US2931835A - Quaternary phosphonium polyphosphates - Google Patents
Quaternary phosphonium polyphosphates Download PDFInfo
- Publication number
- US2931835A US2931835A US576758A US57675856A US2931835A US 2931835 A US2931835 A US 2931835A US 576758 A US576758 A US 576758A US 57675856 A US57675856 A US 57675856A US 2931835 A US2931835 A US 2931835A
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- US
- United States
- Prior art keywords
- polyphosphate
- quaternary phosphonium
- phosphonium
- cations
- solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 239000001205 polyphosphate Substances 0.000 title claims description 24
- 229920000388 Polyphosphate Polymers 0.000 title claims description 23
- 235000011176 polyphosphates Nutrition 0.000 title claims description 23
- 125000005496 phosphonium group Chemical group 0.000 title description 9
- -1 PHOSPHONIUM CATIONS Chemical class 0.000 claims description 13
- 150000001768 cations Chemical class 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- 150000004714 phosphonium salts Chemical group 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910001414 potassium ion Inorganic materials 0.000 claims description 2
- 229910001415 sodium ion Inorganic materials 0.000 claims description 2
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical group [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 14
- OQZCJRJRGMMSGK-UHFFFAOYSA-M potassium metaphosphate Chemical compound [K+].[O-]P(=O)=O OQZCJRJRGMMSGK-UHFFFAOYSA-M 0.000 description 13
- 235000019828 potassium polyphosphate Nutrition 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 12
- 239000000314 lubricant Substances 0.000 description 12
- 150000003254 radicals Chemical class 0.000 description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
- 235000002639 sodium chloride Nutrition 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000003729 cation exchange resin Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- NIHVNKYHRZLDMR-UHFFFAOYSA-N hexadecyl(tripropyl)phosphanium Chemical compound CCCCCCCCCCCCCCCC[P+](CCC)(CCC)CCC NIHVNKYHRZLDMR-UHFFFAOYSA-N 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910000963 austenitic stainless steel Inorganic materials 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 229960002668 sodium chloride Drugs 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical class [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 229910001209 Low-carbon steel Inorganic materials 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- MTHGNUJZMIVGLC-UHFFFAOYSA-N didecyl(dimethyl)phosphanium Chemical compound CCCCCCCCCC[P+](C)(C)CCCCCCCCCC MTHGNUJZMIVGLC-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- QPFQQVUSISSKRU-UHFFFAOYSA-M hexadecyl(tripropyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](CCC)(CCC)CCC QPFQQVUSISSKRU-UHFFFAOYSA-M 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910001867 inorganic solvent Inorganic materials 0.000 description 1
- 239000003049 inorganic solvent Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- CBFCDTFDPHXCNY-UHFFFAOYSA-N octyldodecane Natural products CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229920001921 poly-methyl-phenyl-siloxane Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- FQLQNUZHYYPPBT-UHFFFAOYSA-N potassium;azane Chemical compound N.[K+] FQLQNUZHYYPPBT-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- DAUOXRUBCACRRL-UHFFFAOYSA-N tetradecylphosphane Chemical compound CCCCCCCCCCCCCCP DAUOXRUBCACRRL-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J47/00—Ion-exchange processes in general; Apparatus therefor
- B01J47/016—Modification or after-treatment of ion-exchangers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
-
- C—CHEMISTRY; METALLURGY
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- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/40—Fatty vegetable or animal oils
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/40—Fatty vegetable or animal oils
- C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
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- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
- C10M2211/024—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aromatic
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- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/06—Perfluorinated compounds
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- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
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- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
- C10M2223/061—Metal salts
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- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
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- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/043—Siloxanes with specific structure containing carbon-to-carbon double bonds
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/044—Siloxanes with specific structure containing silicon-to-hydrogen bonds
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/10—Semi-solids; greasy
Definitions
- This invention relates to quaternary phosphonium polyphosphate compounds which are new compounds.
- a quaternary phosphonium polyphosphate salt having (E D k units forming substantially linear groups, each (F5 unit being associated with a' cation, a major pro-' potassium or other cations associated with the (P0 units. These cations may be present as a result of their incomplete substitution in a polyphosphate salt by quaternary phosphonium cations, or they may be deliberately introduced during thepreparation of the compounds of the present invention.
