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Publication numberUS3331896 A
Publication typeGrant
Publication dateJul 18, 1967
Filing dateSep 15, 1964
Priority dateSep 15, 1964
Also published asDE1518948A1, DE1518948B2
Publication numberUS 3331896 A, US 3331896A, US-A-3331896, US3331896 A, US3331896A
InventorsJr Fred S Eiseman, Leslie M Schenck
Original AssigneeGen Aniline & Film Corp
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Method of preparing alkali soluble phosphate esters of hydroxylic organic compounds
US 3331896 A
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Description  (OCR text may contain errors)

United States Patent 3 331 896 METHOD or PREPARING ALkALr soLUBLE PHUSlPl-IATE ESTERS 0F HYDROXYLIC 0R- GANHC C(DMPOUNDS Fred S. Eiseman, .lr., Maplewood, and Leslie M. Schenck, Mountainside, Ni, assignors to General Aniline 8; Film Corporation, New York, N.Y., a corporation of Delaware No Drawing. Filed Sept. 15, 1964, Ser. No. 396,700 10 Claims. (Cl. 260-980) This invention relates to a method of preparing alkali soluble surface active compositions containing mixtures of primary and secondary phosphate esters of hydroxylic organic compounds.

It is known that hydroxylic organic compounds can be esterified with a number of diiferent phosphating agents including phosphoric acid, P 0 PCl POCI and the like. The use of phosphoric acid or solutions of P 0 in phosphoric acid as phosphating agent generally yields inconsistent mixtures of different types of esters, including esters of pyrophosphoric acid, phosphoric acid, primary, secondary and tertiary phosphates, and the like. When P 0 has been employed, considerably greater molar ratios of the hydroxy compounds were regarded as necessary to bring the solid P 0 into solution.

To eliminate the use of an excess of the hydroxylic organic compound, it has been proposed in US. Patent 3,004,056 to react 1 mole of P 0 With 2 to 4.5 moles of a nonionic surface active agent derived from the condensation of at least 1 mole of an alkylene oxide with 1 mole of a hydroxylic organic compound under substantially anhydrous conditions at a temperature below about 110 C. Substantially no tertiary phosphate ester is formed by this process and little or no P 0 remains in the composition. Depending upon the particular ratio of P 0 to the nonionic surface active agent employed, and the nature of such nonionic, the product contains from 30 to 80% of a primary ester, from to 45% of secondary ester and from 0 to 40% by weight of unreacted nonionic surface active agent which for certain uses is actually advantageous. The P 0 is employed in dry, solid form as a granular powder or other finely divided or particulate form. In the phosphating reaction with the nonionic surface active agent, the P 0 however, may be first dispersed in an inert diluent such as benzene, xylene, ether, pentane or low and high boiling hydrocarbon fractions.

The phosphation reaction can advantageously be carried out in the presence of a small or catalytic amount of phosphorous containing compound selected from the group consisting hypophosphorous acid, salts of hypophosphorous acid, phosphorous acid and salts and esters of phosphorous acid in an amount ranging from about 0.01 to 5% and preferably about 0.1 to 2% by Weight based on the weight of the nonionic surface active agent being phosphated as disclosed in US. Patent 3,004,057. When hypophosphorous acid is employed, it is preferred to use a to 50% aqueous solution thereof.

The phosphate esters of hydroxylic organic compounds prepared in accordance with the procedures described in aforementioned patent including US. 3,033,889 are all subject to the major disadvantage of being essentially insoluble in moderately concentrated solutions of aqueous alkali. This is true of practically all other surfactants such as oxyalkylene ethers of phenols or alcohols, or the sulfate esters of these ethers. Thus, their use in such operations as metal cleaning, kier boiling, bottle Washing, as mercerizing assistants, and the like has been severely limited.

It is the principal object of the present invention to ice provide a process for preparing alkali soluble phosphate esters of alcohols and of nonionic surface active agents.

