Multifunctional phospholipid surfactants

Details Multifunctional phospholipid surfactants Multifunctional phospholipid surfactants

2002-05-06

2004-01-27

Carr, Deborah D. (Department: 1621)

Cleaning compositions for solid surfaces, auxiliary compositions

Cleaning compositions or processes of preparing

For cleaning a specific substrate or removing a specific...

C510S123000, C554S080000

Reexamination Certificate

active

06683032

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to novel compositions and, more particularly, to a class of compounds having specific quaternized amine based upon a phosphate ester. The use of a phosphate ester based upon a fatty alcohol or fatty alcohol alkoxylate as the material used to prepare a phospholipid results in heretofore-unknown compounds. The products are very good wetting agents, have improved hydrolytic stability, are extremely substantitive to human skin and are well tolerated by human tissue making them suitable for use preparation of barrier products for personal care applications. In short they are ideal surfactants for use in many personal care applications.
BACKGROUND OF THE INVENTION
Phosphate ester and quaternary amine compounds are well known and have been widely used for many years More recently, various betaine-type derivatives having, in general, quaternized alkyl amine groups and at least one phosphorous-containing anion in the molecule referred to hereinafter as “synthetic phospholipids”, have been disclosed The in U.S. Pat. Nos. are U.S. Pat. Nos. 3,856,893 and 3,928,509 to Diery et al. Diery discloses that the phosphonate compounds of his invention are active anti-microbial compounds. Later amido amine and imidazoline derivatives were disclosed for example, in U.S. Pat. Nos. 4,215,064; 4,233,192 and 4,380,637 to Lindemann et al., U.S. Pat. Nos. 4,209,449; 4,336,385 and 4,503,002 to Mayhew et al., and U.S. Pat. Nos. 4,243,602; 4,283,542 and 4,336,386 to O'Lenick et al. These synthetic phospholipids are suggested as exhibiting an outstanding combination of surfactant characteristics as well as being well tolerated by human tissue, i.e., they exhibit exceptionally low ocular irritation and oral toxicity. While these known phospholipids have been found useful as surfactants in a variety of personal care, they have not exhibited an ability to protect the skin from irritation or provide barrier properties to the skin, protecting it from the negative effects of chemicals and environmental effects.
It is very desirable to provide a material from aqueous solution that have a combination of surfactant properties, including foaming, detergency and wetting. The compounds of the present invention provide a wide range of surfactant properties in a single molecule and consequently are referred to as biominimetric-multi-functional surface-active agents. They can be formulated into a plethora of personal care products ranging from baby wipes to body washes and other skin products. In addition the structure of the compounds provides for outstanding substantivity and the phospholipid nature of the molecule allow for very mild natural like materials that can be used in products where low irritation is important.
SUMMARY OF THE INVENTION
Objective of the Invention
It is the objective of the invention to provide a novel phospholipid that contains in the same molecule a phosphated fatty alcohol or fatty alcohol alkoxylate and a process of its use which comprises contacting the hair with an effective surface active concentration of the novel phospholipid. The effective conditioning concentration ranges from between 0.1 and 25% by weight.
In accordance with the present invention we have now been discovered novel phospholipid compound, which conform to the following structure: A phospholipid, which conforms to the following structure;
wherein;
R
1
is R
5
—(OCH
2
CH
2
O)
a
—(CH
2
CH(CH
3
)O)
b
—(OCH
2
CH
2
O)
c
—
a, b and c are independently integers ranging from 0 to 20;
x, and z are integers independently ranging from 1 to 2;
y is 0 or 1, with the proviso that x+y+z=3;
R
2
is selected from the group consisting of;
CH
3
—(CH
2
)
d
—
CH
3
—(CH
2
)
e
—C(O)—N(H)—(CH
2
)
3
—
CH
3
(CH
2
)
f
CH═CH—(CH
2
)
g
—
 and
CH
3
(CH
2
)
h
CH═CH—(CH
2
)
i
-C(O)—N(H)—(CH
2
)
3
—
R
3
is selected from the group consisting of —CH
3
, —CH
2
CH
3
, and —(CH
2
CH