- at least one of said organic radicals includes at least one alkyl radical having six or more carbon atoms.
- organic radicals include for example octyl, decyl, dodecyl, tetradecyl, cetyl and lauryl, and radicals such as beta-para-tert.-octyl phen'-.
- the preferred polyphosphate compounds of the present invention include for example, cetyl tripropyl phosphonium polyphosphate,
- compositions of matter which are suitable for use as boundary lubricants and which comprise one or more of the preferred polyphosphate compounds of this invention dissolved or dispersed in a liquid or solid vehicle which is preferably a lubricant.
- Suitable vehicles States atent O "ice may be used as insecticides or to give water repellent finishes to glass or textiles.
- the preferred polyphosphate compounds of this inven tion provide eifective boundary lubricants of ferrous metals and may be used either alone or in admixture with suitable materials.
- Boundary'lubrican'ts are effective in lubricating, surfaces, particularly metal surfaces, which are sliding under conditions of heavy loads and/or slow relative sliding speeds, these conditions usually being known as boundary conditions. Under boundary condi tions, surface contact occurs and frictional forces between sliding surfaces are considerable, resulting in wear and even, in extreme cases, in seizure of the sliding parts.
- boundary lubricants are efiective boundary lubricants of mild steel surfaces and of austenitic stainless steel surfaces such as austenitic stainless steel shafts in journal bearings.
- Potassium polyphosphate for use in the process of the present invention may be prepared by heating potassium dihydrogen orthophosphate at a suitable temperature, for example 650 to 700 C., for a period of preferably about one hour.
- Solubilised polyphosphates suitable for .use in the process of the present invention may be produced by any of the following methods:
- Powdered potassium polyphosphate may be added to water, and contacted with the sodium salt of a cation exchange resin, such as, for example, the sodium salt of a sulphonated polystyrene or of a sulphonated phenolic resin.
- a cation exchange resin such as, for example, the sodium salt of a sulphonated polystyrene or of a sulphonated phenolic resin.
- the potassium polyphosphate on treatment in this manner, goes into solution as a sodium-potassium polyphosphate.
- Potassium polyphosphate is solubilised on treatment with hydrogen peroxide, for example by adding potassium polyphosphate to hydrogen peroxide. It is necessary to neutralise the hydrogen peroxide, which usually contains a small quantity of acid, prior touse by the addition of a small quantity of alkali.
- the solubilised potassium polyphosphate is brought into contact in solution with an aqueous solution ofquaternary phosphonium salt, such as the bromide, for ex ample by mixing with stirring. It is preferred to add the phosphonium salt solution gradually, and to stop when precipitation of the quaternary phosphonium polyphosphate, which comes out of solution during the addition, is complete.
- concentrations of the polyphosphate solution and the quaternary phosphonium salt solution are not critical, but it 'is preferred that they should be approximately equal and approximately 1% by weight.
- the product may then be separated, washed with water and dried.
- the products of the present invention may be prepared by bringing powdered potassium polyphosphate into contact with an aqueous solution of quaternary phosphonium salt, for example the bromide.
- the product swells during this treatment, and may be washed to re- L10: excess quaternary phosphonium salt and potassium ali e.
- the quaternary phosphonium polyphosphatcs of the present invention are in general solids which are insolu-f ble in water, but they may be soluble inorganic solvents such as chloroform.
- EXAMPLE -1 120 grams of air driedion exchange resin soldunder the British registered trademark zeo Karb 215 wereactivated into the ammonium form by treatment. with amn P205 85 NH, 0.2 K 0.1
- EXAMPLE 3 200 mls. of 29% w./v. hydrogen peroxide diluted with 200 mls. of water were neutralised with 2 mls. of normal sodium hydroxide solution, and added to 8 grams of potassium polyphosphate. The mixture was vigorously stirred and after 15 minutes the potassium polyphosphate was completely dissolved. A further 350 mls. of water were added to the solution which then contained 1% by weight of KPO 50 mls. of this solution were treated as in Examples 1 and 2.
