U.S. patent application number 11/372607 was filed with the patent office on 2007-09-13 for low-odor dimethicone copolyol sulfosuccinate surfactant compositions.
Invention is credited to Richard J. Otterson, Kenneth E. Visek.
Application Number | 20070212319 11/372607 |
Document ID | / |
Family ID | 38479186 |
Filed Date | 2007-09-13 |
United States Patent
Application |
20070212319 |
Kind Code |
A1 |
Otterson; Richard J. ; et
al. |
September 13, 2007 |
Low-odor dimethicone copolyol sulfosuccinate surfactant
compositions
Abstract
Dimethicone copolyol sulfosuccinate surfactant compounds having
low-odor characteristics are disclosed. The low-odor dimethicone
copolyol sulfosuccinate is substantially free from propionaldehyde
and acid-releasable precursors of propionaldehyde, thereby
substantially eliminating the cosmetically undesirable odor
characteristic of conventional dimethicone copolyol sulfosuccinate
surfactants. The low-odor dimethicone copolyol sulfosuccinates are
suitable for use as surfactants in household or personal care
products and applications.
Inventors: |
Otterson; Richard J.;
(Frankfort, IL) ; Visek; Kenneth E.; (Stickney,
IL) |
Correspondence
Address: |
OLSON & HIERL, LTD.
20 NORTH WACKER DRIVE
36TH FLOOR
CHICAGO
IL
60606
US
|
Family ID: |
38479186 |
Appl. No.: |
11/372607 |
Filed: |
March 10, 2006 |
Current U.S.
Class: |
424/70.12 |
Current CPC
Class: |
C08G 77/46 20130101;
A61Q 19/00 20130101; A61K 8/899 20130101; C08L 83/08 20130101; C08G
77/392 20130101 |
Class at
Publication: |
424/070.12 |
International
Class: |
A61K 8/89 20060101
A61K008/89 |
Claims
1. A low-odor composition suitable for use in cosmetic and personal
care applications comprising a compound having a dimethicone
copolyol portion and a sulfosuccinate portion, the compound having
the formula: ##STR11## wherein the composition is substantially
free of propionaldehyde and acid-releasable precursors of
propionaldehyde; R is a polymer of ethylene oxide, a polymer of
propylene oxide, a polymer of butylene oxide, a polymer of
tetrahydrofuran, a polymer of glycerol, or a copolymer of two or
more monomers selected from the group consisting of ethylene oxide,
propylene oxide, butylene oxide, tetrahydrofuran, and glycerol; M+
is an alkali metal cation or ammonium group; x has a value in the
range of 0 to about 100 and y has a value in the range of 1 to
about 100.
2. The composition of claim 1 wherein R is selected from the group
consisting of: --(C.sub.2H.sub.4O).sub.S--C.sub.2H.sub.4--;
--(C.sub.3H.sub.6O).sub.t--C.sub.3H.sub.6--; and
--(C.sub.2H.sub.4O).sub.v--(C.sub.3H.sub.6O).sub.w--Y--; wherein s
and t each independently have a value in the range of 2 to about
30; v and w each independently have a value in the range of 1 to
about 30; and Y is C.sub.2H.sub.4 or C.sub.3H.sub.6.
3. The composition of claim 1 wherein the dimethicone copolyol
portion has a calculated HLB value in the range of about 10 to
about 17.
4. The composition of claim 1 wherein the compound has an
equivalent weight in the range of about 400 to about 3000 grams per
equivalent.
5. A low-odor composition suitable for use in cosmetic and personal
care applications comprising a compound having a dimethicone
copolyol portion and a sulfosuccinate portion, the compound having
the formula: ##STR12## wherein the composition is substantially
free of propionaldehyde and acid-releasable precursors of
propionaldehyde; R is a polymer of ethylene oxide, a polymer of
propylene oxide, a polymer of butylene oxide, a polymer of
tetrahydrofuran, a polymer of glycerol, or a copolymer of two or
more monomers selected from the group consisting of ethylene oxide,
propylene oxide, butylene oxide, tetrahydrofuran, and glycerol;
M'(+2) is an alkaline earth metal cation; x has a value in the
range of 0 to about 100 and y has a value in the range of 1 to
about 100.
