U.S. patent application number 16/032596 was filed with the patent office on 2018-11-08 for glyceryl and glycol acid compounds.
The applicant listed for this patent is Mary Kay Inc.. Invention is credited to Anton A. MENTLIK, James SWANZY.
Application Number | 20180318192 16/032596 |
Document ID | / |
Family ID | 38544295 |
Filed Date | 2018-11-08 |
United States Patent
Application |
20180318192 |
Kind Code |
A1 |
MENTLIK; Anton A. ; et
al. |
November 8, 2018 |
GLYCERYL AND GLYCOL ACID COMPOUNDS
Abstract
Disclosed is a topical skin composition comprising a glycol
di-salicylate or a glycol di-benzoate compound having the following
structure: ##STR00001## where R is OH or H, n is 1 or 2, and where
the composition further includes a glycol mono-salicylate compound
or a glycol mono-benzoate compound.
Inventors: |
MENTLIK; Anton A.; (Dallas,
TX) ; SWANZY; James; (Arlington, TX) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
Mary Kay Inc. |
Addison |
TX |
US |
|
|
Family ID: |
38544295 |
Appl. No.: |
16/032596 |
Filed: |
July 11, 2018 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
|
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15165772 |
May 26, 2016 |
10045921 |
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16032596 |
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|
13869442 |
Apr 24, 2013 |
9375391 |
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15165772 |
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13594362 |
Aug 24, 2012 |
8431731 |
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13869442 |
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13038074 |
Mar 1, 2011 |
8258121 |
|
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13594362 |
|
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11749869 |
May 17, 2007 |
7932417 |
|
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13038074 |
|
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60747760 |
May 19, 2006 |
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Current U.S.
Class: |
1/1 |
Current CPC
Class: |
A61K 8/375 20130101;
A61K 8/06 20130101; A61Q 19/007 20130101; A61Q 17/04 20130101; A61Q
19/08 20130101; A61K 8/0216 20130101; A61P 17/00 20180101; A61K
8/37 20130101 |
International
Class: |
A61K 8/37 20060101
A61K008/37; A61Q 19/08 20060101 A61Q019/08; A61Q 19/00 20060101
A61Q019/00; A61K 8/02 20060101 A61K008/02; A61K 8/06 20060101
A61K008/06; A61Q 17/04 20060101 A61Q017/04 |
Claims
1. A topical skin composition comprising a glycol di-salicylate or
a glycol di-benzoate compound having the following structure:
##STR00009## where R is OH or H, n is 1 or 2, and where the
composition further includes a glycol mono-salicylate compound or a
glycol mono-benzoate compound.
2. The topical skin composition of claim 1, wherein the composition
is an emulsion.
3. The topical skin composition of claim 2, wherein the composition
is an oil-in-water emulsion.
4. The topical skin composition of claim 2, wherein the composition
is a water-in-oil emulsion.
5. The topical skin composition of claim 1, wherein the composition
is a cream, a lotion, or an ointment.
6. The topical skin composition of claim 1, wherein the composition
is a gel.
7. The topical skin composition of claim 1, wherein the composition
is a solution.
8. The topical skin composition of claim 1, wherein the composition
comprises from about 0.001 to about 20%, by weight, of the glyceryl
di-salicylate.
9. The topical skin composition of claim 1, comprising the glycol
di-salicylate compound, where R is OH and n is 1.
10. The topical skin composition of claim 9, comprising the glycol
mono-salicylate compound having the following structure:
##STR00010##
11. The topical skin composition of claim 1, comprising the glycol
di-benzoate compound, where R is H and n is 1.
12. The topical skin composition of claim 11, comprising the glycol
mono-benzoate compound having the following structure: ##STR00011##
Description
CROSS-REFERENCE TO RELATED APPLICATIONS
[0001] This application is a continuation of U.S. application Ser.
No. 15/165,772, filed May 26, 2016, which is a continuation of U.S.
application Ser. No. 13/869,442, filed Apr. 24, 2013 (now issued as
U.S. Pat. No. 9,375,391), which is a continuation of U.S.
application Ser. No. 13/594,362 (now issued as U.S. Pat. No.
8,431,731), which is a continuation of U.S. application Ser. No.
13/038,074 (now issued as U.S. Pat. No. 8,258,121), which is a
continuation of U.S. application Ser. No. 11/749,869 (now issued as
U.S. Pat. No. 7,932,417), which claims the benefit of U.S.
Provisional Application No. 60/747,760, filed May 19, 2006. The
entire contents of these applications are incorporated into the
present application by reference.
BACKGROUND OF THE INVENTION
A. Field of the Invention
[0002] The present invention relates generally to a compound that
can be used in compositions such as cosmetic skin care
compositions. The compound can include an acid molecule attached to
a glycerol or glycol molecule via an ester linkage.
B. Description of Related Art
[0003] With ageing, chronic exposure to adverse environmental
factors, or malnutrition, the visual appearance, physical
properties, and physiological functions of skin can change in ways
that are considered visually undesirable. The most notable and
obvious changes include the development of fine lines and wrinkles,
loss of elasticity, increased sagging, loss of firmness, loss of
color evenness or tone, coarse surface texture, and mottled
pigmentation. Less obvious, but measurable changes which occur as
skin ages or endures chronic environmental insult include a general
reduction in cellular and tissue vitality, reduction in cell
replication rates, reduced cutaneous blood flow, reduced moisture
content, accumulated errors in structure and function, alterations
in the normal regulation of common biochemical pathways, and a
reduction in the skin's ability to remodel and repair itself. Many
of the alterations in appearance and function of the skin are
caused by changes in the outer epidermal layer of the skin, while
others are caused by changes in the lower dermis.
[0004] Several different approaches have been used to treat damaged
skin caused by aging, environmental factors, chemicals, or
malnutrition. These approaches can oftentimes have various
drawbacks, such as significant irritation to the skin or skin
toxicity.
SUMMARY OF THE INVENTION
[0005] The present invention overcomes deficiencies in the art. In
a non-limiting aspect, the invention relates generally to compounds
that can be used in compositions such as cosmetic and
pharmaceutical compositions. In certain embodiments, the compound
can include an acid molecule attached to a glyceryl or glycol
molecule via an ester linkage. Generic and specific structures of
these compounds are disclosed throughout this specification and
incorporated into this section by reference.
[0006] In certain embodiments, the compounds can be incorporated
into a composition. The composition can be cosmetic composition or
a pharmaceutical composition. The composition can be topically
applied to skin. The compositions can be included in a cosmetic
vehicle. Non-limiting examples of cosmetic vehicles are disclosed
in other sections of this specification and are known to those of
skill in the art. Examples of cosmetic vehicles include emulsions
(e.g., oil-in-water and water-in-oil emulsions), creams, lotions,
solutions (e.g., aqueous or hydro-alcoholic solutions), anhydrous
bases (e.g., lipstick or a powder), gels, and ointments. In other
non-limiting embodiments, the compositions of the present invention
can be included in anti-aging, cleansing, or moisturizing products.
The compositions can also be formulated for topical skin
application at least 1, 2, 3, 4, 5, 6, 7, or more times a day
during use. In other aspects of the present invention, compositions
can be storage stable or color stable, or both.
