Organic compounds -- part of the class 532-570 series – Organic compounds – Fatty compounds having an acid moiety which contains the...
Reexamination Certificate
1999-09-23
2001-01-30
Carr, Deborah D. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Fatty compounds having an acid moiety which contains the...
C554S080000
Reexamination Certificate
active
06180806
ABSTRACT:
BACKGROUND OF THE INVENTION
(1) Field of Invention
The present invention relates to a series of novel glyceryl phosphobetaine compounds which are exceptional surface active agents that provide outstanding foam and are very mild to the hair and skin. The compounds, because they contain a pendant ionizable phosphate group and a quaternary amine compound are amphoteric surfactants that is they contain both a positive and negative charge in the same molecule. These combination of properties makes these polymers ideally suited for use in personal care applications.
The compounds of the present invention are based upon raw materials which are prepared by the reaction of a phosphated mono-chloro glycerin reacted with a tertiary amine to produce the phosphobetaine.
The technology used to produce the phosphobetaine compounds of the present invention is very flexible and allows us to prepare performance tailored molecules for specific applications.
(2) Description of the Arts and Practices
Fatty phosphobetaine compounds have been known since 1974. There are several patents which have issued on this topic.
U.S. Pat. No. 3,856,893 and 3,928,509 both issued to Diery disclose the basic technology used to make phosphobetaine compounds.
Later, amido and imidazoline based phosphobetaine compounds were patented in U.S. Pat. No. 4,209,449 issued in 1980 to Mayhew and O'Lenick. This patent teaches that phosphate quats can be prepared by the reaction of a phosphate salt, three equivalents of epichlorohydrin and in a subsequent step, three equivalents of a tertiary amine.
U.S. Pat. No. 4,215,064 issued in 1980 to Lindemann et al teaches the basic technology that is used for the preparation of amido and imidazoline based phosphobetaine compounds. These compounds can be prepared by the reaction of a phosphate salt, one equivalent of epichlorohydrin and one equivalent of a tertiary amine.
U.S. Pat. No. 4,243,602 issued in 1981 to O'Lenick and Mayhew teaches the basic technology that is used for the preparation of phosphobetaine compounds based upon phosphorous acid salts. These compounds can be prepared by the reaction of a phosphorous acid salt, one equivalent of epichlorohydrin and one equivalent of a tertiary amine.
U.S. Pat. No. 4,261,911 issued in 1981 to Lindemann et al teaches the utilization of phosphobetaine compounds based upon phosphorous acid. These compounds are useful as surfactants.
U.S. Pat. No. 4,283,542 issued in 1981 to O'Lenick and Mayhew teaches the process technology used for the preparation of phosphobetaine compounds. These compounds can be prepared by the reaction of a phosphate salt, one equivalent of epichlorohydrin and one equivalent of a tertiary amine.
U.S. Pat. No. 4,336,386 issued in 1982 to O'Lenick and Mayhew teaches the technology for the preparation of imidazoline derived phosphobetaine compounds based upon phosphorous acid salts. These compounds can be prepared by the reaction of a phosphorous acid salt, one equivalent of epichlorohydrin and one equivalent of an imidazoline.
U.S. Pat. No. 4,503,002 which is related to U.S. Pat. No. 4,209,449 issued in 1985 to Mayhew and O'Lenick teach that phosphate quats can be prepared by the reaction of a phosphate salt, three equivalents of epichlorohydrin and three equivalents of a tertiary amine.
Despite the fact that there was significant patenting of phosphobetaine compounds based upon phosphoric acid salts, phosphorous acids salts, tertiary amine and imidazolines, the technology needed to place a alkyl or acyl moiety into the molecule and make the compounds of the present invention was not appreciated. It was also not until the compounds of the present invention that the concept and technology needed to incorporate the glyceryl group, which adds both to the water solubility, humectancy properties and mildness to skin and eyes.
THE INVENTION
(1) Object of the Invention
It is the object of the present invention to provide a series of novel glyceryl phosphobetaine compounds which are high foaming, low irritation to eyes and skin, have an inverse cloud point and are substantive to the surface of a fibers, and are very effective emulsifiers.
Still another object of the present invention is to provide a series of glyceryl phosphobetaine compounds which have differing solubilities in water and organic solvents. This is achieved by selection of the phosphate used as a raw material and the amine chosen for preparation of the phosphobetaine.
Application of the compounds of the invention can be from solvent, aqueous dispersion or solution, or applied neat in these processes.
2) Summary of the Invention
The present invention relates to a series of novel glyceryl phosphobetaine compounds. The amine group typically will be a quaternized nitrogen. Hence the products are amphoteric, having both an anionic and cationic group present on the same pendant group. The glyceryl group contributes properties to these surfactants resulting in compounds that are outstanding emulsifiers, foaming intensely, are non irritating to eyes and skin and deposits on fiber surfaces and form effective surface modifying finishes. The compounds of the present invention are therefore very well suited to applications in the personal care market.
The compounds of this invention having a pendant amphoteric group is represented by the following formula;
R
1
is alkyl having between 7 and 21 carbon atoms.
The reaction sequence needed to produce the compounds of the present invention starts with the phosphation of chloro-glycerin.
In a subsequent step the chloro-glyceryl-phosphate is reacted with an alkyl amido propyl dimethyl amine to produce the compounds of the present invention.
wherein M is H, Na or K.
PREFERRED EMBODIMENTS
In a preferred embodiment R1 is C
7
H
17
.
In a preferred embodiment R1 is C
9
H
19
.
In a preferred embodiment R1 is C
13
H
27
.
In a preferred embodiment R1 is C
15
H
31
.
In a preferred embodiment R1 is C
19
H
39
.
In a preferred embodiment R1 is C
7
H
17
.
In a preferred embodiment R1 is C
11
H
23
.
In a preferred embodiment R1 is C
17
H
35
.
In a preferred embodiment R1 is C
21
H
43
.
REFERENCES:
patent: 5136093 (1992-08-01), Smith
Chem. Abstr., 130:311858, 1999.
Chem. Abstr., 92:200147, 1980.
Imperante John
O'Lenick, Jr. Anthony J.
Carr Deborah D.
Phoenix Research Corp.
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