6. The composition of claim 5 wherein R is selected from the group
consisting of: --(C.sub.2H.sub.4O).sub.S--C.sub.2H.sub.4--;
--(C.sub.3H.sub.6O).sub.t--C.sub.3H.sub.6--; and
--(C.sub.2H.sub.4O).sub.V--(C.sub.3H.sub.6O).sub.w--Y--; wherein s
and t each independently have a value in the range of 2 to about
30; v and w each independently have a value in the range of 1 to
about 30; and Y is C.sub.2H.sub.4 or C.sub.3H.sub.6.
7. The composition of claim 5 wherein the dimethicone copolyol
portion has a calculated HLB value in the range of about 10 to
about 17.
8. The composition of claim 5 wherein the compound has an
equivalent weight in the range of about 400 to about 3000 grams per
equivalent.
9. A low-odor composition suitable for use in cosmetic and personal
care applications comprising a compound having a dimethicone
copolyol portion and a sulfosuccinate portion, the compound having
the formula: ##STR13## wherein the composition is substantially
free of propionaldehyde and acid-releasable precursors of
propionaldehyde; X+ is an ammonium group derived from an amino
alcohol, an amine ethoxylate or an amine propoxylate; R is a
polymer of ethylene oxide, a polymer of propylene oxide, a polymer
of butylene oxide, a polymer of tetrahydrofuran, a polymer of
glycerol, or a copolymer of two or more monomers selected from the
group consisting of ethylene oxide, propylene oxide, butylene
oxide, tetrahydrofuran, and glycerol; M+ is an alkali metal cation
or ammonium group; x has a value in the range of 0 to about 100 and
y has a value in the range of 1 to about 100.
10. The composition of claim 9 wherein the ammonium group, X+, is
derived from at least one amine selected from the group consisting
of monoethanolamine, diethanolamine, triethanolamine,
monoisopropanolamine and diglycolamine.
11. The composition of claim 9 wherein R is selected from the group
consisting of: --(C.sub.2H.sub.4O).sub.S--C.sub.2H.sub.4--;
--(C.sub.3H.sub.6O).sub.t--C.sub.3H.sub.6--; and
--(C.sub.2H.sub.4O).sub.V--(C.sub.3H.sub.6O).sub.W--Y--; wherein s
and t each independently have a value in the range of 2 to about
30; v and w each independently have a value in the range of 1 to
about 30; and Y is C.sub.2H.sub.4 or C.sub.3H.sub.6.
12. The composition of claim 9 wherein the dimethicone copolyol
portion has a calculated HLB value in the range of about 10 to
about 17.
13. The composition of claim 9 wherein the compound has an
equivalent weight in the range of about 400 to about 3000 grams per
equivalent.
14. A low-odor composition suitable for use in cosmetic and
personal care applications comprising a compound having a
dimethicone copolyol portion and a sulfosuccinate portion, the
compound having the formula: ##STR14## wherein the composition is
substantially free of propionaldehyde and acid-releasable
precursors of propionaldehyde; X+ is an ammonium group derived from
an amino alcohol, an amine ethoxylate or an amine propoxylate; R is
a polymer of ethylene oxide, a polymer of propylene oxide, a
polymer of butylene oxide, a polymer of tetrahydrofuran, a polymer
of glycerol, or a copolymer of two or more monomers selected from
the group consisting of ethylene oxide, propylene oxide, butylene
oxide, tetrahydrofuran, and glycerol; x has a value in the range of
0 to about 100 and y has a value in the range of 1 to about
100.
15. The composition of claim 14 wherein the ammonium group, X+, is
derived from at least one amine selected from the group consisting
of monoethanolamine, diethanolamine, triethanolamine,
monoisopropanolamine and diglycolamine.