[0007] In certain embodiments, the compositions of the present
invention can include from about 0.001% to about 20%, by weight or
volume, of glyceryl/acid or glycol/acid compounds, or a combination
of both. It should be recognized, however, that the amount of the
compounds in a composition can be modified below, within, or above
this range based on the desired results (e.g., 1, 2, 3, 4, 5, 6, 7,
8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24,
25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41,
42, 43, 44, 45, 46, 47, 48, 49, 50, 55, 60, 65, 70, 75, 80, 85, 90,
95, 96, 97, 98, 99%, or more, by weight or volume of the
composition). Therefore, the amount of a glyceryl/acid or
glycol/acid compound can include less than 0.001% or more than 5%,
by weight or volume. In other aspects, the compositions can include
0.002, 0.003, 0.004 . . . 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12,
13, 14, 15, 16, 17, 18, 19, 20, 25, 30, 35, 40, 45, 50, 60, 70, 80,
90, 95, 96, 97, 98, 99%, or more or, or any range derivable
therein, by weight or volume of glyceryl or glycol salicylate or a
combination of both. In other embodiments, the compositions of the
present invention can further include a camitine molecule. The
camitine molecule can be acylated (e.g., acetyl-1-camitine). In
certain aspects, the ratio of any ingredient within the composition
when compared to another ingredient can be from about 1:1, 2:1,
3:1, 4:1, 5:1, 6:1, 7:1, 8:1, 9:1, 10:1, 11:1, 12:1, 13:1, 14:1,
15:1, 16:1, 17:1, 18:1, 19:1, 20:1, 21:1, 22:1, 23:1, 24:1, 25:1,
26:1, 27:1, 28:1, 29:1, 30:1, 31:1, 32:1, 33:1, 34:1, 35:1, 36:1,
37:1, 38:1, 39:1, 40:1, 50:1, 60:1, 70:1, 80:1, 90:1, 100:1, or
more or any number derivable therein, by weight or volume of the
total composition. In other aspects, the ratio of any ingredient
within the composition when compared to another ingredient can be
from about 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, 1:10, 1:11,
1:12, 1:13, 1:14, 1:15, 1:16, 1:17, 1:18, 1:19, 1:20, 1:21, 1:22,
1:23, 1:24, 1:25, 1:26, 1:27, 1:28, 1:29, 1:30, 1:31, 1:32, 1:33,
1:34, 1:35, 1:36, 1:37, 1:38, 1:39, 1:40, 1:50, 1:60, 1:70, 1:80,
1:90, 1:100, or more or any number derivable therein, by weight or
volume of the total composition.
[0008] The compositions of the present invention can also be
modified to have a desired oxygen radical absorbance capacity
(ORAC) value. In certain non-limiting aspects, the compositions of
the present invention can be modified to have an ORAC value per mg
of at least about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14,
15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 35,
40, 45, 50, 55, 60, 70, 80, 90, 95, 100, 200, 300, 400, 500, 600,
700, 800, 900, 1000, 2000, 3000, 4000, 5000, 6000, 7000, 8000,
9000, 10000, 15000, 20000, 30000, 50000, 100000 or more or any
range derivable therein.
[0009] In other non-limiting aspects of the present invention, the
compositions can further include a vitamin, a mineral, an essential
fatty acid, an amino acid (including essential and non-essential
amino acids), a flavinoid, and/or a protein, or a combination
thereof. Non-limiting examples of vitamins include the B vitamins
(e.g., B1, B2, B6, B12, niacin, folic acid, biotin, and pantothenic
acid), vitamin C, vitamin D, vitamin E (e.g., tocopherol or
tocopheryl acetate), vitamin A (e.g., palmitate, retinyl palmitate,
or retinoic acid), and vitamin K. Non-limiting examples of minerals
include iron, potassium, phosphorus, magnesium, manganese,
selenium, and calcium. Non-limiting examples of essential fatty
acids include Omega 3 (linolenic acid), Omega 6 (linoleic acid) and
Omega 9 (oleic acid) essential fatty acid, or a combination
thereof. Non-limiting examples of amino acids include essential
amino acids (e.g., lysine, leucine, isoleucine, methionine,
phenylalanine, threonine, tryptophan, valine, histidine, or
arginine) and non-essential amino acids (e.g., serine, asparagine,
glutamine, aspartic acid, glutamic acid, alanine, tyrosine,
cysteine, glycine, or proline). Non-limiting examples of flavinoids
include anthocyanin compounds (e.g., cyanidin-3-glucoside and
cyanidin-3-rutinoside).
[0010] The compositions in non-limiting aspects can have a pH of
about 6 to about 9. In other aspects, the pH can be 1, 2, 3, 4, 5,
6, 7, 8, 9, 10, 11, 12, 13, or 14. The compositions can include a
triglyceride. Non-limiting examples include small, medium, and
large chain triglycerides. In certain aspects, the triglyceride is
a medium chain triglyceride (e.g., caprylic capric triglyceride).
The compositions can also include preservatives. Non-limiting
examples of preservatives include methylparaben, propylparaben, or
a mixture of methylparaben and propylparaben.
[0011] Also disclosed is a method of treating or preventing a skin
condition comprising topical application of a composition
comprising a glyceryl/acid compound and/or a glycol/acid compound,
wherein the topical application of the composition treats the skin
condition. Non-limiting examples of skin conditions include
pruritus, spider veins, lentigo, age spots, senile purpura,
keratosis, melasma, blotches, fine lines or wrinkles, nodules, sun
damaged skin, dermatitis (including, but not limited to seborrheic
dermatitis, nummular dermatitis, contact dermatitis, atopic
dermatitis, exfoliative dermatitis, perioral dermatitis, and stasis
dermatitis), psoriasis, folliculitis, rosacea, acne, impetigo,
erysipelas, erythrasma, eczema, and other inflammatory skin
conditions. In certain non-limiting aspects, the skin condition can
be caused by exposure to UV light, age, irradiation, chronic sun
exposure, environmental pollutants, air pollution, wind, cold,
heat, chemicals, disease pathologies, smoking, or lack of
nutrition. The skin can be facial skin or non-facial skin (e.g.,
arms, legs, hands, chest, back, feet, etc.). The method can further
comprise identify a person in need of skin treatment. The person
can be a male or female. The age of the person can be at least 1,
2, 3, 4, 5, 6, 7, 8, 9, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60,
65, 70, 75, 80, 85, 90, 95, or more years old, or any range
derivable therein.
[0012] The compositions of the present invention can also be used
in methods for exfoliate the skin. This allows the user to shed
dead skin cells and also encourages the skin's natural sloughing
process. An advantage of this process is that it reveals and
exposes "younger," fresher skin. The shedding process unclogs
pores, keeps skin clean and helps reduce acne breakouts.
[0013] The methods of the present invention can also include
topically applying an amount effective to: increase the stratum
corneum turnover rate of the skin; decrease skin roughness;
increase collagen synthesis in fibroblasts; increase cellular
anti-oxidant defense mechanisms (e.g., exogenous additions of
anti-oxidants can bolster, replenish, or prevent the loss of
cellular antioxidants such as catalase and glutathione in skin
cells (e.g., keratinocytes, melanocytes, langerhans cells, etc.)
which will reduce or prevent oxidative damage to the skin,
cellular, proteins, and lipids); inhibit melanin production in
melanocytes; reduce or prevent oxidative damage to skin (including
reducing the amount lipid peroxides and/or protein oxidation in the
skin); enhance desmosomal degradation, leading to an increase in
corneocyte desquamation; increase cytokines, hyaluronic acid, cell
proliferation, collagen production and epidermal proliferation;
normalize corneocyte cohesion; enhance lipid synthesis in the
intercellular areas; target the sebum in the sebaceous glands; and
activate fibroblasts.
[0014] The compositions of the present invention can also be used
in a regimen alone or with other compositions (e.g., skin care
compositions). For instance, the composition of the present
invention can be applied in the morning and/or evening at
predetermined intervals and/or amounts. Alternatively, the
compositions of the present invention can be applied in the morning
and a second skin care composition can be applied in the evening
and vice versa.
