Note: Descriptions are shown in the official language in which they were submitted.
CA 02146422 1998-02-20
NON-AOUEOUS EMOLLIENT COMPOSITIONS FOR TOPICAL
APPLICATION
BACKGROUND OF THE INVENTION
The present invention relates to fatty alkoxylate
esters of aliphatic and aromatic dicarboxylic and
tricarboxylic acids possessing unique emolliency
properties. The fatty alkoxylate esters of the present
invention are particularly useful in the formulation of
cold creams, after shaves, anti-perspirants, lotions,
skin moisturizers, electric pre-shaves, topical
pharmaceutical ointments, lipsticks, hand and nail
lotions and cleansing creams. The present invention
further relates to topical preparations prepared from
the fatty alkoxylate esters of the present invention.
Fatty acid esters of diols and polyols such as are
disclosed in U.S. Patent Nos. 4,803,010 to Ogino,
4,774,017 to Siebert, 4,614,622 to Huettinger and
4,079,403 to Tsutsumi are widely used as emulsifying
thickeners. While these compounds function effectively
as thickeners and emulsifiers, they lack emolliency.
German Patent No. 2,834,645 discloses fatty alcohol
esters of citric acid, a tricarboxylic acid. The
compounds are disclosed as being viscosity-stable
cosmetic emulsifiers and thickeners; however, they lack
the unique emolliency properties of the ester
compositions described herein. Numerous other fatty
citric acid esters are listed in the Cosmetic, Toiletry
and Fragrance Association International Cosmetic
Ingredient Directory, such as trioctyl citrate,
trioctydodecyl citrate, tristearyl citrate, triisostearyl
citrate and trilauryl citrate. However,
~146 ~22
none of these citrates have the unique properties of the
ester compositions described and claimed herein.
Mineral oil is widely used in personal care
products as an emollient because of its low cost.
However, mineral oil has an undesirable oily feel which
is carried over into the finished product.
There exists a need for products that will
reduce the oily feel of mineral oil without reducing its
emolliency. Other than solid particle materials such as
DRY-FLO~ (aluminum starch octenylsuccinate) which is
made by National Starch and Chemical of Bridgewater, New
Jersey, there exists no other products which reduce the
oily feel of mineral oil, petrolatum, and the like.
SUMMARY OF THE INVENTION
These needs are met by the present invention,
which provides fatty alkoxylate esters of aliphatic and
aromatic dicarboxylic and tricarboxylic acids which
possess an exceptional dry emollient feel when compared
to prior art emulsifying thickeners of similar molecular
weight. It is therefore an object of the present
invention to provide agents having improved emollient
properties in the nature of two or more polyalkoxylated
fatty alcohol chains covalently bonded by ester linkages
to the carboxylic acid groups of aliphatic and aromatic
dicarboxylic and tricarboxylic acids. Another object of
the present invention is to provide a class of agents
with superior emollient properties adaptable for use in
formulating topical preparations and the like.
In accordance with one embodiment of the
present invention, there is provided a fatty alkoxylate
ester in which a diester or a triester of an aliphatic
or aromatic dicarboxylic acid or tricarboxylic acid is
formed by reacting the acid with a stoichiometric excess
of one or more polyalkoxylated fatty alcohols.
Preferred fatty alkoxylate esters of the present
invention are citric acid esters having the structural
- ~146422
-3-
- formula of Formula I:
ICH3
CH2 -C- ( O-CH2 -CH2 ) X- ( O-CH-CH2 ) yO~R2
HO-C-C-(o-cH2-cH2)x-(o-cH-cH2)y-o-R2 (I)
CH2-C-Rl CH3
a
wherein Rl is -OH or a polyalkoxylated fatty alcohol
chain having the structural formula of Formula II:
IH3
-(O-CH2-CH2)X-(O-cH-cH2)y ~ 2 (II)
R2 is a saturated or unsaturated, substituted or
unsubstituted, aliphatic or aromatic fatty moiety
containing from 8 to 22 carbon atoms; each x and y are
independently zero or integers from 1 to 100, inclusive;
the sum of x and y in each fatty alkoxy ester chain is
independently between 1 and 200, inclusive; and the sum
of all x's and y's does not exceed 600.