- Cetyl tripropyl phosphonium polyphosphate was tested as a boundary lubricant in the following way. Coefficients of friction. were measured between 20 and 200 C. on 'a kinetic boundary friction apparatus, the moving surfaces being ofaustenitic stainless steel and moving at a relative speed of 0.08 cm. per second. Measurements were made using no lubricant and using vehicles only as lubricants. Further measurements were made using cetyl tripropyl phosphonium polyphosphate alone as a lubricant, and also in the form of a 5% dispersion by weight in the vehicles tested.
- the dispersions tested were made by mixing the two components by stirring, if necessary with heating to moderate temperatures for a short time.
- Lubricant Coefficient oi friction Percent Poiy- Percent vehicle 20 100 120 140 160 180 200 phosphate 0. O 0. C. C. O. 0.
- M0-M1nerai oil viscosity 350 cs. at 70F.. 12 ca. at 200F.
- PPS-Polymethyl-phenyl slloxane viscosity 2500s. at 100 F., 25 cs. at 210 F. OPP-cetyl tripropyl phosphonium polyphosph ate.
- EXAMPLE 2 2.5- grams of potassium polyphosphate were, added to mls. of a solution containing sufficient sodiumchloride to give a potassiumzsodium atomic ratio of 1:2. The mixture was slowly stirred for hour, the solution poured'otf and 180 mls. of water added. After rapid agitation, nearly all of the swollen residue passed into solution. A small amount of undissolved material was separated by filtration. 5.0 mls. ofj'thisi solution were treated in the same way as in Example 1 by the addition It will be seen that the vehicl'e-polyphosphate compositions are effective boundary lubricants and even at a concentration as lowas 5%, there is an improvement over the vehicle-used alone which becomes moremarked at higher temperatures. It can further be seen that the effectiveness of the compositions in most cases is maintained over a wide temperature range.
- a quaternary phosphonium polyphosphate salt having (1 6 units forming. substantially linear groups, each (1 69* unit being-associated with a cation, the major proportion of such cations being quaternary phosphonium cations, in each of which the four valences of the phosphorous atom are attached to organic radicals selected from the group consistingof alkyl radicals and monocyclic arylo'xyalkyl groups and themino'r proportion of such cationsbeing selected from the group-consisting of hydrogen; ammonium, sodium and potassium ions 2.
- a compound according to claim 1 in which at least one of said organic radicals includes at least one alkyl Refer Cited in the file of this patent radical having at least six carbon atoms. 5
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Description
QUATERNARY PHosPHoNrUM POLYPHOSPHATES Peter William Brett Sennnens, Norton-on-Tees, England, assignor to Imperial Chemical Industries Limited, Loin don, England, a corporation of Great Britain No Drawing. Application April 9, 1956 Serial No. 576,758
Claims priority, application GreatBritain April 20, 1955 6 Claims. ((21. 260-6065) This invention relates to quaternary phosphonium polyphosphate compounds which are new compounds.
According to the present invention, there is provided a quaternary phosphonium polyphosphate salt having (E D k units forming substantially linear groups, each (F5 unit being associated with a' cation, a major pro-' potassium or other cations associated with the (P0 units. These cations may be present as a result of their incomplete substitution in a polyphosphate salt by quaternary phosphonium cations, or they may be deliberately introduced during thepreparation of the compounds of the present invention. In a preferred group of polyphosphate compounds of the present invention at least one of said organic radicals includes at least one alkyl radical having six or more carbon atoms. Such organic radicals include for example octyl, decyl, dodecyl, tetradecyl, cetyl and lauryl, and radicals such as beta-para-tert.-octyl phen'-.
oxyethyl in which the alkyl radical having the required minimum number of carbon atoms forms part of a larger radical which may include other alkyl or aryl radicals, and/or other functional groups. The preferred polyphosphate compounds of the present invention include for example, cetyl tripropyl phosphonium polyphosphate,
didecyl dimethyl phosphonium polyphosphate and tetradecyl phosphonium polyphosphate.
