R ^ COOR ^, wherein R ^ 30 represents an ethoxylated alkylphenol radical of the formula wherein a is 0 - 12 and b is 1 - 2k, or represents an ethoxylated alkanol radical of the formula 6, wherein c is 7 - 22 and b is 1 - 2h and wherein R 1 is straight or branched chain alkyl of 1-21 carbon -atams, phenyl or tolyl. 3. Preparation according to claim 1, characterized in that it is a spin-treatment, in fibers consisting of 20 µl parts of cycloaliphatic diester, 20-0%. parts of high-boiling aromatic ester, 10-20 parts by weight of oxygen dispersant and 20-30 parts by weight of emulsifier, dispersant and / or anti-static agent. The preparation according to claim 1, characterized in that it is a spin finish, in fibers consisting of: parts of 10 cycloaliphatic bis (2-ethylhexyl) ester 25-35 propylene glycol dibenzoate 25 - 35 ethoxylated nonylphenol laurate 10-20 ethoxylated castor oil k - è 15 ethoxylated hydrogenated castor oil 8-12 ethoxylated nonylphenol phosphate 8-12 . Preparation according to Claim 1, 20, characterized in that it is a lubricant consisting in fibers of 10-30 parts by weight of cycloaliphatic diester, 25-60 parts by weight. parts of high boiling aromatic ester, 10-30 parts by weight of colorant dispersant and 10-30 parts by weight of emulsifier, dispersant and / or antistatic agent. Preparation according to claim 1, characterized in that it is a knitting lubricant comprising 5-15 parts by weight of cycloaliphatic diester, 30-50 parts by weight of high-boiling aromatic ester, 5-15 parts by weight of colorant dispersant, 10- Contains 30 parts of ethylene-propylene oxide copolymer and 10-20 parts of 30 emulsifier, dispersant and / or antistatic agent. Preparation according to claim 1, characterized in that it is a dyeing aid, in fibers consisting of 15 -1 (-0 parts by weight of cycloaliphatic diester, 20 - 55 parts by weight of high-boiling aromatic ester, 10 - 25 parts by weight. colorant dispersant and 10 - 30 parts of emulsifier, dispersant 8104516 * - 43 - and / or anti-static agent. 8. Preparation according to claim 7S, characterized in that in the eyeloaliphatic diester R substituted or unsubstituted alkyl with k ~ 20 carbon atoms, the high-boiling aromatic ester is a dibenzoate, ditoluate or mono- or diethylene or propylene glycol, the dye dispersant the agent is an ester of an ethoxylated alkylphenol and an emulsifier, dispersant and / or antistatic agent are composed of ethoxylated castor oil, ethoxylated, hydrogenated castor oil and / or potassium salt of a phosphated, ethoxylated eyeliphatic diester. Preparation according to claim 1, characterized in that it essentially consists of: Wt. # 15 eyeloaliphatic bis (2-ethylhexyl) ester 15-25 propylene glycol dibenzoate 30 - 50 ethoxylated nonylphenol urate 15-20 ethoxylated hydrogenated castor oil 5-15 ethoxylated castor oil 5-15 Synthetic fiber or synthetic fabric, characterized in that this article is coated with a composition according to claim 1 to an adhesion of 0.25-5% by weight of the fiber or fabric. 11. Synthetic fiber or synthetic fabric, characterized in that this article is coated with a composition according to claim 1 to an adhesion of 0.1-1.5% by weight of the fiber or fabric. 12. Synthetic fiber or synthetic fabric, characterized in that this article is coated with a composition according to claim 1, wherein the minimum percentage of extractable material is 0.075 wt.% Eyeloaliphatic diester, 0.075 wt.% High boiling aromatic ester and 0.050 wt. dye dispersant. 13. Method for processing synthetic, twisted, twisted fiber fibers into goods and ------ M 8104516 i - 44 - dyeing of the goods thus produced, characterized in that the fiber is coated during spin pretreatment with the composition according to claim 3 to an inclusion of Q, U - 0.75 wt% and this composition is used as the sole treatment agent. 1fc. Method according to claim 13, characterized in that the fiber is polyester. Method according to claim 13, characterized in that the fiber is polyamide. 16. A process for processing synthetic fibers into knitted goods and subsequently dyeing the knitted goods, characterized in that a composition according to claim is used as a lubricant, up to an inclusion of 0.5-1.5 wt.