The present invention provides fatty
alkoxylate esters possessing an exceptional aesthetic
emollient feel that has long been desired by cosmetic
chemists for use in personal care products. Therefore,
in accordance with another embodiment of the present
invention, there is provided an aqueous composition for
topical application including one or more active
ingredients, water and an emollient fatty alkoxylate
ester of the present invention. Still yet another
embodiment of the present invention provides a
non-aqueous composition for topical application
including one or more active ingredients and an
emollient fatty alkoxylate ester of the present
invention. The improved emollient feel of these esters
enables cosmetic formulation chemists to produce
products for topical application that out-perform
similar products in aesthetic feel.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENT
The emollient agents of the present invention
are fatty alkoxylate esters of aliphatic or aromatic,
- ~ 2146422
dicarboxylic or tricarboxylic acids. Aliphatic
dicarboxylic acids suitable for use in the present
invention contain from 2 to 22 carbon atoms. Aliphatic
tricarboxylic acids suitable for use in the present
invention contain from 4 to 22 carbon atoms. Aromatic
dicarboxylic acids suitable for use in the present
invention contain from 8 to 22 carbon atoms, and
aromatic tricarboxylic acids suitable for use in the
present invention contain from 9 to 22 carbon atoms.
Preferred aliphatic dicarboxylic acids contain from
3 to 8 carbon atoms. Preferred aliphatic tricarboxylic
acids contain from 4 to 8 carbon atoms. Examples of
suitable aliphatic dicarboxylic acids include malonic
acid, succinic acid and maleic acid.
Preferred aromatic dicarboxylic acids contain
from 8 to 12 carbon atoms. An example of a suitable
aromatic dicarboxylic acid is phthalic acid.
1,2-phthalic acid, having the lowest melting point of
the phthalic acid isomers, is preferred. Preferred
aromatic tricarboxylic acids contain from 9 to 18 carbon
atoms, and more preferably contain from 9 to 15 carbon
atoms.
Tricarboxylic acids are preferred over
dicarboxylic acids, and the dicarboxylic and
tricarboxylic acids are preferably hydroxyl-substituted.
Therefore, the most preferred aliphatic acid is the
hydroxyl-substituted tricarboxylic acid, citric acid.
The fatty alkoxylate esters of the present
invention are formed by reacting the above-described
dicarboxylic and tricarboxylic acids with
polyalkoxylated fatty alcohols. The polyalkoxylated
fatty alcohols preferably have between about 1 and about
100 moles of the alkoxylating moieties present for each
fatty alcohol moiety and are preferably either
polyethoxylated, polypropoxylated or both
polyethoxylated and polypropoxylated. Therefore,
preferred polyalkoxylated fatty alcohols in accordance
- 21~42~
with the present invention have the structural formula
of Formula III:
~H3
H-(O-CH2-CH2)X-(O-CH-CH2)y ~ R2 (III)
wherein R2 is a saturated or unsaturated, substituted or
unsubstituted aliphatic or aromatic fatty moiety
containing from 8 to 22 carbon atoms. X and y are
independently zero or integers from 1 to 100, inclusive,
and the sum of x and y is between 1 and 100, inclusive.
The polyalkoxylated fatty alcohol depicted
above is prepared by the polyalkoxylation of a saturated
or unsaturated, substituted or unsubstituted, aliphatic
or aromatic fatty alcohol having the structural formula
of Formula IV:
R2-OH (IV)
As is well understood by those of ordinary skill in the
art, fatty alcohols are derived from fatty acids, and
for this reason, groups such as R2 are defined as fatty
moieties. Fatty alcohols are often commercially
prepared from a mixture of fatty acids and contain a
mixture of fatty moieties. Therefore, in accordance
with the present invention, R2 for each polyalkoxylated
fatty alcohol chain may be the same or different.
Saturated, unsubstituted, aliphatic fatty
moieties containing from 8 to 18 carbon atoms are
preferred, and such fatty moieties containing from
10 to 16 carbon atoms are even more preferred. The
myristyl fatty moiety containing 14 carbon atoms is most
preferred.
For diesters of dicarboxylic acids, aliphatic
fatty moieties containing from 14 to 22 carbon atoms are
suitable for use with the present invention. Diesters
of dicarboxylic acids with ethoxylated 6-carbon alcohols
are disclosed by U.S. Patent No. 4,061,612 as being
useful as plasticizers with extended temperature ranges
in elastomers. This is attributable to the short
6-carbon alcohol chains, which provide a low molecular
~1~6422
--6--
weight diester with low viscosity that consequently has
the solvent properties required of a plasticizer.
