Ethyl Benzyl Quaternary Amines of Amido Amines for Improved Antifungal properties

Abstract

Ethyl benzyl quaternaries having superior anti-fungal properties versus their benzyl quaternary analogs. The ethylbenzyl amidoamine quaternaries of the present invention are easily produced without significant waste and with minimal capital, while possessing improved antimicrobial properties. These molecules are useful in a range of applications such as fungicides, personal care as treatments for acne, dandruff, psoriasis and other fungal skin born conditions, as well as in feminine products where an antifungal is required that is gentle on the sensitive tissues, as well as HIV prevention. These molecules are also excellent hair conditioners and laundry fabric softeners.

Claims

1. The salt of the quaternary ammonium compound of the following structure: ##STR00001## wherein R and R.sup.1 are independently chosen from alkyl, alkenyl, alkynyl, branched or linear, cyclic or acyclic from 1-22 carbons wherein Q is chosen from —CH.sub.3, —CH.sub.2CH.sub.3, —CH.sub.2—C.sub.6H.sub.5, or —CH(CH.sub.2—CH.sub.3)—C.sub.6H.sub.5.

2. The salt of the quaternary ammonium compound of claim 1 wherein Q=—CH.sub.3.

3. The salt of the quaternary ammonium compound of claim 1 wherein Q=—CH.sub.2CH.sub.3.

4. The salt of the quaternary ammonium compound of claim 1 wherein Q=—CH.sub.2—C.sub.6H.sub.5.

5. The salt of the quaternary ammonium compound of claim 1 wherein Q=—CH(CH.sub.2—CH.sub.3)—C.sub.6H.sub.5.

6. The salt of the quaternary ammonium compound of claim 1 wherein Q=—CH.sub.3 and one of R or R′ is alkyl.

7. The salt of the quaternary ammonium compound of claim 1 wherein Q=—CH.sub.2CH.sub.3 and at least one of R or R′ is alkyl.

8. The salt of the quaternary ammonium compound of claim 1 wherein Q=—CH.sub.2—C.sub.6H.sub.5 and at least one of R or R′ is alkyl.

9. The salt of the quaternary ammonium compound of claim 1 wherein Q=—CH(CH.sub.2—CH.sub.3)—C.sub.6H.sub.5 and at least one of R or R′ is alkyl.

10. The salt of the quaternary ammonium compound of claim 1 wherein Q=—CH.sub.3 and R is not equal to R′.

11. The salt of the quaternary ammonium compound of claim 1 wherein Q=—CH.sub.2CH.sub.3 and R is not equal to R′.

12. The salt of the quaternary ammonium compound of claim 1 wherein Q=—CH.sub.2—C.sub.6H.sub.5. and R is not equal to R′.

13. The salt of the quaternary ammonium compound of claim 1 wherein Q=—CH(CH.sub.2—CH.sub.3)—C.sub.6H.sub.5 and R is not equal to R′.

14. The salt of the quaternary ammonium compound of claim 1 wherein R═R′.

Description

DESCRIPTION OF THE FIGURES

[0006] FIG. 1 shows the synthesis of EB quaternary from amidoamines, n is an integer. R is alkyl, linear or branched, saturated or unsaturated, cyclic or acylic from 1 to 21 carbons.

[0007] FIG. 2 shows the use of dimethylpropylamine as the amidoamine. R is alkyl, linear or branched, saturated or unsaturated, cyclic or acylic from 1 to 21 carbons.

[0008] FIG. 3 shows the amidoamine quaternary from lauric acid and DMAPA. R is alkyl, linear or branched, saturated or unsaturated, cyclic or acylic from 1 to 21 carbons.

[0009] FIG. 4 shows the use of aminoethylpiperadine as the diamine. R and R 1 are independently chosen from alkyl, linear or branched, saturated or unsaturated, cyclic or acylic from 1 to 21 carbons.

[0010] FIG. 5 shows the synthesis of dialkyl amidoamine quaternaries. R and R 1 are independently chosen from alkyl, linear or branched, saturated, cyclic or acylic or unsaturated from 1 to 21 carbons.

[0011] FIG. 6 shows the synthesis of dialkyl quats from N,N-Bis(2-aminoethyl)methylamine. R and R 1 are independently chosen from alkyl, linear or branched, saturated or unsaturated, cyclic or acylic from 1 to 21 carbons.

[0012] FIG. 7 shows the synthesis of dialkyl quats from N-(3-aminopropyl)-N-methylpropane-1,3-diamine. R and R.sup.1 are independently chosen from alkyl, linear or branched, saturated or unsaturated, cyclic or acylic from 1 to 21 carbons.

DETAILED DESCRIPTION OF THE INVENTION

[0013] Ethyl benzyl quaternaries (EB quats) and their salts, as well as salt free EB quats offer a distinct advantage over methyl and benzyl quaternaries. The EB quats have superior anti-fungal performance and, the amidoamine quats, can be made in cost effective manner with minimal capital. FIG. 1 shows the general principle, showing a linear, alkyl diamine, but this need not be the case. However, the preferred embodiment of the invention is the condensation of fatty acid and dimethylaminopropyl amine (DMAPA), followed by reaction with ethyl benzyl chloride as shown in FIGS. 2 and 3. Other diamines and even other polyamines so long as a primary or secondary amine is present and a tertiary amine. Another example would be the use aminoethylpiperadine as shown in FIG. 4. FIG. 5 shows the synthesis of dialkyl amidoamine quaternaries. The diamido compounds are stearically hindered and thus, more difficult to prepare. A longer reaction time is required to reach the diamide as the temperature must be mostly held at around 80 C under about 20 LB of vacuum. Higher temperatures in the DMAPA case, will lead to loss of DMAPA. Activated forms of fatty acids may also be utilized, such as acid chlorides (sufficient base neutralization must occur during the reaction or sufficient base must be present before the reaction to neutralize the HCl generated and prevent amine neutralization. Aldehydes may also be used. Starting from oils did result in some diamide, but not in sufficient quality versus the longer the reaction time. The ethyl quaternary is formed with an ethyl sulfate salt for the purposes of demonstrating that various counter anions are possible and all are within the scope of the invention.

[0014] Another way of achieving dialkyl amidoamine quats is to condense N,N-Bis(2-aminoethyl)methylamine with two moles of fatty acid, followed by quaternization of the tertiary amine as taught in FIG. 6. FIG. 7 shows the synthesis of dialkyl quats from N-(3-aminopropyl)-N-methylpropane-1,3-diamine, which has the advantage of being easier to prepare than N,N-Bis(2-aminoethyl)methylamine. N-(3-aminopropyl)-N-methylpropane-1,3-diamine is readily made in good yield by reacting 2 moles of acrylonitrile with methyl amine and reducing with hydrogen over a sponge nickel catalyst.

[0015] The molecules described herein are useful in a range of applications. The molecules find utility as fungicides in personal care as treatments for acne, dandruff, psoriasis, and other fungal skin born conditions, as well as use in feminine products where an antifungal is required that is gentle on the sensitive tissues, as well as HIV prevention. These molecules are also excellent hair conditioners and laundry fabric softeners. Other applications include agriculture as a sporicide, algicide, and fungicide. Oil field applications include treatment of clay to make hydrophilic drilling muds, and in aqueous systems, prevent clay from swelling. In asphalt emulsions as a cationic surfactant.

[0016] Several descriptions and illustrations have been presented to enhance understanding of the present invention. One skilled in the art will know that numerous changes and variations are possible without departing from the spirit of the invention. Each of these changes and variations are within the scope of the present invention.