Bis-Quaternary Ammonium Compounds

A 12 liter round bottom flask equipped with a mechanical stirrer, thermometer, reflux condenser and dropping funnel was charged with 2,824 grams of stearyl dimethyl amine (equivalent weight 297); 1,610 grams of isopropanol and 1,610 grams of deionized water. With agitation, 406 grams of concentrated (37.2%) hydrochloric acid was slowly added. After 15 minutes, a sample was removed and analyzed for free amine and aminehydrochloride. In this particular case, employing acid/base titration, a difference of 0.15 meg/g in favor of the amine was observed. Neutralization of half of the residual free amine was desired. This required an additional 51 grams of concentrated hydrochloric acid.

Epichlorohydrin (438 grams) was charged into a pressure equalizing dropping funnel; the mixture was heated to 55.degree. C. and the epichlorohydrin was added dropwise to the mixture over a 1.5 hour period. The temperature rose through a modest exotherm to 85.degree. C. Analysis at this point indicated 3.2% amine hydrochloride and 5.2% free amine. On standing overnight, analysis indicated 1.98% amine hydrochloride and 2.5% free amine. The amine hydrochloride value was employed to calculate an addition of epichlorohydrin. A total of 39 more grams were added dropwise at 70.degree. C. and the mixture agitated an additional four hours. Final analysis was as follows:

Activity (Epton Titration): 46.9% (Equivalent weight 361.5)

% Free Amine: 0.83 (Equivalent weight 297)

% Amine HCl: 0.53 (Equivalent weight 333.5)

% Solids (2 hrs. 150.degree. C.): 51.1

pH (1% aqueous soln): 5.1

Upon standing at ambient temperatures, the clear yellow liquid solidified into a white paste.

A three liter round bottom flask equipped as above was charged with 461 grams of lauryl dimethyl amine (equivalent weight 218), 299 grams of isopropanol and 233 grams of deionized water. With stirring, 96.8 grams of hydrochloric acid were slowly added. Analysis by acid-base titration indicated an equivalent of free amine and amine hydrochloride to be present. The mixture was heated to 80.degree. C., and 98 grams of epichlorohydrin was slowly charged over an hour and a half. After 8-10 hours of mixing at 80.degree. C., analysis indicated:

% Solids (105.degree. C., 1.5 Hours): 52.0

% Actives (Epton: equivalent weight 265) 43.5

% Free Amine (equivalent weight 218): 0.88

Amine Hydrochloride (equivalent weight 254.4): 0.32

A three liter round bottom flask equipped as above was charged with 422 grams of lauryl dimethyl amine, 563 grams of isopropanol alcohol and 501 grams of deionized water. With agitation, 185 gram of concentrated 37% hydrochloric acid was added. This addition raised the temperature to 80.degree. C. At this point, 175 grams of epichlorohydrin was added over a 1/2 hour period. Analysis indicated acceptable conversion to the quat-halohydrin chloride salt. To this mixture was added 577 grams of stearyl dimethyl amine. The mixture was reacted out at 80.degree. C. for 8-10 hours. In order to bring the free amine and amine HCl into specification, an additional 15 grams of epichlorohydrin was required. Final analysis was as follows:

% Solids (105.degree. C., 1.5 hrs.): 52.9

% Actives (equivalent weight 319.5): 46.8

% Amine HCl (equivalent weight 291.5): 0.9

% Free Amine (mw 255): 1.1

pH (10% Aq soln): 6.8

A three liter round bottom flask equipped as above was charged with 394 grams of stearamidopropyl dimethyl amine (equivalent weight 365), 500 grams isopropanol and 500 grams deionized water. To this, with agitation, was added 54.9 grams of concentrated HCl. The mixture was heated to 80.degree. C. and 103.9 grams of epichlorohydrin was added over a 1/2 hour period. After 8-10 hours at 80.degree. C., the product analyzed as follows:

% Solids (105.degree. C., 1.5 hrs.): 34.1

% Actives (equivalent weight 429.5): 30.1

% Amine HCl (equivalent weight 401.5): 0.1

% Free Amine (equivalent weight 365): 0.3

The products of examples 1-3 were evaluated as germicides by the AOAC Phenol Coefficient method against Staphylococcus aureus and Pseudomonas aeruginosa with the following results:

Examples 1 and 3 were further evaluated against a variety of textile dye bath softeners and "Downy" on acrylic and polycotton fabric at equal add on concentrations. Subjective results reviewed by a panel of 3-4 individuals identified examples 1 and 3 to be as effective as the commercial products in softening ability.

A hair conditioner was prepared. The composition was as follows:

The procedure used to prepare the hair conditioner was as follows. The hydroxyethyl cellulose was slowly added to cold water with agitation. After mixing the resulting mixture for a sufficient amount of time, it was heated to the range from about 80.degree. C.-90.degree. C. The bis-compound was added to the heated mixture. The cetyl alcohol was melted and added to the heated mixture. The pH of the resulting mixture was adjusted to the range of between from 5.0-6.0 with a 50% solution of citric acid. Perfume may be added as desired.

The above composition was panel tested versus an equivalent formula containing the most widely utilized hair conditioner ingredient, stearalkonium chloride. The formula was adjusted to contain an equal level of active conditioner. The results are as follows:

The comment most often received was that the above composition resulted in a softer feel and better control of the hair than with the stearalkonium chloride.

A skin lotion was prepared. The composition was as follows:

The procedure used to prepare the skin lotion was as follows. The ingredients of Portion A were blended together and heated to 70.degree. C. with agitation. Each of the ingredients of Portion B were heated separately to 75.degree. C. The stearamine oxide and water were mixed together and the pH of the resulting mixture was adjusted to between from 5.5 to 6.0 by the addition of citric acid. Portion B was blended into Portion A with rapid agitation and while cooling to 35.degree. C. stirred, and at which temperature the perfume, if desired, is generally added.

The above formula was panel tested versus the same composition without the bis-compound. The addition of the latter resulted in better initial and after feel.

The above composition was also panel tested versus a leading national brand. The composition containing the bis-compound was overwhelmingly preferred.

Other "bis-quats" can be prepared in a similar manner as described in Examples 1, 2, 3 and 4 using other epoxides and other tertiary amines with equally good yields.