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UNITED STATES PATENT OFFICE 2,128,946 TETRAPHOSPHORCAC) ESTERS Morris B

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UNITED STATES PATENT OFFICE 2,128,946 TETRAPHOSPHORCAC) ESTERS Morris B - if 3 {: 3 S ; 4 £, A2) g f sub. Patented Sep 8, 1938 2,128,946 care." UNITED STATES PATENT OFFICE 2,128,946 TETRAPHOSPHORCAC) ESTERS Morris B. Katzman, Chicago, Ill. No Drawing. Application April 9, 1937, Serial No. 135,931 23 (Claims. (C. 260-46) My invention relates to a new class of chemi More specifically, the most preferable of the cal substances. It relates more in particular to compounds of my invention may be defined as . a class of chemical, substances having the prop tetraphosphoric acid esters of polyhydroxy sub erties of interface modifiers as, for example, when stances wherein at least one hydroxy group of employed in a treating bath containing textile, the polyhydroxy substance has its hydrogen sub leather or ores. Many of the compounds of my stituted by a lipophile group. The lipophile group 5 invention are also effective to decrease the spat- nay include any organic acid group, particular tering of margarine, to increase the oiliness of ly fatty acid groups having preferably at least lubricating oils and greases, such as are derived four carbon atoms such as the fatty acid radi O from mineral oils, to act as emulsifying agents calls of the following acids: caproic acid, capric, O for cosmetic and other emulsions, to reduce vis- caprylic, valeric, butyric, abietic, naphthenic, hy cosity of chocolate and the like, to retard the droxystearic, benzoic, benzoylbenzoic, naphthoic, rancidification of oils, fats, and vitamin prepara- toluic, higher molecular weight saturated and tions which are subject to deterioration by oxi- unsaturated fatty acids including palmitic acid, dation, to act as assistants in the textile and re- Stearic, lauric, melissic, oleic, myristic, ricinoleic, 5 5 lated industries and, in general, to function linoleic acid or mixed fatty acids derived from wherever interface modification is sought or de- animal or vegetable fats and fish oils such as sired. lard, oleo oil, coconut oil, corn oil, cottonseed The substances of my invention have many oil, partially or completely hydrogenated vege useful application in the arts where frothing, table oils such as cottonseed oil, corn oil, sesame 20 20 foaming, wetting, penetrating, detergent, emul- oil and fatty acids of various waxes such as bees sifying, and other interface modifying functions Wax and carnauba waX; or the lipophile group. are required. They are in general possessed of may be an alkyl radical derived from an alcohol t at least two groups, one having a hydrophile corresponding to any of the preceding acids, such function and the other having a lipophile func- as octanol, cetyl alcohol, stearyl alcohol, oleyl 25 tion in the molecule. The hydrophile function alcohol, lauryl alcohol, higher saturated and un- 25 is performed primarily by a tetra-phosphoric Saturated aliphatic alcohols derived from natural acid or tetraphosphate group, giving the mole- fats and oils, cholesterol, Sperm oil, etc. cule as a whole an affinity for aqueous materials. Specific examples of polyhydroxy substances, The lipophile group is any radical having a defl- the residues of which may serve as linkages be 30 nite affinity for oils and fats and may comprise tween the lipophile groups, and the hydrophile 30 radicals such as acyl or alkyl derived from a fatty tetraphosphate groups, besides those previously acid or its corresponding alcohol. The hydro- mentioned, are as follows: mucic acid, tartaric phile tetraphosphate group may be and prefer- acid saccharic acid, gluconic. acid, glucuronic ably is linked to the lipophile group by means acid, gulonic acid, mannoic acid, trihydroxyglu 35 of a polyhydroxy substance. I have found poly- taric acid, glyceric acid, and the like, as well as 35 hydroxy substances such as sugars, sugar alco- carboxylic oxidation products of polyglycerols hols, glycols, polyglycols, glycerol, polyglycerols, which may be represented by the formulae: and hydroxycarboxylic acids to be particularly QH OE. O. 40 substancesuitable. Anand ester the linkagetetraphosphate joins the polyhydroxygroup. The Ho-Cio-Cio-Cio-C-OH 40 linkage between the polyhydroxy substance and gh OE O. O. the lipophile group may be either an ester or Ho-CII-bil-CH-O-CH-CH-CH-0-cr-en-3-oh ether linkage. cated,All ofare the esters products of tetraphosphoric of my invention, acid, as which indi- Ho-Chi-CH-CH-OH Ho-CH-CH-6-OH 45 acid may be represented by the following struc tural formula: CH, ch, rO > O N / O -C-OH E-C-OE 50 Ho-r o=d-OH Hid-oh 50 go O OB pH 9 Ho-r Ho-5-bH-CH-O-CH-bH-E-OH p (Jo O OH OE OH. O 55 O) HO-PN HO-C-CH-CH-O-CH-CH-CH-O-C-C-C-OH8-d &H-CH: bH s go O OH OH O . t HO-P/ IO-C-CH-CH-O-C-CH-CH-O-C-C-OI and sugars such as: xylose, galactose, fructose, 60 2 2,128,946 maltose, glucose, sorbitol, dulcitol, arabitol and 28. Tetraphosphoric acid ester of octyl alcohol. other sugar alcohols such as hexahydric alco 29. Tetraphosphoric acid ester of lauryl alcohol. hols derived from sugars, and other substances 30. Tetraphosphoric acid ester of oleyl alcohol. having free hydroxy groups. The above poly 31. Tetraphosphoric acid ester of steary glycerols and their oxidation products are pro alcohol. duced by polymerizing glycerine, preferably by 32. Tetraphosphoric acid esters of mixture of heating with about 1% of alkali at temperatures alcohols derived from reduction of sperm from 250 C. to 260 C. for about three hours in oil. the presence of an inert gas. This reaction mix 33. Tetraphosphoric acid esters of mixture of O ture will give a mixture of various polyglycerols, alcohols derived from reduction of cocoa O the size of the molecules depending upon the nut oil. time of polymerization. The mixture of poly 34. Tetraphosphoric acid ester of ricinoley glycerols is then oxidized with mild oxidizing alcohol. agents to convert at least one of the primary hy 35. Tetraphosphoric acid ester of butyl alcohol. 5 droxy groups to a carboxylic group, 36. Tetraphosphoric acid ester of cholesterol. Examples of Substances of my invention are as The procedural details of the methods by follows: means of which the materials of my invention 1. Tetraphosphoric acid ester of mono-olein, may be made may be varied. The exact method ammonium salt. employed should be determined primarily by con 2. Tetraphosphoric acid ester of diethylene Sidering the type of reacting constituents and 20 glycol mono-ricinoleate, triethanolamine the final Substance to be produced. In introduc salt. & ing the tetraphosphate radical, for example, a Tetraphosphoric acid ester of mono-aurin, material containing an esterifiable hydroxy group SOdium salt. is reacted with tetraphosphoric acid. Either one 25 Tetraphosphoric acid ester of mono-acetin, or more tetraphosphate radicals may be intro 25 Sodium salt. duced, depending upon the Substance desired. Tetraphosphoric acid ester of di-butyrin, Furthermore, the molal ratios of the reacting Sodium salt. constituents may be varied to produce products Tetraphosphoric acid ester of cetyl ether of having varied properties. A condensing agent 30 SOrbitol. and/or a solvent may be added where required. 30 Tetraphosphoric acid ester of ethylene gly In order that those skilled in the art may even Col. In Ono-Stearate. more fully understand the scope of my invention, 8. Tetraphosphoric acid ester of ethyl ether of I shall describe various specific embodiments of ethylene glycol. my invention in detail. It is to be understood, 35 9. Tetraphosphoric acid ester of octanoic acid however, that the following examples are given ester of diethylene glycol. dnly by Way of illustration and are not to be con 10. Tetraphosphoric acid ester of mixed cocoa strued as limitative of the true scope of my in nut oil fatty acid estér of diethylene glycol, vention which is set out in the appended claims. ammonium salt. W It is evident that proportions of reacting in 40 11. Tetraphosphoric acid ester of butyl ether of gredients, temperatures of reaction, time of re diethylene glycol, Sodium salt. action, and the like represent factors which may 40 12. Tetraphosphoric acid ester of sucrose mono be varied, all Within the skill of those versed in the Oleate, Sodium salt. art in the light of my teachings herein. 13. Tetraphosphoric acid ester of mixed cocoa Eacample I 45 nut oil fatty acid mono- or diglycerides or mixtures of mono- and diglycerides, am 50 parts by weight of monostearin were heated monium or triethanolamine Saits. to 90 degrees C. and to Said monostearin was 14. Di-tetraphosphoric acid ester of sucrose di added slowly, while stirring, 50 parts by weight stearate, ammonium salt. of tetraphosphoric acid, previously heated to 90 50 15. Tetraphosphoric acid ester of mono-oleic degrees C. The temperature rose to about 115 acid ester of diglycerol, sodium salt. degrees C. and the mass became viscousand light 50 16. Tetraphosphoric acid ester of mono-octyl brown in color. Stirring was continued for sev ether of glycerol, potassium salt. eral minutes until the product cooled down to ap 17. Tetraphosphoric acid ester of di-caproin, proximately 90 degrees C. When the reaction 55 SOdin Salt. mixture begins to drop in temperature, it is an 18. Di-tetraphosphoric acid ester of mono indication that at least the major portion of the 55 cetylglycerol, potassium salt. reaction has proceeded to completion. The final 19. Tetraphosphoric acid ester of lauryl ether product, which was practically odorless, very sub of diethylene glycol, sodium salt. stantially reduced the spattering of margarine 60 20. Tetraphosphoric acid ester of mono-melis and likewise reduced the Surface tension of water. sic acid ester of mannitol, ammonium salt.
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