US3887475A

US3887475A - Softening agent for textiles having a tetrahydropyrimidinium salt component

Info

Publication number: US3887475A
Application number: US337195A
Authority: US
Inventors: Ulrich Cuntze; Adolf May; Eckhard Milewski
Original assignee: Hoechst AG
Current assignee: Hoechst AG
Priority date: 1972-03-02
Filing date: 1973-03-01
Publication date: 1975-06-03
Anticipated expiration: 1992-06-03
Also published as: GB1427094A; BE796226A; BR7301498D0; IT979644B; DE2210085A1; JPS4898192A; ATA176673A; NL7302563A; FR2174273B1; CA988659A; AT329723B; FR2174273A1; CH582779A5

Abstract

The softening of textiles by treating them with an aqueous solution of tetrahydropyrimidinium salts of the formula

IN WHICH R means alkyl or alkenyl of 7 to 21 carbon atoms, R means alkyl or alkenyl of 8 to 22 carbon atoms or an Nacylaminopropyl radical of the formula

Description

United States Patent [1 1 (Iuntze et al.

[ June 3,1975

[ SOFTENING AGENT FOR TEXTILES HAVING A TETRAHYDROPYRIMIDINIUM SALT COMPONENT [75] Inventors: Ulrich Cuntze, l-lofheim, Taunus;

Adolf May, Diedenbergen, Taunus', Eckhard Milewski, Schwalbach, Taunus,, Germany [73] Assignee: Hoechst Aktiengesellschaft,

Frankfurt am Main, Germany [22] Filed: Mar. 1, 1973 [21] Appl. N0.: 337,195

[30] Foreign Application Priority Data Primary Examiner-Stephen J. Lechert, Jr. Attorney, Agent, or Firm-Connolly and Hutz 57 ABSTRACT The softening of textiles by treating them with an aqueous solution of tetrahydropyrimidinium salts of the formula in which R means alkyl or alkenyl of 7 to 21 carbon atoms, R means alkyl or alkenyl of 8 to 22 carbon atoms or an N-acylaminopropyl radical of the formula ci-i, 'cH, cH, NH-co R,

at least one of the radicals R and R having more than 14 carbon atoms, R means methyl or ethyl and A means a salt-forming anion.

4 Claims, No Drawings SOFTENING AGENT FOR TEXTILES HAVING A TETRAHYDROPYRIMIDINIUM SALT COMPONENT It is known that washed textiles, especially those of cellulosic fibers, show a hardening of the handle after drying. This is especially the case when washing has been effected on a washing machine.

It is also known that this undesired hardening of the handle can. be avoided by treating the textile materials after washing with a rinsing bath containing cationic substances that contain at least 2 long chain aliphatic radicals in the molecule. In practice, the dialkyldimethyl-ammonium salts which are dispersible in water are used. However, these produucts have the disadvantage of not being fluid as concentrated solutions, which is the prefered commercial form, but of having a pasty consistency and, in addition, of being usable and workable at elevated temperatures only.

It is known that certain imidazolinium compounds which are fluid as concentrated solutions can be used as softeners for textile materials. These imidazolinium compounds are, for example, l-alkylamido-ethyl-2- alkyl-3-methyl-3-methylimidazolinium-methosulfates, whose softening effect is much lower than that of dialkyl-dimethylaammonium salts.

Now, we have found that softening agents on the basis of tetrahydropyrimidinium compounds of the general formula 1 N-ca (I) of which radicals R and R, at least one contains more than 14 carbon atoms, R represents a methyl or ethyl radical and A represents a salt-forming anion, in particular C1" or R OSO do not have the abovedescribed disadvantages.

The present invention furthermore relates to fluid concentrates of softeners for textiles which consist essentially of about 50 to 80 percent by weight, preferably 60 to 75 percent by weight, of a tetrahydropyrimidinium salt of the above-defined general formula l in a polar organic solvent.

As such polar organic solvents for the preparation of the concentrates of softeners for textiles, there may be used above all lower aliphatic alcohols or glycols, in particular ethanol, isopropanol, isobutanol, ethylene glycol, propylene glycol or polyethylene glycols which are liquid at room temperature.

The tetrahydropyrimidinium compounds of the general formula 1 can be prepared by the reaction of about 1 to 1.2 moles of a compound of the formula III (Ill) with 1 mole of a long chain aliphatic carboxylic acid of the formula R c' (Iv) In the formula 111, R represents an N- acylaminopropyl radical of the formula H NC1-1 C1-1 CH or an alkyl or alkenyl radical of 8-22 carbon atoms. The reaction of the components is effected by melting them together, while stirring, at temperatures of about to 200C, preferably 160 to 180C. The conden-- sation reaction is completed after about 5 to 10 hours. The end of the reaction can be determined with the aid of the acid number; this number should be below 8 mg KOH/g.