Another object is to provide surface active compositions containing mixtures of primary and secondary phosphate esters of hydroxylic organic compounds which are soluble in moderately concentrated aqueous alkali, such solutions being useful as cleaning and Wetting agents.

Other objects and advantages will become evident from the following description.

We have discovered that the foregoing objects are attained by phosphating 0.3 to 1.5 moles of a hydroxy containing organic compound such as a branched or straight chain primary aliphatic alcohol of from 3 to 20 carbon atoms, a cycloaliphatic alcohol of from 4 to 8 carbon atoms, or one mole of a nonionic surface active agent having the molecular configuration of a condensation product of at least one mole of an alkylene oxide of from 2 to 4 carbon atoms with one mole of either an aliphatic primary alcohol of from 3 to 20 carbon atoms, cycloaliphatic alcohol of from 4 to 8 carbon atoms, phenol, alkyl phenol or aliphatic fatty acid of at least 8 carbon atoms, with 1 mole of P 0 as present in polyphosphoric acid at a temperature ranging from about room temperature to about C. A small amount of hypophosphorous acid, or its salts, may be used for color inhibition during the reaction. By the use of polyphosphoric acid, the resulting phosphate ester mixture is soluble to the extent of at least 1% in aqueous solutions of caustic soda, potassium hydroxide, lithium hydroxide, ammonium hydroxide, etc., of 13% to 30% concentration. The aqueous alkaline solutions of the phosphate ester mixture are especially adaptable as surface active agents in metal cleaning, kier boiling, bottle washing, mercerizing operations and other cleaning and wetting applications where an aqueous alkaline solution of a surface active agent is a prime requirement.

Inasmuch as the present invention is applicable as an improvement of the processes disclosed in US. Patents 3,004,056, 3,004,057 and 3,033,889, the entire subject matter of said patents is incorporated herein by reference thereto with respect to the nonionic surface active agents employed as reactants in the phosphation reaction, the conditions of reaction, and the manner of carrying out the reaction, all of which are employed in the present process by theme of 110%120% polyphosphoric acid as the phosphating agent.

As noted above, the aliphatic primary alcohols of from 3 to 20 carbon atoms include propanol, butanol, octanol, decanol, octadecanol, 2,3,4-trimethyl, pentanol, and the like. Cycloaliphatic alcohols such as cyclobu-tanol, cyclohexanol, cycloheptanol, etc., including ethyleneglycol monoalkyl ethers wherein the alkyl ether contains from 1 to 6 carbon atoms such as ethyleneglycolmonomethyl ether, -monoethyl ether, -monopropyl ether, -monobutyl ether, -monoamyl ether and -monohexyl ether. The branched chain aliphatic alcohols which may be used in lieu of straight chain primary aliphatic alcohols are those of the type incorporated in US. Patent 3,033,889, the entire disclosure of which is incorporated herein by reference thereto.

The polyphosphoric acid utilized as the phosphating agent in accordance with the present invention is an equilibrium mixture of orthophosphoric, pyrophosphoric and higher linear phosphoric acids. The polyphosphoric acids commercially available range from 110% to 120% H PO and contain from about 80% to 86.5% P 0 Superphosphoric is equivalent to 105% H PO containing 76% P 0 Ordinary phosphoric acid ranges from 75% to 85% H PO containing from 54 to 61.5% of P 0 The following table shows, by commercial analyses, the percent of the H PO content aswell as the percent of P available in 110% to 120% polyphosphoricacid:

