Guerbet functionalized phospholipids

Details Guerbet functionalized phospholipids Guerbet functionalized phospholipids

2002-07-08

2003-09-16

Vollano, Jean F. (Department: 1621)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Carbohydrate doai

C514S077000

Reexamination Certificate

active

06620794

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to novel compositions and, more particularly, to a class of compounds having specific quatemized amine based upon a guerbet amido amine linked to specific phosphate esters. Guerbet acids are a specific group of branched acids that have no unsaturation present in the group, but nonetheless are liquid, and are outstanding skin care emollients, providing great spreadability on the skin. In addition this material is not toxic to human skin and is well tolerated by human tissue making it suitable for use in the preparation 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. Patents are U.S. Pat Nos. 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.
Guerbet alcohols have been known for over 100 years now. Marcel Guerbet pioneered the basic chemistry in the 1890s. It has allowed for the synthesis of a regiospecific beta branched hydrophobe which introduces high purity, branching into the molecule. The ability to capitalize upon this reaction sequence and develop derivatives has resulted in many materials that find use in applications where liquidity and lubrication are important. The various market segments include metal lubrication, plastic mold release, paper processing, synlube, and personal care. The chemistry results in a unique class of materials that remains underutilized to this day.
Guerbet Alcohols, the oldest and best-understood material in the class of compounds, have been known since the 1890's when Marcel Guerbet first synthesized these materials. The reaction sequence, which bears his name, is related to the Aldol Reaction and occurs at high temperatures under catalytic conditions. The overall reaction can be represented by the following equation;
A relatively new Guerbet derivative is the Guerbet acid. They are prepared by the oxidation of Guerbet alcohols to produce primary carboxylic acids. One method by which this can be achieved is the dehydrogenation of the alcohol with alkali metal salts, called oxidative alkali fusion, which gives excellent yields of carboxylic acids.
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. The added properties of not being subjected to rancidity, an oxidative process that affects unsaturated compounds, and having outstanding spreadability on the skin make these compounds unique cosmetic additives.
SUMMARY OF THE INVENTION
Objective of the Invention
It is the objective of the invention to provide a novel guerbet based phospholipid and a process of its use, which comprises using it as an emollient and softener for skin in personal care applications.
Detailed Description of the Invention
In accordance with the present invention we have now been discovered novel phospholipid compound, which conform to the following structure:
wherein;
R is
c and d are each integers ranging from 3 to 19 with the proviso that d=c+2.
The present invention is directed toward a process for conditioning skin that comprises contacting the skin with an effective conditioning amount of a phospholipid compound, which conforms to the following structure:
wherein:
R is
c and d are each integers ranging from 3 to 19 with the proviso that d=c+2.
The effective conditioning concentration ranges from 0. 1% to 15%. by weight of the phospholipid. In a preferred embodiment the effective conditioning concentration ranges from 1.0% to 5% by weight of the phospholipid.
Preferred Embodiments
In a preferred embodiment the effective emulsifying concentration ranges from 0.5% to 25% by weight with 3 to 15% being the preferred concentration.
In a preferred embodiment of the novel phospholipid c is 13 and d is 15.
In a preferred embodiment of the novel phospholipid c is 17 and d is 19.
In a preferred embodiment of the novel phospholipid c is 3 and d is 5.
In a preferred embodiment of the novel phospholipid c is 4 and d is 6.
In a preferred embodiment of the novel phospholipid c is 5 and d is 7.
In a preferred embodiment of the novel phospholipid c is 7 and d is 9.
In a preferred embodiment of the process c is 13 and d is 15.
In a preferred embodiment of the process c is 17 and d is 19.
In a preferred embodiment of the process c is 3 and d is 5.
In a preferred embodiment of the process c is 4 and d is 6.
In a preferred embodiment of the process c is 5 and d is 7.
In a preferred embodiment of the process c is 7 and d is 9.
DETAILED DESCRIPTION OF THE INVENTION
The present invention is directed to novel phospholipid compounds, which conform to the following structure:
wherein;
R is
c and d are each integers ranging from 3 to 19 with the proviso that d=c+2.
The compounds of the present invention are prepared by reacting first reacting a guerbet acid with dimethylaminopropyl amine (DMAPA) to give a tertiary amine intermediate.
Guerbet Amidoamine
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.
wherein;
R is:
c and d are each integers ranging from 3 to 19 with the proviso that d=c+2.
The compounds of the present invention are made reaction of the intermediate above with the guerbet amido-amine under aqueous conditions. The product of the invention is thereby attained.
The compatibility of these 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: 4209449 (1980-06-01), Mayhew et al.
patent: 4243602 (1981-01-01), O'Lenick
patent: 4382036 (1983-05-01), Lindemann et al.
patent: 4822529 (1989-04-01), Saiki et al.
patent: 5019281 (1991-05-01), Singer et al.
patent: 5415855 (1995-05-01), Critchley et al.
patent: 6180806 (2001-01-01), O'Lenick et al.
patent: 6451775 (2002-09-01), Smith et al.

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