If compounds of the formula 111 in which R stands for an aminopropyl radical are used for the reaction with a carboxylic acid of formula IV, the compound obtained by this condensation is further reacted at about 120 to 180C, preferably at to C, during a period of time of about 3 to 6 hours, with about 1 further mole of a carboxylic acid of the formula The completion of this reaction is likewise determined with the aid of the acid number which should be below 8 mg KOl-l/g. After having been allowed to cool and after addition of about 20 to 50 percent by weight, suitably 25 to 40 percent by weight, of a polar organic solvent such as isopropanol or propylene-glycol, the reaction product is combined with l to 1.1 mole of dimethylor diethyl sulfate. Instead of with the dialkyl sulfates. quaternization may also be carried with chloro-methyl using super-atmospheric pressure. The concentrates of tetrahydropyrimidinium salts obtained in this manner constitute fluid solutions at concentrations of up to about 75 percent by weight.

The tetrahydropyrimidinium salts of the formuls l are soluble or dispersible in water. They may be applied as softeners for textiles in known manner by impregnating the material to be treated by immersion or spraying with aqueous solutions or dispersions of these tetrahydropyrimidinium salts. ln general, about 0.01 to 0.7 percent, preferably 0.05 to 0.2 percent. referred to the weight of the textile material, of compounds of the formula l are applied onto the textile material. In the preferred application of the softeners as additions to the last rinsing water after washing at a goods to liquor ratio of about 1:5 to 1:10 as usual for these purposes, the concentration of the tetrahydropyrimidinium salts amounts to about 0.02 to 1.5 g/l of rinsing bath.

The aqueous solutions or dispersions of the softeners for textiles of the invention, which in general contain about 1 to 30 percent by weight, in most cases 4 to percent by weight, of pyrimidinium compounds of the formula I and about 0.3 to 30 percent by weight of a polar organic solvent, may also contain other components or auxiliary agents which have been admixed either to the concentrates of the tetrahydropyrimidinium salts or have been added separately to the aqueous solutions or dispersions or to the treatment baths destined for utilization, and which may serve, for example, for an additional influence on the handle or on other properties of the textiles to be treated or for an adjustment of the viscosity, of the regulation of the pH-value or of the increase of the stability of the solutions to cold. Such other components may be, for example cationic or non-ionogenic surface-active substances, electrolytes, organic complex formers, optical brighteners or solubilizers.

After impregnation with the baths which contain the softeners for textiles of the invention, the textile material is dried in the usual manner.

. The tetrahydropyrimidinium salts of the invention have proved to be particularly good washing after- 1 treatment agents. When used for this purpose, they are EXAMPLE 1 191 g of tallow fat propylene diamine and 135 g of tallow fatty acid were heated for 8 hours to 180 C, while stirring. The condensation product showed an acid number of 2.0 mg KOl-l/g. The reaction product was allowed to cool to 80 C, combined with 93 g of isopropanol and then 77 g of diethylsulfate were added dropwise, while stirring. A liquid concentrate was obtained which contained 74 percent by weight of the softener and which was easily dispersible in cold water.

EXAMPLE 2 93 g of tallow fat propylene diamine and 70 g of stearic acid were'stirred for 8 hours at 180 C. The acid number of the reaction product was determined with reference to 0 mg KOH/g. The whole was allowed to cool to 75C, combined with 50 g of isopropanol and quaternized in an autoclave at 120C with methyl chloride. A fluid concentrate was obtained which was dispersible in cold water and which contained 72.5 percent by weight of softener.

EXAMPLE 3 93 g of tallow fat propylene diamine and 55 g (0.25 mole) of fatty acid (mixture of C to C carboxylic acids) were stirred for 7 hours at 180 C. The acid number of the condensation product was determined with reference to 0 mg KOH/g. The whole was allowed to cool to C, combined with 50 g of isopropanol and then 31 g of dimethyl sulfate were added dropwise at 60 C. A fluid concentrate was obtained which was dispersible in cold water and which contained 74 percent by weight of solids.

EXAMPLE 4 68.8 g of tallow fatty acid and 33 g of di-propylenetriamine were stirred for 3 hours at C and for 4 hours at 180 C. The acid number was determined with reference to 0 mg KOl-l/g. Then, 68.8 g of tallow fatty acid were added and the mixture was stirred for 4 hours at C. The acid number was determined with reference to 7 mg KOH/g. The mixture was allowed to cool to 80 C, combined with 55 g of isopropanol and 32 g of dimethyl sulfate were added at 60C. A fluid concentrate was obtained which was dispersible in cold water and which contained 74 percent by weight of solids.

EXAMPLE 5 83 g of coco-nut propylene diamine and 72.5 tallow fatty acid were stirred for 8 hours at C. The acid number of the condensation product was determined with reference to 0 mg KOH/g. The mixture was allowed to cool to 70 C, combined with 50 g ofisopropano] and then 38.5 g of dimethyl sulfate were added dropwise at 50C. A fluid concentrate was obtained which was dispersible in cold water and which contained 75 percent by weight of solids.