% And use this lubricant as the sole treating agent. Method according to claim 16, characterized in that the fiber is polyamide. A method according to claim 16, characterized in that the fiber is polyester. 20 19 · Method for applying a cone oil to synthetic fibers after twisting or during winding and for subsequently processing the yarn into goods and dyeing those goods, characterized in that the only fiber treatment agent used is a cone oil used according to claim 1 consisting essentially of 5-10 parts by weight of cycloaliphatic diester, 5-10 parts by weight of high-boiling aromatic ester, 2-5 parts by weight of colorant dispersant, 60-70 parts by weight of ethylene oxide. propylene oxide copolymer and 10-20 parts by weight of emulsifier, dispersant and / or antistatic agent. 20. A method for increasing the color yields and decreasing the heat history bareconds in the dyeing of goods, made from a twisted, spin-finished synthetic fiber, characterized in that the preparation according to claim 3 is used as a spin-finish. used without adding lubricant, colorant dispersing 8104516 'V - 45 agent, paint aid or paint carrier. 21. A method for increasing the color yields and decreasing the heat history barreseconds by dyeing goods made from a twisted synthetic fiber provided with spin finish, characterized in that the preparation according to claim b is used as spin finish. used without adding lubricant, colorant dispersant, paint aid or paint carrier. 22. A method of manufacturing a fabric or article from a synthetic fiber or synthetic fabric, characterized in that in sequence: a. The fiber or fabric is coated with 1-2% knitting or weaving aid, that 5-15 parts by weight of the cycloaliphatic diester of the formula I, wherein E is a substituted or unsubstituted straight or branched chain alkyl of b to 20 carbon atoms, polyoxyalkylene of the formula H0 (CH2 CH2 O4 ^ CHgCHg-, I ° (03Hg0) nC3Hr, HOtCH ^ oyCjHgO ^ OjHg- or 110 (0 ^ 0 ^ (0 ,, ^ 0 ^ CgH ^ - or phosphated polyoxyalkylene, where n is 2 - 22 and the sum of p + q equal to n, 30 to 50 parts by weight of a high-boiling aromatic ester of the formula ArC00-R ^ -00CAr or ArCQORg, in which Ar represents a monocyclic aryl with up to 10 carbon atoms, R ^ alkylene of 2-8 carbon atoms, or polyoxyalkylene of the formula - CrEL (0-C Hn), wherein r is 2 or 3 dr r dr s and is s to 15 and Rg represents alkyl or alkenyl having 8-30 carbon atoms, 5-15 parts by weight kl dust dispersant of the formula R ^ COOR ^, wherein R ^ represents an ethoxylated alkyl phenol radical of the formula 5, wherein a is 0 - 12 and b is 1 - 2b or an ethoxylated alkanol radical of the formula CH ^ (C12) c-0- ( CHgCHgO) ^ CHgCHg-, wherein c 7-22 and 30 d is 1 - 2¾ and wherein R 2 represents a straight or branched chain alkyl of 1 - 21 carbon atoms, phenyl or tolyl and 10 - 30 parts by weight of emulsifier, dispersant and / or anti-static agent, b. processing the fiber into a fabric or knit and 35 e. dye the woven or knitted object. 8104516 - 46 - λ «c A method of decreasing the heat historical properties and the crystallinity of a synthetic fiber while decreasing the temperature, wherein. the fiber can be twisted and lowering the temperature at which the fiber absorbs dye, characterized in that a composition is applied to the fiber up to an inclusion of 0.4-0.75 wt. a cycloaliphatic diester of the formula 1, wherein R contains straight or branched chain alkyl of 4-20 carbon atoms, polyoxyalkylene of the formula HO (CH2CH2O) nCH2CH2-, HO (C ^ HgOHO (CHgCHgO) p (0 ^) ^ 0 ^ - or H0 (C ^ HgO) (CgHj.0) or phosphated polyoxyalkylene, where n is 2 - 22 and the sum of p + q is n and contains a high boiling aromatic ester of the formula ArC00-R ^ - OOCAr or ArCOORg, wherein Ar represents a monocyclic aryl 15 with up to 10 carbon atoms, R 1 alkylene of 2 to 8 carbon atoms or polyoxyalkylene of the formula -CrH 2 R 2 O-CrH 2r s where r is 2 or 3 and s is 15 , and R2 represents alkyl or alkenyl of 8-30 carbon atoms, wherein the ratio of cycloaliphatic di-ester to high-boiling aromatic ester is 0.1: 1 to 2: 1. and the combination of cycloaliphatic diester and high-boiling aromatic ester comprises 10-90 wt.