The 14 to 22 carbon alcohols alkoxylated
diesters of the present invention have high molecular
weights and viscosities, and lack the solvent properties
to function effectively as a plasticizer. Instead, the
higher molecular weight and viscosity results in a
diester having desireable emollient properties. Such
emollient properties cannot be obtained from the lower
molecular weight low viscosity diesters disclosed by
U.S. Patent No. 4,061,612.
Saturated, unsubstituted aliphatic moieties
are preferred for the diesters of dicarboxylic acids of
the present invention, and such fatty moieties
containing from 14 to 18 carbon atoms are more
preferred. Even more preferred are fatty moieties
containing from 14 to 16 carbon atoms. The myristyl
fatty moiety containing 14 carbon atoms is most
preferred.
In the above-depicted polyalkoxylated fatty
alcohol of Formula III, x and y are preferably
independently selected from integers from 0 to 100,
inclusive, and more preferably independently selected
from integers from 0 to 10, inclusive. The sum of x and
y is preferably between 1 and 200, inclusive, and more
preferably between 1 and 20, inclusive.
As will be readily appreciated by those of
ordinary skill in the art, the dicarboxylic acid-based
esters of the present invention will be esterified on
both carboxylic acid groups by the above-depicted
polyalkoxylated fatty alcohol. The tricarboxylic acid-
based compounds of the present invention will be
esterified on either two or three carboxylic acid groups
with the above-depicted polyakoxylated fatty alcohol.
As described above, the sum of x and y in each
polyalkoxylated fatty alcohol chain of Formula II is
independently between 1 and 100, inclusive. However,
the sum of all x's and y's in every polyalkoxylated
~6~22
fatty alcohol chain of Formula I should not exceed 600.
The sum of all x's and y's preferably do not exceed 300,
and more preferably do not exceed 60.
As noted above, preferred fatty alkoxylate
esters in accordance with the present invention are di-
and tri-fatty alkoxylate esters of citric acid having
the structural formula of Formula I depicted above,
wherein Rl is -OH or a polyalkoxylated fatty alcohol
chain having the structural formula of Formula II,
wherein R2, x and y are the same as described above with
respect to Formula IV. The sum of each x and y in each
polyalkoxylated fatty alcohol chain and the sum of all
x's and y's in every polyalkoxylated fatty alcohol chain
are the same as described above with respect to
Formulas I and II.
With respect to Formulas I, II and III, when
R2 is a myristyl moiety, x is preferably zero and each y
is preferably an integer independently selected from 1
to 100, inclusive, and more preferably an integer
independently selected from 1 to 10. The sum of all y's
preferably does not exceed 300, and more preferably does
not exceed 30.
The fatty alkoxylate esters of the invention
described above are prepared by initially reacting,
either sequentially, or in their mixed forms, saturated
or unsaturated, substituted or unsubstituted, aliphatic
or aromatic fatty alcohols containing from 8 to 22
carbon atoms, with an epoxide, preferably ethylene
oxide, propylene oxide, or mixtures thereof, in the
presence of an acidic or basic catalyst. It is typical
of propylene oxide to branch upon opening of the epoxide
ring. This branching tends to impart liquidity to the
compound. Catalysts suitable for this reaction are
well-known in the art and include, for example,
inorganic alkalis such as alkali metal oxides and
hydroxides, e.g., potassium hydroxide, sodium methoxide,
sodium borohydride, protic and Lewis acids, e.g., boron
trifluoride, stannic chloride and sulfuric acid.
~1~6422
- Amines, quaternary ammonium compounds, water and otheracids may also be employed. Mixtures of catalysts may
also be employed. Certain reactive substrates known in
the art, for example, acetylenic alkanols, may eliminate
the need for such catalysts.
Preferably, a basic catalyst is used in this
reaction and most preferably from about 0.1 to about
2.0 weight percent of potassium or sodium hydroxide,
sodium methoxide, sodium borohydride or mixtures
thereof, based on the weight of the alcohol. The
reaction is carried out under anhydrous conditions to
avoid formation of by-products, and at a temperature
which is, preferably, in the range of from about 110~C
to about 200-C, although higher temperatures may be
utilized. The reaction can be carried out at
substantially atmospheric pressure, although it is
preferably carried out in an autoclave at pressures of
from about 10 psig to about 80 psig. The amount of
ethylene oxide or propylene oxide introduced to the
reaction zone, and the duration of reaction time,
determines the number of moles of such components added
to the fatty moiety, R2, of the fatty alcohol.