For determining the softening action of the compounds specified in Examples 1 to 5, textile materials that had been treated in corresponding manner were tested by several persons with regard to handle. These persons gave marks on the degree of softness of the tissue samples ranging between 1 (very hard handle) and 5 (optimum soft handle). The tests were carried out as follows: marked test tissues (terry towelling specimen each having a weight of about 20 g) were at first washed at 80 C and at a goods to liquor ratio of l 10 with 6 g/l ofa commercial detergent and rinsed 5 times with cold water (about 15 hardness (German Hardness)). The treatment of the textiles was effected with the last rinsing bath to which the aqueous dispersions of the compounds of the invention had been added. The concentration of the respective active substance was 0.1 g/l, the goods to liquor ratio was 1:10. After an action period of 5 minutes, the test samples were taken out from the bath, centrifuged and dried at 70 to 80 C in a drying cabinet. The evaluation of the handle by the judgingg persons was effected after storage of the test samples for 24 hours in a climate chamber at a temperature of 20 C and a relative air humidity of 60 percent.

The test results shown in the following table are average values obtained from 5 parallel tests.

TABLE Treating agent Mark of handle Example 1 Example 2 Example 3 Example 4 Example 5 untreated sample Comparison TABLE-Continued Treating agent Mark of handle "Commercial softener on the basis of l-tallow fat-ulkyl-umido-cthyl-2-tullow fut-alkyl-3-mcthyl-imidazolinium methosulfutc.

We claim:

1. Fluid concentrates of softeners for textiles, which contain as essential components about 50 to 80 percent by weight of tetrahydropyrimidinium salts of the formula l in which R represents alkyl or alkenyl of 7 to 21 carbon atoms, R, represents alkyl or alkenyl of 8 to 22 carbon atoms or an N-acylaminopropyl radical of the formula in which R has the meaning given above, R represents a methyl or ethyl radical and A represents Cl" or R OSO which tetrahydropyrimidinium salts of the formula 1 contain at least one alkyl or alkenyl radical of more than 14 carbon atoms, and about to 50 percent by weight of a lower aliphatic alcohol or a glycol.

2. A fluid concentrate as claimed in claim 1 wherein the tetrahydropyrimindinium salt is the compound of formula l wherein R is CH,,, A is CH -OSO R is the alkyl radical of tallow fatty amine and R is the alkyl radical of tallow fatty acid.

3. Fluid concentrates of softeners for textiles, which contain as essential components about 50 to 80 percent by weight of tetrahydropyrimidinium salts of the forin which R represents alkyl or alkenyl of 7 to 21 carbon atoms, R represents alkyl or alkenyl of 8 to 22 carbon atoms or an N-acylaminopropyl radical of the formula CH CH CH NHCOR in which R has the meaning given above, R represents a methyl or ethyl radical and A" represents Cl or R -OSO which tetrahydropyrimidinium salts of the formula I contain at least one alkyl or alkenyl radical of more than 14 carbon atoms, and about 20 to 50 percent by weight of ethanol, isopropanol, isobutanol, ethylene glycol, propylene glycol or polyethylene glycol.

4. Fluid concentrates of softeners for textiles, which contain as essential components about 50 to percent by weight of tetrahydropyrimidinium salts of the formula I (+lR2 N-CH 2 N-CH in which R represents alkyl or alkenyl of 7 to 21 carbon atoms, R, represents alkyl or alkenyl of 8'to 22 carbon atoms or an N-acylaminopropyl radical of the formula II in which R has the meaning given above. R represents a methyl or ethyl radical and A represents Cl or R OSO which tetrahydropyrimidinium salts of the formula 1 contain at least one alkyl or alkenyl radical of more than 14 carbon atoms, and about 20 to 50 percent by weight of isopropanol.

Claims

1. FLUID CONCENTRATES OF SOFTENERS FOR TEXTILES, WHICH CONTAIN AS ESSENTIAL COMPONENTS ABOUT 50 TO 80 PERCENT BY WEIGHT OF TETRAHYDROPYRIMIDINIUM SALTS OF FORMULA I 1-R2,2-R,3-R1-3,4,5,6-TETRAHYDROPYRIDINIUM A(-), IN WHICH R REPRESENTS ALKYL OR ALKENYL OF 7 TO 21 CARBON ATOMS, R1 REPRESENTS ALKYL OR ALKENYL OF 8 TO 22 CARBON ATOMS OR AN N-ACYLAMINOPROPYL RADICAL OF THE FORMULA (II)

1. Fluid concentrates of softeners for textiles, which contain as essential components about 50 to 80 percent by weight of tetrahydropyrimidinium salts of the formula I

2. A fluid concentrate as claimed in claim 1 wherein the tetrahydropyrimindinium salt is the compound of formula I

3. Fluid concentrates of softeners for textiles, which contain as essential components about 50 to 80 percent by weight of tetrahydropyrimidinium salts of the formula I