US2617830A - Polyglycol ethers of 7-ethyl-2-methyl-undecanol-4 - Google Patents

Description

Patented Nov. 11, 1952 2,617,830 POLYGLYCOL ETHERS oi? 7 ErHYL-2 METHlKLfUNDECANOL- l Milton Kosniin, Dayton, ome, assienor-to mom santo Chemical Companmstaliouis, Mot,- a/P001 poration of Delaware 'No'Draw ing. Application luheiill, 1950,. I

Serial No. 171,560

5 Claims. (01. etcere)- The present invention relates to compounds having high surface-activity in aqueous solutions and to processes for preparing the said compounds. V

In my prior Patents Nos 2,508,035 and 2,508,036. issued May 16, 1950, I have disclosed polyglycol ethers of certainbranched chain alcohols, namely, -ethyl 'no'nanol-2 and 2-n-propyl heptanol.

These products are produced by condensing of the present and related products the dtergency of Gardinol which is a commercial detergent product, by sulfating the mantis derived by hydrogenation of cocoanut oil fatty acids. 7

The detergency of thepresent andrelatedproducts-as determinedby the; Harris method isillus trated inthe following. table:

The present products are prepared by conethylene oxide with the respective alcohols. While densi-ng. ethylene oxide:with-7-ethyle2-methylun- Detergency-Percent of Gardinol Prod'dt 'lested 3" 5'0 300 5 3'06 v p. p.--m; p.-;p;;m.- p. ;p.-m;. -1). ppm.

n-"Dt'rad'canol-l-IO rnoles ethylene oxide; 110 109 ;1 27 n-Tetradecanol+l5 .moles ethylene oxide- 102 103 108 128 2-n-Ii5opyl-heptanol+5 moles ethylene- 50 45' '1-11 106 ox e: 2-n-liopyl-heptanol+l0 moles ethylene 100' 78 99" 100 ox e. I I 2-n-1 5opyl-heptano1+l5 moles ethylene 102 87 93 100 0x1 e. s-Etlhlyll nonanol-2+5 moles ethylene 36 37 106 112 Oil 0. S-Etlayl nonanol-2+l0 moles ethylene 114 110 111 oi: e. v i fi-Etihiyl unusual-21:15 moles ethylene 110 101 101 116 ox e. 7-Ethyl 2-methyl undecanol-4+5 moles U 120 I 7 120 128 ethylene oxide. 7-Ethy1e2-methyllundecanoI-4+10 moles 124 v 127 131 :1-37 {ethylene oxide. ,4 i, v 7 Ethyl z-methyl undecanol 4+15 moles .124 118 124 r187 ethylene oxide.

. z'lliabuilder consisted of40 parts of tetrasodium pyrophosphate, 40 parts of starch forea'ch 20 parts of the active constituent.

these compounds show especially low andi therefore advantageous wetting .out speeds when aqueous solutions thereof are tested by the Braves test, these products have been found to be somewhat deficient in detergency. v

I have now found that if at least 5, but less than 21, moles of ethylene oxide be condensed with 7-ethyl-2-methyl undecanol-4 that a series of products is obtained which exhibit not only excellent wetting-outproperties but also excellent detergency. As amatter of fact, the detergency of the present products is superior to that of the corresponding products made from n-tetradecanol.

Relative detergency may be measured by any quantitative method; however for the purpose of evaluating the present and related products I have used the method described by Jay C. Harris in Soap and Sanitary Chemicals for August and September 1943. By the application of this method it is possible to evaluate the detergency of a product in terms of any standard detergent For convenience I have compared the detergency decanol-4 until at least 5mdles, but not in excess of 20 moles, have been condensed with the alcohol. The condensation may be carried out by mixing ethylene oxide either as gas or liquid with the alcohol and heating to a temperature of from 110 to C. The condensation reaction is aided by the presence of a catalyst. For this purpose any alkaline materials, such l-as an alkali metal hydroxide or alcoholate may be; used.

The catalyst may be employed in relatively small amounts, usually from 0.5% to 1% being employed. The catalyst is added to the liquid ale cohol at the beginning of the reaction.

The products so produced are secondary alcohol ethers and are believed to have the structure:

CHsCHzCHaCHgCHCHrCHzCHCHgCHCHa Ha i loh sHi 3 where n is an integer having a value of from 4 to 19.

The following examples will further illustrate this invention:

* EXAMPLE 1' 150.9 g. (0.705 mole) of 7-ethyl-2-methyl undecanol-4 was placed in a glass flask, 1.5 g. of powdered KOH added and the contents .then heated to 120 C. A stream of gaseous ethylene oxide was passed into the alcohol by means-of a gas dispersing tube and the stream continued until 155.1 g. of ethylene oxide had combined. The mass became hot due to the exothermic reaction heat and the temperature was controlled bycooling the flask by the application of cold water to the exterior. In this way the temperature was maintained at about 150during the progress of the reaction. 7 v v r .The product obtained corresponds to the pentaethylene glycol ether of 7-ethyl-2-methyl undecanol-4.

EXAMPLE 2 A portion of the product obtained above, weighing-153 g., was furthertreated with 77.5 g. of ethylene oxide using the same apparatus as described above. The product obtained corresponded to the decaethylene glycol ether of '7- ethyl-Z-methyl undecanol-4.

EXAMPLE 3 A of the product obtained in Example 2,

weighing 139.5 g.. was-treated with 46.7 g. of ethylene oxide in the manner described above. The product corresponded to the pentadecyl ethylene glycol ether of 'I-ethyl-Z-methyl un- 'decanol-4.,

The speed of wetting, as measured by the Draves test of the products when dissolved in water to form a 0.5% solution gave the follow- What I claim' is: ,1. C ompounds having the formula:

(1H, on;oniongomonomomonemotion.

. v Ha where n has a value of at least 4 but not in excess 2. Compounds having the formula:

5. The process which comprises passing ethylene oxide into '7-ethyl-2-methyl undecanol-4 at a temperature between C. and C. until at least 5 moles, but less than 21 moles, of said ethylene oxide have combined with each mole of said 7-ethyl-2-methyl undecanol-4.

MILTON KOSMIN.

REFERENCES CITED The following references are of record in the file of this patent:

UNITED STATES PATENTS Number Name Date 1,696,874 Young Dec. 25, 1928 1,970,578 Schoeller et al Aug. 21, 1934 2,226,119 De Groote et al. Dec. 24, 1940 2,316,842 Coleman Apr. 20, 1943 2,355,823 Schlegel Aug. 15, 1944 2,491,533 Swern Dec. 20, 1949 2,527,970 S0kO1' Oct. 31,1950

Claims (1)

1. COMPOUND HAVING THE FORMULA: