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Publication numberUS3775446 A
Publication typeGrant
Publication dateNov 27, 1973
Filing dateDec 16, 1970
Priority dateFeb 17, 1968
Publication numberUS 3775446 A, US 3775446A, US-A-3775446, US3775446 A, US3775446A
InventorsC Macura, F Schmitz, A Wegerhoff
Original AssigneeGlanzstoff Ag
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Acyl-amino-propyl-dialkylammonium dialkyl phosphates
US 3775446 A
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Description  (OCR text may contain errors)

United States Patent 3,775,446 ACYL-AMINO-PROPYL-DIALKYLAMMONIUM DIALKYL PHOSPHATES Arno Wegerhoif, Worth am Main, Franz-Josef Schmitz, Erlenbach, and Carl Macura, Klingenherg, Germany, assignors to Glanzstolf AG, Wuppertal, Germany No Drawing. Original application Feb. 17, 1969, Ser. No. 799,999, now Patent No. 3,634,117. Divided and this application Dec. 16, 1970, Ser. No. 98,896 Claims priority, application Germany, Feb. 17, 1968,

P 17 19 543.6 Int. Cl. C07f 9/02; D06m 13/26 US. Cl. 260403 8 Claims ABSTRACT OF THE DISCLOSURE Acyl-amino-propyl dialkylammonium dialkyl phosphates as surface active agents and their application to textile materials, especially polyester and polyamide fibrous materials, as a finishing agent, for example, in combination with an aqueous emulsion of a textile lubricating agent.

The present application is a division of application Ser. No. 799,999, which was filed on Feb. 17, 1969, and which issued as US. Pat. No. 3,634,117.

The use of amine salts of polyethoxyalkyl phosphoric acid esters of the formula 3 O=I|0(CHCH,0),H:|

b I an anti-electrostatic finishing agents for polyethylene terephthalate filaments and fibers has been described in German patent specification No. 1,084,231. The amine portion of this phosphoric acid ester salt consists of a monoamine, e.g. an alkyl amine or an alkylol amine. Diethanolamine salts of mixtures of alkyl esters of pentavalent phosphorous acids or acid anhydrides, characterized by the presence of --P--O--P-- linkages, are described in US. patent specification No. 2,742,379 as having antistatic properties in their application to hydrophobic textile materials.

N-substituted diamines can form the cation of the quaternary ammonium salts II of the formula:

which also have antistatic properties (see US. Pat. No. 3,082,227). In these salts of the Formula II, the radical R is an aliphatic or alicyclic hydrocarbon of at least 7 carbon atoms, two of the primed Rs may be a lower alkyl but at least one is a monohydroxyalkyl of 2 or 3 carbon atoms, and Y is the anion of an inorganic acid.

There are literally thousands of organic compounds in addition to those mentioned above which possess antistatic properties and which have therefore been suggested for application to hydrophobic synthetic polymer products, especially textile materials, in order to reduce the electrostatic charging of these products as they are being processed and/or during subsequent use. It is extremely difficult, however, to find suitable antistatic agents which are fully compatible with other finishing agents such as lubricants, sizes, emulsifiers and the like. Moreover, many antistatic agents possess other properties which make them relatively unsatisfactory in such applications, e.g. where the antistatic agent contributes to the corrosion of machinery used in processing the treated textile materials or where it is not stable or resistant to subsequent heat treatment steps. These and similar problems as well as the desirability of improving the antistatic effect must be "ice taken into consideration in attempting to provide satisfactory finishing agents of this type.

One object of the present invention is to provide a class of organic compounds which are highly useful in a finishing or lubricating composition for textile materials, and to provide a process for treating such textile materials to achieve an improved antistatic efiect.

Another object of the invention is to provide an antistatic agent which can also function as an emulsifying agent for textile lubricants and which possesses a number of desirable properties for this use or similar applications.

Still other objects and advantages of the invention are explained in greater detail hereinafter.

