AN ESTER PRODUCT OF POLYGL YCEROL
The present invention relates to an ester product of polyglycerol with Cs and C10 fatty
acids & lactic acid and its use in the preparation of stable personal care compositions.
BACKGROUND OF THE INVENTION
United States Patent Application Publication number 2017/0071836 (applicant M/w
Henkel AG, referred to herein as '836) exemplifies use of fatty acyl lactylates as
cosmetic cleansing agents. However, the present invention prepares a polyglycerol
ester product and its use in stabilizing personal care compositions.
Chinese Patent application No. 106588648 discloses preparation of polyglycerol
esters wherein the polyglycerol is a tetramer. However, it suggests use of the
polyglycerol esters as moisturizers. However, the present invention prepares a
polyglycerol ester product and its use in stabilizing personal care compositions.
OBJECT OF THE INVENTION
The object ofthe present invention is to provide an ester product of polyglycerol with
C8 and C1o fatty acids & lactic acid for the preparation of stable personal care
com positions.
Another object of the present invention is to provide stable personal care
compositions comprising an ester product of polyglycerol with Cs and C10 fatty acids
2
I 1---... t J
& lactic acid which facilitates wetting, dispersion and reduced settling of hydrophobic
pigments during storage.
SUMMARY OF THE INVENTION
An ester product of polyglycerol with Cs and Cw fatty acids & lactic acid; wherein the
polyglycerol is with an average polymeric degree of 3 to 10.
An ester product of polyglycerol with Cs and Cw fatty acids & lactic acid with ester
selected from glycerol with C8 and Cw fatty acids and/or polyglycerol with lactic acid
and C12 fatty acid in the preparation of stable personal care compositions.
Additionally, the personal care compositions comprising the ester product of the
present invention will be free of preservatives.
DESCRIPTION OF THE INVENTION
Personal care compositions with mild preservatives are in demand by consumers.
It is known that sulfates in personal care compositions may damage cells and strip
away natural oils and hair proteins & ethanolamide based surfactants may comprise
nitroso compounds which are considered harmful when in contact with skin.
In view of the same we have developed a personal care composition which is stable
and mild. Thepersonal care composition ofthe present invention is user friendly as it
is preservative free, sulfate free, amide free, ethylene oxide free, silicone free,
paraben free and formaldehyde free.
3
I -, .. f~~ ) ·-.=;'
·"- ·._.- ...:..... ·--'
According to one embodiment of the present invention is an ester product of
polyglycerol with Cs and C10 fatty acids & lactic acid; wherein the polyglycerol is with
an average polymeric degree of 3 to 10.
Typically, the polyglycerol comprises 20 to 40 weight % of glycerol.
The combined Cs and C1ofatty acids will be 5-15 parts by weight of the polyglycerol.
The lactic acid is 3 to 8 parts by weight of the polyglycerol.
The ester product of polyglycerol with Cs and C10 fatty acids & lactic acid; wherein the
polyglycerol is with an average polymeric degree of 3 to 10 facilitates dispersion of
hydrophobic pigments by improving wettability in personal care compositions.
A good wetting agent first and foremost gives good particle separation in the bulk.
As a consequence, intra-particle agglomeration and settling are reduced or
eliminated. This would typically be seen on stability studies of the finished product
such as personal care compositions either at ambient or accelerated conditions as a
liquid separation, solid agglomerates, or a precipitate.
Improved dispersion of hydrophobic pigments inhibits settling of hydrophobic
pigments leading to stable personal care compositions.
The ester product of polyglycerol with Cs and C10 fatty acids & lactic acid; wherein the
polyglycerol is with an average polymeric degree of 3 to 10 disperses hydrophobic
pigments in 40 to 80% concentration.
A personal care composition comprising
(a) 0.1 to 5 weight % of an ester product of polyglycerol with Cs and Cw fatty acids & lactic
acid; wherein the polyglycerol is with an average polymeric degree of 3 to 10;
4
. (b) at least one hydrophobic pigment;
(c) at least one excipient; and
(d) water;
wherein the weight % is with regards to the composition and the composition is
physically stable at ambient conditions.
Physical stability is measured visually in the form of liquid separation, solid
agglomerates, or a precipitate.
The personal care composition of the present invention is selected from shampoo,
lotions, creams, veggie wash, different personal care preparation scalp cleanser,
lotions, creams, veggie. wash, different personal care preparation, hair cleanser,
shower preparations, shower gels, foam baths, gels, body wash, facial cleanser, face
wash, makeup remover, cleansing wipe, sunscreen, foundation and the like.
The excipients used in the personal care composition of the present invention are
selected from anionic, cationic, zwiterrionic, nonionic, amphoteric surfactants;
superfatting agents, stabilizers, biogenic active ingredients, humectants;
preservatives, pearlizing agents, dyes and pigments, fragrances, solvents, opacifiers,
further thickeners and dispersants, protein derivatives such as gelatin, collagen
hydrolysates, polypeptides, fatty alcohols, odor masking agents and enzymes.