In Formulas I, II and III, x represents the
number of moles of ethylene oxide which are incorporated
into each polyalkoxylate fatty alcohol chain. Likewise,
y represents the number of moles of propylene oxide that
are incorporated into the polyalkoxylated fatty alcohol
chain. As will be readily appreciated by those of
ordinary skill in the art, stoichiometric quantities of
fatty alcohols, ethylene oxide and propylene oxide are
reacted together, and stoichiometric quantities of the
polyalkoxylated fatty alcohol and dicarboxylic acid or
tricarboxylic acid are reacted together.
Preferably, the reaction is carried out
sequentially in that the fatty alcohol is first reacted
with the-propylene oxide and after complete reaction,
the ethylene oxide is introduced into the reaction.
After complete reaction of the ethylene oxide, an acid,
6 4 2 2
g
e.g., phosphoric acid or acetic acid, is introduced into
the reaction mixture to neutralize the basic catalyst.
The resulting polyalkoxylated fatty alcohol is
then reacted with a suitable dicarboxylic or
tricarboxylic acid. Examples of suitable acids are
listed above and include malonic acid, succinic acid,
maleic acid, phthalic acid and citric acid. The most
preferred acid is citric acid.
A conventional esterification reaction of the
acid with the polyalkoxylated fatty alcohol is carried
out. This may be accomplished with or without catalyst.
Preferred catalysts are methane sulfonic acid and
para-toluene sulfonic acid.
The esterification is typically performed by
combining stoichiometric quantities of the
polyalkoxylated fatty alcohol and the acid to be
esterified. As is well understood by those of ordinary
skill in the art, when two polyalkoxylated fatty alcohol
chains are to be added to the acid, the polyalkoxylated
fatty alcohol and acid to be esterified should be
combined in a molar ratio of 2:1. When three
polyalkoxylated fatty alcohol chains are to be added to
the acid, the polyalkoxylated fatty alcohol and acid to
be esterified should be combined in a molar ratio of
3:1. However, a slight stoichiometric excess should be
employed to insure complete esterification and a low
acidity. The polyalkoxylated fatty alcohol is a liquid,
therefore a reaction solvent is not needed.
The polyalkoxylated fatty alcohol, acid and
catalyst are combined with mixing to form a reaction
mixture. The reaction mixture is heated with mixing at
a temperature between about 155~C and about 250 C, and
preferably at a temperature between about 170-C and
220-C until, for the dicarboxylic acids and fully
esterified tricarboxylic acids, an acid value of less
than 8 mg KOH, and preferably less than 5 mg KOH is
obtained. The reaction mixture is then cooled below
85~C and washed with water, preferably without
il 4S 422
--10--
neutralizing the catalyst. Higher temperatures should
be avoided to prevent loss of the polyalkoxylated fatty
alcohols and, consequently, incomplete esterification
and higher than desired acidity. The ester layer is
separated and heated under vacuum until a moisture
content of less than 0.2 percent is obtained.
As noted above, the polyalkoxylated fatty
alcohols can be prepared by reacting mixed forms of
fatty alcohols containing from 8 to 22 carbon atoms with
mixtures of ethylene oxide and propylene oxide.
Therefore, the resulting polyalkoxylated fatty alcohol
can contain a mixture derived from the ethoxylation and
the propoxylation of mixtures of fatty alcohols
containing from 8 to 22 carbon atoms.
The fatty alkoxylate esters of the present
invention are particularly useful as agents that confer
superior emollient properties adaptable for use in a
number of topical preparations. The esters are useful
in the formulation of cold creams, after shaves,
anti-perspirants, lotions, skin moisturizers, electric
pre-shaves, topical pharmaceutical ointments, lipsticks,
hand and nail lotions, cleansing creams, eye makeup
formulations, cream rinses, sunscreens, cosmetic
emulsions or gels in general, hairdressing preparations,
foam baths and the like.
