U.S. patent application number 13/506522 was filed with the patent office on 2012-08-16 for sorbitol polyesters having liquid and solid domains.
Invention is credited to Andrew J. O'Lenick, Anthony J. O'Lenick, JR., Kevin A. O'Lenick.
Application Number | 20120208775 13/506522 |
Document ID | / |
Family ID | 46148013 |
Filed Date | 2012-08-16 |
United States Patent
Application |
20120208775 |
Kind Code |
A1 |
O'Lenick; Kevin A. ; et
al. |
August 16, 2012 |
Sorbitol polyesters having liquid and solid domains
Abstract
The present invention is directed to a series of sorbitol esters
that have two different molecular weight ester chains, one solid
and one liquid, which when combined into a single molecule make a
polymer that is solid, but has very unique flow properties. These
materials find applications as additives to formulations in
personal care products where there is a desire to have a structured
film (provided by the solid fatty group) and flow properties,
(provided by the liquid fatty group). These compounds by virtue of
their unique structure provide outstanding skin feel.
Inventors: |
O'Lenick; Kevin A.; (Dacula,
GA) ; O'Lenick; Andrew J.; (Dacula, GA) ;
O'Lenick, JR.; Anthony J.; (Dacula, GA) |
Family ID: |
46148013 |
Appl. No.: |
13/506522 |
Filed: |
April 25, 2012 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
|
|
12653457 |
Dec 16, 2009 |
8192727 |
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13506522 |
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61270597 |
Jul 13, 2009 |
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Current U.S.
Class: |
514/23 ;
536/1.11 |
Current CPC
Class: |
C07C 69/608 20130101;
C07C 2601/16 20170501; A61Q 19/00 20130101; A61Q 5/12 20130101;
C07C 2601/14 20170501; A61K 8/375 20130101 |
Class at
Publication: |
514/23 ;
536/1.11 |
International
Class: |
A61K 8/49 20060101
A61K008/49; A61Q 5/12 20060101 A61Q005/12; C07H 7/02 20060101
C07H007/02; A61Q 19/00 20060101 A61Q019/00 |
Claims
1. A polyester made by the esterification reaction of: (a) sorbitol
conforming to the following structure: ##STR00025## (b) a di acid
selected from the group consisting of: ##STR00026## hydrogenated
dimer acid, conforming to the following structure: ##STR00027## and
mixtures thereof; (c) a fatty acid that is liquid at room
temperature, selected from the group consisting of oleic acid
conforming to the following structure:
HO--C(O)--(CH.sub.2).sub.8--CH.dbd.CH--(CH.sub.2).sub.6--CH.sub.3
and iso-stearic acid conforming to the following structure:
##STR00028## and mixtures thereof; (d) a fatty acid that is solid
at room temperature HO--C(O)--(CH.sub.2).sub.a--CH.sub.3 a is an
integer ranging from 14 to 20.
2. A process for conditioning hair and skin which comprises
contacting the hair or skin with an effective conditioning
concentration of a polyester made by the esterification reaction
of: (a) sorbitol conforming to the following structure:
##STR00029## (b) a di acid selected from the group consisting of:
##STR00030## hydrogenated dimer acid, conforming to the following
structure: ##STR00031## and mixtures thereof; (c) a fatty acid that
is liquid at room temperature, selected from the group consisting
of oleic acid conforming to the following structure:
HO--C(O)--(CH.sub.2).sub.8--CH.dbd.CH--(CH.sub.2).sub.6-CH.sub.3
and iso-stearic acid conforming to the following structure:
##STR00032## and mixtures thereof; (d) a fatty acid that is solid
at room temperature HO--C(O)--(CH.sub.2).sub.a--CH.sub.3 a is an
integer ranging from 14 to 20.
Description
RELATED APPLICATIONS
[0001] This application is a divisional patent application of Ser.
No. 12/653,457 filed Dec. 16, 2009, which in turn claims priority
to and benefit of U.S. Provisional Application No. 61/270,597 filed
Jul. 13, 2009, the disclosure of which is incorporated herein for
all purposes.
FEDERAL SPONSORSHIP
[0002] There is no federal sponsorship on the present
invention.
FIELD OF THE INVENTION
[0003] The present invention is directed to a series of sorbitol
esters that have two different molecular weight ester chains, one
solid and one liquid, which when combined into a single molecule
make a polymer that is solid, but has very unique flow properties.
These materials find applications as additives to formulations in
personal care products where there is a desire to have a structured
film (provided by the solid fatty group) and flow properties,
(provided by the liquid fatty group). These compounds by virtue of
their unique structure provide outstanding skin feel.
BACKGROUND OF THE INVENTION
[0004] Sorbitan esters are known. They are derived from a cyclic
material called Sorbitan derived from the dehydration of sorbitol.
Sorbitan conforms to the following structure:
##STR00001##
[0005] Sorbitan is esterified using fatty acids to make sorbitan
esters. A typical sorbitan ester is shown:
##STR00002##
[0006] Sorbitan esters with different kinds of fatty acids and
various degrees of esterification are known. Those are generally
used as emulsifier for example in making cream.