The monionic surface active agents employed as reactants with the 1l0%-120% polyphosphoric acid are well known in the art and disclosed not only in the aforementioned patents-but in numerous other patents and publica tions. In general they are obtained by reacting atleast 1 mole of an alkylene oxide such as ethylene oxide, propylene oxide, butylene oxide and the like with 1 mole of an aliphatic alcohol, phenol, alkylated phenol or alphatic fatty acid. Numerous compounds of this type are described in US. Patents 2,213,477 and 2,593,112, the entire subject matter of said patents being incorporated herein by reference thereto as showing polyalkylene. oxide derivatives of phenolic compounds in which the total number of alkyl carbon atoms is between 4 and 20. As examples of such phenolic compounds may be mentioned normal and isomeric butyl, amyl, dibutyl, and diamyl phenols and cresols, tripropyl phenols and cresols, heptyl, octyl, nonyl,

decyl, unde-cyl, dodecyl, tetradecyl, cetyl, oleyl, octadecyl, and the like, phenols and cresols in addition to dihexyland trihexyl-phenol prepared from hexene-l and phenol, diisoheptyl phenol, dioctyl phenol, dinonyl phenol, dioctyl-p-cresol, dioctylocresol, didecyl-phenol, didecylp-cresol, didodecyl-phenol, and the like. Of particular value are the polyalkylene oxide derivatives of secondary and tertiary alkyl substituted phenols and cresols obtained by condensing olefins of the type obtained in petroleum refining with phenols or cresols. In the case of products obtained by condensing phenol or cresol with olefins of from 3 to 5 carbon atoms such as .propylene, butylene or amylene, it is sometimes desirable to employ the dialkylated phenols or cresols, while in the case of compounds obtained by condensing a phenol or cresol with an olefin containing 8 or more carbon atoms, the mono-substituted derivatives are sometimes preferred. Particularly desirable derivatives can be obtained fromthe phenols and cresols containing a substituent derived from olefinscontaining from 8 to 18 carbon atoms such as diisobutylene and other alkylenes such as nonylene, decylene, undecylene, dodecylene, pentadecylene, octadecylene and mixtures thereof, and may advantageously be the dimers and trirners obtained by polymerization of such low molecular weight olefins as propylene, butylene, isobutylene, amylene or mixtures thereof.

The polyalkylene oxide derivatives described in U.S. Patent 1,970,578 are particularly adaptable to the method of the present invention. As examples of aliphatic fatty acids, both saturated and unsaturated, whose polyalkylene oxide derivatives may be phosphated in accordance with the present invention include those derivatives prepared from caprylic,lauric, oleic, ricinoleic, palmitic, stearic, behenic acid, erucic and the like, or mixtures thereof, such as the mixtures obtained from animal and vegetable fats and oils ,or by the oxidation of such petroleum fractions as paraflin wax.

Another group of nonionic surface active agents which may be phosphated are those of the Pluronic type as disclosed for example in US. Patent 2,674,619 and other patents-In general, in preparing these agents a suitable.

1,2-alkylene oxide or substituted alkylene oxide, as for example butylene oxide, amylene oxide, phenyl ethylene oxide (oxystyrene), cyclohexene oxide, cyclooctene oxide,

or preferably propylene oxide, ora mixture thereof, is

polymerized in the presence of an alkaline catalyst such as sodium hydroxide, preferably at elevated temperatures and pressures to produce the corresponding water insoluble' polypropylene glycol or substituted polypropylene glycol having a molecular weight of about 300 to 3,000. The resulting polyglycol is then reacted under similar conditions with the required number of moles of ethylene oxide to yield the desired nonionic surface active agent which is then'phosphated. These. polyglycols. should generally have a molecular weight ranging from about 1,200 to 15,000and preferably about 2,000 to 10,000. Alternatively, ethylene diamine, propylene diamine, other alkylene diamines and polyalkylene polyamines, in addition to ethylene glycol, propylene glycol, 1,4-butanediol, hexamethylene glycoland other diols may be reacted with the required number of moles of propylene oxide or substituted propylene oxide to produce, the corresponding water-insoluble polypropylene glycols and substituted polypropylene glycols having a molecular weight of about 300 to 3,000 as described above, followed by reaction with the required number of moles of ethylene oxide. It will be understood that these Pluronic types of nonionic surface active agent will ordinarily be of the diol type containing two terminal hydroxy (ethanol) groups. Both of these terminal hydroxy groups may be alkoxylated,

preferably ethoxylated, and then phosphated in accord-.