It has now been found, in accordance with the invention, that especially improved results can be achieved in terms of antistatic effect with a finishing agent and compositions containing the same by means of a phosphate of the Formula III, especially when applied as a preparatory and finishing agent for fibrous or filamentary polyester and polyamide textile materials; in which formula R represents a primary n-alkyl group of 5 to 17 carbon atoms, i.e. an alkyl group of from C H to C H R and R each represent a lower alkyl radical of 1 to 3 carbon atoms;

R represents a lower alkyl radical of 2 to 4 carbon atoms; and

R represents an alkyl radical of 2 to 18 carbon atoms,

preferably a primary n-alkyl group.

Of particular technical and commercial significance are the phosphoric acid ester amine salts which may be identified as l-lauramidopropyl-dimethylammonium-(3)- ethyl primary-n-alkyl phosphates which have the structural formula:

in which R, is alkyl and preferably the primary n-alkyl group of about 2 to 18 and preferably 4 to 14 carbon atoms.

Depending on the length of the alkyl chains in the cation and anion, respectively, the amine salts used in accordance with the invention are either cationicallyactive or anionically-active, or may be both cationically and anionically active.

The elfectiveness of these compounds is not limited to the improved electrostatic properties imparted to polyester and polyamide yarns, filaments or fibers and to textiles containing these materials, but also extends to other filaments and fibers so as to greatly facilitate their mechanical handling during drawing or carding operations or in knitting and weaving machinery. The amino phosphoric acid ester salts of the Formulae III or IV, when used according to the invention, thus reduce the static and sliding friction of a wide variety of natural and synthetic fibers and also that of metal or rubber, so as to be generally useful as an antistatic agent. The finishing or antistatic agents of the invention are also extremely resistant to heat. For example, during the heat fixing or setting of synthetic thermoplastic filaments, the phosphate compounds of the invention do not cause any yellowing of the fibrous material finished with these compounds. Also, these finishing agents do not cause any alteration in the electrical and mechanical properties of the filaments during heat treatment.

The emulsifying properties of the phosphate compounds permit, inter alia, the preparation of stable emulsions of mineral oil or similar hydrocarbon lubricants in water. In this respect, these phosphates are generally useful as emulsifiers or dispersing agents beyond textile applications, especially where a good antistatic effect is also desired.

When applied to unalloyed steel components, e.g. by vaporization of a 1% aqueous solution on a steel plate, the amine salts according to the invention actually prevent rust formation. Thus, the dialkyl phosphates listed in Table I below have a notable corrosion-inhibiting action. By comparison, the quaternary ammonium salts 11 according to US. Pat. No. 3,082,227 are not too satisfactory in this respect, and in fact, the salts of strong inorganic acids as disclosed in this patent actually promote the formation of rust.

The anti-electrostatic effect is particularly pronounced with the 1 lauramidopropyl dimethylammonium-(3)- ethyl primary-n-alkyl phosphates of the structural Formula IV, especially when these amine salts form a thin surface layer on polyesters, e.g. polyethylene terephthalate, or on polyamide (nylon) yarns, filaments or fibers, including fabrics or other textile products. Those salts having R of 2 up to 6 carbon atoms, e.g. the primary n-C H group, are fully soluble in water. With larger alkyl radicals R e.g. up to 18 carbon atoms, they can still be dispersed in water, so that the impregnation of any materials to be treated is best accomplished in an aqueous solution or dispersion.

Strips of a polycaprolactam fabric, which have been treated under controlled conditions with aqueous solutions of these phosphates, then dried and rubbed over stainless steel pins, show a distinctly lower electrostatic charging than a comparison strip of polycaprolactam fabric which has a surface film or coating of the sodium salt of the copolymer of styrene and maleic acid which is a well known antistatic agent (see Example 1 below).

