Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Ether doai
Reexamination Certificate
2001-01-02
2002-03-26
Hartley, Michael G. (Department: 1619)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Ether doai
C424S401000
Reexamination Certificate
active
06362233
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention is directed to a series of methoxy capped water-soluble emollient products that exhibit resistance to hydrolysis with water. The present invention also provides a process for treating skin, which comprises contacting the skin with an effective emollient amount of the compounds of the present invention.
Glycerin ethoxylates are per se poor emolients. This is thought to be related to the fact that hydroxyl groups make the molecule too polar to be substantive to the skin and provide conditioning effects. An approach that has met with limited success is the reaction of the hydroxyl group with acetic anhydride to produce an acetoxy-capped product. The difficulty is that the products produced using this technology have free acetic acid, which has a typical biting odor and therefore must be removed. In addition and more importantly the acetoxy-capped products have a limited pH range over which they are stable to hydrolysis. The hydrolysis process occurs at pH below 6 and cleaves off the acetoxy group giving the smelly acetic acid and the ineffective hydroxyl-containing product. Since the compounds used as skin emolients are generally delivered at a pH of around 5 (natural skin pH) the acetoxy capped materials hydrolyze and are unacceptable in products that are not used rapidly. Since most personal care compounds are not used instantly when produced, product instability is not acceptable. It was not until the compounds of the present invention which feature methoxy capped products that are stable to hydrolysis was it possible to make stable products containing water soluble emolients. Acetoxy capped products are esters having a —C(O)CH
3
group on the hydroxyl group. Methoxy groups are ethers and feature the hydrolytically stable —OCH
3
group.
THE INVENTION
Objective of the Invention
The present invention is directed to a series of methoxy capped water-soluble emollient products that exhibit resistance to hydrolysis with water. It is also an objective of the present invention to provide a process for treating skin which comprises contacting the skin with an effective emollient amount of the compounds of the present invention.
SUMMARY OF THE INVENTION
The present invention is directed to a series of methoxy capped water-soluble emollient products that exhibit resistance to hydrolysis with water. It is also an objective of the present invention to provide a process for treating skin, which comprises contacting the skin with an effective emollient amount of the compounds of the present invention.
DETAILED DESCRIPTION OF THE INVENTION
The compounds of the present invention conform to the following structure:
wherein:
a, b and c are independently integers ranging from 0 to 20 with the proviso that a +b+c be at least 1.
The present invention also comprises a process for treating skin which comprises contacting the skin with an effective emollient amount of compounds conforming to the following structure:
wherein:
a, b and c are independently integers ranging from 0 to 20 with the proviso that a +b+c be at least 1. The effective emollient concentration ranges from 0.1% to 25% by weight.
The compounds of the present invention are made by reacting an ethoxylated glycerin with methyl chloride as follows;
wherein:
a, b and c are independently integers ranging from 0 to 20 with the proviso that a +b+c be at least 1.
The present invention also comprises a process for treating skin, which comprises contacting the skin with an effective emollient amount of compounds conforming to the following structure;
wherein.
a, b and c are independently integers ranging from 0 to 20 with the proviso that a +b +c be at least 1.
The present invention also comprises a process for treating skin, which comprises contacting the skin with an effective emollient amount of compounds conforming to the following structure,
+3CH
3
OH+3NaCl
Preferred Embodiments
In the first set of preferred embodiments directed toward the methoxy capped glyceryl compound conforming to the following structure:
wherein:
In a preferred embodiment a is 1, b is 0 and c is 0.
In a preferred embodiment a is 1, b is 2 and c is 1.
In a preferred embodiment a is 7, b is 0 and c is 0.
In a preferred embodiment a is 20, b is 20 and c is 20.
In a preferred embodiment a is 10, b is 10 and c is 0.
In a preferred embodiment a is 0, b is 10 and c is 0.
In a preferred embodiment 1 wherein a is 10, b is 2 and c is 10.
In a preferred embodiment a is 2, b is 2 and c is 5.
In another set of preferred embodiments directed to a process for treating skin which comprises contacting the skin with an effective emollient amount of compounds conforming to the following structure;
wherein;
a, b and c are independently integers ranging from 0 to 20 with the proviso that a +b+c be at least 1.
In a preferred embodiment the effective emollient concentration ranges from 0.1% to 25% by weight.
In a preferred embodiment of this set a is 1, b is 0 and c is 0.
In a preferred embodiment of this set a is 1, b is 2 and c is 1.
In a preferred embodiment of this set a is 7, b is 0 and c is 0.
In a preferred embodiment of this set a is 20, b is 20 and c is 20.
In a preferred embodiment of this set a is 10, b is 10 and c is 0.
In a preferred embodiment of this set a is 0, b is 10 and c is 0.
In a preferred embodiment of this set 1 wherein a is 10, b is 2 and c is 10.
In a preferred embodiment of this set a is 2. b is 2 and c is 5.
REFERENCES:
patent: 4046914 (1977-09-01), Hallgren et al.
Abstract of JP 2001107075 A; Abe et al, “Aqueous Working Fluid”, Apr. 17, 2001.
Imperante John
O'Lenick, Jr. Anthony J.
Hartley Michael G.
Phoenix Research Corporation
Willis Michael A.
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