[0015] Also disclosed are methods for using the glyceryl/acid
compounds and glycol/acid compounds as moisturizing agents,
film-forming agents, UV absorption agents, and/or skin treatment
agents. For instance, the compounds can maintain and/or increase
the hydration (such as water content) of skin. The compounds can
also lubricate the skin. The compounds can form a film or barrier
on the outer surface of the skin which can reduce or prevent the
evaporation of water from the skin. In certain aspects, the film
can have tactile properties which make the skin feel soft or
smooth. The compounds can also be used as UV absorption agents and
can be used in methods for increasing the UV absorption
characteristics of a composition such as, for example, a sunscreen
composition. The compounds can be used in methods for increasing
the SPF of a sunscreen composition. In certain aspects, the
compounds can be used to increase the efficiency of existing
sunscreen products and/or sunscreen agents that are used in such
products. Alternatively, the compounds can be used as a standalone
sunscreen agent. In certain embodiments, the compounds can be used
in methods for reducing or preventing cosmetic compositions from
chemical or physical deterioration that is induced by ultraviolet
light. The compounds and/or compositions of the present invention
can diffract or absorb a broad spectrum of UV radiation. For
example, the compounds and/or compositions can absorb or diffract
UVA (approximately 315 to 400 nm), UVB (approximately 280 to 315)
and/or UVC (approximately 10 to 280 nm) light. In certain aspects,
the compounds and/or compositions can absorb or diffract UV light
ranging from about 1 to about 400 nm, or any integer or range
therein (e.g., 2, 10, 20, 30, 40, 50, 60, 70, 80, 90, 100, 110,
120, 130, 140, 150, 160, 170, 180, 190, 200, 210, 220, 230, 240,
250, 260, 270, 280, 290, 300, 310, 320, 330, 340, 350, 360, 370,
380, 390, 399).
[0016] Also contemplated are kits that include the compositions of
the present invention. In certain embodiments, the composition is
comprised in a container. The container can be a bottle, dispenser,
or package. The container can dispense a pre-determined amount of
the composition. In certain aspects, the compositions is dispensed
in a spray or mist, dollop, or liquid. The container can include
indicia on its surface. The indicia can be a word, an abbreviation,
a picture, or a symbol.
[0017] Also contemplated is a product comprising a composition of
the present invention. In non-limiting aspects, the product can be
a cosmetic product. The cosmetic product can be those described in
other sections of this specification or those known to a person of
skill in the art. Non-limiting examples of products include a
moisturizer, a cream, a lotion, a skin softener, a foundation, a
night cream, a lipstick, a cleanser, a toner, a sunscreen, a mask,
or an anti-aging product.
[0018] It is contemplated that any embodiment discussed in this
specification can be implemented with respect to any method or
composition of the invention, and vice versa. Furthermore,
compositions of the invention can be used to achieve methods of the
invention.
[0019] The term "alkyl" includes straight-chain alkyl groups,
branched-chain alkyl groups, cycloalkyl (alicyclic) groups, alkyl
heteroatom-substituted cycloalkyl groups, and cycloalkyl
heteroatom-substituted alkyl groups.
[0020] The term "alkoxy" includes a group having the structure
--OR, where R is an alkyl group. Non-limiting examples of alkoxy
groups include --OCH.sub.3, --OCH.sub.2CH.sub.3,
--OCH.sub.2CH.sub.2CH.sub.3, --OCH(CH.sub.3).sub.2,
--OCH(CH.sub.2).sub.2, etc.
[0021] The term "hydroxyalkyl" includes an alkyl group having at
least one hydroxy group.
[0022] The term "about" or "approximately" are defined as being
close to as understood by one of ordinary skill in the art, and in
one non-limiting embodiment the terms are defined to be within 10%,
within 5%, within 1%, and/or within 0.5%.
[0023] The terms "inhibiting" or "reducing" or any variation of
these terms, when used in the claims and/or the specification
includes any measurable decrease or complete inhibition to achieve
a desired result.
[0024] The term "effective," as that term is used in the
specification and/or claims, means adequate to accomplish a
desired, expected, or intended result.
[0025] The use of the word "a" or "an" when used in conjunction
with the term "comprising" in the claims and/or the specification
may mean "one," but it is also consistent with the meaning of "one
or more," "at least one," and "one or more than one."
[0026] The use of the term "or" in the claims is used to mean
"and/or" unless explicitly indicated to refer to alternatives only
or the alternatives are mutually exclusive, although the disclosure
supports a definition that refers to only alternatives and
"and/or."
[0027] As used in this specification and claim(s), the words
"comprising" (and any form of comprising, such as "comprise" and
"comprises"), "having" (and any form of having, such as "have" and
"has"), "including" (and any form of including, such as "includes"
and "include") or "containing" (and any form of containing, such as
"contains" and "contain") are inclusive or open-ended and do not
exclude additional, unrecited elements or method steps.
[0028] Other objects, features and advantages of the present
invention will become apparent from the following detailed
description. It should be understood, however, that the detailed
description and the examples, while indicating specific embodiments
of the invention, are given by way of illustration only.
Additionally, it is contemplated that changes and modifications
within the spirit and scope of the invention will become apparent
to those skilled in the art from this detailed description.
DESCRIPTION OF ILLUSTRATIVE EMBODIMENTS
[0029] In today's image conscious society, people are continually
looking for a product that can protect or improve the visual
appearance of their skin. Often times, aged skin, uneven skin tone,
or skin damaged by environmental factors such as UV light, chronic
sun exposure, environmental pollutants, chemicals, disease
pathologies, or smoking, is associated with unattractive skin.
Compounds of the present invention can be used in all types of
cosmetic compositions/formulations for treating, preserving, or
preventing the appearance of aged or damaged skin.
[0030] For instance, the compounds of the present invention can
have a wide variety of uses in compositions that are applied to
skin. Non-limiting examples include using the compounds as a
moisturizing agent, a film-forming agent, a UV absorption agent,
and a skin treatment agent. As a moisturizing agent, the compounds
can help maintain and/or increase the hydration of skin, thereby
making the skin softer and more pliable. The compounds can also act
as lubricants for the skin to treat, reduce, or prevent skin
flaking and dry skin.
[0031] As a film-forming agent, the compounds can be used to form a
film or barrier on the outer surface of the skin. This can be
beneficial to the skin by reducing or preventing the evaporation of
water from the skin. Additionally, the film can have tactile
properties that make the skin feel soft and smooth.
[0032] As a UV absorption agent, the compounds can be used to
protect the cosmetic composition from chemical or physical
deterioration induced by ultraviolet light. The compounds can also
be used as a sunscreen agent in sunscreen compositions. The
compounds can also increase the sun protection factor (SPF) of a
sunscreen composition that already includes a sunscreen agent.
[0033] As a skin treatment agent, the compounds can be used as
active ingredients in topical skin care compositions. Non-limiting
examples of skin conditions that can be treated with the compounds
of the present invention are disclosed throughout this
specification.
[0034] These and other aspect of the invention are described in
further non-limiting detail below.
A. Glyceryl/Acid and Glycol/Acid Compounds
[0035] 1. Glyceryl/Acid Compounds
[0036] A glyceryl/acid compound of the present invention can be
derived from glycerol molecule which has the following
structure:
##STR00002##
The acid portion of the glyceryl/acid compounds can be attached via
an ester linkage of the OH group of the glycerol molecule and the
COOH group of the acid molecule. In non-limiting aspects, a
glyceryl/acid compound can have the following generic chemical
structure:
##STR00003##
where R, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6
can each independently be an H, an acid molecule, a hydroxy, a
halogen, an oxo (e.g., ether), an alkoxy, a silyloxy, an acyl, an
aryl, an acetyl, a carbonyl, a cyano, a heterocyclyl, an amido, an
aminocarbonyl, an amino, --NH-alkyl, --N(alkyl).sub.2,
--NH-(substituted alkyl), --N-(substituted alkyl).sub.2, --NH-aryl,
--N(aryl).sub.2, an azido, a trialkylsilyloxy, an acyloxy, a
acylamino, a bis-acylamino, an ester, a NO, a NO.sub.2, or a sulfo
(e.g., thioether, thioester, thiocarbonyl, sulfonamido, sulfonyl,
etc.). In certain aspects, the acid molecule is selected from the
group consisting of salicylic acid, cinnamic acid, and benzoic
acid, and derivatives and substituted acids thereof. Other
non-limiting examples of acids that can be used in the context of
the present invention are described in International Cosmetic
Ingredient Dictionary and Handbook, 10.sup.th Ed., 2004, which is
incorporated by reference. In certain aspects, at least one of R,
R.sub.4, and R.sub.6 is an acid, R and R.sub.4 are acids, R and
R.sub.6 are acids, R.sub.4 and R.sub.6 are acids, or R, R.sub.4,
and R.sub.6 are all acids. Non-limiting examples of certain
glyceryl/acid compounds of the present invention are illustrated
below:
##STR00004## ##STR00005##
[0037] The glyceryl/acid compounds and derivatives and
modifications of the same can be prepared by using convention
chemical synthesis techniques (see, e.g., Organic Chemistry,
5.sup.th Ed.).
[0038] 2. Glycol/Acid Compounds
[0039] A glycol/acid compound of the present invention can be
derived from a glycol molecule. Glycols are a generic class of
dihydric alcohols. Non-limiting examples of glycols that can be
used in the context of the present invention include: ethylene
glycols (e.g., 1, 2 ethane diol (monoethylene glycol),
2-hydroxyethoxy)ethan-2-ol (diethylene glycol); polyethylene
glycols (PEGs); propylene glycols (e.g., 1, 2 propane diol, 1, 3
propane diol, etc.); and butylene glycols (e.g., 1, 2 butane diol,
1,3 butane diol, 1, 4 butane diol, etc.). Other non-limiting
examples of glycols that can be used in the context of the present
invention are described in International Cosmetic Ingredient
Dictionary and Handbook, 10.sup.th Ed., 2004, which is incorporated
by reference. It certain aspects, the glycol that is used can have
similar physical and chemical characteristics to glycerol.
[0040] The acid portion of the glycol/acid compounds can be
attached via an ester linkage of the OH group of the glycol
molecule and the COOH group of the acid molecule. In non-limiting
aspects, a glycol/acid compound can have the following generic
chemical structure:
##STR00006##
where n can be 2, 3, 4, 5, 6, 7, 8, 9, 10, or more, or any range
therein. In certain aspects, n is an integer from 2 to 4. Y.sub.1,
Y.sub.2, Y.sub.3, and Y.sub.4, can each independently be OY.sub.5,
an H, an acid molecule attached via an ester linkage, a hydroxy, a
halogen, an oxo (e.g., ether), an alkoxy, a silyloxy, an acyl, an
aryl, an acetyl, a carbonyl, a cyano, a heterocyclyl, an amido, an
aminocarbonyl, an amino, --NH-alkyl, --N(alkyl).sub.2,
--NH-(substituted alkyl), --N-(substituted alkyl).sub.2, --NH-aryl,
--N(aryl).sub.2, an azido, a trialkylsilyloxy, an acyloxy, a
acylamino, a bis-acylamino, an ester, a NO, a NO.sub.2, or a sulfo
(e.g., thioether, thioester, thiocarbonyl, sulfonamido, sulfonyl,
etc.). In certain aspects, the acid molecule is selected from the
group consisting of salicylic acid, cinnamic acid, and benzoic
acid, and derivatives and substituted acids thereof. Other
non-limiting examples of acids that can be used in the context of
the present invention are described in International Cosmetic
Ingredient Dictionary and Handbook, 10.sup.th Ed., 2004, which is
incorporated by reference. Y.sub.5 can be anyone of the groups
identified for Y.sub.1, Y.sub.2, Y.sub.3, and Y.sub.4. In certain
aspects Y.sub.5 is an acid group. In other embodiments, at least
two of Y.sub.1, Y.sub.2, Y.sub.3, and Y.sub.4 is a hydroxyl group.
Non-limiting examples of certain particular glycol/acid compounds
of the present invention are illustrated below:
##STR00007## ##STR00008##
[0041] The glycol/acid compounds and derivatives and modifications
of the same can be prepared by using convention chemical synthesis
techniques (see, e.g., Organic Chemistry, 5.sup.th Ed.).
[0042] 3. Modifications and Derivatives of Glyceryl/Glycol/Acid
Compounds
[0043] Modifications or derivatives of the glyceryl/acid and
glycol/acid compounds disclosed throughout this specification are
contemplated as being useful with the methods and compositions of
the present invention. Derivatives and modifications may be
prepared and the properties of such derivatives and modified
compounds may be assayed for their desired properties by any method
known to those of skill in the art.
[0044] In certain aspects, "derivative" refers to a chemically
modified glyceryl/acid or glycol/acid compound that still retains
the desired effects of the compound prior to the chemical
modification. Such derivatives may have the addition, removal, or
substitution of one or more chemical moieties on the glyceryl,
glycol, and/or acid portion of the compounds. Non-limiting examples
of the modifications that can be made to these portions of the
compounds include the addition or removal of alkyl groups, carboxyl
groups, carbonyl groups, hydroxyl groups, nitro groups, amino
groups, amide groups, azo groups, sulfate groups, sulfonate groups,
sulfono groups, sulfhydryl groups, sulfonyl groups, sulfoxido
groups, phosphate groups, phosphono groups, phosphoryl groups,
and/or halide groups. Additional modifications can include an
addition or a deletion of one or more atoms of the atomic
framework, for example, substitution of an ethyl by a propyl or
substitution of a phenyl by a larger or smaller aromatic group. In
a cyclic or bicyclic structure, hetero atoms such as N, S, or O can
be substituted into the structure instead of a carbon atom.
B Compositions
[0045] The compounds of the present invention can be incorporated
into all types of compositions (e.g., cosmetic and pharmaceutical
compositions). A person of ordinary skill would recognize that the
compositions can include any number of combinations of
glyceryl/acid compounds, glycol/acid compounds, and/or additional
ingredients, or derivatives thereof. The concentrations of the
glyceryl/acid compounds, glycol/acid compounds, and/or additional
ingredients, or derivatives thereof, can vary for a given
composition. This variation can oftentimes depend on the desired
characteristics of the final composition. In non-limiting
embodiments, for example, the compositions may include in their
final form, for example, at least about 0.0001%, 0.0002%, 0.0003%,
0.0004%, 0.0005%, 0.0006%, 0.0007%, 0.0008%, 0.0009%, 0.0010%,
0.0011%, 0.0012%, 0.0013%, 0.0014%, 0.0015%, 0.0016%, 0.0017%,
0.0018%, 0.0019%, 0.0020%, 0.0021%, 0.0022%, 0.0023%, 0.0024%,
0.0025%, 0.0026%, 0.0027%, 0.0028%, 0.0029%, 0.0030%, 0.0031%,
0.0032%, 0.0033%, 0.0034%, 0.0035%, 0.0036%, 0.0037%, 0.0038%,
0.0039%, 0.0040%, 0.0041%, 0.0042%, 0.0043%, 0.0044%, 0.0045%,
0.0046%, 0.0047%, 0.0048%, 0.0049%, 0.0050%, 0.0051%, 0.0052%,
0.0053%, 0.0054%, 0.0055%, 0.0056%, 0.0057%, 0.0058%, 0.0059%,
0.0060%, 0.0061%, 0.0062%, 0.0063%, 0.0064%, 0.0065%, 0.0066%,
0.0067%, 0.0068%, 0.0069%, 0.0070%, 0.0071%, 0.0072%, 0.0073%,
0.0074%, 0.0075%, 0.0076%, 0.0077%, 0.0078%, 0.0079%, 0.0080%,
0.0081%, 0.0082%, 0.0083%, 0.0084%, 0.0085%, 0.0086%, 0.0087%,
0.0088%, 0.0089%, 0.0090%, 0.0091%, 0.0092%, 0.0093%, 0.0094%,
0.0095%, 0.0096%, 0.0097%, 0.0098%, 0.0099%, 0.0100%, 0.0200%,
0.0250%, 0.0275%, 0.0300%, 0.0325%, 0.0350%, 0.0375%, 0.0400%,
0.0425%, 0.0450%, 0.0475%, 0.0500%, 0.0525%, 0.0550%, 0.0575%,
0.0600%, 0.0625%, 0.0650%, 0.0675%, 0.0700%, 0.0725%, 0.0750%,
0.0775%, 0.0800%, 0.0825%, 0.0850%, 0.0875%, 0.0900%, 0.0925%,
0.0950%, 0.0975%, 0.1000%, 0.1250%, 0.1500%, 0.1750%, 0.2000%,
0.2250%, 0.2500%, 0.2750%, 0.3000%, 0.3250%, 0.3500%, 0.3750%,
0.4000%, 0.4250%, 0.4500%, 0.4750%, 0.5000%, 0.5250%, 0.0550%,
0.5750%, 0.6000%, 0.6250%, 0.6500%, 0.6750%, 0.7000%, 0.7250%,