With medium length alkyl radicals R e.g. 6 to 8 carbon atoms, the lauramidopropyl dimethylammoniumdialkyl phosphates IV are soluble both in water and hydrocarbon solvents, e.g. turpentines or so-called white spirit as well as mineral oils in general, and exhibit especially good emulsifying properties because of their boundary surface activity. For example, when the ethyl primary-n-hexylphosphate V is combined with an ethoxylated oleyl alcohol VI which contains about 2 ethylene oxide groups per alcohol molecule, an emulsifier system is formed which permits mineral oils or similar lubricants to be emulsified in water. An optimum emulsifying action has been produced when 10 parts by weight of the ethoxylated oleyl alcohol VI are used to 13 parts by Weight of the amine salt V. With a ratio by weight of this emulsifier system to mineral oil of 23:30, a 10% by weight emulsion of the mineral oil in water is transparent. With increasing mineral oil content, the aqueous emulsions assume a milky cloudiness because of particle enlargement. In a comparison sample using only the ethoxylated oleyl alcohol, mineral oil and water, and in which no ammonium phosphate such as Compound V is present, it is not possible to obtain a stable emulsion.

Aqueous emulsions of these components are particularly suitable for use as finishing and lubricating compositions in the processing of synthetic yarns, filaments or fibers, since they lower the friction and protect steel contact surfaces from rust formation, as well as decreasing the electrostatic charging. In addition to the use of the ammonium dialkyl phosphates III alone, mixtures of these compounds with other emulsifiers are also feasible. In particular, mixtures of V and VI have been found especially useful as dressings for the processing of polyester staple fibers. The addition of the ethoxylated oleyl alcohol VI to the amine phosphate salt V increases the slippability as compared to fibers dressed only with the salt V. With a compo i ion consisti g of eq a p t y w ight of V and VI, addition of about 0.1% by weight to a dried 3-denier polyethylene terephthalate fibrous material is sufficient in order to almost completely eliminate electrostatic charging during carding. By comparison, when using a commercial product which is an ethoxylated stearic acid ester, the electrostatic charging is substantially higher even after application of 4 times as much of the active agent (see Example 3 below).

Mixtures of 1 part by weight of the dialkylphosphate V to about 1 to 2 parts by weight of the ethoxylated oleyl alcohol VI also provide good finishing agents for those polyester or polyamide fibers which are processed on cards or by the converter method. Such finishing compositions reduce the static and sliding friction of the fibers both relative to one another and also to metal or rubber. This makes it possible to process these fibers satisfactorily, for example, on a Rieter converter, followed by machines which are customary in the spinning of combed yarn.

Mixtures of phosphoric acid ester amine salts of the structural Formula IV and ethyloxylated oleyl alcohol VI do not cause any yellowing of polyethylene terephthalate fibers or other thermoplastic fibers after these have been set or heat treated for one hour at 150 C. Furthermore, the electrical and mechanical properties of such fibers or filaments are not modified by this heat treatment.

A comparison of the salts III of the acylated l-dimethylamino-3-propylamine and dialkyl phosphoric acids according to the invention with the phosphoric acid ester diethanolamine salts described in US. Pat. No. 2,742,379 shows the decided superiorit of the salts III over the known diethanolamine salts of the cited patent, particularly as finishing agents with an anti-electrostatic effect. Thus, the l-lauramidopropyldimethylammonium-(3)-ethyl primary-n-alkyl phosphates IV, at relatively low atmospheric humidities, have a better anti-electrostatic action on fabrics consisting of polyamide or polyester fibers than the compounds according to US. Pat. No. 2,742,379. Also, the anti-electrostatic effect of the amine salts III used according to the present invention on woven fabrics, e.g. consisting of polyester fibers, has been proven to be more heat resistant than that of the prior art compounds.

The tertiary amines with an acid amide group, which are required as the intermediate product for the preparation of the acylated tertiary ammonium dialkyl phosphates III, can be produced in accordance with the following procedure, generally by reacting higher fatty acids with dimethylamino-propylamine:

3.8 kg. (19 mols) of lauric acid and 2.54 kg. (25 mols) of dimethylamino-propylamine are heated for 1 hour at 145 C. and the mixture is boiled gently. Within another 4 hours, the temperature is slowly raised to 200 C. The excess amine is then distilled off, together with the water produced in the reaction. The last residues of the dimethylamino-propylamine can also be removed under vacuum, the pressure being slowly reduced within an hour to 13 to 15 mm. Hg. The residue of l-lauramidopropyl-3- dimethylamine, which is similar to a grain or curd soap, melts at 335 to 35.5 C.