16. The composition of claim 14 wherein R is selected from the
group consisting of: --(C.sub.2H.sub.4O).sub.S--C.sub.2H.sub.4--;
--(C.sub.3H.sub.6O).sub.t--C.sub.3H.sub.6--; and
--(C.sub.2H.sub.4O).sub.v--(C.sub.3H.sub.6O).sub.w--Y--; wherein s
and t each independently have a value in the range of 2 to about
30; v and w each independently have a value in the range of 1 to
about 30; and Y is C.sub.2H.sub.4 or C.sub.3H.sub.6.
17. The composition of claim 14 wherein the dimethicone copolyol
portion has a calculated HLB value in the range of about 10 to
about 17.
18. The composition of claim 14 wherein the compound has an
equivalent weight in the range of about 400 to about 3000 grams per
equivalent.
19. A method of producing a relatively low-odor dimethicone
copolyol sulfosuccinate that is substantially free from
propionaldehyde and acid-releasable precursors of propionaldehyde,
the method comprising the steps of: reacting a dimethicone copolyol
with maleic anhydride to form a maleic monoester, the dimethicone
copolyol being substantially free of propionaldehyde and
acid-releasable precursors of propionaldehyde; and sulfonating the
maleic monoester with a compound selected from the group consisting
of an alkali metal sulfite, an alkaline earth sulfite, ammonium
sulfite, an amino sulfite, and a combination of any of the
foregoing with an amino alcohol.
20. The method of claim 15 wherein the dimethicone copolyol has an
equivalent weight in the range of about 350 to about 1100 grams per
equivalent.
21. The method of claim 15 wherein the dimethicone copolyol has a
calculated HLB value in the range of about 10 to about 17.
22. A household or personal care product comprising at least one
low-odor composition of claim 1 and a physiologically tolerable
vehicle.
23. A household or personal care product comprising at least one
low-odor composition of claim 5 and a physiologically tolerable
vehicle.
24. A household or personal care product comprising at least one
low-odor composition of claim 9 and a physiologically tolerable
vehicle.
25. A household or personal care product comprising at least one
low-odor composition of claim 14 and a physiologically tolerable
vehicle.
Description
FIELD OF THE INVENTION
[0001] This invention relates to sulfosuccinate surfactants. More
particularly, this invention relates to silicone-based
sulfosuccinate surfactants having low-odor characteristics.
BACKGROUND OF THE INVENTION
[0002] Sulfosuccinate surfactants have been used in the cosmetic
industry primarily to improve the mildness of skin cleansers,
shampoos and other personal care products. Such surfactants are
usually diesters or monoesters, with the monoester being preferred
because of its mildness and foam enhancement properties. Prior to
the development of dimethicone copolyol sulfosuccinates, which are
disclosed in U.S. Pat. No. 4,717,498 to Maxon, which is
incorporated herein by reference, primarily two half ester or
monoester derivatives had been used for shampoos. Such derivatives
included derivatives of monoalcohol amides, such as oleamide MEA,
oleamide IPA and undecylenamide MEA, and derivatives of fatty
alcohols and ethoxylated alcohols, such as lauryl, laureth and
oleyl alcohols.
[0003] The sulfosuccinates obtained from diesters and monoesters
vary considerably in their foaming, viscosity building, solubility
and conditioning properties. In general, they are gentle to the
skin and eyes when compared to high foaming surfactants, and are
usually blended with such high foaming surfactants to obtain
compositions that exhibit some degree of both mildness and foaming
properties. Dimethicone copolyol sulfosuccinates, on the other
hand, have useful foaming characteristics, while also being quite
mild to the skin. One factor which has limited the use of
dimethicone copolyol sulfosuccinates in cosmetics is that such
surfactants typically exhibit a characteristic odor, which can be
objectionable in some personal care and cosmetic products.
[0004] There is an ongoing need, therefore, for dimethicone
copolyol sulfosuccinate surfactants that have relatively low-odor
characteristics suitable for use in cosmetic applications. The
present invention fulfills this need.
