US2094489A - Wetting-out - Google Patents

Description

Patented Sept. 28, 1937 PATENT OFFICE.

WETTING-OUT-,

WASHING-,

CLEAN SING-9 LATHERING-, AND DISPERSING AGENTS Richard Hueter, Hans Waldfrieden, Rosslau/ alt, Germany,

assignor, by mesne assignments, to Unichem Chemikalien Handels A.-G., Zurich, Switzerland,a corporation of Switzerland No Drawing. ApplicationMarch 16, 1933, Serial 13 Claims.

The present invention has for an object the provision of improved wetting-out, washingcleansing-, foamingand dispersing agents. The wetting-out and emulsifying agents suitable for washing and cleansing purposes hitherto employed include sulphuric acid esters of the higher molecular fatty alcohols as well as higher molecular alkyl sulphonic acids in their original state or in the form of their neutralization products.

Compared with the aforesaid estcrlike sulphuric acid derivatives, it is true that the salts of the alkyl sulphonic acids distinguish themselves by extremely increased stability, but in the cold they are much less soluble so that their employment is limited to operations which can be carried out at higher temperatures, e. g., at temperatures of more thanabout 60 C. Moreover from experience to date, it appears that the feel, i. e.,

the softness and pliancy of the textiles treated with sulphonic acid salts is not as satisfactory as in the case when materials are treated with sulphnric acid ester.

Now it has been found that the alkyl ethers of the hydroxyalkylsulphonic acids formed with higher molecular alcohols, compared with the said alkylsulphonic acids, are of a better solubility in the cold, and besides possess good stability against acids, lime and magnesia salts. These com-.- pounds are therefore preferable for use for textile-chemical operations to be carried out at lower temperatures, e.'g., for the cleansing of wool and silk, for the dyeing of artificial silk and the like.

These new compounds are formed by the alkoxylation of mono-hydroxyor poly-hydroxyalkylsulphonic acids with higher molecular fatty alcohols, e. g., by the alkoxylation of hydroxyethane-sulfonic acid or di-hydroxypropanesulphonic acid.

In accordance with the preferred procedure one commences with glycide compounds such as, e. g., ethylene oxideor propylene oxide; one breaks down the ethylene oxide ring by alkoxylation and forms at the same time a hydroxyl group. The hydroxyl group after esteriflcation with halogen hydracid is in turn replaced by the sulphonic acid group. These transformations are based on the following reaction equations:

+HCl +NaiSOa In Germany March 18, 1932 to react with fatty alcohol mixtures in the presence of a small amount of sulphuric acid and with the aid of an autoclave and a slight excess of sodium sulphite, converting the reaction mixture obtained from the higher boiling components by washing with water and by fractional distillation in vacuo into sulfonic acid derivatives. Alkylchlorethylethers more difiicult to prepare may be converted in the same manner with sodium sulalcohols are dodecyl-, myristyland cetyl alcohol and the alcohol mixtures obtained by high pressure reduction from natural greases such as cocoa fat and palm kernel oil. Unsaturated alcohols such as oleyl alcohol and its homologues are, however, likewise to be taken into consideration. Polyhydroxy saturated or unsaturated alcohols may also be used, such as hydroxystearyl alcohol or ricinoleyl alcohol (dihydroxyoctadecene) obtained by reducing castor oil according to the reduction method of Bouvealt and Blane.

The new products, in the form of the alkaline salts, comprise crystalline masses of excellent capillary active properties. In the following a description is given for a particular method for the manufacture of such a product and a manner in which it may be used, it being understood, however, that the scope of the invention is not limited to the therein described manner of performance or the'proportional quantities.

Ezrampla-ZSO parts by weight of a fatty alcohol mixture (first runnings of the fatty alcohol mixtures obtained by catalytic reduction of cocoafat and distilling up to 130 C. at 3 mm. pressure of mercury) are heated for 16 hours to 115-120 C. in an open vessel together with 150 parts by weight of epichlorhydrine and 6 parts by weight of concentrated sulphuric acid. The reaction mixture is freed from sulphuric acid by boiling with water and is purified from by-products by fractional distillation. The main fraction boiling between 150 and 195 C. at 12 mm. pressure of mercury contains 13.2% of chlorine and is re- There is still a simpler way of obtaining the OINB acted at C. in well-known manner with the a calculated amount ofsodlum sulphite in a concentrated aqueous solution. The thus obtained reaction product is clearly soluble even in hard water at to C. and it develops a stable lather.

When the product obtained in accordance with the procedure of the above example is used for wetting-out of makopearlyarn, the goods are brought into a bath containing 0.1% of this product. The wetting-out occurs immediately and the materials are readily penetrated by the subsequent treatment baths (bleachin8-, dyeing baths and the like).