The dialkyl phosphoric acids used for neutralizing this amine intermediate are obtained by methods generally well known and similar to that given in German patent specification No. 1,084,231 for the production of polyethoxy ethyl phosphoric acids. For neutralization purposes, i.e. to produce the amine salt III, equimolar quantities of amine and dialkyl phosphoric acid are stirred together at 50 to 60 C. for about 15 minutes.

The invention is further illustrated but not limited by the following examples. All parts and percentages are by weight unless otherwise indicated.

EXAMPLE 1 Strips measuring 5 x cm. of a polycaprolactam woven fabric are dipped at room temperature into various baths of an 0.5% aqueous solution of a number of the different 1 lauramido-propyl-dimethylammonium (3)- ethyl primary-n-alkyl phosphates IV (see Table 1). The amine salts which are used differ only in the length of the alkyl radical R in the phosphate anion. The fabric strips are then wrung out until they contain about 100% moisture, dried for 20 hours in air and rubbed on stainless steel pins. The rubbing movement can be effected using a suitable mechanical device, always under the same mechanical conditions. With an atmosphere of 44% relative humidity at 23 C., the maximum charges listed in Table l are measured with a Feldmuhle instrument, with a spacing being provided between the fabric and the measuring head of the instrument of 30 mm.

In addition to the maximum charges, Table 1 also gives the charges prior to the rubbing operation, designated as precharge, and the discharge times. In those cases where the electrostatic charge was low, the discharge was generally so quick that the field decay could not be accurately controlled with the measuring arrangement being used. Such a rapid field decay is given in all of the Tables 1, 2, 4, 5 and 6 below as a time reading of 1 second, i.e. less than one second. With a slower field decay which can be clearly measured, the discharge times are set forth as being measured from the termination of the rubbing movement, at which time it has reached the maximum charge, until there has been a discharge to +0.5 or 0.5 kv./m. or to the indicated value.

The determination of the applied amounts of the anti static agent is effected by weighing the untreated and im pregnated fabric strips, and the amount is set forth as percentage by weight with reference to the dry fabric. The Copolymer A is the sodium salt of the copolymer of styrene and maleic acid which is a readily available commercial product normally used as an antistatic agent for polyamides, and which is used for a comparison of the anti-electrostatic effects. The discharge of the strips of polycaprolactam fabric, finished with the ammonium dialkyl phosphates IV, takes place substantially more quickly than with the substrate treated with the sodium salt of the copolymer.

TABLE 1 Maximum charging and discharge capacity of strips of polycaprolactam fabric, impregnated with the salts IV of 1-lauramidopropyl-dimethylamine-( 3) and ethyl primaryn-alkyl phosphoric acids, and with Copolymer A (the sodium salt of the copolymer of styrene and maleic acid) as a comparison substance:

Charging at Finishing agept: Amine salt Amount Pre- Maximum Discharge with R4 as applied char 11 char in time listed below (percent) (kv. m. (kvjmg (sec.)

0. 52 +0. 02 4. 1 0. 45 +0. 06 6. 0 1 0. 75 +0. 02 0. 4 1 0.52 +0.03 1.5 1 0. 71 0. 1 0. 1 0. 43 +0. 04 1. 5 1 Copolymer A (comparlson) 0.43 1. 9 9. 2 1 -7.3

1 Kv./1S0 sec.

EXAMPLE 2 Instead of strips of polycaprolactam fabric as used in Example 1, fabric strips of polyethylene terephthalate fibers were examined in the same way as in Example 1. The results are given in Table 2. Serving as a comparison product was the stearamidopropyl-dimethyl-B-hydroxyethylammonium-(3)-phosphate VII, which is known and is also obtainable commercially as an antistatic agent.