0.7500%, 0.7750%, 0.8000%, 0.8250%, 0.8500%, 0.8750%, 0.9000%,
0.9250%, 0.9500%, 0.9750%, 1.0%, 1.1%, 1.2%, 1.3%, 1.4%, 1.5%,
1.6%, 1.7%, 1.8%, 1.9%, 2.0%, 2.1%, 2.2%, 2.3%, 2.4%, 2.5%, 2.6%,
2.7%, 2.8%, 2.9%, 3.0%, 3.1%, 3.2%, 3.3%, 3.4%, 3.5%, 3.6%, 3.7%,
3.8%, 3.9%, 4.0%, 4.1%, 4.2%, 4.3%, 4.4%, 4.5%, 4.6%, 4.7%, 4.8%,
4.9%, 5.0%, 5.1%, 5.2%, 5.3%, 5.4%, 5.5%, 5.6%, 5.7%, 5.8%, 5.9%,
6.0%, 6.1%, 6.2%, 6.3%, 6.4%, 6.5%, 6.6%, 6.7%, 6.8%, 6.9%, 7.0%,
7.1%, 7.2%, 7.3%, 7.4%, 7.5%, 7.6%, 7.7%, 7.8%, 7.9%, 8.0%, 8.1%,
8.2%, 8.3%, 8.4%, 8.5%, 8.6%, 8.7%, 8.8%, 8.9%, 9.0%, 9.1%, 9.2%,
9.3%, 9.4%, 9.5%, 9.6%, 9.7%, 9.8%, 9.9%, 10%, 11%, 12%, 13%, 14%,
15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24%, 25%, 26%, 27%,
28%, 29%, 30%, 35%, 40%, 45%, 50%, 60%, 65%, 70%, 75%, 80%, 85%,
90%, 95%, or 99% or any range derivable therein, of at least one of
the glyceryl/acid compounds, glycol/acid compounds, and/or
additional ingredients, or derivatives thereof. In certain
non-limiting aspects, the percentages can be calculated by weight
or volume of the total composition. A person of ordinary skill in
the art would understand that the concentrations can vary depending
on the addition, substitution, and/or subtraction of the
glyceryl/acid compounds, glycol/acid compounds, and additional
ingredients, or derivatives thereof.
C Additional Ingredients
[0046] In addition to the glyceryl/acid compounds and/or
glycol/acid compounds disclosed throughout this specification,
compositions of the present invention can include additional
ingredients such as cosmetic ingredients and pharmaceutical active
ingredients. Non-limiting examples of these additional ingredients
are described in the following subsections.
[0047] 1. Cosmetic Ingredients
[0048] The CTFA International Cosmetic Ingredient Dictionary and
Handbook (2004) describes a wide variety of non-limiting cosmetic
ingredients that can be used in the context of the present
invention. Examples of these ingredient classes include: fragrances
(artificial and natural), dyes and color ingredients (e.g., Blue 1,
Blue 1 Lake, Red 40, titanium dioxide, D&C blue no. 4, D&C
green no. 5, D&C orange no. 4, D&C red no. 17, D&C red
no. 33, D&C violet no. 2, D&C yellow no. 10, and D&C
yellow no. 11), adsorbents, lubricants, solvents, moisturizers
(including, e.g., emollients, humectants, film formers, occlusive
agents, and agents that affect the natural moisturization
mechanisms of the skin), water-repellants, UV absorbers (physical
and chemical absorbers such as paraaminobenzoic acid ("PABA") and
corresponding PABA derivatives, titanium dioxide, zinc oxide,
etc.), essential oils, vitamins (e.g. A, B, C, D, E, and K), trace
metals (e.g. zinc, calcium and selenium), anti-irritants (e.g.
steroids and non-steroidal anti-inflammatories), botanical extracts
(e.g. aloe vera, chamomile, cucumber extract, ginkgo biloba,
ginseng, and rosemary), anti-microbial agents, antioxidants (e.g.,
BHT and tocopherol), chelating agents (e.g., disodium EDTA and
tetrasodium EDTA), preservatives (e.g., methylparaben and
propylparaben), pH adjusters (e.g., sodium hydroxide and citric
acid), absorbents (e.g., aluminum starch octenylsuccinate, kaolin,
corn starch, oat starch, cyclodextrin, talc, and zeolite), skin
bleaching and lightening agents (e.g., hydroquinone and niacinamide
lactate), humectants (e.g., sorbitol, urea, and manitol),
exfoliants, waterproofing agents (e.g., magnesium/aluminum
hydroxide stearate), skin conditioning agents (e.g., aloe extracts,
allantoin, bisabolol, ceramides, dimethicone, hyaluronic acid, and
dipotassium glycyrrhizate). Non-limiting examples of some of these
ingredients are provided in the following subsections.
[0049] a. Preservatives
[0050] Non-limiting examples of preservatives that can be used in
the context of the present invention include quaternary ammonium
preservatives such as polyquarternium-1 and benzalkonium halides
(e.g., benzalkonium chloride ("BAC") and benzalkonium bromide),
parabens (e.g., methylparabens and propylparabens), phenoxyethanol,
benzyl alcohol, chlorobutanol, phenol, sorbic acid, thimerosal or
combinations thereof.
[0051] b. Moisturizers
[0052] Non-limiting examples of moisturizing agents that can be
used with the compositions of the present invention can be found in
the International Cosmetic Ingredient Dictionary, 10.sup.th Ed.,
2004. Examples include amino acids, chondroitin sulfate,
diglycerin, erythritol, fructose, glucose, 1,2,6-hexanetriol,
honey, hyaluronic acid, hydrogenated honey, hydrogenated starch
hydrolysate, inositol, lactitol, maltitol, maltose, mannitol,
natural moisturizing factor, salts of pyrollidone carboxylic acid,
potassium PCA, sodium glucuronate, sodium PCA, sorbitol, sucrose,
trehalose, urea, and xylitol.
[0053] c. Emollients
[0054] Non-limiting examples of emollients include, but are not
limited to, vegetable oils, mineral oils, silicone oils, synthetic
and natural waxes, petrolatum, lanolin, aluminum magnesium
hydroxide stearate (which can also function as a water repellent),
and fatty acid esters. Non-limiting examples of vegetable oils
include safflower oil, corn oil, sunflower seed oil, and olive
oil.
[0055] d. Antioxidants
[0056] Non-limiting examples of antioxidants include, but are not
limited to, acetyl cysteine, ascorbic acid, ascorbic acid
polypeptide, ascorbyl dipalmitate, ascorbyl methylsilanol
pectinate, ascorbyl palmitate, ascorbyl stearate, BHA, BHT, t-butyl
hydroquinone, cysteine, cysteine HCl, diamylhydroquinone,
di-t-butylhydroquinone, dicetyl thiodipropionate, dioleyl
tocopheryl methylsilanol, disodium ascorbyl sulfate, distearyl
thiodipropionate, ditridecyl thiodipropionate, dodecyl gallate,
erythorbic acid, esters of ascorbic acid, ethyl ferulate, ferulic
acid, gallic acid esters, hydroquinone, isooctyl thioglycolate,
kojic acid, magnesium ascorbate, magnesium ascorbyl phosphate,
methylsilanol ascorbate, natural botanical anti-oxidants such as
green tea or grape seed extracts, nordihydroguaiaretic acid, octyl
gallate, phenylthioglycolic acid, potassium ascorbyl tocopheryl
phosphate, potassium sulfite, propyl gallate, quinones, rosmarinic
acid, sodium ascorbate, sodium bisulfite, sodium erythorbate,
sodium metabisulfite, sodium sulfite, superoxide dismutase, sodium
thioglycolate, sorbityl furfural, thiodiglycol, thiodiglycolamide,
thiodiglycolic acid, thioglycolic acid, thiolactic acid,
thiosalicylic acid, tocophereth-5, tocophereth-10, tocophereth-12,
tocophereth-18, tocophereth-50, tocopherol, tocophersolan,
tocopheryl acetate, tocopheryl linoleate, tocopheryl nicotinate,
tocopheryl succinate, and tris(nonylphenyl)phosphite.
