Dimer amidopropyl dimethyl phospholipids as barrier compounds

Details Dimer amidopropyl dimethyl phospholipids as barrier compounds Dimer amidopropyl dimethyl phospholipids as barrier compounds

2001-06-04

2001-12-18

Pryor, Alton (Department: 1616)

Drug, bio-affecting and body treating compositions

Topical sun or radiation screening, or tanning preparations

C424S450000, C514S077000, C514S078000, C514S108000, C514S554000, C514S079000, C436S071000, C554S079000

Reexamination Certificate

active

06331293

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to novel compositions and, more particularly, to a class of compounds having specific quaternized amine based upon a dimer acid amido amine linked to specific phosphate esters. Dimer acid is a C-36 diacid having a cyclic structure and two amine groups that allow for the synthesis of a high molecular weight material phospholipid composition which is extremely substantitive to human skin and are well tolerated by human tissue making them suitable for use preparation of barrier products for personal care applications.
BACKGROUND OF THE INVENTION
Phosphate ester and quaternary amine compounds are well known and have been widely used for many years More recently, various betaine-type derivatives having, in general, quaternized alkyl amine groups and at least one phosphorous-containing anion in the molecule referred to hereinafter as “synthetic phospholipids”, have been disclosed The in U.S. Pat. Nos. are 3,856,893 and 3,928,509 to Diery et al. Diery discloses that the phosphonate compounds of his invention are active anti-microbial compounds. Later amido amine and imidazoline derivatives were disclosed for example, in U.S. Pat. Nos. 4,215,064; 4,233,192 and 4,380,637 to Lindemann et al., U.S. Pat. Nos. 4,209,449; 4,336,385 and 4,503,002 to Mayhew et al., and U.S. Pat. Nos. 4,243,602; 4,283,542 and 4,336,386 to O'Lenick et al. These synthetic phospholipids are suggested as exhibiting an outstanding combination of surfactant characteristics as well as being well tolerated by human tissue, i.e., they exhibit exceptionally low ocular irritation and oral toxicity. While these known phospholipids have been found useful as surfactants in a variety of personal care, they have not exhibited an ability to protect the skin from irritation or provide barrier properties to the skin, protecting it from the negative effects of chemicals and environmental effects.
It is very desirable to provide a material from aqueous solution that will protect the skin from environmental irritants such as ozone, and other pollutants. The compounds of the present invention can be formulated into body washes and other skin products and protect the skin from damage. In addition the di-nature of the compounds provides for outstanding substantivity and the phospholipid nature of the molecule allow for very mild natural like materials that can be used in products where low irritation is important.
SUMMARY OF THE INVENTION
Objective of the Invention
It is the objective of the invention to provide a novel dimer acid based phospholipid and a process of its use which comprises contacting the skin with an effective barrier providing concentration of the novel phospholipid.
In accordance with the present invention we have now been discovered novel phospholipid compound, which conform to the following structure:
The present invention is directed to a process of protecting skin, which comprises contacting the skin with an effective barrier providing concentration of a novel phospholipid compound, which conform to the following structure:
Preferred Embodiments
In a preferred embodiment the effective barrier providing concentration ranges from 0.5% to 25% by weight with 1 to 5% being the preferred concentration.
In another preferred embodiment the barrier compounds contains an anionic surfactant selected from the group consisting of alcohol sulfates. Alcohol ether sulfates and alpha olefin sulfonate.
In still another preferred embodiment the barrier compounds contains a non-ionic surfactant selected from the group consisting of alkanolamids, and fatty alcohol ethoxylated
DETAILED DESCRIPTION OF THE INVENTION
The present invention is directed to novel phospholipid compounds, which conform to the following structure:
The compounds of the present invention are prepared by reacting first reacting dimer acid with dimethylaminopropyl amine (DMAPA) to give a tertiary amine intermediate.
This intermediate is then reacted with 3-chloro-2hydroxypropyl-phosphate made in accordance with the procedure outlined in U.S. Pat. No. 4,283,542 to O'Lenick, incorporated herein by reference.
The compounds of the present invention are made reaction of the intermediate above with the dimmer diamido-amine under aqueous conditions. The product of the invention is thereby attained.
The compatibility of this novel phospholipid compounds of the invention with human tissue, i.e., dermal and eye tissue has also been tested. In these tests, 48-hour human patch dermal evaluations (5% in water), in vitro ocular evaluations (3% in water) and repeated insult patch tests (3% in water) determined that the compounds are substantially non-irritating to humans, they are safe and suitable for use in eye area products and are not a skin sensitizer to humans.


REFERENCES:
patent: 3856893 (1974-12-01), Diery et al.

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