ples it is to be noted that the reaction product consists of a mixture containing from about 70% to about of monoester, from about 9% to about 28% of diester and from about 0.1% to about 12% of-unreacted nonionic surface active agent or unreacted aliphatic alcohol. These components are characterized by the following general formulae:

unreacted nonionic surface active agent or unreacted aliphatic alcohol wherein R is the residue of an aliphatic or aromatic compound which contained a reactive hydrogen atom or the residue of an aliphatic alcohol, and n represents either zero or an integer of from 1 to 20.

EXAMPLE I A'total of 340 grams of polyphosphoric acid (containing 2 moles of P 0 were added to 436 grams (2.0 moles) of the condensation product of one mole of isooctyl alcohol with 2 moles: of ethylene oxide over a period of one hour. Temperature was held below 70 C. with external cooling. Following the addition, the charge was heated to 90-95? C. and held at this temperature for four hours.

Product was soluble to the extent of 1% in 20% aqueous caustic soda.

Percent Monoester 89.8 Diester 8.9 Nonionic 1.9

Wetting time by AATCC STM 43l9523 min. at 1% in 20% NaOH.

5 EXAMPLE u A total of 212 grams of 115% polyphosphoric acid (containing 1.25 moles of P were added to 654 grams (3.0 moles) of the condensation product of one mole of isooctyl alcohol with 2 moles of ethylene oxide over a period of one hour. Temperature was held below 70 C. with external cooling. Following the addition, the charge was heated to 90-95" C. and held at this temperature for four hours.

Product was insoluble in 13% aqueous caustic soda.

Percent Monoester 77.0 Diester 6.1 Nonionic 16.2

From the foregoing example, it is clearly apparent that by deviation from the limits of mole ratio of the nonionic surface active agents prescribed above, the resulting reaction product is insoluble in the aqueous caustic soda.

EXAMPLE III A total of 117 grams of 115% superphosphoric acid (containing 0.625 mole of P 0 were added to 327 grams (1.5 moles) of the condensation product of one mole of isooctyl alcohol with 2 moles of ethylene oxide over a period of one hour. Temperature was held below 70 C. with external cooling. Following the addition, the charge was heated to 9095 C. and held at this temperature for four hours.

Product was insoluble in 13% aqueous caustic soda.

Percent Monoester 76.7

Diester Nonionic 33.2

The above example shows that by deviation from the limits of mole ration of the nonionic surface active agents prescribed above, the resulting reaction product is insoluble in aqueous caustic soda.

EXAMPLE IV A total of 170 grams of 115 polyphosphoric acid (containing 1 mole of P 0 were added to 598 grams (1.0 mole) of the condensation product of one mole of decyl alcohol with moles of ethylene oxide in the presence of 2.0 grams hypophosp-horous acid over a period of one hour. Temperature was held below 70 C. with external cooling. Following the addition, the charge was heated to 90-95 C. and held at this temperature for four hours.

Product was soluble to the extent of 1% in 13% aquer ous caustic soda.

Percent Monoester 85.2 Diester 12.1 Nonionic 2.9

EXAMPLE V A total of 187 grams of 105% superphosphoric acid (containing 1 mole of P 0 were added to 598 grams (1.0 mole) of the condensation product of one mole of decyl alcohol with 10 moles of ethylene oxide in the presence of 2.0 grams hypophosphorous acid over a period of one hour. Temperature was held below 7 0 C. with external cooling. Following the addition, the charge was heated to 90-95" C. and held at this temperature for four hours.

Product was insoluble in 13% aqueous caustic soda.

Percent Monoester 54.0 Diester 5.9 Nonionic 42.0

The above example also shows that by employing a superphosphoric acid of a lower percent of P 0 a reaction product is obtained which is insoluble in aqueous caustic soda.