As will be seen from Table 2, the fabric strips treated with the dialkyl phosphates IV become charged to a substantially smaller degree than those finished with the comparison substance. There is no diiference with regards to the speed of the discharge.

6 TABLE 2 Maximum charging and discharging capacity of fabricstrips of polyethylene terephthalate fibers, impregnated with the salts IV of llauramidopropyl-dimethylamine-( 3) A mixture which proved suitable for use as a dressing or finishing agent for polyethylene terephthalate fibers is a mixture of equal parts by weight of l-lauramidopropyldimethylammonium-(3)-ethyl primary-n-hexyl phosphate V and an oleyl alcohol which has been etherified with 2 mols of ethylene oxide VI. Polyethylene terephthalate fibers (3.0 denier; staple lengtl1=60 mm.) are dressed for 30 seconds at 70 C. in aqueous solutions containing dissolved therein the mixture defined above. The bath ratio is 1:20, and the bath concentrations which are used are given in Table 3. After centrifuging to about 7% absorption of the bath solution, the fibers are dried for 15 minutes at C. with air circulation and conditioned for 24 hours in an atmosphere of air maintained at 54 to 58% relative humidity and a temperature of 22 to 24 C. A commercially available finishing agent for polyester fibers, based on an ethoxylated stearic acid ester is used as the comparison substance. The finished fibrous flocks are carded and the electrostatic charges on the resulting non-woven fiber fleece are measured with a Feldmuhle instrument under the same conditions. The results are given in Table 3, together with the bath concentrations and the electrical resistivities measured on the fibrous flocks at 65% relative humidity and 20 C. With the exception of the comparison sample, the capacity of the fibers for carding is quite suitable in all three cases. It is known that electrostatic charges below about 10,000 v./m. represent a limiting value for this purpose. With the comparison example, a bath concentration of more than 6% had to be used in order to produce an adequate antielectrostatic efiect. However, the larger application of such a textile auxiliary has been found from experience to impair the working properties of the fibers because the static friction on metal and rubber is too great.

TABLE 3 Electrical resistivities of finished polyethylene terephthalate fibrous and electrostatic charges, measured during carding of the non-woven fibrous fleece material:

7 EXAMPLES 4 AND Comparison tests were made in these examples with the anti-electrostatic finishing agents according to the invention and US. Pat. No. 2,742,379.

The phosphoric acid ester amine salts III according to the invention were prepared as set forth herein, and the comparison products were obtained according to US. Pat. No. 2,742,379.

An examination of the antistatic effects of the preparations under different air humidity conditions was carried out.

For the investigation of the antistatic effects, fabric strips of polyethylene terephthalate fibers (Example 4) and polycaprolactam fibers (Example 5) were impregnated by the method described in Example 1 with the l-lauramidopropyl dimethyl-ammonium-(3)-ethyl primary-n-alkyl phosphates IV and, after drying in air, they were conditioned for 24 hours in air:

at 20 C. and 30% relative humidity, and at 20 C. and 65% relative humidity.

The radical R in the cation of the dialkylphosphate IV was selected as n-hexyl-(l), n-octyl-(l) and n-decyl-(l), respectively, in order to test three different compounds of the invention.

The electrostatic charge was produced, always under the same mechanical conditions, by rubbing on stainless steel pins, and the same procedure was used for estimating the antistatic efficiency as in Examples 1 and 2. This charge was measured with a Feldmuhle measuring instrument under the atmospheric conditions indicated,

Electro- Finishing agent: Atmospheric static Maxi- Amine salt IV Amount conditions premum with R4 as applied C./percent charging chargin listed below (percent) rel. hum.) (kv./m (kv./m.