[0057] e. Thickening Agents
[0058] Thickening agents, including thickener or gelling agents,
include substances which that can increase the viscosity of a
composition. Thickeners include those that can increase the
viscosity of a composition without substantially modifying the
efficacy of the ingredients within the composition. Thickeners can
also increase the stability of the compositions of the present
invention. Non-limiting examples of additional thickeners that are
known to those of ordinary skill in the art can be used in the
context of the present invention (e.g., U.S. Pat. Nos. 5,087,445;
4,509,949; 2,798,053; International Cosmetic Ingredient Dictionary
and Handbook, 10.sup.th Ed., 2004). Examples include carboxylic
acid polymers, crosslinked polyacrylate polymers, polyacrylamide
polymers, polysaccharides, and gums. Examples of carboxylic acid
polymers include crosslinked compounds containing one or more
monomers derived from acrylic acid, substituted acrylic acids, and
salts and esters of these acrylic acids and the substituted acrylic
acids, wherein the crosslinking agent contains two or more
carbon-carbon double bonds and is derived from a polyhydric
alcohol. Examples of commercially available carboxylic acid
polymers include carbomers, which are homopolymers of acrylic acid
crosslinked with allyl ethers of sucrose or pentaerytritol (e.g.,
Carbopol.TM. 900 series from B. F. Goodrich).
[0059] f. Silicone Containing Compounds
[0060] In non-limiting aspects, silicone containing compounds
include any member of a family of polymeric products whose
molecular backbone is made up of alternating silicon and oxygen
atoms with side groups attached to the silicon atoms. By varying
the --Si--O-- chain lengths, side groups, and crosslinking,
silicones can be synthesized into a wide variety of materials. They
can vary in consistency from liquid to gel to solids.
[0061] The silicone containing compounds that can be used in the
context of the present invention include those described in this
specification or those known to a person of ordinary skill in the
art. Non-limiting examples include silicone oils (e.g., volatile
and non-volatile oils), gels, and solids. The silicon containing
compound can be a silicone oil such as a polyorganosiloxane.
Non-limiting examples of polyorganosiloxanes include dimethicone,
cyclomethicone, polysilicone-11, phenyl trimethicone, trimethyl
silylamodimethicone, stearoxytrimethylsilane, or mixtures of these
and other organosiloxane materials in any given ratio in order to
achieve the desired consistency and application characteristics
depending upon the intended application (e.g., to a particular area
such as the skin, hair, or eyes). A "volatile silicone oil"
includes a silicone oil have a low heat of vaporization, i.e.
normally less than about 50 cal per gram of silicone oil.
Non-limiting examples of volatile silicone oils include:
cyclomethicones such as Dow Corning 344 Fluid, Dow Corning 345
Fluid, Dow Corning 244 Fluid, and Dow Corning 245 Fluid, Volatile
Silicon 7207 (Union Carbide Corp., Danbury, Conn.); low viscosity
dimethicones, i.e. dimethicones having a viscosity of about 50 cst
or less (e.g., dimethicones such as Dow Corning 200-0.5 cst Fluid).
The Dow Corning Fluids are available from Dow Corning Corporation,
Midland, Mich. Cyclomethicone and dimethicone are described in
International Cosmetic Ingredient Dictionary, 10.sup.th Ed., 2004
as cyclic dimethyl polysiloxane compounds and a mixture of fully
methylated linear siloxane polymers end-blocked with
trimethylsiloxy units, respectively. Other non-limiting volatile
silicone oils that can be used in the context of the present
invention include those available from General Electric Co.,
Silicone Products Div., Waterford, N.Y. and SWS Silicones Div. of
Stauffer Chemical Co., Adrian, Mich.
[0062] 2. Pharmaceutical Actives
[0063] Pharmaceutical active agents are also contemplated as being
useful with the compositions of the present invention. Non-limiting
examples of pharmaceutical active agents include anti-acne agents,
agents used to treat rosacea, analgesics, anesthetics, anorectals,
antihistamines, anti-inflammatory agents including non-steroidal
anti-inflammatory drugs, antibiotics, antifungals, antivirals,
antimicrobials, anti-cancer actives, scabicides, pediculicides,
antineoplastics, antiperspirants, antipruritics, antipsoriatic
agents, antiseborrheic agents, biologically active proteins and
peptides, burn treatment agents, cauterizing agents, depigmenting
agents, depilatories, diaper rash treatment agents, enzymes, hair
growth stimulants, hair growth retardants including DFMO and its
salts and analogs, hemostatics, kerotolytics, canker sore treatment
agents, cold sore treatment agents, dental and periodontal
treatment agents, photosensitizing actives, skin protectant/barrier
agents, steroids including hormones and corticosteroids, sunburn
treatment agents, sunscreens, transdermal actives, nasal actives,
vaginal actives, wart treatment agents, wound treatment agents,
wound healing agents, etc.
D Vehicles
[0064] Compositions of the present invention can be incorporated
into all types of vehicles. Non-limiting examples of suitable
vehicles include emulsions (e.g., water-in-oil,
water-in-oil-in-water, oil-in-water, oil-in-water-in-oil,
oil-in-water-in-silicone, water-in-silicone, silicone-in-water
emulsions), creams, lotions, solutions (both aqueous and
hydro-alcoholic), anhydrous bases (such as lipsticks and powders),
gels, and ointments or by other method or any combination of the
forgoing as would be known to one of ordinary skill in the art
(see, e.g., Remington's, 1990 and International Cosmetic Ingredient
Dictionary and Handbook, 10.sup.th Ed., 2004)). Variations and
other appropriate vehicles will be apparent to the skilled artisan
and are appropriate for use in the present invention. In certain
aspects, it is important that the concentrations and combinations
of the compounds, ingredients, and agents be selected in such a way
that the combinations are chemically compatible and do not form
complexes which precipitate from the finished product.
E Cosmetic Products and Articles of Manufacture
[0065] The composition of the present invention can also be used in
many cosmetic products including, but not limited to, sunscreen
products, sunless skin tanning products, hair products, finger nail
products, moisturizing creams, skin benefit creams and lotions,
softeners, day lotions, gels, ointments, foundations, night creams,
lipsticks, cleansers, toners, masks, or other known cosmetic
products or applications. Additionally, the cosmetic products can
be formulated as leave-on or rinse-off products. In certain
aspects, the compositions of the present invention are stand-alone
products.
F Kits
[0066] Kits are also contemplated as being used in certain aspects
of the present invention. For instance, emulsion compositions of
the present invention can be included in a kit. A kit can include a
container. Containers can include a bottle, a metal tube, a
laminate tube, a plastic tube, a dispenser, a pressurized
container, a barrier container, a package, a compartment, a
lipstick container, a compact container, cosmetic pans that can
hold cosmetic compositions, or other types of containers such as
injection or blow-molded plastic containers into which the
dispersions or compositions or desired bottles, dispensers, or
packages are retained. The kit and/or container can include indicia
on its surface. The indicia, for example, can be a word, a phrase,
an abbreviation, a picture, or a symbol.
[0067] The containers can dispense a pre-determined amount of the
emulsion composition. In other embodiments, the container can be
squeezed (e.g., metal, laminate, or plastic tube) to dispense a
desired amount of the emulsion composition. The emulsion
composition can be dispensed as a spray, an aerosol, a liquid, a
fluid, or a semi-solid. The containers can have spray, pump, or
squeeze mechanisms. A kit can also include instructions for
employing the kit components as well the use of any other emulsion
compositions included in the container. Instructions can include an
explanation of how to apply, use, and maintain the emulsion
compositions.
EXAMPLES
[0068] The following examples are included to demonstrate certain
non-limiting aspects of the invention. It should be appreciated by
those of skill in the art that the techniques disclosed in the
examples which follow representative techniques discovered by the
inventor to function well in the practice of the invention.