2
O)
j
—(CH
2
CH(CH
3
)O)
k
—(OCH
2
CH
2
O)
m
—H
R
4
is selected from the group consisting of —CH
3
, —CH
2
CH
3
, and —(CH
2
CH
2
O)
j
—(CH
2
CH(CH
3
)O)
k
—(OCH
2
CH
2
O)
m
—H
R
5
is selected from the group consisting of
CH
3
—(CH
2
)
r
—
CH
3
(CH
2
)
s
CH═CH—(CH
2
)
t
—
 and
CH
3
(CH
2
)
u
—C
6
H
5
—O—
d is an integer ranging from 7 to 21;
e is an integer ranging from 6 to 20;
f and g are independently integers ranging from 2 to 20;
h and i are independently integers ranging from 2 to 20;
j, k and m are independently integers ranging from 0 to 20, with the proviso that j+k+m be greater than or equal to 1;
r is an integer ranging from 6 to 21;
s and t are integers ranging from 2 to 20
u is an integer ranging from 7 to 21.
The invention is also directed to a process for cleaning and conditioning hair, which comprises contacting the hair with an effective conditioning amount of a phospholipid, which conforms to the following structure;
wherein;
R
1
is R
5
—(OCH
2
CH
2
O)
a
—(CH
2
CH(CH
3
)O)
b
—(OCH
2
CH
2
O)
c
—
a, b and c are independently integers ranging from 0 to 20;
x, and z are integers independently ranging from 1 to 2;
y is 0 or 1, with the proviso that x+y+y=3;
R
2
is selected from the group consisting of;
CH
3
—(CH
2
)
d
—
CH
3
—(CH
2
)
e
—C(O)—N(H)—(CH
2
)
3
—
CH
3
(CH
2
)
f
CH═CH—(CH
2
)
g
—
 and
CH
3
(CH
2
)
h
CH═CH—(CH
2
)
i
—C(O)—N(H)—(CH
2
)
3
—
R
3
is selected from the group consisting of —CH
3
, —CH
2
CH
3
, —(CH
2
CH
2
O)
j
—(CH
2
CH(CH
3
)O)
k
—(OCH
2
CH
2
O)
m
—H
R
4
is selected from the group consisting of —CH
3
, —CH
2
CH
3
, —(CH
2
CH
2
O)
n
—(CH
2
CH(CH
3
)O)
p
—(OCH
2
CH
2
O)
q
—H
R
5
is selected from the group consisting of
 CH
3
—(CH
2
)
r
—
CH
3
(CH
2
)
s
CH═CH—(CH
2
)
t
—
 and
CH
3
(CH
2
)
u
—C
6
H
5
—O—
d is an integer ranging from 7 to 21;
e is an integer ranging from 6 to 20;
f and g are independently integers ranging from 2 to 20;
h and i are independently integers ranging from 2 to 20;
j, k and m are independently integers ranging from 0 to 20, with the proviso that j+k+m be greater than or equal to 1.
r is an integer ranging from 6 to 21;
s and t are integers ranging from 2 to 20;
u is an integer ranging from 7 to 21.
Preferred Embodiments
In a preferred embodiment, R
2
is CH
3
—(CH
2
)
d
—.
In a preferred embodiment, R
2
is CH
3
—(CH
2
)
e
—C(O)—N(H)—(CH
2
)
3
—.
In a preferred embodiment, R
2
is CH
3
(CH
2
)
f
CH═CH—(CH
2
)
g
—.
In a preferred embodiment, R
2
is
CH
3
(CH
2
)
h
CH═CH—(CH
2
)
i
-C(O)—N(H)—(CH
2
)
3
—.
In a preferred embodiment, R
3
is —CH
3
.
In a preferred embodiment, R
3
is —CH
2
CH
3
,
In a preferred embodiment, R
3
is
—(CH
2
CH
2
O)
j
—(CH
2
CH(CH
3
)O)
k
—(OCH
2
CH
2
O)
m
—H.
In a preferred embodiment, R
4
is —CH
3
.
In a preferred embodiment, R
4
is —CH
2
CH
3
.
In a preferred embodiment, R
4
is
—(CH
2
CH
2
O)
n
—(CH
2
CH(CH
3
)O)
p
—(OCH
2
CH
2
O)
q
—H.
In a preferred embodiment, R
3
and R
4
are both —CH
3
In a preferred embodiment, R
3
and R
4
are both
—(CH
2
CH
2
O)
n
—(CH
2
CH(CH
3
)O)
p
—(OCH
2
CH
2
O)
q
—H.
In a preferred embodiment, R
3
and R
4
are both —CH
2
CH
3
.
In a preferred embodiment the effective conditioning concentration ranges from 0.1 to 25% by weight.
DETAILED DESCRIPTION OF THE INVENTION
The present invention is directed to novel phospholipid compounds, which conform to the following structure: In accordance with the present invention we have now been discovered novel phospholipid compound, which conform to the following structure:
wherein;
R
1
is R
5
—(OCH
2
CH
2
O)
a
—(CH
2
CH(CH
3
)O)
b
—(OCH
2
CH
2
O)
c
—
a, b and c are independently integers ranging from 0 to 20;
x, and z are integers independently ranging from 1 to 2;
y is 0 or 1, with the proviso that x+y+z=3;
R
2
is selected from the group consisting of;
CH
3
—(CH
2
)
d
—
CH
3
—(CH
2
)
e
—C(O)—N(H)—(CH
2
)
3
—
CH
3
(CH
2
)
f
CH═CH—(CH
2
)
g
—
 and
CH
3
(CH
2
)
h
CH═CH—(CH
2
)
i
-C(O)—N(H)—(CH
2
)
3
—
R
3
is selected from the group consisting of —CH
3
, —CH
2
CH
3
, and —(CH
2
CH
2
O)
j
—(CH
2
CH(CH
3
)O)
k

Affiliated with

Also associated with

Rating

Multifunctional phospholipid surfactants does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Multifunctional phospholipid surfactants, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Multifunctional phospholipid surfactants will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3247903