Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Reexamination Certificate
1999-10-01
2002-11-05
Rotman, Alan L. (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
C560S182000, C560S204000
Reexamination Certificate
active
06476254
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to the field of chemical manufacture and in particular, cosmetics. It provides products having good pigment wetting and spread properties.
BACKGROUND OF THE INVENTION
Producing sunscreens and cosmetics offers a great number of challenges. Cosmetics, such as, for example, a lipstick, may require that material be easy to apply but once applied, it should not spread, smear or creep. To accomplish same, it is desirable to develop certain agents which, as additives, have a low skin spread factor. Unfortunately, it is also often necessary when making cosmetics to include pigments. The use of such pigment provides additional complications, particularly since the pigments need to be wetted. Pigment wetting agents generally have a low viscosity and tend to interfere with a low skin spread factor and complicate formulations significantly.
Fatty alkoxylated esters of aliphatic and aromatic dicarboxylic and tricarboxylic acids have been known for use in sunscreens, cosmetics and the like for their emollient properties. See U.S. Pat. Nos. 5,382,377, 5,455,025 and 5,597,555. However, while these compounds are excellent emollients and useful in formation of sunscreens, cosmetics and the like, not all of them have good pigment wetting properties, low skin spread factors, or preferably both. Ideally, additives for cosmetics and, in particular, skin products such as sunscreens, will also act as good solvents for such other additives as benzophenones. Therefore there exists a continued need for the discovery and use of various compounds which have good pigment wetting, low skin spread factors or preferably both.
SUMMARY OF THE INVENTION
These needs are met by the present invention, which provides fatty alkoxylated esters of aliphatic and aromatic dicarboxylic acids which possess exceptional pigment wetting and/or a low skin spread factor. In a particularly preferred embodiment, these compounds are also good solvents for compounds such as benzophenones. These compounds have two polyalkoxylated fatty alcohol chains covalently bonded by ester linkages to the carboxylic acid groups of aliphatic and aromatic dicarboxylic acids. See Formula I.
R1 and R2 are fatty alcohol groups and can be the same or different, and are saturated or unsaturated, substituted or unsubstituted, aliphatic of aromatic fatty groups containing from 8 to 36 carbons. X and y may both be from 0 to 40. Preferably, x and y can each be 15 but the total of x and y does not exceed 25. However, at least two alkoxy units must be present in each polyalkoxylated fatty alcohol group. A representative dicarboxylic acid is illustrated in formula I in square brackets. However, any dicarboxylic acids having between 2 to 36 carbons as described herein may be used to form the dicarboxylate esters of the present invention.
In addition, while the above Formula I illustrates all of the ethoxy units in a group and all of the propoxy units in a group, their order need not be as such. Indeed, these groups may be placed in any order, randomly, in blocks and in alternating patterns. Purely for illustrative purposes, the ethoxy units (E) and propoxy units (P) of one of the alkoxylated fatty alcohol groups may be arranged as follows: EEEP, EEPE, EPEE, PEEE, EEEPEPPPE, PEPPPEEEEPE and the like. Neither the number of E and P units, nor their orders, needs to be the same in each of the two polyalkoxylated fatty alcohols of each ester.
In a particularly preferred embodiment, x is 1 or greater and y may be 0 or greater. More preferably, the number of ethoxy units is greater than the number of propoxy units. Generally, in this embodiment, x to 40 ethoxy units are provided and 0 to 30 propoxy units are provided. Of course, since at least two alkoxy units are needed to form a polyalkoxylated fatty alcohol group, x is 1 unless the number of propoxy units is 0, in which case, x is 2. Again, x and y can each be 15 with the total of x and y not exceeding 25.
These esters possess superior properties making them suitable for use in formulating topical personal care preparations such as cosmetics, sunscreens and the like. In a particularly preferred embodiment, there is provided the composition of matter of Formula IV.
wherein B is 0 to 10 which may be saturated or unsaturated, substituted or unsubstituted, and R
1
and R
2
may be the same or different and each are fatty alcohols of 10 to 22 carbons which may be saturated or unsaturated, substituted or unsubstituted, x is 1 to 40 and y is 0 to 30 with the proviso that if y is 0, x is at least 2 and with the further proviso that x is greater than y. In a particularly preferred compound, x is 10, y is 2, B is 4 and R
1
and R
2
are each 14 carbons long and, in particular, myristyl alcohol. This compound can also be referred to as Bis (PPG
2
, PEG
10
Myristyl) adipate. Other advantageous compounds are formed when B is 4, R
1
and R
2
are 14 to 16 carbons, x is 4 to 6 and y is 2 to 4. Again this is with the proviso that x is greater than y.
Another particularly preferred compound of the present invention is D3PA in which, in Formula IV, x is 0, y is 3, and B and R
1
/R
2
are as described immediately above. Other advantageous compounds are formed where B is 4, R
1
and R
2
are 14 to 16 carbons, x is 2 to 6 and y is 2 to 6.
In accordance with another embodiment of the present invention, there is provided a fatty alkoxylated ester in which a diester of an aliphatic or aromatic dicarboxylic acid is formed by reacting the acid with a stoichiometric excess of one or more polyalkoxylated fatty alcohols.
The present invention provides fatty alkoxylated esters possessing exceptional pigment wetting properties and/or low skin spread factors both of which have long been desired by chemists for use in personal care products. Therefore, in accordance with another embodiment of the present invention, there is provided a composition for topical application including one or more active ingredients, and fatty alkoxylated ester agents of the present invention. Most preferably, the one or more active ingredients include pigments and/or sunscreening agents.
REFERENCES:
patent: 4061612 (1977-12-01), Bertozzi et al.
patent: 5302377 (1994-04-01), Pereira et al.
patent: 5382377 (1995-01-01), Raehse et al.
patent: 5455025 (1995-10-01), Pereira et al.
patent: 5597555 (1997-01-01), Pereira et al.
Obukowho Patrick
Pereira Abel G.
Croda Inc.
Lerner David Littenberg Krumholz & Mentlik LLP
Oh Taylor V.
Rotman Alan L.
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