US3671308A

US3671308A - Textile softening agents

Info

Publication number: US3671308A
Application number: US845505A
Authority: US
Inventors: Helmut Diery; Bernhard Kiefer; Siegbert Rittner; Manfred Seidel
Original assignee: Hoechst AG
Current assignee: Hoechst AG
Priority date: 1968-07-29
Filing date: 1969-07-28
Publication date: 1972-06-20
Anticipated expiration: 1989-06-20
Also published as: DE1934177B2; DE1934177C3; CH510775A; BR6911126D0; NL6911400A; DE1934177A1; GB1237612A; FR2013934A1; AT287644B; BE736731A; FR2013934B1; CH1143269A4

Abstract

PROCESS FOR THE SOFTENING OF TEXTILE MATERIALS CONSISTING OF OR CONTAINING CELLULOSE FIBERS, WHEREIN THESE MATERIALS ARE TREATED WITH SOLUTIONS OR DISPERSIONS OF REACTION PRODUCTS OF AT LEAST 3 MOLS OF FORMALDEHYDE AND 1 MOL OF A N-ALKYL-UREA OR A N-ALKYL-BIURET CONTAINING 14 TO 22 CARBON ATOMS IN THE ALKYL RADICAL.

Description

United States Patent Int. Cl. D06m 15/54 US. Cl. 117-1395 A 4 Claims ABSTRACT OF THE DISCLOSURE Process for the softening of textile materials consisting of or containing cellulose fibers, wherein these materials are treated with solutions or dispersions of reaction products of at least 3 mols of formaldehyde and 1 mol of a N-alkyl-urea or a N-alkyl-biuret containing 14 to 22 carbon atoms in the alkyl radical.

The present invention relates to new textile softening agents.

It is known from German Pat. 762,964 that the products resulting from the reaction of mono-octadecyl-urea or stearoyl-urea with formaldehyde may be used as means for making materials from cellulose fibers Water-repellent. These water-repellent effects are obtained only if the alkylureas have been reacted With less than 3 mols of formaldehyde. 'With' such alkylmethylol-ureas, similarly good hydrophobizing effects are produced on cellulose fibers as with the reaction products of long chain aliphatic acid amides with formaldehyde, for example the stearic acid amide methylol compounds.

The present invention is based on the unexpected finding that the reaction products of at least 3 mols of formaldehyde with 1 mol of N-alkyl-ureas of N-alkyl-biuret compounds with long chain alkyl radicals, when applied onto textile materials, impart to these materials a soft full handle.

Hence, the object of the invention is a process for the softening of cellulose fibers or of textile materials consisting of or containing such cellulose fibers, wherein these materials are treated with solutions or dispersions of reaction products of at least 3, preferably 3.2 to 4 mols, of N-alkyl-ureas or N-alikyl-biuret compounds which contain about 14 to 22 carbon atoms in the alkyl radical. For the textile softening agents used according to the invention, it is an absolute prerequisite that for their preparation the N-alkyl-urea or N-alkyl-biuret compounds are reacted with at least 3 mols of formaldehyde. The products obtained by the reaction with less than 3 mols of formaldehyde still have hydrophobising properties, but they rapidly lose their softening effect with decreasing proportion of formaldehyde.

The reaction products used according to the present invention, when applied in the form of aqueous dispersions or in the form of solutions in inert organic solvents onto textile materials such as fibers, filaments, fabrics or other products that consist of or contain cellulose, impart onto these materials an agreeable, very soft, flowing and smooth handle. The textile materials which may be treated with the softening agents of the present invention may consist of or contain cotton, staple fibers, polynosic fibers or other fibers of regenerated cellulose, or mixture of such fibers with synthetic fibers such as polyamide, polyester, cellulose triacetate and similar fibers.

3,671,308 Patented June 20, 1972 'ice The textile softening agents according to the invention may be prepared by known methods. For example, in a first reaction step, a fatty amine containing about 14 to 22 carbon atoms, for example octadecylamine, may be condensedwith urea or biuret under separation of ammonia. The condensation is effected generally at temperatures in the range of from about to C. In a second reaction step, 1 mol of the reaction products obtained is methylolised with at least 3 mols of formaldehyde or formaldehyde yielding substances, for example p-formaldehyde, formaline or trioxane. The methylolation can be effected in aqueous solution, in organic solvents, in the melt or according to other known methods. 3.2 to 4 mols of formaldehyde are used preferably per mol of the N-alkyl-urea compound or of the biuret compound. However, it is also possible to increase the proportion of form aldehye further to about 6 mols, without deterioration of the softening properties of the reaction products obtained. But the use of higher amounts of formaldehyde does not bring further improvements, so that for economical reasons no more than about 4 mols of formaldehyde per mol of the alkyl-ureaor alkyl-biuret-compound are used.