According to a further feature of the present invention new compositions of matter are provided which are suitable for use as boundary lubricants and which comprise one or more of the preferred polyphosphate compounds of this invention dissolved or dispersed in a liquid or solid vehicle which is preferably a lubricant. Suitable vehicles States atent O "ice may be used as insecticides or to give water repellent finishes to glass or textiles.
The preferred polyphosphate compounds of this inven tion provide eifective boundary lubricants of ferrous metals and may be used either alone or in admixture with suitable materials. Boundary'lubrican'ts are effective in lubricating, surfaces, particularly metal surfaces, which are sliding under conditions of heavy loads and/or slow relative sliding speeds, these conditions usually being known as boundary conditions. Under boundary condi tions, surface contact occurs and frictional forces between sliding surfaces are considerable, resulting in wear and even, in extreme cases, in seizure of the sliding parts. The efi'ectiveness of these preferred compounds as boundary lubricants is therefore a most important property. They are efiective boundary lubricants of mild steel surfaces and of austenitic stainless steel surfaces such as austenitic stainless steel shafts in journal bearings.
Potassium polyphosphate for use in the process of the present invention may be prepared by heating potassium dihydrogen orthophosphate at a suitable temperature, for example 650 to 700 C., for a period of preferably about one hour.
Solubilised polyphosphates suitable for .use in the process of the present invention may be produced by any of the following methods:
(a) Powdered potassium polyphosphate may be added to water, and contacted with the sodium salt of a cation exchange resin, such as, for example, the sodium salt of a sulphonated polystyrene or of a sulphonated phenolic resin. The potassium polyphosphate, on treatment in this manner, goes into solution as a sodium-potassium polyphosphate.
(b) Instead of using a sodium'salt of a cation exchange "resin as described in (a), it is possible to use an ammonium salt of a cation exchange resin. On treatment which are lubricants include for example, mineral or vegetable oils or greases, esters of aliphatic dicarboxylic acids, polyalkylene glycols, polymethyl-phenyl siloxanes,
mixtures of substantially completely halogenated aromatic hydrocarbons such as that sold under the British regis tered trademark Florube 1, or any combination of these. The relative proportions of vehicle in these com positions may be varied over a wide range.
' in this manner the potassium polyphosphate goes into solution as ammonium-potassium polyphosphate.
(c) The use of the salt of a cation exchange resin as in (a and (b), has the disadvantage that the resin must either be discarded or regenerated. An alternative method which avoids the use of a cation exchange resin is to allow powdered potassium polyphosphate to stand in contact with a solution of a-sodium salt, for example sodium chloride. The product swells during this treatment, and may be dissolved in water to give a viscous solution suitable for use in the process of the present invention.
(d) Potassium polyphosphate is solubilised on treatment with hydrogen peroxide, for example by adding potassium polyphosphate to hydrogen peroxide. It is necessary to neutralise the hydrogen peroxide, which usually contains a small quantity of acid, prior touse by the addition of a small quantity of alkali.
The solubilised potassium polyphosphate is brought into contact in solution with an aqueous solution ofquaternary phosphonium salt, such as the bromide, for ex ample by mixing with stirring. It is preferred to add the phosphonium salt solution gradually, and to stop when precipitation of the quaternary phosphonium polyphosphate, which comes out of solution during the addition, is complete. The concentrations of the polyphosphate solution and the quaternary phosphonium salt solution are not critical, but it 'is preferred that they should be approximately equal and approximately 1% by weight. The product may then be separated, washed with water and dried.
As an alternative to first solubilising potassium polyphosphate, the products of the present invention may be prepared by bringing powdered potassium polyphosphate into contact with an aqueous solution of quaternary phosphonium salt, for example the bromide. The product swells during this treatment, and may be washed to re- L10: excess quaternary phosphonium salt and potassium ali e.
-The quaternary phosphonium polyphosphatcs of the present invention are in general solids which are insolu-f ble in water, but they may be soluble inorganic solvents such as chloroform.
EXAMPLE -1 120 grams of air driedion exchange resin soldunder the British registered trademark zeo Karb 215 wereactivated into the ammonium form by treatment. with amn P205 85 NH, 0.2 K 0.1
of a 1% aqueous solution of cetyl tripropyl phosphonium bromide. The product was collected in the same way as in Example 1.
