The present invention relates to a series of novel glyceryl phosphobetaine compounds which are exceptional f 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.

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;
 ##STR1##
 R.sup.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.
 ##STR2##
 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.
 ##STR3##
 wherein M is H, Na or K.
 PREFERRED EMBODIMENTS
 In a preferred embodiment R1 is C.sub.7 H.sub.17.
 In a preferred embodiment R1 is C.sub.9 H.sub.19.
 In a preferred embodiment R1 is C.sub.13 H.sub.27.
 In a preferred embodiment R1 is C.sub.15 H.sub.31.
 In a preferred embodiment R1 is C.sub.19 H.sub.39.
 In a preferred embodiment R1 is C.sub.7 H.sub.17.
 In a preferred embodiment R1 is C.sub.11 H.sub.23.
 In a preferred embodiment R1 is C.sub.17 H.sub.35.
 In a preferred embodiment R1 is C.sub.21 H.sub.43.

EXAMPLES
 CHLORO GLYCERIN
 Chloro glycerin is a raw material used in the preparation of the
 intermediate used to make the products of the present invention. It is an
 article of commerce available from Phoenix Chemical Somerville, N.J. and
 others.
 It conforms to the following structure:
EQU HO--CH.sub.2 --CH(OH)CH.sub.2 Cl
 It is also called alpha-monochlorohydrin, 3-chloro-1,2,-propanediol,
 3-chloro-1,2-dihydroxypropane, 3-chloro-propane glycol. It has a molecular
 weight 110.5, and is listed in the Merck Index.
 Polyphosphoric acid
 Polyphosphoric acid is an item of commerce. It is commercially available
 from a variety of sources. It is also called phospholeum, 115% phosphoric
 acid and tetraphosphoric acid. It is listed in the Merck Index.
 Preparation of chloro-glyceryl-phosphate
 The phosphation of chloro glycerine is carried out as follows:
 Example 1
 To a suitable vessel with good agitation is added 110.5 grams of
 chloroglycerin. The material is heated to 60.degree. C. Next, add 100.0
 grams of polyphosphoric acid. The polyphosphoric acid is very thick and is
 added slowly to insure the a uniform mixture. After the mixture becomes
 uniform heat to 90.degree. C. The mixture will clear. Hold at 90.degree.
 C.-100.degree. C. for 3 hours. The product is used without additional
 purification.
 Preparation of Glyceryl Phosphobetaines
 The chloro-glyceryl-phosphate (example 1) is reacted with an amido amine in
 aqueous solution at a pH of between 7 and 11, with a preferred pH of
 8.5-10.5.
 Amido Amines
 The amidoamine compounds of the present invention are items of commerce
 commercially available from Phoenix Chemical, Somerville, N.J. and others.
 Phoenix Chemical sells such products under the Catemol tradename.

Example 2 R1 is C.sub.7 H.sub.17.
 Example 3 R1 is C.sub.9 H.sub.19.
 Example 4 R1 is C.sub.13 H.sub.27.
 Example 5 R1 is C.sub.15 H.sub.31.
 Example 6 R1 is C.sub.19 H.sub.39.
 Example 7 R1 is C.sub.8 H.sub.17.
 Example 8 R1 is C.sub.11 H.sub.23.
 Example 9 R1 is C.sub.17 H.sub.35.
 Example 10 R1 is C.sub.21 H.sub.43.
 General Procedure
 To the specified number of grams of water is added 200.0 grams of
 chloro-glyceryl-phosphate (example 1) under good agitation. The batch is
 heated to 80.degree. C. Next, add the specified number of grams of the
 specified amido amine Example (2-10). The pH is adjusted to between 8.5
 and 10.5 with the specified base (KOH or NaOH). The temperature is then
 kept between 80-90.degree. C. and the pH is kept between 8.5 and 10.5 for
 about 6-8 hours. The reaction progress is monitored by inorganic chloride
 concentration. The reaction is considered complete when the amount of
 chloride ion reaches 98% of theoretical.