SUMMARY OF THE INVENTION
[0005] The present invention provides low-odor compositions
including a dimethicone copolyol sulfosuccinate having a
dimethicone copolyol portion and a sulfosuccinate portion. The
low-odor compositions of the present invention include a
dimethicone copolyol sulfosuccinate of the formula: ##STR1##
wherein R is a polymer of ethylene oxide, a polymer of propylene
oxide, a polymer of butylene oxide, a polymer of tetrahydrofuran, a
polymer of glycerol, or a copolymer of two or more monomers
selected from the group consisting of ethylene oxide, propylene
oxide, butylene oxide, tetrahydrofuran, and glycerol; M+ is an
alkali (Group IA) metal cation (e.g., sodium, potassium or lithium)
or an ammonium group; x has a value in the range of 0 to about 100;
and y has a value in the range of 1 to about 100. Preferably, the
compound has an equivalent weight in the range of about 400 to
about 3000 grams per equivalent, wherein the term "equivalent
weight" refers to the average molecular weight (i.e., grams of
compound per mole) divided by the number of moles of alkoxylated
monomer units (i.e., the value of "y") in the molecule.
[0006] Preferably, R is a polyoxyalkylene moiety selected from the
group consisting of: --(C.sub.2H.sub.4O).sub.s--C.sub.2H.sub.4--;
--(C.sub.3H.sub.6O).sub.t--C.sub.3H.sub.6--; and
--(C.sub.2H.sub.4O).sub.v--(C.sub.3H.sub.6O).sub.w--Y--; wherein s
and t each independently have a value in the range of 2 to about
30; v and w each independently have a value in the range of 1 to
about 30; and Y is C.sub.2H.sub.4 or C.sub.3H.sub.6. The
C.sub.3H.sub.6 and C.sub.3H.sub.6O moieties can be linear or
branched, preferably branched. The
--(C.sub.2H.sub.4O).sub.v--(C.sub.3H.sub.6O).sub.w--Y-- group can
be a block copolymer, a random copolymer or an alternating
copolymer of C.sub.2H.sub.4O and C.sub.3H.sub.6O moieties.
[0007] The dimethicone copolyol portion of the dimethicone copolyol
sulfosuccinate can have any hydrophilic/lipophilic balance (HLB),
as calculated by methods well known in the art. Preferably, the
dimethicone copolyol portion of the dimethicone copolyol
sulfosuccinate has a calculated HLB value in the range of about 10
to about 17.
[0008] It has been found that the sensory, cosmetically
undesirable, odor characteristic of prior art dimethicone copolyol
compositions is primarily due to propionaldehyde present in the
surfactant composition or released from the surfactant composition
under acidic conditions. The low-odor dimethicone copolyol
compositions of the present invention are substantially free from
propionaldehyde and acid-releasable precursors thereof, such as
propionaldehyde enol ethers, which affords a cosmetically
acceptable, suitably low-odor sensory characteristic to the
composition.
[0009] A variation of the composition of the dimethicone copolyol
sulfosuccinate surfactants of the present invention is represented
by the formula: ##STR2## wherein X+ is an ammonium group derived
from an amino alcohol, preferably derived from an amino alcohol
selected from the group consisting of monoethanolamine,
diethanolamine, triethanolamine, monoisopropanolamine and
diglycolamine; while M+, R, x, and y are as defined above.
[0010] Another variation of the sulfosuccinate surfactant of the
present invention is represented by the formula: ##STR3## wherein
M'(+2) is an alkaline earth (Group II) cation, for example,
calcium, magnesium or barium, rather than an alkali metal cation;
while R, x, and y are as defined above.
[0011] Yet another form of the sulfosuccinate surfactant of the
present invention is represented by the following formula: ##STR4##
wherein X+, R, x, and y are as defined above. Typically, the
ammonium group, X+, is obtained from a sulfite salt containing an
amino alcohol.