The emollient agent of the present invention
is primarily useful as a replacement for the mineral oil
and petrolatum emollient agents of the prior art. The
emollient agent works well on its own or with reduced
levels of mineral oil or petrolatum. A distinct
improvement in emolliency properties of mineral oil or
petrolatum-based products is noticeable when as little
as 25~ of the mineral oil or petrolatum has been
replaced by the emollient agents of the present
invention. Therefore, topical compositions in
accordance with the present invention can include a
second emollient agent of mineral oil, petrolatum, and
the like present with the emollient of the present
~6 4~2
invention in a ratio of up to about 4:1 of the second
emollient agent to the emollient agent of the present
invention.
Aqueous topical preparations in accordance
with the present invention include the essential
compounds of the emollient agent of the present
invention and one or more active ingredients, with the
balance being water. As mentioned above, a second
emollient agent of mineral oil, petrolatum and the like
can optionally be included. Suitable active agents for
use in topical preparations include sunscreens,
moisturizers, film formers, detergents, thickening
agents, emulsifiers, antiseptic agents, conditioning
agents, deodorant actives, reducing agents for permanent
wave products and the like. The detergent may include a
variety of surfactants of the anionic type, non-ionic
type, amphoteric type and mixtures thereof.
Suitable anionic detergents include sodium
lauryl sulfate, sodium oleyl succinate, ammonium lauryl
sulfosuccinate, sodium lauryl ether sulfate, ammonium
lauryl sulfate, sodium dodecylbenzene sulfonate,
triethanolamine dodecylbenzene sulfinate, sodium
N-lauroyl sarcosinate, sodium laureth sulfate and
triethanolamine lauryl sulfate. Suitable amphoteric or
ampholytic detergents include N-lauryl-N'carboxymethyl-
N-(2-hydroxyethyl) ethylenediamine, cocobetaine, the
Miranol compounds in U.S. Patent Nos. 2,528,378 and
2,781,354, cocoamidopropyl hydroxysultaine, lauroampho
diacetate and cocoamidopropyl betaine. Other suitable
amphoteric detergents include the quaternary
cycloimidates, betaines and sultaines disclosed in U.S.
Patent No. 3,964,500. Nonionic surfactants include
polysorbate 20, laurylamide DEA and sucrose monococate.
The topical preparations of the present
invention, in addition to including the main components
of the emollient agent of the present invention, one or
more active ingredients, water and the optional second
emollient agent, may also include coloring agents,
6~22
-12-
fragrances, proteins, humectants, salts, preservatives,
essential oils and the like. These additional
components may be added in various amounts as is well-
known in the cosmetic formulation art.
Typical aqueous topical preparations in
accordance with the present invention include the
emollient agents of the present invention, alone, or
with the second emollient agent, in a range of from
about 0.20 to about 40.0 percent by weight of the
composition, preferably from about 3.0 to about 20.0
percent by weight of the composition. The one or more
active ingredients may be present in an amount from
about 0.20 to about 40.0 percent by weight of the
composition, preferably from about 3.0 to about 20.0
percent by weight of the composition. As noted
previously, the second emollient agent, when present, is
blended with the emollient agent of the present
invention in a ratio of up to about 4:1 of the second
emollient agent to the emollient agent of the present
invention.
Non-aqueous topical preparations in accordance
with the present invention may also be prepared. Such
preparations include the essential compounds of the
emollient agent of the present invention and one or more
of the above-listed active ingredients. A second
emollient agent of mineral oil, petrolatum, and the like
may again optionally be included, as may the above-
described coloring agents, fragrances, proteins,
humectants, salts, preservatives, essential oils and the
like.
Typical non-aqueous topical preparations in
accordance with the present invention include ~he
emollient agents of the present invention, alone, or
with the second emollient agent, in a range of from
about 0.20 to about 99.0 percent by weight of the
composition, preferably from about 10 to about
90.0 percent by weight of the composition, and more
preferably from about 25 to about 75 percent by weight
'- ~146422
-13-
- of the composition. The one or more active ingredients may be present in an amount from about 0.20 to about
99.0 percent by weight of the composition, preferably
from about 10 to about 90.0 percent by weight of the
composition, and more preferably froma bout 25 to about
75 percent by weight of the composition.
