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Title:
SOLUTIONS OF STEARAMIDOPROPYL DIMETHYL PYRROLIDONYL METHYL AMMONIUM CHLORIDE IN A POLYHYDRIC ALCOHOL
Document Type and Number:
WIPO Patent Application WO/1993/016045
Kind Code:
A1
Abstract:
A solution of stearamidopropyl dimethyl pyrrolidonyl methyl ammonium chloride in a polyhydric alcohol at a concentration of about 1-30 % by weight in glycerol.

Inventors:
ANDERSON LOWELL R (US)
CHAUDHURI RATAN K (US)
LOGIN ROBERT B (US)
Application Number:
PCT/US1993/000765
Publication Date:
August 19, 1993
Filing Date:
January 26, 1993
Export Citation:
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Assignee:
ISP INVESTMENTS INC (US)
International Classes:
A61K8/49; A61Q19/00; C07D207/12; C07D207/27; C07D207/26; (IPC1-7): C07D207/12; C07D211/76
Foreign References:
US4732990A1988-03-22
US4590069A1986-05-20
US4885158A1989-12-05
US5008104A1991-04-16
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Claims:
WHAT IS CLAIMED IS:
1. A solution of about 130% by wt. of the compound stearamidopropyl dimethyl pyrrolidonyl methyl ammonium chloride in a polyhydric alcohol.
2. A solution according to claim 1 wherein said polyhydric alcohol is selected from glycerol, ethylene glycol, propylene glycol and polyalkylene alcohols.
3. A method of making the solution of claim 1 which comprises: (a) slurrying said compound into excess acetone, (b) filtering the slurry to provide a filter cake of said compound, (c) forming a solution of said filter cake in a polyhydric alcohol, and (d) dropping said solution into an evacuated reaction vessel to substantially remove residual acetone therefrom.
4. A method according to claim 3 wherein said polyhydric alcohol is selected from glycerol, ethylene glycol and propylene glycol.
5. A method according to claim 1 wherein the solution obtained includes about 130% by wt. of said compound.
Description:
SOLUTIONS OF STEARAMIDOPROPYL DIMETHYL

PYRROLIDONYL METHYL AMMONIUM CHLORIDE

IN A POLYHYDRIC ALCOHOL

Stearamidopropyl dimethyl pyrrolidonyl methyl ammonium chloride is a solid compound which is useful in cosmetic applications as a surfactant and/or conditioner. However, its use is limited because of the difficulty of formulating such solid into commercial cosmetic compositions.

Accordingly, what is provided herein is a solution of stearamidopropyl dimethyl pyrrolidonyl methyl ammonium chloride in a polyhydric alcohol, suitably at a concentration of about 1-30% by weight, preferably 2-20%, and, optimally, about 5-15%, wherein said polyhydric alcohol is a di-, tri-, or tetra hydric alcohol, preferably glycerol.

The desired solution is made by slurrying said compound into excess acetone, filtering the slurry to provide a filter cake of the compound, forming a solution of the filter cake in a polyhydric alcohol, and dropping the solution into an evacuated reaction vessel to substantially remove residual acetone therefrom. In a preferred form of the invention, the remaining acetone in the solution is less than 0.7%.

A preferred solution comprises about 5-15% of said compound in glycerol.

Solubilization of stearamidopropyl dimethyl f pyrrolidonyl methyl ammonium chloride in a polyhydric alcohol is accomplished by slurrying the compound into k J excess acetone, filtering the slurry to provide a filter cake of the compound containing about 30-40% acetone. The

filter cake then is dissolved in a polyhydric alcohol such as a di-, tri- or tetra- hydric alcohol, e.g. a di-, tri- and tetra- alkylene or polyalkylene alcohol, including such polyhydric alcohols as glycerol, ethylene glycol or propylene glycol, or alkylene derivatives thereof. A preferred polyhydric alcohol is glycerol. Thereafter, the solution is dropped into an evacuated reaction vessel to substantially remove residual acetone therefrom. In this manner, the foam produced is dissipated as the liquid enters the reactor and the foam height is controlled by the rate of addition. The resulting product is always under full vacuum and hence loses acetone more readily.

The solution obtained by this procedure contains less than about 0.7% acetone, and the compound in a concentration of about 1-30%, preferably 2-20%, and, optimally, about 5-15%, by weight of the solution.

EXAMPLE

50 g. of stearamidopropyl dimethyl pyrrolidonyl methyl ammonium chloride was slurried into 200 ml of acetone and filtered to remove excess acetone. The resulting filter cake contained about 30-40% acetone. This material was then added to a stirred vessel containing 400 g. of glycerol at 35°C. Dissolution was immediate. The resultant solution was then added to a 1 1. evacuated flask (<1 mm) at a suitable rate to minimize excessive foaming. Pumping was continued for 30 minutes while addition of the solution was complete.

The final solution was a quaternary salt-glycerol composition at a 1:8 ratio, with quaternary salt of 10.27%, residual acetone of 0.2%, pH (50% aqueous) of 4.15, viscosity (cps-25°C.) of 2320 cps, and % solids (calc.) of 11.1%, as a clear yellow solution.