[0007] Sorbitol, one of the reactants used to make the compounds of
the present invention is linear. It contains six hydroxyl groups as
shown below:
##STR00003##
[0008] It is known that sorbitan fatty acid esters can be produced
by direct, base-catalyzed reaction of sorbitol with a fatty acid at
elevated temperatures.
[0009] U.S. Pat. No. 2,390,395 to Soltzberg describes the
preparation of monoanhydro sorbitol which is rich in 1,4-sorbitan
by anhydrization of sorbitol under reduced pressure at
120.degree.-150.degree. C. in the presence of an acid catalyst.
[0010] U.S. Pat. No. 2,387,842 to Soltzberg discloses the
preparation of "sorbide" by heating sorbitol solution at reduced
pressure (88-95 mm of mercury absolute) in the presence of an acid
catalyst (sulfuric acid) until 2 moles of water per mole of
sorbitol are removed.
[0011] U.S. Pat. No. 6,384,248 to O'Lenick, Jr. discloses
Meadowfoam based sorbitan esters
[0012] U.S. Pat. No. 6,013,813 to O'Lenick Jr. discloses Guerbet
acid based sorbitan esters.
[0013] The patents referenced disclose sorbitan derivatives.
[0014] U.S. Pat. No. 7,473,707 to O'Lenick et al discloses specific
alkoxylated sorbitan esters (Spider Esters) useful in delivering
skin actives.
[0015] None of these patents provide polyester derivatives of mixed
fatty esters of sorbitol as envisioned by the present
invention.
THE INVENTION
Objective of the Invention
[0016] The present invention has as its objective a series of
sorbitan polyesters that have both liquid and solid fatty groups
contained thereon and are crosslinked by dimer acid.
[0017] The present invention also has an objective a process for
treating hair and skin with the sorbitan polyesters that have both
liquid and solid fatty groups contained thereon and are crosslinked
by dimer acid.
[0018] Other objectives will become clear as one reads the
specification and claims herein.
SUMMARY OF THE INVENTION
[0019] The present invention discloses a polyester made by the
reaction of a mixture of liquid and solid fatty acids reacted with
sorbitol and dimer acid.
DETAILED DESCRIPTION OF THE INVENTION
[0020] The present invention relates to a polyester that conforms
to the following structure:
##STR00004##
[0021] R.sup.1 is a mixture of between 15 and 60%
-(CH.sub.2).sub.a--CH.sub.3 and between 85 and 40% of fatty acids
selected from the group consisting of
##STR00005##
and mixtures thereof
[0022] a is an integer ranging from 14 to 20;
[0023] R.sup.2 is selected from the group consisting of;
##STR00006##
hydrogenated dimer acid, conforming to the following structure:
##STR00007##
and mixtures thereof;
[0024] x is an integer ranging from 1 to 20.
[0025] Another aspect of the present invention is a process for
conditioning hair and skin which comprises contacting the hair or
skin with an effective conditioning concentration of a polyester
that conforms to the following structure:
##STR00008##
[0026] R.sup.1 is a mixture of between 15 and 60%
--(CH.sub.2).sub.a--CH.sub.3 and
between 85 and 40% of fatty acids selected from the group
consisting of
##STR00009##
and mixtures thereof;
[0027] a is an integer ranging from 14 to 20;
[0028] R.sup.2 is selected from the group consisting of;
##STR00010##
hydrogenated dimer acid, conforming to the following structure:
##STR00011##
and mixtures thereof;
[0029] x is an integer ranging from 1 to 20.
[0030] In a preferred embodiment said effective conditioning
concentration ranges from 0.1% to 20% by weight.
[0031] The products of the present invention are made by the
esterification reaction of:
[0032] (a) sorbitol conforming to the following structure:
##STR00012##
[0033] (b) a di acid selected from the group consisting of:
##STR00013##
hydrogenated dimer acid, conforming to the following structure:
##STR00014##
and mixtures thereof;
[0034] (c) a fatty acid that is liquid at room temperature,
selected from the group consisting of oleic acid conforming to the
following structure:
[0035]
HO--C(O)--(CH.sub.2).sub.8--CH.dbd.CH--(CH.sub.2).sub.6--CH.sub.3
and iso-stearic acid conforming to the following structure:
##STR00015##
and mixtures thereof;
[0036] (d) a fatty acid that is solid at room temperature
HO--C(O)--(CH.sub.2).sub.a--CH.sub.3 a is an integer ranging from
14 to 20.