EXAMPLE 3 200 mls. of 29% w./v. hydrogen peroxide diluted with 200 mls. of water were neutralised with 2 mls. of normal sodium hydroxide solution, and added to 8 grams of potassium polyphosphate. The mixture was vigorously stirred and after 15 minutes the potassium polyphosphate was completely dissolved. A further 350 mls. of water were added to the solution which then contained 1% by weight of KPO 50 mls. of this solution were treated as in Examples 1 and 2.
Cetyl tripropyl phosphonium polyphosphate was tested as a boundary lubricant in the following way. Coefficients of friction. were measured between 20 and 200 C. on 'a kinetic boundary friction apparatus, the moving surfaces being ofaustenitic stainless steel and moving at a relative speed of 0.08 cm. per second. Measurements were made using no lubricant and using vehicles only as lubricants. Further measurements were made using cetyl tripropyl phosphonium polyphosphate alone as a lubricant, and also in the form of a 5% dispersion by weight in the vehicles tested.
The results obtained are given in the table below.
The dispersions tested were made by mixing the two components by stirring, if necessary with heating to moderate temperatures for a short time.
Coefi'icient of friction between auste'nitic stainless steel surfaces-surface speed 0.08 cm./sec.
Lubricant Coefficient oi friction Percent Poiy- Percent vehicle 20 100 120 140 160 180 200 phosphate 0. O 0. C. C. O. 0.
Nil Nil "1.11 1. 27 1. 24 1. 30 1. 28 1. 25 1. 28 1. 31 Nil 100% M 0.12 0. 12 0. 12 0.12 0.13 0.16 0.19 0. 20 OPP 95% M0 0. 11 0.11 0.09 O. 08 0. 08 0. 08 0.07 0.12 N 11 100% DS 0. 14 0. 15 0. 18 0. 18 0. 19 0. 21 0. 23 0. 23 6% GP? 95% DS -0. 12 0.10 '0. 0.08 0.08 0.07 0.08 0.03 N i] 100% PAG 0. 0. 21 0. 21 0. 0. 19 0; 22 0. 20 0. 23 5% OPP 95% P 0. 14 0. 12 0. 10 0. 09 0. 09 0. 10 0. 12 N11 100% 0 0. 15 0. 15 0. 16 0. 17 0. 19 0. 17 0.20 0. 18 5% OPP 95% X 0. 14 0. 12 0. 10 0. 10 0. 11 0. 11 0. 10 0. 10 Nil 100% FPS 0.20 0.20 0.26 0.43 0.53 0.01 0.87 0.98 5% OPP 95% PPS 0. 16 0.16 0. 21 0.17 0.23 0.23 0. 23 0. 23 100% OPP N 0.00 0. 00 0.00 0.06 0. 05
References:
M0-M1nerai oil, viscosity 350 cs. at 70F.. 12 ca. at 200F.
DS-Di(ethyl hexyl) sebacate. a PAG-Poiyalky1ene glycol, viscosity 61.7 as at 100 F., 11 cs. at 210 F. CXFlorube" 1, (British registered Trademark).
PPS-Polymethyl-phenyl slloxane, viscosity 2500s. at 100 F., 25 cs. at 210 F. OPP-cetyl tripropyl phosphonium polyphosph ate.
EXAMPLE 2 2.5- grams of potassium polyphosphate were, added to mls. of a solution containing sufficient sodiumchloride to give a potassiumzsodium atomic ratio of 1:2. The mixture was slowly stirred for hour, the solution poured'otf and 180 mls. of water added. After rapid agitation, nearly all of the swollen residue passed into solution. A small amount of undissolved material was separated by filtration. 5.0 mls. ofj'thisi solution were treated in the same way as in Example 1 by the addition It will be seen that the vehicl'e-polyphosphate compositions are effective boundary lubricants and even at a concentration as lowas 5%, there is an improvement over the vehicle-used alone which becomes moremarked at higher temperatures. It can further be seen that the effectiveness of the compositions in most cases is maintained over a wide temperature range.