[0012] The compositions of the present invention are preferably
prepared by reacting the ethoxylated polyether side chains of a
low-odor dimethicone copolyol with maleic anhydride to form a
monoester, and then converting the monoester to a sulfosuccinate by
sulfonation of the double bond with a metallic or amino alcohol
sulfite. The dimethicone copolyol starting material utilized in the
reaction is preferably substantially free from propionaldehyde and
acid-releasable precursors thereof, such as propionaldehyde enol
ethers. Metallic sulfite and amino salts can also be used either
alone or in combination for sulfonation of the double bond. The
resulting sulfosuccinate is a silicone-based surfactant, which
exhibits mildness to the skin, excellent foam stabilizing
properties, and has a low-odor characteristic suitable for use in
household or personal care products and applications.
DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS
[0013] The term "low-odor dimethicone copolyol" refers herein to
dimethicone copolyol type compounds that are substantially free of
propionaldehyde and acid-releasable precursors of propionaldehyde.
The term "low-odor" as applied to surfactant compositions of this
invention means that the discernible sensory odor characteristic of
the composition is improved, and deemed cosmetically desirable,
relative the discernible odor of a counterpart composition having a
relatively high content of propionaldehyde, or acid precursors
thereof (e.g., greater than about 3200 ppm).
[0014] The dimethicone copolyol sulfosuccinate compositions of the
present invention preferably are prepared by reacting the
ethoxylated polyether side chains of a dimethicone copolyol with
maleic anhydride to form a monoester. The side chains involved in
this reaction are a polymer or copolymer of ethylene oxide,
propylene oxide, butylene oxide, tetrahydrofuran, and/or glycerol.
Preferably, the side chains involved in this reaction are a polymer
or copolymer of ethylene oxide and/or propylene oxide. The
dimethicone copolyol preferably is substantially free of
propionaldehyde and acid-releasable precursors thereof. The
condensation reaction with maleic anhydride is represented by the
following equation. ##STR5##
[0015] In the above equation, the R group side chains are polymers
or copolymers ethylene oxide, propylene oxide, butylene oxide,
tetrahydrofuran, and/or glycerol, with the preferred R group being
selected from the group consisting of:
--(C.sub.2H.sub.4O).sub.S--C.sub.2H.sub.4--;
--(C.sub.3H.sub.6O).sub.t--C.sub.3H.sub.6--; and
--(C.sub.2H.sub.4O).sub.V--(C.sub.3H.sub.6O).sub.w--Y--; wherein s
and t each independently have a value in the range of 2 to about
30; v and w each independently have a value in the range of 1 to
about 30; and Y is C.sub.2H.sub.4 or C.sub.3H.sub.6. In the
dimethicone copolyol sulfosuccinate surfactants of the present
invention, the C.sub.3H.sub.6 and C.sub.3H.sub.6O moieties can be
linear or branched, preferably branched. The
--(C.sub.2H.sub.4O).sub.V--(C.sub.3H.sub.6O).sub.w--Y-- group can
be a block copolymer, a random copolymer or an alternating
copolymer of C.sub.2H.sub.40 and C.sub.3H.sub.6O moieties.
[0016] Preferably, x has a value in the range of 0 to about 100 and
y has a value in the range of 1 to about 100. More preferably, x
has a value in the range of 1 to about 50, and y has a value in the
range of 1 to about 50. The values of x, y, s, t, v and w
preferably are selected to produce a dimethicone copolyol
sulfosuccinate product with an equivalent weight in the range of
about 400 to about 3000 grams per equivalent. Preferably, the
dimethicone copolyol portion of the compound has a calculated HLB
value in the range of about 10 to about 17.
[0017] The low odor dimethicone copolyol sulfosuccinate surfactants
of the invention can be random copolymers, block copolymers or
alternating copolymers (i.e., the "x" and "y" monomer units can be
randomly distributed, arranged in blocks, or arranged in repeating
or alternating patterns).