As N-alkyl-ureaand N-alkyl-biuret compounds, there may be used those which correspond to the general formula R NHCO-NH--R in which R, stands for an alkyl radical containing 14 to 22 carbon atoms and R stands for hydrogen or the radical CONH For the application onto the textile materials, the softening agents of the invention are dissolved in suitable organic solvents or dispersed in water. The aqueous dispersions may be prepared with the aid of nonionic and/ or anionic dispersing agents or stabilized in this manner.

The solutions or dispersions of the softening agents may be applied onto the textile material in any desired manner, for example by spraying or impregnation and squeezing. The quantity of softening agents of the invention applied may vary within wide limits and depends on the textile material to be treated and on the softening effect to be obtained. In general, the softening agents are applied onto the textile material in quantities ranging from about 0.01 to 1%, preferably 0.1 to 0.5%, referred to the weight of the textile material.

The softening agents of the invention impart onto the textile material treated wash-resistant effects already when used alone and particularly also when used together with an acid catalyst which includes acids and acid-forming substances such as magnesium chloride, zinc chloride, zinc nitrate, diammonium phosphate, ammonium nitrate, and similar compounds. When used together with known wash and wear resins, for example dimethylol-urea, dimethyloldihydroxyethylene-urea, dimethylol-dihydroxyethyleneurea, dimethylol-propylene-urea and similar compounds, they improve the wet and dry crease resistance, the fastness to rubbing and the resistance to tearing and the tensile strength.

Another important advantage with regard to application of the softening agents of the invention is their particularly good compatibility with other finishing agents. Thus, there may be added to the finishing bath containing the softening agents of the invention also other auxiliary agents, for example filling and smoothing agents, wetting agents, emulsifiers, water softeners, so-called soil releasers, optical brighteners, catalysts, synthetic resin precondensation products and other additives, without impairment of the original softening effect. The softening agents may be applied from one bath which also contains the additives or from a separate bath, i.e. separately from the additives; in the last case it is advantageous to apply the softening agent at last. The softening agents may also be applied onto fabrics, for example on 3 a foulard or a similar apparatus or by the exhaust method. Finally, the fibrous materials may be treated with an engraved or Schreiner calender, and, depending on their composition, at temperatures in the range of from about 20 to 220 C.

The following examples serve to illustrate the invention but they are not intended to limit it thereto:

EXAMPLE 1 A cotton fabric having a weight of 120 g. per square meter was immersed in a bath containing, per liter,

13 g. of a 20% aqueous dispersion of a reaction product of 1 mol of N-octadecyl-urea with 3. 6 mols of formaldehyde, the preparation of which is described hereinafter, and 3 g. of polyvinyl alcohol as filling agent.

The fabric was then squeezed to about 80% of weight increase and dried for 3 minutes at 110 C. The fabric showed then a soft flowing full handle.

GREASE ANGLE ACCORDING TO GERMAN INDUSTRIAL STANDARD 53 890 Initial efiect dry Washing dry 60 minutes Unloading Handle Warp Weft Warp Weft Untreated- Empty, 42 49 38 47 rough, flabby. Treated- Full, supple-.- 44 54 44 55 ."With practically the same result, there may be used in the treatment described above instead of the reaction product of octadecyl-urea and formaldehyde also a reaction product of N-dodecyl-urea with formaldehyde, the preparation of which is described hereinafter under (b).

(a) Preparation of the reaction product of N-octadecylurea with formaldehyde 128 parts by weight of octadecylamine and 33 parts by weight of urea were heated to 129-131 C. in a reaction vessel provided with stirrer, thermometer and gas inlet and outlet means. At 105 to 110 C., the molten mass became homogenous and the reaction began under vigorous evolution of ammonia. The ammonia set free was passed over from the reaction vessel into 2 N sulfuric acid by means of a stream of nitrogen. As soon as about 8.5 g. of ammonia had been separated the temperature of the molten mass was lowered to 105-110 C. and then 54 parts by weight of p-formaldehyde were introduced portionwise. Subsequently, there were added as dispersing agents 64 parts by weight of a condensation product of 1 mol of sperm oil fatty acid and 1 mol of N-methyltaurin and 10.4 parts by weight of an addition product of about 35 mols of ethylene oxide and 1 mol of stearyl alcohol. Finally, 750 parts by weight of water having a temperature of 75 to 80 C. were allowed to run, in the course of 30 minutes, into the well stirred molten reaction mass and the whole was further stirred for 3 hours at 50 C. The stable aqueous dispersion thus obtained had a content of N-octadecyl-urea-formaldehyde condensation product of about 20% by weight.