For cleansing of woolen piece goods one employs a bath which contains about 1,5 g. of the aforementioned product per litre of water. If there are considerable quantities of free fatty acids in the wool, an admixture of ammonia or soda is recommended. Material which has been dryed with dye stuffs sensitive to alkali, can be treated in the same bath, if the latter has previously been rendered acid by an addition of formic acid. The indicated cleansing bath develops an excellent deterging effect and imparts a soft and pliant feel to the thus treated material.

For cleansing of raw wool one usefully employs a 0,2% bath with 0,1% cyclo-hexanol and 0,1% of the above mentioned high molecular ether of the lwdroxyalkylsulphonic acid. By this the material is perfectly degreased. The presence of lime soap in the wool does no harm in the present case, since it is likewise dispersed by the bath.

What I claim is:-

1. The method of producing a di-alkyl ether sulfonic acid salt which comprises preparing an ether from a glycide and a fatty alcohol having 8 or more carbon atoms in the molecule, and reacting a chloride of said ether in which the chlorine is attached to the glycide radical of said ether with sodium sulflte to produce a sodium salt of the sulfonated ether. 1

2. The method of producing a dialkyl ether sulfonic acid salt which comprises reacting'epichlorhydrine with a fatty alcohol having 8 or more carbon atoms in the molecule in the presence of sulfuric acid and converting the product with sodium sulflte to produce sulfonic compounds.

3. A wetting and cleansing textile treatment agent consisting of an ether having in its formula on one side of the etherial oxygen atom a fatty alkyl radical containing 8 or more carbon atoms and on the other side a radical of an hydroxy propane sulfonate salt, the cation of which is an alkaline metal imparting water solubility properties to the ether.

4. As wetting, washing, cleansing, latherlng and dispersing agents, the products of the formula rt-o-cnhcnon-cmsoix wherein R is an alkyl radical of at least 8 carbon atoms and X is hydrogen or an alkali metal.

5. A wetting and cleansing textile treating agent comprising the sulfonate of propane etherifled withan alcohol radical selected from the group consisting of fatty alcohol radicals of at least 8 carbon atoms and naph-.

acid derivativ'es of ethers comprising forming a chloride of an ether by a process which includes reacting a glycide with a fatty alcohol having at least 8 carbon atoms in the molecule, said chlorine atom being joined to the glycide radical of the ether, then sulfonating said ether through replacement of the chloride radical with a sul-' fonate radical by reacting with a sulflte salt.

8. Wetting and cleansing textile treating agents consisting of alkali metal salts of sulfuric acid derivatives of ethers of glycerine with fatty alcohols corresponding to the fatty acids contained in an 011 selected fromv the group consisting of cocoanut and palm kernel oils, the sulfuric acid radical being joined-to the glycerine radical.

9. An ether of an alkyl radical with dihydroxy propyl sulfonic acid in which the alkyl radical joins through an oxygen atom of one of said hydroxy groups and is derived from cocoanut oil by reduction of the fatty acids therein to the corresponding fatty alcohols.

10. Alkyl ethers of poly hydroxy alkyl sulfonic acids in which the alkyl radicals on the one hand have more than 8 carbon atoms and are derived from and correspond to the mixture' of fatty alcohols obtained by reduction of an oil selected from the group consisting of cocoanut and palm kernel oils and the poly hydroxy alkyl radicals on the other hand are derivable from and corresponding to the glycerine radical, the sulfuric acid radical being joined to the glycerine radical.

11. The process of producing alkyl ethers of poly hydroxy alkyl sulfonic acids which comprises reducing cocoanut oil to alcohols, reacting a mixture of such alcohols with epichlorhydrine in the presence of sulfuric acid and reacting the resulting product with sodium sulflte to produce the sulfonic acid.

12. The compound of the formula R-CHz-SOJX sistingof an H atom and a cathion of a neutralizing agent.

13. Thecompound of the formula R-CHz-SOzX I where R represents an alkyl group containing one or more hydroxy groups one of which is etherifled with a hydroxy stearyl and where X is a member of the group consisting of an H atom and a cathion of a neutralizing agent.

RICHARD HUE'IER.

CERTIFICATE OF CORRECTION. Patent No. '2',0 9L .,h89. September 28, 1957.

' RICHARD HUETER.

It is hereby certified that error appears in the printed specification of the above numbered patent requiring correction as follows: Page 2, first column, line 19-, for "dryed" reeddy'ed; andsecomd column, line 62, claim 13, after stearyl" insert alcohol; and that the said LetterePatent should be read with these corrections therein thatv the same may conform to the record of the case in the. Potent Office.

. Signed andeealed this 8th day of February, A. 19.19 8;

' Henry-Van Aredale,

' (-Se'al) I Acting Commissioner ofPatents.