6 EXAMPLE VI Percent Monoester 83.5 Diester 5.9 Nonionic 6.2

EXAMPLE VII A total of 220 grams of 115% polyphosphoric acid (containing 1.3 moles of P 0 were added to 605 grams (1.3 moles) of the condensation product of one mole of tridecyl alcohol with 6 moles of ethylene oxide over a period of one hour. Temperature was held below 70 C. with external cooling. Following the addition, the charge was heated to '95 C. and held at this temperature for four hours.

Product was soluble to the extent of 1% in 13% aqueous caustic soda.

Percent Monoester 77.8 Diester 19.3 Nonionic 1.6

EXAMPLE VIII A total of 127 grams of 115% polyphosphoric acid (containing 0.75 mole of P 0 were added to 645 grams (0.75 mole) of the condensation product of one mole of tridecyl alcohol with 15 moles of ethylene oxide over a period of one hour. Temperature was held below 70 C. with external cooling. Following the addition, the charge wa heated to 90-95 C. and held at this temperature for four hours.

Product was soluble to the extent of 1% in 13% aqueous caustic soda.

Percent Monoester 79.0 Diester 9.0 Nonionic 11.9

EXAMPLE IX A total of 300 grams of superphosphoric acid (containing 1.6 moles of P 0 were added to 457 grams (1.6 moles) of the condensation product of one mole of nonyl phenol with 1.5 moles of ethylene oxide over a period of one hour. Temperature was held below 70 C. with external cooling. Following the addition, the charge was heated to 9095 C. and held at thi temperature for four hours.

Product was insoluble in 13% aqueous caustic soda.

Percent Monoester 69.8 Diester 18.9 Nonionic 21.0

From the foregoing example it is again apparent that by employing superphosphoric acid of a lower percent of P 0 the resulting reaction product is insoluble in aqueous caustic soda.

EXAMPLE X A total of 170 grams of polyphosphoric acid (containing one mole of P 0 were added to 306 grams (0.5 mole) of the condensation product of one mole of nonyl phenol with 9 moles of ethylene oxide over a period of one hour. Temperature was held below 70 C. with external cooling. Following the addition, the charge 7 was heated to 90-95" C. and held at this temperature for four hours.

Product was soluble to the extent of 1% in 13% aqueous caustic soda.

Percent Monoester 91.0 Diester 8.7 Nonionic 0.6

EXAMPLE XI A total of 170-grams of 115% polyphosphoric acid (containing one mole of P were added to 459 grams (0.75 mole) of thecoudensation product of one mole ofv nonyl phenolwith 9 moles of ethylene oxide over a period of one hour. Temperature was held below 70 C. with external cooling. Following the addition, the charge was heated to 90-95 C. and held at this temperature for four hours.

Product was soluble to the extent of 1% in 13% aqueous caustic soda.

Percent Monoester 89.4 Diester M 10.1 Nonionic 0.9

EXAMPLE XII A total of 170 grams of 115% polyphosphoric acid (containing one mole of P 0 were added to 612 grams (1.0, mole) of the condensation product of one mole of nonyl phenol with 9 moles of. ethylene oxide over a period of one hour. Temperature was held below 70 C. with external cooling. Following the addition, the charge a was heated to 90--95 C. and held at this temperature for four hours.

Product was soluble to the extent of 1% in 13% aqueous caustic soda.

Percent Monoester 87.3 Diester 9.3 Nonionic 4.2

EXAMPLE XIII Percent Monoester 74.0 Diester 21.7 Noni-onic 4.6

EXAMPLE XIV A total of 340 grams of 115% polyphosphoric acid (containing 2 moles of P 0 were added to 464 grams (2.0 moles) of the condensation product of one mole of cyclohexanol with 3 moles of ethylene oxide over a period of one hour. Temperature was held below 70C. with external cooling. Following. the addition, the charge was heated to 90-95 C. and held at this temperature for four hours.