[0018] The low-odor compositions of the present invention are
substantially free from propionaldehyde and acid-releasable
precursors thereof, such as propionaldehyde enol ethers. Examples
of acid-releasable propionaldehyde precursors include, without
limitation, an enol ether of propionaldehyde, such as a compound of
Formula (I): ##STR6## wherein R is
--(C.sub.2H.sub.4O).sub.S--C.sub.2H.sub.4--;
--(C.sub.3H.sub.6O).sub.t--C.sub.3H.sub.6--; or
--(C.sub.2H.sub.4O).sub.V--(C.sub.3H.sub.6O).sub.W--Y--; wherein s
and t each independently have a value in the range of 2 to about
30; v and w each independently have a value in the range of 1 to
about 30; and Y is C.sub.2H.sub.4 or C.sub.3H.sub.6. The
C.sub.3H.sub.6 and C.sub.3H.sub.6O moieties can be linear or
branched, preferably branched. The
--(C.sub.2H.sub.4O).sub.V--(C.sub.3H.sub.6O).sub.w--Y-- group can
be a block copolymer, a random copolymer or an alternating
copolymer of C.sub.2H.sub.4O and C.sub.3H.sub.6O moieties.
[0019] Dimethicone copolyol sulfosuccinate compositions of the
present invention can be prepared by condensation of a low-odor
dimethicone copolyol with maleic anhydride to form a monoester with
at least one R group in the dimethicone copolyol molecule,
preferably with a majority of the R groups, and more preferably
with each R group in the molecule. The olefinic bond in the maleic
monoester is then sulfonated to afford the sulfosuccinate.
[0020] A preferred condensation reaction proceeds by reacting about
1 to about 1.3 moles of maleic anhydride with about 1 equivalent of
a dimethicone copolyol. The dimethicone copolyol is heated to a
temperature in the range of about 45 to about 70.degree. C., with
the preferred temperature being in the range of about 60 to about
65.degree. C. Preferably, the dimethicone copolyol is substantially
free of propionaldehyde and acid-releasable precursors of
propionaldehyde, such as an enol ether precursor of propionaldehyde
(e.g., a compound of Formula (I), and the like). The maleic
anhydride can be dissolved in an aprotic solvent (e.g.,
tetrahydrofuran, dioxane, glyme, diglyme, a chlorinated hydrocarbon
such as dichloromethane, and the like), if desired, or can be
utilized without added solvent. The reaction mixture of dimethicone
copolyol and maleic anhydride is maintained at a temperature in the
range of about 40 to about 70.degree. C., preferably about 50 to
about 65.degree. C. under conditions and according to practices
known to those skilled in the art until a constant acid value or
number is obtained.
[0021] The resulting maleic monoester of dimethicone copolyol is
then converted into a sulfosuccinate surfactant of the present
invention by sulfonating the double bond of the maleic monoester
with a metallic sulfite salt, ammonium sulfite, an amine sulfite
salt, or a combination thereof. The preferred conversion is
accomplished by reacting the olefinic bond of the maleic anhydride
portion of the dimethicone copolyol monoester with approximately
equal molar amount of an alkali metal sulfite in an aqueous
solution in the following manner: ##STR7## wherein M+ is an alkali
(Group IA) metal cation, for example, sodium, potassium or lithium,
or ammonium group, while R, x and y are as defined above.
[0022] The alkali metal sulfite preferably is dissolved in water at
a temperature of about 40 to about 60.degree. C., more preferably
about 40 to about 50.degree. C. After the alkali metal sulfite is
thoroughly dissolved, the maleic monoester of dimethicone copolyol
is added to the solution while maintaining the reaction mixture in
a fluid state. The mixture is allowed to react for approximately
one half hour to about three hours, or until the concentration of
the free alkali metal sulfite is about 3% or less, with the
preferred concentration being less than about 1%.