However, those of skill in the art should appreciate that changes
can be made in the specific embodiments which are disclosed and
still obtain a like or similar result without departing from the
spirit and scope of the invention.
Example 1
Methods of Making Glyceryl/Acid or Glycol Acid Compounds
[0069] An esterification process can be used for producing
glyceryl/acid and glycol/acid compounds. A glyceryl or glycol
molecule and an acid molecule are added to a multi-necked round
bottom flask equipped with a heating mantle, a condenser, a
Dean-Stark trap and a thermometer. A solvent is chosen that will
allow a high enough reflux temperature to accommodate the reaction.
The reaction is run until the calculated amount of water is
collected in the trap signifying that the limiting reagent is
exhausted. The by-product can be compounds other than water in some
processes. For instance, if a methyl salicylate is used in place of
salicylic acid, methanol will be the by-product rather than water,
and the methanol may escape through the condenser or remain in the
reaction flask. The methanol can be removed when the ester is
extracted.
Example 2
UV Absorption Data for Glyceryl Mono-Salicylate
[0070] UV absorption data for glyceryl mono-salicylate is
summarized in Table 1 below:
TABLE-US-00001 TABLE 1 (UV absorption data*) Glyceryl
Mono-Salicylate Data Avg. Mol. Wt. 242.95 Molar Absorptivity
(.lamda. max 238 nm) 12065.7 Molar Absorptivity (.lamda. max 307
nm) 6126.4 *Data obtained by using a UV/Vis spectrometer using
standard USP 197U testing procedures.
Example 3
Compositions
[0071] Non-limiting examples of compositions of the present
invention are described in Tables 1-3.
TABLE-US-00002 TABLE 2* (Exfoliation composition) Ingredient %
Concentration (by weight) SD Alcohol 40-B 56.00 Glyceryl
mono-salicylate** 7.50 Water 29.00 Mineral oil 3.00 Sepigel 305
(thickener) 4.00 *The composition was prepared as follows:
Ingredients were cold-mixed and added to a beaker in the listed
order prior to the addition of the next ingredient. The pH of the
composition was adjusted to approximately 4.3 by using 1N HCl
solution. **Glyceryl mono-salicylate can be substituted with other
glyceryl/acid and glycol/acid compounds.
TABLE-US-00003 TABLE 3* (Moisturizer**) % Concentration Ingredient
(by weight) Phase A Water 66.44 Xanthum gum 0.10 Methyl paraben
0.15 Propyl paraben 0.10 Citric acid 0.01 Phase B Cetyl alcohol
4.00 Glyceryl stearate + PEG 100 4.00 Octyl palmitate 4.00
Dimethicone 1.00 Tocopheryl acetate 0.20 Phase C SD Alcohol 40-B
15.00 Glyceryl mono-salicylate*** 5.00 *The composition was
prepared as follows: Phases A and B were heated to approximately
70.degree. C.-75.degree. C. in separate beakers while mixing. Phase
B was added to Phase A when both phases were at approximately
70.degree. C.-75.degree. C. The Phase A + B mixture was cooled to
<40.degree. C. while mixing. Phase C was subsequently added to
the Phase A + B mixture, and the mixture was cooled to room
temperature (approximately 20.degree. C.-25.degree. C.) while
mixing. **Formulation showed statistically significant
moisturization for 6 hours after application to skin when compared
to the baseline control (p < 0.05) (data not shown). ***Glyceryl
mono-salicylate can be substituted with other glycelyl/acid and
glycol/acid compounds.
TABLE-US-00004 TABLE 4 (Generic formulation)* % Concentration
Ingredient (by weight) Phase A Water 84.44 Xanthum gum 0.1
M-paraben 0.15 P-paraben 0.1 Citric acid 0.01 Phase B Cetyl alcohol
4.0 Glyceryl stearate + PEG 100 4.0 Octyl palmitate 4.0 Dimethicone
1.0 Tocopheryl acetate 0.2 Phase C Glyceryl mono-salicylate** 2.0
*The composition can be prepared as follows: Sprinkle Xanthum gum
in water and mix for 10 min. Subsequently, add all ingredients in
phase A and heat to 70-75.degree. C. Add all items in phase B to a
separate beaker and heat to 70-75.degree. C. Mix phases A and B at
70-75.degree. C. Continue mixing and allow composition to cool to
30.degree. C. Subsequently, add phase C ingredient while mixing.
**Glyceryl mono-salicylate can be substituted with other
glyceryl/acid and glycol/acid compounds.
TABLE-US-00005 TABLE 5 (Generic formulation)* % Concentration
Ingredient (by weight) Phase A Water 78.6 M-paraben 0.2 P-paraben
0.1 Na2 EDTA 0.1 Shea butter 4.5 Petrolatum 4.5 Glycerin 4.0
Propylene Glycol 2.0 Finsolve TN 2.0 Phase B Sepigel 305 2.0 Phase
C Glyceryl mono-salicylate** 2.0 *Add ingredients in phase A to
beaker and heat to 70-75.degree. C. while mixing. Subsequently, add
the phase B ingredient with phase A and cool to 30.degree. C. with
mixing. Subsequently, add phase C ingredient while mixing.
**Glyceryl mono-salicylate can be substituted with other
glyceryl/acid and glycol/acid compounds.
TABLE-US-00006 TABLE 6 (Generic formulation)* % Concentration
Ingredient (by weight) Phase A Water 84.44 Xanthum gum 0.1
M-paraben 0.15 P-paraben 0.1 Citric acid 0.01 Phase B Cetyl alcohol
4.0 Glyceryl stearate + PEG 100 4.0 Octyl palmitate 4.0 Dimethicone
1.0 Tocopheryl acetate 0.2 Phase C Glyceryl mono-salicylate** 1.0
Glycol mono-salicylate** 1.0 *The composition can be prepared as
follows: Sprinkle Xanthum gum in water and mix for 10 min.
Subsequently, add all ingredients in phase A and heat to
70-75.degree. C. Add all items in phase B to separate beaker and
heat to 70-75.degree. C. Mix phases A and B at 70-75.degree. C.
Continue mixing and allow composition to cool to 30.degree. C.
Subsequently, add phase C ingredient while mixing. **Glyceryl
mono-salicylate and/or glycol mono-salicylate can be substituted
with other glyceryl/acid and glycol/acid compounds.
TABLE-US-00007 TABLE 7 (Generic formulation)* Ingredient %
Concentration (by weight) Phase A Water 78.6 M-paraben 0.2
P-paraben 0.1 Na2 EDTA 0.1 Shea butter 4.5 Petrolatum 4.5 Glycerin
4.0 Propylene Glycol 2.0 Finsolve TN 2.0 Phase B Sepigel 305 2.0
Phase C Glyceryl mono-salicylate** 1.0 Glycol mono-salicylate** 1.0
*Add ingredients in phase A to beaker and heat to 70-75.degree. C.
while mixing. Subsequently, add the phase B ingredient with phase A
and cool to 30.degree. C. with mixing. Subsequently, add phase C
ingredient while mixing. **Glyceryl mono-salicylate and/or glycol
mono-salicylate can be substituted with other glyceryl/acid and
glycol/acid compounds.
Example 4
Determining Efficacy of Glyceryl/Acid or Glycol/Acid Compounds and
Compositions
[0072] The efficacy of the glyceryl/acid or glycol/acid compounds
and compositions containing the same can be determined by methods
known to those of ordinary skill in the art. The following are
non-limiting procedures that can be used in the context of the
present invention. It should be recognized that other testing
procedures can be used, including, for example, objective and
subjective procedures.
