Fatty quat based on ante-iso compounds

Details Fatty quat based on ante-iso compounds Fatty quat based on ante-iso compounds

2001-03-29

2003-05-13

Page, Thurman K. (Department: 1615)

Drug, bio-affecting and body treating compositions

Live hair or scalp treating compositions

Cationic surfactant containing

C424S070100, C424S070140, C424S070110, C424S401000, C514S285000

Reexamination Certificate

active

06562328

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to the field of quaternary ammonium compounds (“quats”) and, in particular, their use in additives for personal care products such as shampoos, conditioners, skin care products and the like.
BACKGROUND OF THE INVENTION
Human hair contains a thin protective fatty layer of an ante-iso fatty acid, 18-methyl eicosanoic acid (18-MEA), covalently bound to the cuticle. Chemical or mechanical damage to the hair removes portions of this fatty layer making the hair less manageable, less healthy looking and more susceptible to environmental stresses. In the treatment of hair, it is desirable to replenish these ante-iso fatty acids, particularly 18-MEA.
18-MEA is relatively rare in nature and is found in small amounts in materials such as lanolin. Lanolin contains a mixture of fatty acids, including amongst other things, ante-iso fatty acids, as well as hydroxy fatty acids, iso-hydroxy fatty acids, iso fatty acids and unsubstituted fatty acids. U.S. Pat. No. 4,069,347, issuing to McCarthy et al., discloses compositions of quat derivatives of fatty acids derived from lanolin. These lanolin-derived quats are described as being useful, when combined with specific branched-diols, in the preparation of clear cosmetic formulations. These include shampoos and clear hair rinse formulations.
SUMMARY OF THE INVENTION
In one aspect, the present invention relates to quats derived from either fatty acid compounds consisting essentially of ante-iso fatty acids or fatty acid mixtures enriched in ante-iso fatty acids.
These quats impart desirable properties when used as additives to personal care products including hair grooming preparations and skin care products. Personal care products which include an additive of quats consisting essentially of ante-iso fatty acids or comprising fatty acid mixtures enriched in ante-iso fatty acid content are also contemplated.
A number of new discoveries have been made with important consequences for personal care products. First, it has been discovered that of all the various components contained in lanolin, it is the ante-iso fatty acids which, when quaternized, have the most profound effect upon the health and manageability of hair and/or skin. It has also been discovered that additives which consist essentially of quats of one or more ante-iso fatty acids, without significant quantities (greater than 5%) of the quats of other fatty acid species traditionally found in lanolin, yield superior personal care products. Of course, the personal care products containing these quat based additives can, and often will, include other fatty acids and fatty acid quats in varying amounts for other reasons.
It has further been discovered that of these ante-iso fatty acids, 18-MEA (having a C-21 chain), is particularly useful and provides dramatically improved results over, for example, quaternized lanolin acids derived directly from lanolin. Thus, additives containing a relatively large proportion of 18-MEA when compared to, for example, lanolin are extremely effective additions to personal care products.
However, these ante-iso fatty acids and, in particular, 18-MEA, are not typically found in nature in large quantities. These materials are also generally not found in sources from which they can be easily extracted in large quantities. U.S. Pat. No. 5,476,649, issuing to Naito et al., the text of which is hereby incorporated by reference, discloses various synthetic methods for preparation of ante-iso acids. The various synthetic preparations disclosed all call for the use of reagents and solvents such as benzene, xylene, triphenylphosphine, phosphorous tribromide, etc., that create handling and disposal difficulties due to their toxicity. These manufacturing procedures are difficult, time consuming, costly and solvent intensive. Still, where available, additives produced almost exclusively from ante-iso fatty acid quats, particularly those with fatty acid chains longer than 15 carbon atoms, and more preferably those made with 18-MEA, are desirable.
While it is desirable to make and use additives of quats made almost exclusively from ante-iso fatty acids, it has also been unexpectedly found that significant improvements in hair and skin care products, make-up, cosmetics and the like, can be obtained without the need for formulations limited to substantially only these quats. Desirable and unexpected results are also obtained by using quats resulting from mixtures of ante-iso acids with other fatty acid species, such as the mixtures that are found in lanolin, so long as the content of the ante-iso acids, and accordingly, the content of their corresponding quats, is enriched relative to lanolin. This can be done by, for example, processing lanolin acids, such as those disclosed in McCarthy et al., U.S. Pat. No. 4,069,347, the text of which is incorporated herein by reference, and enriching them by the addition of more ante-iso acid quats such as those produced in Naito et al. A relative increase in the content of ante-iso fatty acids can also be accomplished by removing some quantity of less desirable fatty acid species, such as by concentration techniques like molecular distillation. This approach can be accomplished without the use of solvents. When concentrating, for example, lanolin acids, it is most preferred to use techniques which result in a decrease in the relative proportion of iso-hydroxy fatty acids and hydroxy fatty acids thereby enriching the relative proportion of the ante-iso fatty acids.
It has also been found that many quats produced from ante-iso enriched mixtures are compatible with anionic surfactants. For the purposes of this application, “compatible with anionic surfactants” means that a clear solution, one without significant precipitation or turbidity, results once the quat is mixed with the surfactant. This is surprising since it was previously thought that with standard lanolin acid quats, such as those described in McCarthy et al., it was the presence of significant amounts of hydroxy fatty acid quats that made them anionic surfactant compatible. Since in accordance with the present invention, the iso-hydroxy fatty acids and the hydroxy fatty acids are generally removed, or their relative proportions reduced, it is completely unexpected to see continued anionic surfactant compatibility.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
Ante-iso acids conform to the following formula:
where “z” can be any positive whole number, and R is an alkyl group, substituted or un-substituted, straight chain or branched, saturated or unsaturated. This alkyl group may be substituted or unsubstituted.
Hydroxy fatty acids include at least one —OH group attached to the fatty acid chain. Iso fatty acids are similar to ante-iso fatty acids except that the attached alkyl group is located closer to the carbonyl group, usually on the next adjacent carbon.
The ante-iso acids used to produce the quat compounds in accordance with the present invention can be individually essentially pure (either all ante-iso fatty acids or a mixture of substantially only ante-iso fatty acids) or part of a fatty acid mixture that is generally comprised of acids illustrated, by example in Table I.
TABLE I
Carbon
Ante-iso
Normal Acids
Chain
Acids (%)
(%)
Iso-Acids
C
8-15
<5
<5
<5
C
16
 0-10
0.1-20 
0.1-20 
C
17
0-5
0-5
0.1-10 
C
18
 0-10
0.1-20 
0.1-20 
C
19
 0-50
 0-10
 0-10
C
20
0-5
 0-10
 1-40
C
21
 0-95
0-5
0-5
C
22
0-5
 0-10
 1-20
C
23
 0-25
0-5
 0-10
C
24
0-5
 1-15
 1-20
C
25
 0-30
0.1-10 
0.1-10 
C
26
0-5
0.1-10 
0.1-20 
C
27
 0-10
0-5
0-5
TOTAL
 8-95
1.5-50 
3.5-60 
In the present application, hydroxy fatty acids or iso-hydroxy fatty acids are preferably minimized to levels at least about 10% lower than that typically found in lanolin and more preferably substantially eliminated. Additionally, the ante-iso fatty acids are preferably kept at levels greater than those

Affiliated with

Also associated with

Rating

Fatty quat based on ante-iso compounds does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Fatty quat based on ante-iso compounds, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Fatty quat based on ante-iso compounds will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3086839