Download synthetic phosphobetaines technology

SYNTHETIC PHOSPHOBETAINES
TECHNOLOGY
(PHOENOTAINE C-35 / PHOENOTAINE D-35)
Specialty phospholipids made from soy lecithin are used extensively in cosmetics
for their ability to act as emulsifiers, lubricants, dispersing agents, and emollients.
In recent years, they have assumed important roles in the formation of liposome
dispersions used in fine cosmetic and drug applications. Phospholipids are
excellent choices for cosmetic use since they are natural, toxicologically safe,
and do not produce skin irritation or cause sensitization effects. The naturally
occurring materials from soy while useful have some drawbacks in terms of
formulation. They have some problems with ease of emulsification and
applications.
Phospholipids refers to compounds having one or more ionizable phosphate
groups and one or more cationic groups. This term applies to compounds
regardless of the number of these groups. Phosphobetaines are a specific type
of phospholipids in which there is only one ionizable phosphate group and only
one cationic group.
Phoenix Chemical has undertaken a project aimed at providing Synthetic
PhosphoBetaines (The SPB project). The use of synthetic organic chemistry to
modify the basic properties of phospholipids has resulted in functional materials
that can be used as replacements, enhancers, emulsifiers, and extenders of
natural phospholipids.
As one looks at the product line the natural product phosphatidyl choline needs
to be kept in mind. Compounds in our SPB line need to be compared to this
material.
R C(O) O CH2
R'C(O) O CH
CH3
H2C O P(O) O (CH2)2N+ CH3
O
Phosphatidyl Choline
CH3
It is important to note the functional groups present in phosphatidyl choline. It is
the structural attributes of the molecule that determines the functionality. The
molecule has (a) hydrophobic groups (the two acyl groups), (b) hydrophilic
groups (the quat group and the phosphate group), and (c) the presence of the (+)
and (-) groups in the same molecule make this material an amphoteric surfactant.
This is quite significant when one realizes that 99% of all surfactant activities in
the cell is carried out by amphoteric surfactants. This includes cell wall activities.
Industrially, we use comparatively little amphoteric materials.
Phoenix EPB Compounds (Ester PhosphoBetaines)
Phoenix EPB compounds conform to the following structure:
CH3
HO
R C(O) O (CH2CH2O)X P(O) O CH2
CH CH2
-O
N+R'
CH3
These molecules have (a) two hydrophobic groups R and R’ at opposite ends of
the molecule (gemini surfactants), (b) hydrophilic groups ( the quat group, the
phosphate group and the polyoxyalkylene group), and (c) the presence of the (+)
and (-) groups in the same molecule making this material an amphoteric
surfactant and (d) an ester group. The molecule can be modified in terms of:
(a) Hydrophobic Modification
(b) Hydrophilic Modification
(c) HLB Balance
R and R’,
“x” value
ratios of (a) to (b)
providing the formulator with new flexibility in making emulsions.
PHOENIX AMIDO PHOSPHO BETAINES (APB) COMPOUNDS
Phoenix APB compounds conform to the following structure:
+
O
RCNH(CH2)3
CH3
N
CH3
O
CH2CHCH2O
PONa
OH
2
3Cl
These molecules have (a) a hydrophobic group R, (b) hydrophilic groups (the
quat group, and the phosphate group), and (c) the presence of the (+) and ( - )
groups in the same molecule making this material an amphoteric surfactant and
(d) an amido group. The molecule can be modified in terms of:
(a) Hydrophobic Modification
(b) Hydrophyllic Modification
(c) HLB Balance
By modifying the R (alkyl) group one can
modify either property
providing the formulator with new flexibility in making emulsions. The conversion
of the ester group into the more hydrolytically stable amido group provides wider
formulation latitude. Phoenix synthetic phosphobetaines are propylene glycol free
and unique in that they are monofunctional as compared to di and trifunctional
phospholipids currently in the market. These products are covered by U.S.
patent 6,180,806, entitled Glyceryl Phosphobetaine Compounds, issued January
30, 2001, to Phoenix Research Corp.
Phosphobetaines are compatible with anionic surfactants such as sodium lauryl
ether sulfate (SLES), forming a complex that enhances deposition on hair and
contributes to hair conditioning and manageability. This effect is also postulated
to take effect on the epidermis.
Two materials are currently being offered; one is a Sodium Cocamidopropyl PGDimonium Chloride Phosphate and the other a Sodium Dilinoleamidopropyl PGDimonium Chloride Phosphate.
Trade Name
INCI
CAS #
EINECS
PHOENOTAINE® C-35
Sodium Cocamidopropyl PG-Dimonium Chloride Phosphate
83682-78-4
280-518-3
Trade Name
INCI
CAS #
PHOENOTAINE® D-35
Sodium Dilinoleamidopropyl PG-Dimonium Chloride Phosphate
Not Assigned
Amino phospholipids are recommended for use as extremely mild surfactants,
especially in baby products such as shampoos, bath and shower gels, body
wash, bath beads, and products used in personal care.
ATTRIBUTES
At 5% levels favorable properties contributed by PHOSPHOBETAINES in
shampoos and bath products are:
1. Mildness
2. Counter irritant for SLES
3. Foam enhancement
4. Mild detergent
5. Conditioning
TENTATIVE SPECIFICATIONS
PHOENOTAINE®
Appearance (@25°C)
Solids (%)
pH (10% in 25% IPA)
Color (Gardner)
Foreign Matter
% NaCl
C-35
Clear Yellow Liquid
37-39
6.0-8.0
6 Max
Free Of
4.0 Min.
D-35
Clear Amber Liquid
29-31
5-7
8 Max
Free Of
5.0 Min.
SOLUBILITIES
PHOENOTAINE® C-35 D-35
Water
s
s
Propylene Glycol
s
s
IPA
s
s
Mineral Oil
i
i
Isopropyl Myristate
i
i
Silicone Fluid
i
i
s = Soluble
i = Insoluble
SAFETY DATA
Skin irritation and skin sensitization data developed via RIPT studies with 50
human subjects follows:
PHOENOTAINE®
* Skin Irritation
* Skin Sensitization
C-35
Non-Primary Irritant
Non-Primary Sensitizer
D-35
Non-Primary Irritant
Non-Primary Sensitizer
* Studies conducted by AMA Labs., 216 Congers Rd. New City, NY 10956
02/28/03
Rev. 02/06/07
While the information herein is believed to be reliable, PHOENIX CHEMICAL, INC. does not guarantee its accuracy. Purchasers are urged to conduct their own tests. PHOENIX
CHEMICAL, INC. warrants its materials, as described herein, shall conform to the written specifications for such materials. PHOENIX CHEMICAL, INC. makes no other
warranty, either expressed or implied, as to the materials’ merchantability or fitness for purpose. In no event shall PHOENIX CHEMICAL, INC.’s liability for breach of this
warranty exceed the purchase price of the material for which such breach is claimed. Nothing contained herein is intended as a recommendation to use PHOENIX CHEMICAL,
INC. products so as to infringe any patent and no liability for customer’s violation of patent or other rights is assumed.