Product was soluble to the extent of 1% in 13% aqueous caustic soda.

Percent Monoester 76.5

Diester 20.1 Nonionic 9.2

EXAMPLE XV A total of 510 grams of 115% poly phosphoric acid (containing 3 moles of P 0 were added to 354 grams (3.0 moles) of the condensation product of one mole of butyl alcohol with 1 mole of ethylene oxide over a period of one hour. Temperature was held below 70 C.,

with external cooling. Following the addition, the charge was heated to -95 C. and held at this temperature for four hours.

Product was solubleto the extent of 1% in 30%.

aqueous caustic soda.

Percent Monoester 71.0 Diester 27.2 Nonionic 0.1v

Wetting time by AATCC STM 43-19526 sec. at 1% in 20% NaOH; 8 sec. at, /2%.

EXAMPLE XVI I A total of 425 grams of polyphosphoric acid (containing 2.5 moles of P 0 were added to 405 grams (2.5 moles) of the condensation product of one mole of 'butyl alcohol with 2 moles of ethylene oxide over a period of one hour. Temperature was held below 70 C. with external cooling. Following the addition, the-charge was heated to 9095 C. and held at this temperature for four hours.

Product was soluble to extent of 1% in 30% aqueous caustic soda.

Percent Monoester 73.8 Diester 27.2 Nonionic 0.1-

Wetting time by AATCC STM -'431952.7 sccpat 1% in 20% NaOH; 20 sec. at /2%.

EXAMPLE XVII A total of 408 grams of 115 polyphosphoric acid (containing 2.4 moles of P 0 were added to 370 grams (2.4 moles) of the condensation product of one mole of isoamyl alcohol with 1.5 moles of ethylene oxide over a period of one hour. Temperature was held below 70 C. with external cooling. Following the addition, the charge was heated to 9095 C. and held at this temperature for four hours.

Product was soluble to extentof 1% in 30% aqueous caustic soda.

Percent, Monoester 78.0 Diester 22.2 Nonionic 0.4

Wetting time by AATCC STM 43195212 sec. at 1% in 20% NaOH.

EXAMPLE XVIII A total of 355 grams of 115 .polyphosphoric acid (containing 2.1 moles of P 0 were added to 416 grams (21 moles) of the condensation product of one mole of isoamyl alcohol with 25 moles of ethylene oxide over a period of one hour. Temperature was held below 70 C. with external cooling. Following the addition, the charge was heated to 90-95 C. and held at this temperature for four hours. a

Product was soluble to extent of 1% in 30% aqueous caustic soda.

Percent Monoester 75.8 Diester 22.5 Nonionic 0.4

Wetting time by AATCC STM 43-195224 sec. at 1% in 20% NaOH.

EXAMPLE XIX A total of 340 grams of 115% polyphosphoric acid (containing 2 moles of P 0 were added to 176 grams (2.0 moles) of isoamyl alcohol over a period of one hour. Temperature was held below 70 C. with external cool- Following the addition, the charge was heated to 9095 C. and held at this temperature for four hours. Product was soluble to extent of 1% in 20% aqueous caustic soda.

Wetting time by AATCC STM 43195246 sec. at 1% in 20% NaOH.

EXAMPLE XX A total of 272 grams of 115% polyphosphoric acid (containing 1.6 moles of P 0 were added to 122 grams (1.6 moles) of methyl Cellosolve over a period of one hour. Temperature was held below 70 C. with external cooling. Following the addition, the charge was heated to 9095 C. and held at this temperature for four hours.

Product was soluble to the extent of 1% in 20% aqueous caustic soda.

Percent Monoester 76.6 Diester 16.8 Methyl Cellosolve 7.7

Wetting time by AATCC STM 4319525 min. at 1% in 20% NaOH.