As with the aqueous topical preparations, the
second emollient agent, when present, may be blended
with the emollient agent of the present invention in a
ratio of up to about 4:1 of the second emollient agent
to the emollient agent of the present invention.
one non-aqueous composition in accordance with
the present invention is a bath oil consisting entirely
of from about 25 to about 99 percent by weight of the
emollient agent of the present invention, from about
1 to about 75 percent by weight of mineral oil and
optional coloring agents, fragrances, essential oils and
the like. Preferred bath oils contain about 99 percent
by weight of the emollient agent of the present
invention.
A non-aqueous bath oil composition consisting
entirely of the emollient agent of the present
invention, with optional coloring agents, fragrances,
essential oils and the like may also be prepared.
The topical preparations of the present
invention are formulated utilizing techniques that are
well-known in the cosmetic formulating art. Typically,
the ingredients are combined with mixing and the
addition of heat if necessary until a uniform,
homogeneous product is formed. The water-soluble and
water-insoluble ingredients are mixed together
separately and combined with suitable emulsifying
ingredients, such as the fatty alkoxylate esters of the
present invention, to form emulsions.
The following non-limiting examples set forth
hereinbelow illustrate certain aspects of the present
invention. They are not to be considered limiting as to
the scope and nature of the present invention.
lg6~22
-14-
EXAMPLES
EXAMPLE 1
Pre~aration of Tri-PPG-3 Myristyl Ether Citrate
Propylene oxide was bubbled into 685 g of
myristyl alcohol in the presence of potassium hydroxide
catalyst until three moles of propylene oxide were added
per mole of myristyl alcohol, thus obtaining a pale,
yellow liquid (PPG-3 myristyl ether) as the major
product.
A four-necked flask was charged with 1,210 g
of the PPG-3 myristyl ether and 190 g of citric acid. A
catalytic amount of methane sulfonic acid was added to
effect esterification, and the resulting reaction
mixture was heated with stirring at 190~C until an acid
value of less than 8 mg KOH was obtained. The reaction
mixture was cooled to 85~C and washed with water. The
ester layer was separated and heated under vacuum until
a moisture content of less than 0.2 percent was
obtained. Filter clay was added and the product was
vacuum filtered, yielding tri-PPG-3 myristyl citrate, a
clear, pale yellow liquid.
EXAMPLE 2
PreParation of DI-PPG-3 Myristyl Maleate
A four-necked flask was charged with 946 g of
the PPG-3 myristyl ether of Example 1 and 54 g of maleic
anhydride. A catalytic amount of methane sulfonic acid
was added and the reaction mixture was heated at 120~C
until an acid value of less than 8 mg KOH was obtained.
The product was cooled to 85~C and washed with water.
The ester layer was separated and heated under vacuum
until a moisture content of less than 0.2 percent was
obtained. Filter clay was added and the product was
vacuum filtered, yielding di-PPG-3 myristyl maleate, a
clear, pale yellow liquid.
The following examples, while not intended to
be limiting, demonstrate topical preparations formulated
in the nature of hand lotions and a hair conditioner in
accordance with the present invention. All quantities
1 2 2
-15-
listed are a percentage by weight unless otherwise
indicated.
EXAMPLE 3
PreParation Of Hand Lotion
5A moisturizing hand lotion was prepared in
accordance with the optimum formulation set forth below.
Acceptable formula variations for the preparation of
such hand lotions are also illustrated.
Inqredient Range Preferred OPtimum
Part A
Incroquat Behenyl TMS 1.0-10.02.0-7.0 3.5
Polawax 1.0-10.02.0-7.0 3.0
Stearyl Alcohol 0-5.0 0.5-3.0 1.0
Tri-PPG-3 Myristyl 1.0-15.02.5-10.0 5.0
Citrate
Mineral Oil 0-10.0 2.0-7.0 3.0
Petrolatum 0-10.0 2.0-7.0 4.0
Part B
Deionized Water 5.0-9.0 60-85 74.5
Glycerin 1.0-15.02.5-10 5.0
Part C
Germaben II 0.1-4.00.5-2.0 1.0
Incroquat Behenyl TMS, a behenyl trimonium
methosulfate in cetearyl alcohol and Polawax, an
emulsifying wax (NF), are available from Croda, Inc.
Germaben II, a diazolidinyl urea, methyl paraben and
propyl paraben-based preservative is available from
Sutton Labs of Chatham, New Jersey.