-n-C5H|3 0. 46 20/30 +0. 02 +4 'H'CQH" 0. 34 20/30 +0. 02 0. 5 -n-C H 0. 31 20/30 +0.03 -0. 1

0.32 20/30 +0. 04 -15 0. 24 20/30 +0. 02 -14 0. 24 20/30 +0.02 8 0. 46 20/65 +0. 02 +0. 02 0. 34 20/65 +0. 02 +0. 02 41-01011 0. 31 20/65 +0. 02 +0. 02 Comparison product:

0. 83 20/65 10 =l=0 0. 76 20/65 0. 02 -0. 02 0. 58 20/65 =t=0 i0 TABLE 5 Maximum charging and discharge capacity of fabric strips of polycaprolactam, impregnated with the salts IV of l-lauramidopropyl-dimethyiarnine-(3) and ethyl primary-n-alkyl phosphoric acids, and with the Comparison Products I, II and III, respectively.

Finishing agent: Amine IV with R4 as listed salt below Disch arge time to =l=0.6 kv./m. (sec.)

Atmospheric conditions OJpercent (percent) rel. hum.)

Electrostatic charr/gin charge (kv. m5 (kv./m.)

20/30 zo/ao 20/30 the distance between the fabric and measuring head being 30 mm.

The substances described in Examples 1, II and III of US. Pat. No. 2,742,379 (hereinafter referred to as Comparison Products I, II and III) were also tested in the same way for their antistatic effectiveness. The results are given in Tables 4 and 5, together with the amounts applied. The determination of the amounts applied was accomplished by weighing the untreated and the impregnated and dried fabric strips. In addition to the maximum charges produced by rubbing, Table 4 and Table 5 also give the so-called precharges, i.e. the electrostatic charges before the rubbing operation, as well as the discharge times (see Examples 1).

TABLE 4 Maximum charging and discharge capacity of fabric strips of polyethylene terephthalate, impregnated with the salts IV of 1-lauramidopropyl-dimethylamine-(3) and ethyl primary-n-alkyl phosphoric acids, and with the Comparison Products I, II and III, respectively. Discharge time with all specimens 1 second.

The comparison of the electrostatic effectiveness of the amine salts IV with the Comparison Products I, II and III shows that, when taking into account the applied quantities, the fabrics finished with the amine salts IV acquire a decidedly lower electrostatic charge than the fabric strips treated with the Comparison Products I, H and III. As shown in Tables 4 and 5, the improvement in the antistatic effectiveness thus produced is established for polyethylene terephthalate fabrics and also for polycaprolactam fabrics. At 20" C. and 30% relative humidity, the effect is more apparent than at 20 C. and 65 relative humidity. Whereas the amine salts IV, at 20 C. and 30% relative humidity. were more effective antistatically on both polyethylene terephthalate fabrics and polycaprolactam fabrics than the Comparison Products I to III, this diiference could only be established in the case of polycaprolactam fabric at 20 C. and 65 relative humidity. As already mentioned, the comparison of the charging values listed in Tables 4 and 5 were made, taking into account the applied quantities.

9 EXAMPLE 6 Tests of the heat stability of the antistatic efiect of the preparations were made.

In order to check the heat stability of the antistatic eifect of the preparations, strips of polyethylene terephthalate fabric were impregnated with the amine salts IV and with the Comparison Products I, II and III, as described in the previous Examples 4 and 5, and after being dried at room temperature, were treated for 45 minutes with hot air at 140 C. The change in the antistatic effect was tested by measuring the charges by the method described in Example 1, and after 24 hours conditioning in air at C. and 30% relative air humidity, before and after the hot air treatment.

Before the hot air treatment, the maximum electrostatic charges, both with the amine salts IV and with the Comparison Products I, II and III, with values in the region of +50 v./m., were approximately equal to the precharging, so that charging diiferences could not be established, because of the relatively good antistatic effect of boh types of finishing agents. This does not contradict the results of Table 4, since the measurement values listed in Table 4 were established using fabric strips with applications of 0.2 to 0.8%, while the determination of the hot air stability on fabric strips took place with applications of about 1% and more. After the hot air treatment, the values given in Table 6 were obtained.