EXAMPLE XXI A total of 272 grams of 115% polyphosphoric acid (containing 1.6 moles of P 0 were added to 144 grams (1.6 moles) of ethyl Cellosolve over a period of one hour. Temperature was held below 70 C. with external cooling. Following the addition, the charge was heated to 9095 C. and held at this temperature for four hours.

Product was soluble to the extent of 1% in 20% aqueous caustic soda.

Percent Monoester 75.3 Diester 19.6 Ethyl Cellosolve 4.7

Wetting time by AATCC STM 431952-5 min. at 1% in 20%.

EXAMPLE XXII Percent Monoester 84.1 Diester 14.2 Nonionic 1.7

EXAMPLE XXIII Example XXII was repeated with the exception that following the addition, the charge was held at 30-35 C. for six hours.

Product was soluble to the extent of 1% in 13% aqueous caustic soda.

Percent Monoester 86.4 Diester 11.3 Nonionic 3.1

EXAMPLE XXIV A total of 170 grams of 115% polyphosphoric acid (containing 1 mole of P 0 were added to 521 grams (1 mole) of the condensation product of 1 mole of oleic acid with 5.43 moles of ethylene oxide over a period of one hour. Temperature was held below 70 C. with external cooling. Following the addition, the charge was 10 heated to 95 C. and held at this temperature for four hours.

Product was soluble to the extent of 1% in 20% aqueous caustic soda.

Percent Monoester 81.0

Diester 8.0

Nonionic 12.6

We claim:

1. The process of preparing alkali soluble phosphate esters of hydroxylic organic compounds which comprises reacting 1 mole of P 0 as present in %120% polyphosphoric acid with 0.3 to 1.5 moles of a hydroxylic organic compound selected from the group consisting of primary aliphatic alcohols from 3 to 5 carbon atoms, cycloaliphatic alcohols of from 4 to 5 carbon atoms, ethyleneglycol monoalkyl ethers wherein the monoalkyl group contains from 1 to 5 carbon atoms, and a nonionic surface active agent having the molecular configuration of a condensation product of at least 1 mole of an alkylene oxide of from 2 to 4 carbon atoms with 1 mole of a hydroxylic organic compound selected from the group consisting of a primary aliphatic alcohol of from 3 to 5 carbon atoms, cycloaliphatic alcohol of from 4 t0 5 carbon atoms, at a temperature of about C. down to about room temperature.

2. A process as defined in claim 1 wherein said hydroxylic organic compound is ethyleneglycol monoethyl ether.

3. A process as defined in claim 1 wherein said hydroxylic organic compound is isoamyl alcohol.

4. A process as defined in claim 1 wherein said hydroxylic organic compound is a nonionic surface active agent having the molecular configuration of a condensation product of one mole of butyl alcohol with two moles of ethylene oxide.

5. A process as defined in claim 1 wherein said bydroxylic organic compound is a nonionic surface active agent having the molecular configuration of a condensation product of 1 mole of isoamyl alcohol with 2.5 moles of ethylene oxide.

6. A process as defined in claim 1 wherein said hydroxylic organic compound is a nonionic surface active agent having the molecular configuration of a condensation product of 1 mole of butyl alcohol with 1 mole of ethylene oxide.

7. A process as defined in claim 1 wherein said hydroxylic organic compound is a nonionic surface active agent having the molecular configuration of a condensation product of 1 mole of isoamyl alcohol with 1.5 moles of ethylene oxide.

8. The process of preparing alkali soluble phosphate esters of cycloaliphatic alcohol which comprises reacting 1 mole of P 0 as present in 110%120% polyphosphoric acid with 0.3 to 1.5 moles of a cycloaliphatic alcohol of from 4 to 5 carbon atoms at a temperature of about 145 C. down to about room temperature.

9. The process of preparing alkali soluble phosphate esters of hydroxylic organic compounds which comprises reacting one mole of P 0 as present in 110%120% polyphosphoric acid with 0.3 to 1.5 moles of ethylene glycol monoalkyl ether, wherein the monoalkyl ether group contains from 1 to 5 carbon atoms, at a temperature of about 145 C. down to about room temperature.