% of the composition and the fiber thus coated is twisted at 180-230 ° C. 24. A method according to claim 23, characterized in that the preparation additionally contains a colorant dispersing agent of the formula R ^ COOR ^, wherein R ^ represents an ethoxylated alkylphenol radical of the formula: wherein a 0-12 and b 1 - 2b, or represents an ethoxylated alkanol radical of the formula 6, wherein c is 7-22 and d is 1 to 24, and where 30 in R 1 represents straight or branched chain alkyl of 1 to 21 carbon atoms, phenyl or tolyl. 25. Process according to claim 24, characterized in that the fiber is coated with a minimum extractable material of 0.075% by weight cycloaliphatic diester, 0.075% by weight of high-boiling aromatic ester and 0.050% by weight of color. -47- c dust dispersant. A method according to claim 24, characterized in that the synthetic fiber is polyester. 27. Polyester fiber treated according to the method of claim 23. 28. A method of decreasing the thermal historical properties and the degree of crystallinity of a synthetic fiber while decreasing the temperature, whereby the fiber can be twisted and decreasing the temperature, at which the fiber absorbs dye, characterized that a composition containing a cycloaliphatic diester of the formula I, wherein R is substituted or unsubstituted straight or branched alkyl of 4-20 carbon atoms, is applied to the fiber to an uptake of 0.4-0.75 wt.%, polyoxyalkylene of the formula HQiCHgCHgO ^ CHgCHg-, HO ^ HgO ^ Hg-, HQ (GHgCH2O) (C3Hg) C ^ Hg or HO (0 ^ 0) (CgBy)) C ^ or phosphated polyoxyalkylene, wherein n is 2 - 22 and the sum of p + q. equals n and contains a high-boiling aromatic ester of the formula ArCOO-R-OOCAr or ArCOORg wherein Ar represents a monocyclic aryl of up to 10 carbon atoms, R-alkylene of 2-8 carbon atoms or polyoxyalkylene of the formula - Cr 1, (0-C Ξ „), where r is 2 or 3 and s is up to 15, represents 2r r 2r s and R 2 represents alkyl or alkenyl of 8-30 carbon atoms, wherein the ratio of cycloaliphatic di-ester to high boiling aromatic ester is from 0.1: 1 to 10: 1 and the combination of cycloaliphatic diester and high boiling aromatic ester comprises 10-90 wt.% of the composition and the fiber thus coated desiccates at 180-230 ° C, provided that, when R is unsubstituted straight or branched chain alkyl, the ratio of cycloaliphatic diester to high boiling aromatic ester is from 2: 1 to 10: 1. 29. Process according to claim 28, characterized in that the preparation additionally contains a colorant dispersing agent of the formula R ^ COOR ^, wherein R ^ represents an ethoxylated alkyl phenol radical of the formula 5S wherein 8104516 - 48 - Λ t- A a Ο - 12 and t is 1 - 24, or represents an ethoxyated alkanol radical of the formula β, wherein c is 7 - 22 and d is 1 - 24 and wherein R 1 is straight or branched chain alkyl of 1 to 21 carbon atoms, phenyl or tolyl proposes. 5 '30. Process according to claim 29, characterized in that the fiber is coated with a minimum extractable material of 0.075 wt% cycloaliphatic diester, 0.075 wt% high boiling aromatic ester and 0.050 wt% dye dispersant. 31. A method according to claim 29, characterized in that the synthetic fiber is polyester. Polyester fiber, treated according to the method of claim 28. 33. Textile treatment composition containing one or more emulsifiers, dispersants and / or antistatic agents in the form of one or more ethoxylated castor oils, ethoxylated hydrogenated castor oils, ethoxylated alkyl phenols, ethoxylated primary and / or secondary alkanols and / or salt of a phosphated ethoxyated primary alkanol and / or alkyl phenol, characterized in that the preparation is a. cycloaliphatic diester of the formula I, wherein R has the formula Ar 'COQiCHgCHgO ^ CHgCHg-, Ar'COOiC ^ HgOj ^ C ^ Hg-, Ar'COOiC ^ O) (C3H6.0) C3Hg-, or Ar'COO ^ HgQ ) (CgH ^ CgH ^ -, where n is 2 - 22 and the sum of p + q. Is equal to n and 25 Ar 'represents unsubstituted or substituted monocyclic aryl in an amount of 10-90% by weight of the fabric treatment -medium. 34. A composition according to claim 33, characterized in that it is a dyeing auxiliary containing 10-25% by weight of a colorant dispersant of the formula R 2 COOR 1, wherein R 1 represents an ethoxyated alkyl phenol residue with. the formula 5 wherein a is 0 - 12 and b is 1 - 24, or represents an ethoxyated alkanol radical of the formula 6, wherein c is 7 - 22 and d is 1 - 24 and wherein R 1 is straight or branched chain alkyl with 1 - 21 ' 35 represents carbon atoms, phenyl or tolyl. 