TABLE 6 Maximum charge and discharging capacity of fabric strips of polyethylene terephthalate, impregnated with amine salts IV of l-lauramidopropyl-dimethylamine-(3) and ethyl primary-n-alkyl phosphoric acids and with the Comparison Products I, II and III, respectively, after hot air treatment for 45 minutes at 140 C., atmospheric conditions: 20 C./ 30% relative humidity.

It can be seen from the values of Table 6 that the antistatic efficiency of the Comparison Products I, II and III is considerably lessened after hot air treatment, whereas the antistatic eifect is only slightly reduced in the case of the amine salts IV. It must also be appreciated that, as already stated, approximately the same good antistatic etfect exists before the hot air treatment.

In carrying out numerous tests in accordance with the preceding examples, it has been found that one can generally employ the finishing agent of the invention, i.e. Compounds III, in an aqueous bath having a concentration of the finishing agent of about 0.5 to 10% by weight. The amount of this finishing agent applied to textile fibers, i.e. as filaments, yarns, fabrics or the like, should ordinarily be about 0.05 to 1% by weight, taken with reference to the dry fibers (after evaporation of the water).

Other finishing or emulsifying agents, such as the ethoxylated oleyl alcohol may also be added to the bath, e.g. in a concentration of about 1 to 5% by weight.

A suitable lubricating agent, such as the known mineral oils, may generally be added to the aqueous finishing composition in amounts of about 1 to 15% by weight, with reference to the water. Since these lubricating agents are usually water-insoluble and relatively instable when emulsified in water, the compositions of the present invention are especially valuable in providing highly stable emulsions which even remain clear With up to about 10% by weight of a mineral oil emulsified in water. In addition to their emulsifying properties, the finishing agents of the invention also have good corrosion-inhibiting properties so as to be especially useful as a preparatory or dressing agent where the textile filaments, yarns, threads, etc., are conducted through many textile operations in contact with steel machinery. The capacity of the textile material to be worked mechanically is also improved.

In all of the examples herein, the primary-n-alkyl groups are generally designated simply as n-alkyl with the empirical formula for the particular alkyl group, e.g. primary-n-hexyl is given as -n-C H These straight chain alkyl radicals are generally preferred for purposes of the present invention, either as the radical R or as the radical R in the structural Formulae III and IV.

Although the working examples above are directed to the Compounds IV as especially preferred finishing agents, good results in terms of antistatic eifect, emulsifying properties and/or heat stability have also been established with other compounds falling within the scope of the structural formula:

TABLE 7 Maximum charging and discharge capacity of fabric strips of polycaprolactam at- Discharge Compound III, Example No.- Amount Maximum time to applied charge 0.5 kv./m. R R R; R3 R4 (percent) (km/in.) (sec.)

11-C H 11 CH3 CH3 C2115 l'i-CioHzr 0. 31 11-0 11 5 CH3 CH1; CzHs n-C 10H21 0. 33 11-0 131321 CH3 O'Hz C2115 n-C 101121 0. 38 n'C11Ha5 CH3 CH3 C2Hs u-C ioHzi 0. 35 n-C H23 0 H CH n-C 4H0 n-C 10H2i 0.40

Copolymer A 0. 33


n-C H 11 C H; CH: C211 n-C 10H 0. 76 n-C1H1 CH3 CH3 CzHs n-C ioHzi (1. 73 n-C 13H CH3 CH3 C2115 11-0 101121 0. 81 n-C 1711 CH3 CH3 CzHs n-C inHzt 0. 75 n-C 11112: C C -0 4H0 n-C mHn 0. 72

Copolymer A 0.71

(comparison) NOTE.Examp1e: A stable aqueous emulsion is prepared as follows: To 3 to 6 p.p.u. mineral oil (viscosity 6.0-6.8 cp. at 20 C., boiling range: 207335C. at 760 mm.) are added 2 p.p.u. of an ethoxlated lauryl alcoho which contains about 5 ethylene oxide groups per alcohol molecule, and p.p.u. l-lauramidopropyl-dimethyl ammonium-(3)-ethyl-n-decy1-(1)phosphate (in formula R-n-CuHza, R1=R2-= CHa, Its-C3115, Rs- 1101121) The mixture is heated under stirring to 50-60 C. By this manner aclear oil is received. The emulsion is ma by adding under stirring 1 to 20 p.p.u. of this oil to p.p.u. water at room temperature.