[0073] Skin moisture/hydration can be measured by using impedance
measurements with the Nova Dermal Phase Meter. The impedance meter
measures changes in skin moisture content. The outer layer of the
skin has distinct electrical properties. When skin is dry it
conducts electricity very poorly. As it becomes more hydrated
increasing conductivity results. Consequently, changes in skin
impedance (related to conductivity) can be used to assess changes
in skin hydration. The unit can be calibrated according to
instrument instructions for each testing day. A notation of
temperature and relative humidity can also be made. Subjects can be
evaluated as follows: prior to measurement they can equilibrate in
a room with defined humidity (e.g., 30-50%) and temperature (e.g.,
68-72 C). Three separate impedance readings can be taken on each
side of the face, recorded, and averaged. The T5 setting can be
used on the impedance meter which averages the impedance values of
every five seconds application to the face. Changes can be reported
with statistical variance and significance.
[0074] Skin clarity and the reduction in freckles and age spots can
be evaluated using a Minolta Chromometer. Changes in skin color can
be assessed to determine irritation potential due to product
treatment using the a* values of the Minolta Chroma Meter. The a*
value measures changes in skin color in the red region. This is
used to determine whether a composition is inducing irritation. The
measurements can be made on each side of the face and averaged, as
left and right facial values. Skin clarity can also be measured
using the Minolta Meter. The measurement is a combination of the
a*, b, and L values of the Minolta Meter and is related to skin
brightness, and correlates well with skin smoothness and hydration.
Skin reading is taken as above. In one non-limiting aspect, skin
clarity can be described as L/C where C is chroma and is defined as
(a.sup.2+b.sup.2).sup.1/2.
[0075] Skin dryness, surface fine lines, skin smoothness, and skin
tone can be evaluated with clinical grading techniques. For
example, clinical grading of skin dryness can be determined by a
five point standard Kligman Scale: (0) skin is soft and moist; (1)
skin appears normal with no visible dryness; (2) skin feels
slightly dry to the touch with no visible flaking; (3) skin feels
dry, tough, and has a whitish appearance with some scaling; and (4)
skin feels very dry, rough, and has a whitish appearance with
scaling. Evaluations can be made independently by two clinicians
and averaged.
[0076] Clinical grading of skin tone can be performed via a ten
point analog numerical scale: (10) even skin of uniform, pinkish
brown color. No dark, erythremic, or scaly patches upon examination
with a hand held magnifying lens. Microtexture of the skin very
uniform upon touch; (7) even skin tone observed without
magnification. No scaly areas, but slight discolorations either due
to pigmentation or erythema. No discolorations more than 1 cm in
diameter; (4) both skin discoloration and uneven texture easily
noticeable. Slight scaliness. Skin rough to the touch in some
areas; and (1) uneven skin coloration and texture. Numerous areas
of scaliness and discoloration, either hypopigmented, erythremic or
dark spots. Large areas of uneven color more than 1 cm in diameter.
Evaluations were made independently by two clinicians and
averaged.
[0077] Clinical grading of skin smoothness can be analyzed via a
ten point analog numerical scale: (10) smooth, skin is moist and
glistening, no resistance upon dragging finger across surface; (7)
somewhat smooth, slight resistance; (4) rough, visibly altered,
friction upon rubbing; and (1) rough, flaky, uneven surface.
Evaluations were made independently by two clinicians and
averaged.
[0078] Skin smoothness and wrinkle reduction can also be assessed
visually by using the methods disclosed in Packman and Gams (1978).
For example, at each subject visit, the depth, shallowness and the
total number of superficial facial lines (SFLs) of each subject can
be carefully scored and recorded. A numerical score was obtained by
multiplying a number factor times a depth/width/length factor.
Scores are obtained for the eye area and mouth area (left and right
sides) and added together as the total wrinkle score.
[0079] Skin firmness can be measured using a Hargens ballistometer,
a device that evaluates the elasticity and firmness of the skin by
dropping a small body onto the skin and recording its first two
rebound peaks. The ballistometry is a small lightweight probe with
a relatively blunt tip (4 square mm-contact area) was used. The
probe penetrates slightly into the skin and results in measurements
that are dependent upon the properties of the outer layers of the
skin, including the stratum corneum and outer epidermis and some of
the dermal layers.
[0080] Skin softness/suppleness can be evaluated using the Gas
Bearing Electrodynamometer, an instrument that measures the
stress/strain properties of the skin. The viscoelastic properties
of skin correlate with skin moisturization. Measurements can be
obtained on the predetermined site on the cheek area by attaching
the probe to the skin surface with double-stick tape. A force of
approximately 3.5 gm can be applied parallel to the skin surface
and the skin displacement is accurately measured. Skin suppleness
can then be calculated and is expressed as DSR (Dynamic Spring Rate
in gm/mm).
[0081] The appearance of lines and wrinkles on the skin can be
evaluated using replicas, which is the impression of the skin's
surface. Silicone rubber like material can be used. The replica can
be analyzed by image analysis. Changes in the visibility of lines
and wrinkles can be objectively quantified via the taking of
silicon replicas form the subjects' face and analyzing the replicas
image using a computer image analysis system. Replicas can be taken
from the eye area and the neck area, and photographed with a
digital camera using a low angle incidence lighting. The digital
images can be analyzed with an image processing program and the
area of the replicas covered by wrinkles or fine lines was
determined.
[0082] The surface contour of the skin can be measured by using the
profilometer/Stylus method. This includes either shining a light or
dragging a stylus across the replica surface. The vertical
displacement of the stylus can be fed into a computer via a
distance transducer, and after scanning a fixed length of replica a
cross-sectional analysis of skin profile can be generated as a
two-dimensional curve. This scan can be repeated any number of
times along a fix axis to generate a simulated 3-D picture of the
skin. Ten random sections of the replicas using the stylus
technique can be obtained and combined to generate average values.
The values of interest include Ra which is the arithmetic mean of
all roughness (height) values computed by integrating the profile
height relative to the mean profile height. Rt which is the maximum
vertical distance between the highest peak and lowest trough, and
Rz which is the mean peak amplitude minus the mean peak height.
Values are given as a calibrated value in mm. Equipment should be
standardized prior to each use by scanning metal standards of know
values. Ra Value can be computed by the following equation:
R.sub.a=Standardize roughness; l.sub.m=the traverse (scan) length;
and y=the absolute value of the location of the profile relative to
the mean profile height (x-axis).
[0083] In other non-limiting aspects, the efficacy of the
compositions of the present invention can be evaluated by using a
skin analog, such as, for example, MELANODERM.TM.. Melanocytes, one
of the cells in the skin analog, stain positively when exposed to
L-dihydroxyphenyl alanine (L-DOPA), a precursor of melanin. The
skin analog, MELANODERM.TM., can be treated with a variety of bases
containing the compositions and whitening agents of the present
invention or with the base alone as a control. Alternatively, an
untreated sample of the skin analog can be used as a control.
[0084] UV absorption of glyceryl/acid or glycol/acid compounds and
compositions containing the same can be determined by UV absorption
assays that are generally known to those of ordinary skill in the
art.
[0085] All of the compounds, compositions, and/or methods disclosed
and claimed can be made and executed without undue experimentation
in light of the present disclosure. While the compounds,
compositions, and methods of this invention have been described in
terms of certain embodiments, it will be apparent to those of skill
in the art that variations may be applied to the compounds,
compositions, and/or methods and in the steps or in the sequence of
steps of the method without departing from the concept, spirit and
scope of the invention. More specifically, it will be apparent that
certain agents which are both chemically and physiologically
related may be substituted for the agents described herein while
the same or similar results would be achieved. All such similar
substitutes and modifications apparent to those skilled in the art
are deemed to be within the spirit, scope and concept of the
invention.
REFERENCES
[0086] The following references, to the extent that they provide
exemplary procedural or other details supplementary to those set
forth herein, are specifically incorporated herein by reference.
[0087] U.S. Pat. No. 2,798,053 [0088] U.S. Pat. No. 4,509,949
[0089] U.S. Pat. No. 5,087,445 [0090] CTFA International Cosmetic
Ingredient Dictionary and Handbook, 10.sup.th Ed., (2004). [0091]
Organic Chemistry, 5.sup.th Ed. [0092] Packman and Gams, J. Soc.
Cos. Chem., 29:70-90, 1978. [0093] Remington's Pharmaceutical
Sciences, 18th Ed. Mack Printing Company, 1289-1329, 1990.
* * * * *