[0023] In another embodiment, the conversion of the maleic
monoester of dimethicone copolyol to a sulfosuccinate is
accomplished by using compounds other than, or in addition to,
alkali metal or ammonium sulfite salts. Specifically, an 5 alkali
metal or ammonium sulfite in conjunction with an amino alcohol can
be used to sulfonate the double bond of the monoester. These
sulfosuccinates can be prepared in the following manner: ##STR8##
wherein M+ is an alkali metal cation or ammonium group and X+ is an
ammonium group derived from an amine(XH), preferably an amino
alcohol such as an amine ethoxylate or an amine propoxylate, while
R, x, and y are as defined above. Preferably, the ammonium group,
X+, is derived from an amine selected from the group consisting of
monoethanolamine, diethanolamine, triethanolamine,
monoisopropanolamine, diglycolamine, an ethoxylate thereof, and a
propoxylate thereof.
[0024] Alkaline earth sulfites also can be used in place of alkali
metal sulfites or ammonium sulfite to convert the maleic monoester
of dimethicone copolyol to a sulfosuccinate. When used alone, the
conversion reaction occurs in the following manner: ##STR9##
wherein M'(+2) is an alkaline earth (Group II) metal cation, for
example, calcium, magnesium or barium, while R, x and y are as
defined above.
[0025] Amino sulfites also can be used without the metallic
sulfites to convert the maleic monoester of dimethicone copolyol to
a sulfosuccinate. When used alone, the conversion reaction occurs
as follows: ##STR10## wherein X+ is an ammonium group derived from
an amine, preferably an amino alcohol such as an amine ethoxylate
and/or an amine propoxylate, more preferably an amino alcohol
selected from the group consisting of monoethanolamine,
diethanolamine, triethanolamine, monoisopropanolamine or
diglycolamine, while R, x and y are as defined above.
[0026] The values for x and y in many commercial dimethicone
copolyol compounds that can be used to produce the compositions of
the present invention cannot be readily determined, because such
values generally are kept as trade secrets and are not released or
made public by the commercial manufacturers of dimethicone
copolyols. However, non-limiting examples of commercial dimethicone
copolyol compounds, which reportedly have a low-odor
characteristic, suitable for preparing a low-odor dimethicone
copolyol sulfosuccinate composition of the present invention
include a purified version of DOW CORNING.RTM. 193 surfactant
manufactured by the Dow Corning Corporation, Midland, Mich., and
SILSURF.RTM. D212-CG, manufactured by Siltech Corporation. A
particularly preferred dimethicone copolyol suitable for preparing
a dimethicone copolyol sulfosuccinate composition of the invention
is DOW CORNING.RTM. UP-1005 Ultra Pure Fluid (INCI Name: PEG-12
Dimethicone), manufactured by the Dow Corning Corporation, which is
substantially free from propionaldehyde and acid-releasable
precursors thereof, such as enol ethers of Formula (I) as described
above.
[0027] Preparation of low-odor dimethicone copolyol type compounds
that are reportedly substantially free of propionaldehyde and
acid-releasable precursors of propionaldehyde are disclosed in U.S.
Pat. No. 5,118,764 to Ichinohe et al.; U.S. Pat. No. 5,225,509 to
Heinrich et al.; U.S. Pat. No. 5,696,192 to Harashima; U.S. Pat.
No. 5,869,727 to Crane et al.; U.S. Pat. No. 6,162,888 to Lee et
al.; U.S. Pat. No. 6,437,162 to O'Lenick, Jr.; and U.S. Pat. No.
6,784,271 to Nakanishi.
[0028] Preferred dimethicone copolyol compounds used to prepare the
low-odor surfactant compositions of the present invention desirably
possess the following characteristics: the dimethicone copolyol
should have an equivalent weight in the range of about 350 to about
1100 grams per equivalent and should be essentially free from any
extraneous solvents, propionaldehyde, and acid-releasable
precursors of propionaldehyde (i.e., compounds that release
propionaldehyde under acidic conditions). Preferably the
dimethicone copolyol is substantially free from enol ethers of
Formula (I).
[0029] Preferably, the hydroxyl number of the dimethicone copolyol
is in the range of about 20 to about 160, more preferably in the
range of about 60 to about 100, most preferably in the range of
about 70 to about 90. If the hydroxyl number of the dimethicone
copolyol is too low, the amount of the other reactants (maleic
anhydride and bisulfite compounds) will be insufficient to react
properly, and the resulting product will have either slight or no
differences in properties from the original dimethicone copolyol.