The invention is hereby claimed as follows: 1. A compound of the formula wherein: R represents a primary n-alkyl group of 5 to 17 carbon atoms;

R and R each represent alkyl of 1 to 3 carbon atoms; 10

R represents alkyl of 2 to 4 carbon atoms; and R represents alkyl of 2 to 18 carbon atoms.

2. A compound as claimed in claim 1 of the formula in which R; is a primary n-alkyl group of 2 to 18 carbon atoms.

3. The compound of claim 2 in which R represents 20 4. The compound of claim 2 in which R represents -I1-C6H13- 5. The compound of claim 2 in which R represents -n-C H 6. The compound of claim 2 in which R represents 1o 21- 7. The compound of claim 2 in which R represents 12 25- 8. The compound of claim 2 in which R represents m zs- References Cited UNITED STATES PATENTS 2,508,924 5/1950 Mertens et al. 260-925 X 3,082,227 3/1963 Sherr 260404.5

ANTON H. SUTTO, Primary Examiner US. Cl. X.R.

1l7--138.8 F, 138.8 N, 139.5 CQ; 2528.8, 8.9; 260 925 "UNITED STATES PATENT OFFICE I CERTIFICATE OF CORRECTION Patent No R 77R l6 Y Dated November-27. 1G7? Invent r( )Arno Welerhofi"; Franz-ilosef Sch mit z a Carl Macura I It is certified that error appears in the above-identified patent and that said Letters Patent are hereby corrected as shown below:

Column 1, line "-33, "an" should read as (golumn 2, lines 20-24,

t should'read 0:1 -03 0 III Column 5, Table 1, lines 50-60, examole "Copolymer A (comparison') column "Precharging (kv./m.)", "-1.9 should read -l.2 and in column "Maximum charging (kv./m. -9.2" should read 7 9 .Q

Column 6, Table 2, lines 10-20, column of "Finishing; agent: Amine salt IV with Ru as listed below", third item,

-n-C H should read -v n C H C'olumnv6, line-61, "fibrous and" should read fibrous flocks and- Column 8, Table 5, lines 35-50, first column, third item,

l n-C H should read --n-C H first column, ninth line, "-n-c sh e Signed and sealed this 26th day of November 1974.

(SEAL) Attest:

McCOY M. GIBSON JR; c. MARSHALL DANN Arresting Officer Commissioner of Patents FORM powso $69) USCOMM-DC 60376-P69 v I U. 5. GOVERNMENT PRINTING OFFICE i969 0-365-5Sl.

Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US4261911 *Nov 30, 1978Apr 14, 1981Johnson & JohnsonPhosphitaines
US4264516 *Jul 17, 1978Apr 28, 1981Ciba-Geigy CorporationQuaternary ammonium salts of antistatic agents or softening agents containing fatty acid radicals, process for the production and use thereof
US4289634 *Jul 25, 1979Sep 15, 1981Chevron Research CompanyDeposit control additives and fuel and lube oil compositions containing them
US4822529 *Sep 10, 1987Apr 18, 1989Takemoto Yushi Kabushiki KaishaQuaternary ammonium alkyl phosphates
U.S. Classification554/41, 558/208
International ClassificationC10M137/08, D06M13/405, D06M13/295, D06M13/292
Cooperative ClassificationC10N2240/62, C10M137/08, C10M2223/043, D06M13/405, D06M7/00, C10M2201/02, D06M13/292, D06M13/295, D06M2200/40
European ClassificationD06M7/00, D06M13/295, D06M13/405, C10M137/08, D06M13/292