[0037] Another aspect of the present invention is a process for
conditioning hair and skin which comprises contacting the hair or
skin with an effective conditioning concentration of a polyester
made by the esterification reaction of:
[0038] (a) sorbitol conforming to the following structure:
##STR00016##
[0039] (b) a di acid selected from the group consisting of:
##STR00017##
hydrogenated dimer acid, conforming to the following structure:
##STR00018##
and mixtures thereof;
[0040] (c) a fatty acid that is liquid at room temperature,
selected from the group consisting of oleic acid conforming to the
following structure:
[0041]
HO--C(O)--CH.sub.2).sub.8--CH.dbd.CH--(CH.sub.2).sub.6--CH.sub.3
and iso-stearic acid conforming to the following structure:
##STR00019##
and mixtures thereof;
[0042] (d) a fatty acid that is solid at room temperature
[0043] HO--C(O)--(CH.sub.2).sub.a--CH.sub.3 a is an integer ranging
from 14 to 20.
[0044] Where there are two different types of ester group present,
one liquid and one solid, the resulting structure cannot
crystallize completely, since the liquid domains in the polymer act
as molecular crystal distorters, resulting in a polymer that
although having the same melting point, flows more easily when
pressure is applied. The resulting solid will be soft and flowable,
rather than hard and un-yielding.
EXAMPLES
Example 1
Sorbitol
[0045] Sorbitol is an item of commerce commercially available from
a variety of sources. It conforms to the following structure:
##STR00020##
[0046] The IUPAC name for sorbitol is d-glucitol. The IUPAC name is
(2R,3R,4R,5S) -hexane-1,2,3,4,5,6-hexol. CAS number 98201-93-5.
Examples 2-3
Example 2
Dimer Acid
[0047] Dimer acid is an item of commerce commercially available
from a variety of sources. It conforms to the following
structure:
##STR00021##
[0048] The CAS NUMBER is 61788-89-4.
Example 3
Hydrogenated Dimer Acid
[0049] Hydrogenated dimer acid, is an item of commerce available
from a variety of sources conforming to the following
structure:
##STR00022##
[0050] The CAS number is 68783-41-5
Example 4
Oleic Acid
[0051] Oleic acid is an item of commerce available from a variety
of sources. It conforms to the following structure;
##STR00023##
[0052] The CAS No. is 112-80-1.
Example 5
iso-stearic acid
[0053] iso-stearic acid is an item of commerce available from a
variety of sources. It conforms to the following structure;
##STR00024##
[0054] The CAS number is 2724-58-5.
Examples 6-9
Fatty Acids that are solid at room temperature
[0055] These acids are an item of commerce available from a variety
of sources. It conforms to the following structure;
[0056] HO--C(O)--(CH.sub.2).sub.a--CH.sub.3 a is an integer ranging
from 14 to 20.
TABLE-US-00001 Example a Common Name MW 6 14 palmitic acid 256 7 16
stearic acid 284 8 18 arachidinic acid 312 9 20 behenic acid
340
[0057] To a suitable reactor equipped with heating and an ability
to distill off water is added the specified number of grams of
sorbitol (Example 1)is added the specified number of grams of the
specified dimer acid (Examples 2-3), next is added the specified
number of grams of the specified liquid acid (Examples 4-5).
Finally, is added the specified number of grams of the specified
solid fatty acid (Examples 6-9). The reaction mass is heated to
180-200.degree. C. and water is distilled off. The reaction mass is
kept at this temperature until the acid value becomes vanishingly
low. The reaction mass is cooled and used without additional
purification.
TABLE-US-00002 Sorbitol Dimer Acid Liquid Acid Solid Acid Example
Ex. Grams Ex. Grams Ex. Grams Ex. Grams x value 10 1 54.6 2 30.0 4
225.5 6 204.8 1 11 1 127.4 2 150.0 4 253.6 7 539.6 5 12 1 218.4 2
300.0 4 394.8 8 436.8 10 13 1 400.4 2 600.0 4 1353.6 9 1258.0 20 14
1 127.4 3 150.0 5 225.6 6 512.0 5 15 1 218.4 3 300.0 5 169.2 7
1136.0 10 16 1 54.6 3 30.0 5 225.6 8 249.0 1 17 1 400.4 3 600.0 5
1128.0 9 1360.0 20
[0058] Ex means example in the table above.
[0059] Products that are of the present invention were low order
soft pastes that liquefied under pressure. Those products that were
made using only solid fatty acids were hard solids that were not
spreadable on the skin or hair. Those made without solid fatty
acids, but only liquid fatty acids, (oleic and iso stearic) were
sticky liquids. Those made with iso-stearic acid were glossy on
hair and skin, while those made with oleic acid were
emollients.
[0060] The compounds are of exceptional interest in the personal
care applications where gloss, rheology that accommodates spreading
and odor are critical.
[0061] While the illustrative embodiments of the invention have
been described with particularity, it will be understood that
various other modifications will be apparent to and can be readily
made by those skilled in the art without departing from the spirit
and scope of the invention. Accordingly, it is not intended that
the scope of the claims appended hereto be limited to the examples
and descriptions set forth hereinabove but rather that the claims
be construed as encompassing all the features of patentable novelty
which reside in the present invention, including all features which
would be treated as equivalents thereof by those skilled in the art
to which the invention pertains.
* * * * *