The ester product of polyglycerol with C8 and C1o fatty acids & lactic acid; wherein the
polyglycerol is with an average polymeric degree of 3 to 10 provides antimicrobial
properties to the personal care composition effective in inhibiting growth of positive
and negative bacteria at 0.05 to 5.0% concentration.
5
T
The bacteria may be selected from Staphylococcus aureus, Bacillus subtilis, E. Coli,
Pseudomonas aeruginosa, Salmonella enteric, Propionebacterium acne, Malassezia
furfur, Streptococcus mutans, Lactobacillis acidophilus, Candida albicans, Aspergillus
niger and the like.
The personal care composition may further comprise ester selected from glycerol
with Cs and C1o fatty acids and/or polyglycerol with lactic acid and C12 fatty acid.
DEFINITION OF TERMS
Dropping point
The dropping point is the temperature at which a substance passes from a semi-solid
to a liquid state.
Pour point
The pour point of a liquid is the lowest temperature at which it becomes semi solid.
This is where the liquid loses its flow characteristics.
Acid Value
Acid value (or neutralization number or acid number or acidity) is the mass of
potassium hydroxide {KOH) in milligrams that is required to neutralize one gram of
chemical substance. The acid number is a measure of the number of carboxylic acid
groups in a chemical compound, such as a fatty acid.
6
Saponification Value
Saponification value or saponification number (SV or SN) represents the number of
milligrams of potassium hydroxide (KOH) required to saponify one gram of fat under
the conditions specified.
Hydroxyl Value
The hydroxyl value of a substance is the amount, in milligrams, of potassium
hydroxide required to neutralize any acid when combined by acylation in 1 g of the
substance under examination.
Iodine Value
The iodine value (or iodine adsorption value or iodine number or iodine index,
commonly abbreviated as IV) is the mass of iodine in grams that is consumed by 100
grams of a chemical substance. Iodine value is used to determine the amount of
unsaturation in fats, oils and waxes.
The following examples illustrate preferred embodiments in accordance with the
present invention without limiting the scope of the invention.
7
I .-. .-. --· --- 1. tJ l. -:'
EXAMPLES
Example 1:
Raw Materials:
Sr no Material Qty (gm)
1 Polyglycerol(crude) 396.0
2 Capric-Caprylic acid 79.2
3 Lauric Acid 26.4
4 Lactic acid 29.6
5 Catalyst 0.520
6 NaOH 0.052
Place in a heating mantle, a four necked round bottom flask fitted with a mechanical
stirrer, temperature sensor, gas sparger and a packed column, add Polyglycerol.
Under stirring introduce Nitrogen gas to maintain inert atmosphere, heat to 75° C.
Add sequentially Capric-Caprylic acid, Lauric acid. Lactic acid, VPA and KOH and raise
the temp to 180° Censuring that the vapour temp at the top of the packed column is
~ 99-100° C. Maintain at this temp till the reaction water steam reduces and raise the
reaction temperature to 200° C ensuring that the vapour temp does not exceed 99-
lQQO (.
Withdraw reaction sample after 3 hrs. to measure Acid Value to monitor the progress
ofthe reaction. Continue the reaction till A.V. reaches< 1 mg KOH/g, cool the reaction
mass and neutralize the same at 90° C with 50:50 NaOH-Water. Continue stirring at
this temperature for ~ 30 minutes and filter the reaction mass. The ester of the
present invention, Finester 2504, is used for the examples below.
Typical characteristic values of Finester 2504 are as follows-
8
Sr. No. Particulars Finester 2504
1 Dropping Point <-soc
2 Acid Value 2.0 Max
3 Sap Value 105
4 Hydroxyl Value 900
5 Iodine Value < 1
TEST METHODS USED
Pour Point: Manual method
The specimen is cooled inside a cooling bath to allow the formation of crystals. At
about goc above the expected pour point, and for every 3 oc after, the test jar is
removed and tilted to check for surface movement. When the specimen does not
flow when tilted, the jar is held horizontally for 5 seconds. If it does not flow, 3 oc is
added to the corresponding temperature, since this is the last measurement when
flow was observed, and the result is the pour point temperature.
An approximate range of pour point can be observed from the specimen's upper and
lower pour point.
This is helpful with products as it gives a temperature window depending on its
thermal history. Within this temperature range, the sample may appear liquid or
solid. This happens because the crystals form more readily when it has been heated
within the past 24 hrs and contributes to the lower pour point.
The upper pour point is measured by pouring the test sample directly into a test jar.
The sample is then cooled and inspected for the pour point.