(b) Preparation of the reaction product of N-dodecyl-urea and formaldehyde 92.6 parts by weight of dodecylamine and 33 parts by weight of urea were condensed in the same apparatus and under the same conditions as those described under (a), at 129-131 C., until about 8.5 parts by weight of ammonia were separated. Then, 54 parts by weight of pformaldehyde were introduced portionwise at 105 to 110 C. into the molten mass and, as dispersing agents, 64 parts by weight of a condensation product of 1 mol of sperm oil fatty acid and 1 mol of N-methyltaurin and 10.4 parts by weight of an addition product of about 30 mols of ethylene oxide and 1 mol of stearyl alcohol were added.

By introducing 610 parts by weight of water having a temperature of 75 to C. in the course of about 30 minutes into the well stirred molten reaction mass and stirring the whole for 3 hours at 50 C., an aqueous paste was obtained which contained about 20% by weight of the condensation product of N-dodecyl-urea and formaldehyde.

EXAMPLE 2 Onto a bleached, mercerized cotton poplin fabric having a weight per square meter of g., there was applied for a high quality finish, from a foulard, an aqueous dis persion containing, per liter, the following components:

20 g. of a 20% dispersion of the reaction product of N-octadecyl-urea and 3.6 mols of formaldehyde, prepared according to Example 1, paragraph (a),

60 g. of dimethylol-4,5-dihydroxy-ethylene-urea as finishing agent, and

12 g. of crystallized magnesium chloride.

The fabric was then squeezed to 80% weight increase and dried at 110 C. The residual moisture was 6%. Finally, the fabric was calendered in the usual manner and condensation was effected for 5 minutes at C.

The fabric showed a full supple handle and good crease resisting properties.

DRY GREASE ANGLE ACCORDING TO GERMAN INDUS- TRIAL STANDARD 53 890 A fabric consisting of 35% of cotton and 65% of polyester fibers was impregnated with a solution containing, per liter 18 g. of 20% aqueous dispersion of a reaction product of N-octadecyl-biuret and formaldehyde, the preparation of which is described hereinafter, and

12 g. of polyvinyl acetate as filler.

The fabric was squeezed to 60% weight increase and dried at 110 C.

The fabric showed an agreeable soft full handle.

Preparation of the reaction product of N-octadecylbiuret and formaldehyde:

128 parts by weight of octadecylamine and 57 parts by weight of biuret were condensed at 138-140 C., in an apparatus as that described in Example 1, paragraph (a), until about 8.5 parts by weight of ammonia were separated. The reaction temperature was then lowered to 110 C., and 80 parts by weight of p-formaldehyde were introduced portionwise into the molten mass and subsequently there were added, as dispersing agent 52 parts by weight of a condensation product of 1 mol of sperm oil fatty acid and 1 mol of N-methyltaurin as well as 8 parts by weight of an addition product of 25 mols of ethylene oxide and 1 mol of stearyl alcohol. By adding 966 parts by weight of water having a temperature of 75-80 C. to the well stirred molten mass and stirring for 3 hours at 50 C., a dispersion was obtained which contained about 20% by weight of the condensation product of N-octadecyl-biuret and formaldehyde.

We claim:

1. Process for the softening of textile materials containing cellulose fibers, comprising applying to said materials a reaction product of at least 3 mols of formaldehyde and 1 mol of a N-alkyl-ureaor a N-alkyl biuret containing 14 to 22 carbon atoms in the alkyl radical.

2. A process as claimed in claim 1, wherein the said reaction product is applied together with an acid forming catalyst.

5 6 3. A process as claimed in claim 1, wherein the textile FOREIGN PATENTS material is impregnated with an aqueous dispersion of 762,964 11/1953 Germany.

the said reaction product.

4. A process as claimed in claim 1, wherein the said IA ARTIN, Primary Examiner reaction product is applied onto the textile materials in 5 a quantity of from 0.01 to 1.0%, referred to the weight of DAVIS Asslstam Exammer the textile material. US Cl References Cited 117-1383 N, 138.8 F, 139.4, 143 A UNITED STATES PATENTS 10 2,165,265 7/1939 Hubert et al. 117-4395 UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No- 1671.508 Dated June 20. i912 Irwent fl Diery. Kiefer. Rittner and Seidel It is certified that error appears in the above-identified patent and that said Letters Patent are hereby corrected as shown below:

In the Heading:

After "Claims priority, application" change "Australia" to--Austria--.

Signed and sealed this 26th day of September 1972.

(SEAL) Attest:

EDWARD N .FLETCHFR,JR. ROBERT GOTTSCHALK Commissioner of Patents Attesting Officer ORM PO'WSO (10-59) uscoMM-oc 60376-F'69 U.5 GOVERNMENT PRINTING OFFICE 2 I959 -365"334