The ingredients of Part A and Part B were
separately mixed with heating to 75~C. The Part B
mixture was then added to the Part A mixture with
thorough mixing. The resulting mixture was cooled to
45-C with continued mixing. The Part C ingredient was
then added with mixing and the resulting mixture was
cooled to room temperature with continued mixing.
'-- 214~ 422
-16-
The resulting hand lotion possessed typical
skin moisturizing properties together with a
surprisingly dry emollient feel.
EXAMPLE 4
Hand Lotion
A second moisturizing hand lotion was prepared
in accordance with the optimum formulation set forth
below. Acceptable formula variations are also
illustrated.
Ingredient Range Preferred OPtimum
Part A
Di-PPG-3 Myristyl 1.0-15.025-10.0 6.5
Maleate
Volpo 10 0.5-6.0 1.0-4.0 2.0
Cetyl Alcohol 0-10.0 1.0-6.0 3.0
Lanolin Alcohol 0-3.0 0.2-1.0 0.5
Glyceryl Stearate 0.5-6.0 1.0-4.0 2.0
Mineral Oil 0-10.0 2.0-6.0 4.0
Part B
Volpo S-20 0.1-5.0 0.5-2.0 0.75
Incromectant AQ 0.1-5.0 0.5-3.0 1.00
Carbopol 934 0.01-1.00.1-0.5 0.20
Glycerin 0-10.0 1.0-6.0 3.00
Deionized Water 50.0-90.060.0-85.0 75.85
Part C
Germaben II 0.1-4.0 0.5-2.0 1.00
TEA 99% 0.01-1.00.1-0.50 0.20
Volpo 10, an oleth-10, Volpo S-20, a
steareth-20 and Incromectant AQ, an acetamidopropyl
trimonium chloride, are all available from Croda, Inc.
Carbopol 934, a carboxyvinyl polymer with active
carboxyl groups, is available from B.F. Goodrich.
The Part A ingredients were combined and
heated to 80 C with mixing. The Part B ingredients were
prepared by first dusting the Carbopol 934 in water and
~ 6 422
-17-
then stirring the mixture until completely dissolved.
The remaining ingredients of Part B were added and
heated to 80 C with mixing. The Part B mixture was
added to the Part A mixture with mixing. The resulting
mixture was then cooled to 45~C with continued mixing.
The Part C ingredients were then added and the resulting
mixture was allowed to cool to room temperature with
continued mixing.
The resulting hand lotion possessed typical
skin moisturizing properties together with a
surprisingly dry emollient feel.
EXAMPLE 5
Hair Conditioner
A hair conditioner was prepared in accordance
with the optimum formulation set forth below.
Acceptable formula variations for the preparation of
such hair conditioners are also illustrated.
Inqredient Ranae Preferred OPtimum
Part A
Stearalkonium Chloride 0.5-5.0 1.0-2.5 1.25
Polawax 1.0-10.02.0-7.0 3.00
Cetyl Alcohol 0-7.5 0.5-5.0 2.00
Crovol Pk-70 0-7.5 0.5-5.0 2.00
Tri-PPG-3 Myristyl 0.5-6.00.75-3.0 1.50
Citrate
Imcromectant AQ 0.2-4.00.5-2.5 1.00
Deionized Water 60.0-95.575.0-90.0 88.25
Part B
Germaben II 0.1-4.00.5-2.0 1.00
Crovol Pk-70, a PEG-45 palm kernel glyceride,
is available from Croda, Inc.
The resulting product possessed characteristic
hair conditioning properties together with a desirable
dry emollient feel.
-~ 21i~6422
-18-
~ EXAMPLE 6
Comparative Example
Trimyristyl Citrate was prepared by
esterifying non-propoxylated myristyl alcohol with
citric acid under the same conditions as described in
Example I, but for the propoxylation step. The product
was a white solid with a melting point of 38 D C. The
product also had very poor emolliency properties on its
own, was marginally compatible with mineral oil at room
temperature, and did not exhibit the reduction in oily
feel of mineral oil as seen with the alkoxylated alcohol
citrate esters. The improved emolliency of the
compounds of the present invention would appear to be
attributable, in part, to the alkoxylation of the fatty
alcohols prior to esterification.
The foregoing description of the preferred
embodiment should be taken as illustrating, rather than
as limiting the present invention as defined by the
claims. Numerous variations and combinations of the
features described above can be utilized without
departing from the present invention.