9
1 7; (~! 7
Acid Value: A.O.C.S. Cd 3d-63 (09)
Saponification Value: A.O.C.S. Cd 3-25(09)
Hydroxyl Value: A.O.C.S. Cd 13- 60 (16)
Iodine Value: A.O.C.S. Tg 1a-64 (09)
Example 2: Sulfate free conditioning shampoo
Ingredient %w/w
Deionized Water 56.75
Dermofeel PA-12 (sodium phytate) 0.10
Amaze XT Dehydoxanthan Gum 2.00
lselux LQ-CLR-SB Sodium Lauroyl Methyllsethionate 10.00
Chembetain CGF Cocamidopropyl betaine 8.00
Finester 2009 Polyglycerin lauroyllactylate 17.00
Finester 2199 Sodium lauroyllactylate 3.00
D-Panthenol 1.00
Finester 2504 Ester of Example 1 2.00
Citric Acid Anh. 0.15
100
Preparation of the shampoo:
1. In main vessel add Deionized Water. Dissolve Dermofeel PA-12.
I pH
2. Add remaining ingredients except Amaze XT and Diocide. Heat to 80 C.
3. Sprinkle in Amaze XT with moderate mixing, allowing air to escape. When all
is added mix faster with mixer deep and without sucking in air.
4. Hold at 80 C for one hour or until thick and uniform. Cool to 35 C. Add
Finester 2504. QS. Mix until uniform
Test values
4.92
[ Viscosity (cps) Brookefield DVLVII+, 6 rpm 606112
10
Example 3: Visual testing for Stability
Clear homogenous mass.
No sedimentation on standing.
Example 4: Microbial testing
Table 1: Summary of Determination of Minimum Inhibitory Concentration/
Minimum Bactericidal Concentration using Broth Dilution Tube Method
Sample Code Test Organism MICValue
Enterococcus hirae ATCC 10541 Inconclusive*
Salmonella enterica ATCC 10708 Inconclusive*
Product- Finester 2504 Pseudomonas aeruginosa ATCC 15442 Inconclusive*
Ester of Example 1
Batch no- 0466012231 candida albicans ATCC 10231 Inconclusive*
Aspergillus brasiliensis ATCC 16404 Inconclusive*
Streptococcus mutans ATCC 25175 Inconclusive*
Malassezia furfur ATCC 14521 Inconclusive*
Key: *- Inconclusive as the presence or absence of growth could not be identified visually;
due to inherent turbidity of the test sample.
11
MBC Value
12.5%
>25%
>25%
12.5%
12.5%
<0.20%
25%

WE CLAIM
1. An ester product of polyglycerol with Cs and Cw fatty acids & lactic acid;
wherein the polyglycerol is with an average polymeric degree of 3 to 10.
2. An ester product of polyglycerol as claimed in claim 1 wherein the polyglycerol
comprises 20 to 40 weight% of glycerol.
3. An ester product of polyglycerol as claimed in claim 1 wherein the combined
Cs and C1o fatty acids are 5-15 parts by weight of the polyglycerol.
4. An ester product of polyglycerol as claimed in claim 1 wherein the lactic acid
is 3 to 8 parts by weight of the polyglycerol.
5. An ester product of polyglycerol as claimed in claim 1 wherein the ester
product facilitates dispersion of hydrophobic pigments in personal care
compositions.
6. An ester product of polyglycerol as claimed in claim 1 wherein the ester
product inhibits settling of hydrophobic pigments in personal care
compositions.
7. An ester product of polyglycerol as claimed in claim 1 wherein the ester product
disperses hydrophobic pigments in 40 to 80% concentration.
12
8. A personal care composition comprising
(a) 0.1 to 5 weight% of an ester product as claimed in claim 1;
(b) at least one hydrophobic pigment;
(c) at least one excipient; and.
(d) water;
wherein the weight% is with regards to the composition and the composition
is physically stable at ambient conditions.
9. A personal care composition as claimed in claim 8 wherein the composition
has antimicrobial properties effective in inhibiting growth of positive and
negative bacteria at 0.05 to 5.0% concentration.
10. A personal care composition as claimed in claim 8 wherein the composition
further comprises ester selected from glycerol with Cs and C10 fatty acids
and/or polyglycerol with lactic acid and C12 fatty acid.
11. A personal care composition as claimed in claim 8 selected from shampoo,
scalp cleanser, hair cleanser, shower preparations, shower gels, foam baths,
gels, body wash, facial cleanser, face wash, makeup remover, cleansing wipe,
sunscreen, foundation and the like.
13
·-:r ::: -
_,_;_ '·-·' 1 7 ';
12. A personal care composition as claimed in claim 8 wherein the excipients are
selected from anionic, cationic, zwiterrionic, nonionic, amphoteric
surfactants; superfatting agents, stabilizers, biogenic active ingredients,
humectants, preservatives, pearlizing agents, dyes and pigments, fragrances,
solvents, opacifiers, further thickeners and dispersants, protein derivatives
such as gelatin, collagen hydrolysates, polypeptides, fatty alcohols, odor
masking agents and enzymes.