If extraneous solvents are present in too large amounts, such
solvents interfere with the reaction to the extent that limited
reaction can occur or the reaction can be partially blocked. The
resulting product then will not possess the desired characteristics
of a low-odor surfactant with useful foaming ability and which is
mild to the skin.
[0030] The dimethicone copolyol starting materials can have any HLB
value. Preferably, the dimethicone copolyol starting material has a
calculated HLB in the range of about 10 to about 17. The HLB
represents a ratio of the silicone portion of the compound to the
ethoxylated side chain portion of the compound (i.e., the R
groups).
[0031] Diester dimethicone copolyol sulfosuccinates can also be
prepared by reacting about 1 mole of the diester with about 1 molar
equivalent of the metallic bisulfite or amine bisulfite.
[0032] Several tests have been conducted using some representative
compositions of the present invention to verify the low-odor
characteristics of some of the compositions of the present
invention.
[0033] Each composition was prepared using the process described
earlier by which about 1 equivalent of dimethicone copolyol was
reacted with about 1 to about 1.3 moles of maleic anhydride, i.e.,
as described in detail in U.S. Pat. No. 4,717,498 to Maxon,
incorporated herein by reference. For example, a low-odor
dimethicone copolyol sulfosuccinate surfactant was prepared from
DOW CORNING.RTM. UP-1005, and compared with a conventional
dimethicone copolyol sulfosuccinate surfactant prepared from
standard, commercial DOW CORNING.RTM. 193, which had a detectable
propionaldehyde odor.
[0034] As used herein, the term "substantially free from", when
used in reference to propionaldehyde and acid-releasable precursors
thereof means a level of propionaldehyde in the head space above a
liquid sample of the product that is low enough to be essentially
free of objectionable odor sensorially discernible to a human
observer. For example, in one test, dimethicone copolyol
sulfosuccinate surfactant of this invention prepared from DOW
CORNING.RTM. UP-1005 was substantially free of objectionable odor
and had a head space concentration of propionaldehyde of about 16
parts per million (ppm) as determined by head-space gas
chromatography. By comparison, conventional dimethicone copolyol
sulfosuccinate surfactant prepared with the typical, non-purified
commercial dimethicone copolyol product, DOW CORNING.RTM. 193, had
propionaldehyde levels in the range of about 2000 to about 4500 ppm
and had readily discernible, objectionable propionaldehyde odors.
Similarly, the calculated propionaldehyde enol ether content
(weight percent) of the dimethicone copolyol sulfosuccinate
prepared from DOW CORNING.RTM. UP-1005 was about zero, compared to
about 10 weight percent for the dimethicone copolyol sulfosuccinate
prepared from non-purified DOW CORNING.RTM. 193.
[0035] Another aspect of this invention is a household or personal
care product comprising at least one low-odor composition of the
invention in a physiologically tolerable (e.g. non-toxic, mild to
the skin, non-allergenic, and the like) vehicle well known in the
cosmetic and personal care arts. The compositions and products can
also include other additives and adjuvants suitable for use in
cosmetics and personal care products. Non-limiting examples of
vehicles, additives and adjuvants suitable for use in household and
personal care products can be found in numerous technical
publications and supplier's literature, such as in any edition of
the well known International Cosmetic Ingredient Dictionary and
Handbook (INCI), published by the Cosmetic, Toiletry, and Fragrance
Association, Inc., Washington, D.C., relevant portions of which are
incorporated herein by reference. Exemplary household and personal
care products, without limitation, include cosmetics, hair and skin
care products, such as cleansers, conditioners, moisturizers, and
the like, oral and personal hygiene products, and household
products, such as cleaners. which come in contact with the skin of
the user.
[0036] The compositions described herein are intended to illustrate
embodiments of the invention and do not limit the scope of the
invention, which is defined by the appended claims. Alternatives to
and equivalents of the specific embodiments described can be made
and considered to be within the scope of the invention as defined
by the claims.
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