10. The process according to claim 9 wherein the ethylene glycol monoalkyl ether is ethylene glycol monobutyl ether.

References Cited UNITED STATES PATENTS 3,004,056 10/1961 Nunn et al. 260-950 3,004,057 10/1961 Nunn 260- 980 CHARLES B. PARKER, Primary Examiner. A. H. SUTTO, Assistant Examiner.

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US3004056 *Nov 12, 1959Oct 10, 1961Gen Aniline & Film CorpSurface active compositions
US3004057 *Dec 1, 1959Oct 10, 1961Gen Aniline & Film CorpSurface active compositions
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US3397051 *May 5, 1966Aug 13, 1968Gaf CorpHerbicidal concentrate composition
US3450803 *Apr 4, 1966Jun 17, 1969Upjohn CoPreparation of poly (hydroxypropyl) polyphosphates
US3532632 *Feb 10, 1967Oct 6, 1970Gaf CorpHydraulic fluids containing nonionic surface action agents and phosphate esters of nonionic surface active agents
US3686371 *May 22, 1969Aug 22, 1972Tadashi HasegawaMethod for producing copolymerizable compound containing functional group of phosphoric acid
US3787319 *Oct 18, 1971Jan 22, 1974Marathon Oil CoAmine/phosphate composition useful as corrosion and scale inhibitor
US4137190 *Apr 4, 1977Jan 30, 1979Gaf CorporationDetergent composition comprising synergistic hydrotrope mixture of two classes of organic phosphate esters
US4152289 *Jul 15, 1977May 1, 1979The Dow Chemical CompanyGelling of organic liquids
US4153649 *Jul 15, 1977May 8, 1979The Dow Chemical CompanyPhosphoric anhydride, hydroxy ether, alcohol, thickening kerosene
US4174283 *Jul 15, 1977Nov 13, 1979The Dow Chemical CompanyPhosphoric ester, aluminum activator, thickening
US4316810 *Jan 7, 1980Feb 23, 1982Halliburton CompanyGelled oil base compositions and methods of preparation and use of same
US4350645 *Nov 25, 1980Sep 21, 1982Kao Soap Co., Ltd.Method for producing a phosphoric monoester
US4493782 *Jul 7, 1983Jan 15, 1985Amchem Products, Inc.Cleansing compositions comprising ethoxylated alcohol monoesters of phosphoric acid
US6410613 *Aug 25, 1998Jun 25, 2002Kureha Kagaku Kogyo Kabushiki KaishaPhosphate compound and preparation process thereof, phosphate copper compound and preparation process thereof, near infrared ray absorber, and near infrared ray-absorbing acrylic resin composition
US6512133 *Oct 25, 2000Jan 28, 2003Chemische Fabrik Budenheim RudolfProcess for the production of phosphoric acid esters or phosphoric acid ester mixtures of polyhydric alcohols and use thereof
US7785462Apr 16, 2010Aug 31, 2010Vary Petrochem, LlcSeparating compositions and methods of use
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US8062512Dec 31, 2009Nov 22, 2011Vary Petrochem, LlcProcesses for bitumen separation
US8147680Nov 23, 2010Apr 3, 2012Vary Petrochem, LlcSeparating compositions
US8147681Nov 23, 2010Apr 3, 2012Vary Petrochem, LlcSeparating compositions
US8268165Nov 18, 2011Sep 18, 2012Vary Petrochem, LlcProcesses for bitumen separation
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Classifications
U.S. Classification558/110, 987/224, 510/469, 558/114, 987/226
International ClassificationC11D1/34, C07F9/08, C07F9/09
Cooperative ClassificationC07F9/09, C07F9/098, C11D1/345, C07F9/091, C07F9/08
European ClassificationC07F9/09A1, C07F9/09B, C07F9/08, C11D1/34C, C07F9/09