8 1 0 4 5 1 6 · \ 1 - 49 - 35. A composition according to claim 33, characterized in that the spinning equipment is essentially composed of (-0-80 parts by weight of cycloaliphatic diester, 10-20 parts by weight of colorant dispersant and 20-30 parts by weight of emulsifier. dispersant and / or anti-static agent. 36. Cycloaliphatic diester of the formula 1, characterized in that R has the formula Ar 'C00 (CH ^ CH ^ O ^ CH ^ CH ^ -, Ar'COOiC ^ Oj ^ Hg-, Ar'COOiCgH ^ O) (C3HgO ) C ^ g-, or Ar'C00 (C ^ H ^ O) ^ (C ^ H ^ O), where n has 2 - 22 and the sum 10 of p + q. is equal to n and Ar "represents substituted or unsubstituted monoeylic aryl. 3T. A process for the treatment of a synthetic fiber, characterized in that a spin-preparation composition containing 1. a cycloaliphatic diester of the formula 1 in which a. R substituted or unsubstituted straight or branched alkyl with k - 20 carbon atoms, polyoxyalkylene of the formula H0 (CH2CH20) nCH2CH2-, H0 (C3H60) nC3H6-, HOiCHgCHgO) (C ^ O) C ^ g- 20 or HO (C ^ HgO) ^ (^ 2¾0) o1 'represents phosphated polyoxyalkylene, where n is 2 - 22 and the sum of p + q. equals n, 2. a high-boiling aromatic ester of the formula ArC00-R ^ -OOCAr or ArCOORg, wherein Ar represents a monoeylic aryl with up to 10 carbon atoms, R ^ alkylene with 2-8 carbon atoms or polyalkylene of the formula “C ^ H ^ CO-C ^ H ^) wherein r is 2 or 3 and s is 15 and R 9 represents alkyl or alkenyl of 8-30 carbon atoms and 3. a dye dispersant of the formula R 2 COOR ^, wherein R ^ represents an ethoxylated alkylphenol radical of the formula VI wherein a is 0 - 12 and b is 1 - 2k, or an ethoxylated alkanol radical of the formula is 6, wherein c is 7 - 22 and d is 1 - 2k and wherein R3 represents straight or branched chain alkyl of 1-21 carbon atoms, phenyl or tolyl, b. the synthetic fibers thus coated disappear at 35 180 - 230 ° C, __ ________ Λ 8104516 Λ - 50 - r e V c. the resulting fiberized fiber into a woven or knitted article and d. paints the object obtained. 38. Process according to claim 37, characterized in that the spin-preparation composition consists essentially of 25-35 parts by weight of cycloaliphatic diester, wherein R is alkyl with k-20 carbon atoms, 25-35 parts by weight of high-boiling aromatic ester, namely ethylene propylene or butylene di-benzoate or ditoluate, 10-20 parts of ethoxylated alkyl-10-phenol ester and 20-30 parts of ethoxylated castor oil, ethoxylated hydrogenated castor oil and phosphated ethoxylated alkylphenol in a weight ratio of 1: 2: 2 to 1: 3: 3- 39. A method according to claim 37, characterized in that the synthetic fiber is polyethylene terephthalate. 1) -0. Method according to claim 37, characterized in that the synthetic fiber is a polyamide. 1 + 1. A process for decreasing the heat e-20 historical properties and the degree of crystallinity of a synthetic fiber while decreasing the temperature, whereby the fiber can be wine-aged and while decreasing the temperature, at which the fiber absorbs dye, characterized in that on the fiber to an uptake of U - 0.75 wt% apply a composition containing a cycloaliphatic diester of the formula 1, wherein R is straight or branched chain alkyl with U - 20 carbon atoms, polyoxyalkylene of the formula HD {CH 2 CH 2 O) nGH2CH2-, HO ^ HgOj ^ Hg - HO (CHgCHgO) ^ (0 ^ 0) ^ 0 ^ - or H0 (C_H ^ 0) (C_H, 0) CJL or phosphated polyoxyalkylene represents -3o p 24 q_24 30, where, n 2 - 22 and the sum of p + q is n and contains a high-boiling aromatic ester of the formula ArC00-R ^ -00CAr or ArCOORg, wherein Ar represents unsubstituted or substituted monocyclic aryl, R ^ alkylene with 2-8 carbon atoms or polyoxyalkylene of the formula -CrH2r ^ 0-CrH2r ^ s' ...... 35 where r 2 or 3 and s is up to 15, and R 2 represents alkyl or 8104516 \ 5-51- alkenyl of 8-30 carbon atoms, the ratio of cycloaliphatic diester to high boiling aromatic ester being 0.1: 1 to 2: 1 and the combination of cycloaliphatic diester and high-boiling aromatic ester constitutes 10-90 wt.% Of the composition, 8104516