I claim:
1. A quaternary phosphonium polyphosphate salt having (1 6 units forming. substantially linear groups, each (1 69* unit being-associated with a cation, the major proportion of such cations being quaternary phosphonium cations, in each of which the four valences of the phosphorous atom are attached to organic radicals selected from the group consistingof alkyl radicals and monocyclic arylo'xyalkyl groups and themino'r proportion of such cationsbeing selected from the group-consisting of hydrogen; ammonium, sodium and potassium ions 2. A quaternary phosphonium polyphosphate' salt as set forth in claim 1 in which the organic radical is a betaquaternary phosphonium cations are 'tetradecyl phosphonip-tertiaryoctylphenoxyethyl radical. um groups.
3. A compound according to claim 1 in which at least one of said organic radicals includes at least one alkyl Refer Cited in the file of this patent radical having at least six carbon atoms. 5
4. A compound according to claim 1 in which the UNITED STATES PATENTS said quaternary 'phosphonium cations are cetyl tripropyl 2,220,851 Schreiber Nov. 5, 1940 phosphonium groups. 2,360,623 Rosen Oct. 17, 1944 5. A compound according to claim 1 in which the said 2,414,263 Kemp Jan. 14, 1947 quaternary phosphonium cations are didecyl dimethyl 10 2,446,647 Stern Apr. 5,1949 phosphonium groups. I 2,703,814 Dye Mar. 8, 1955 16. A compound according to claim 1 in which the said 2,745,877 Bindler May 15, 1956
Claims (1)
1. A QUATERNARY PHOSPHONIUM POLYPHOSPHATE SALT HAVING (PO3)- UNITS FORMING SUBSTANTIALLY LINEAR GROUPS, EACH (PO3)- UNIT BEING ASSOCIATED WITH A CATION, THE MAJOR PROPORTION OF SUCH CATIONS BEING QUATERNARY PHOSPHONIUM CATIONS, IN EACH OF WHICH THE FOUR VALENCIES OF THE PHOSPHOROUS ATOM ARE ATTACHED TO ORGANIC RADICALS SELECTED FROM THE GROUP CONSISTING OF ALKYL RADICALS AND MONOCYCLIC ARYLOXYALKYL GROUPS AND THE MINOR PROPORTION OF SUCH CATIONS BEING SELECTED FROM THE GROUP CONSISTING OF HYDROGEN, AMMONIUM, SODIUM AND POTASSIUM IONS.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB11384/55A GB786902A (en) | 1955-04-20 | 1955-04-20 | Quaternary phosphonium polyphosphates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2931835A true US2931835A (en) | 1960-04-05 |
Family
ID=9985237
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US576758A Expired - Lifetime US2931835A (en) | 1955-04-20 | 1956-04-09 | Quaternary phosphonium polyphosphates |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US2931835A (en) |
| DE (1) | DE1025550B (en) |
| FR (1) | FR1149563A (en) |
| GB (1) | GB786902A (en) |
| NL (2) | NL99057C (en) |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2220851A (en) * | 1940-11-05 | Treatment of hydrocarbon oil | ||
| US2360623A (en) * | 1941-03-01 | 1944-10-17 | Standard Oil Dev Co | Lubricating oil composition |
| US2414263A (en) * | 1943-02-27 | 1947-01-14 | Texas Co | Phosphoric acid esters |
| US2446647A (en) * | 1946-03-27 | 1948-08-10 | Western Electric Co | Apparatus for detecting imperfections in filamentary materials |
| US2703814A (en) * | 1952-03-26 | 1955-03-08 | Monsanto Chemicals | Process of preparing organic phosphorus compounds |
| US2745877A (en) * | 1951-07-06 | 1956-05-15 | Geigy Ag J R | Quaternary phosphonium compounds |
-
0
- NL NL206434D patent/NL206434A/xx unknown
- NL NL99057D patent/NL99057C/xx active
-
1955
- 1955-04-20 GB GB11384/55A patent/GB786902A/en not_active Expired
-
1956
- 1956-04-09 US US576758A patent/US2931835A/en not_active Expired - Lifetime
- 1956-04-19 DE DEI11577A patent/DE1025550B/en active Pending
- 1956-04-20 FR FR1149563D patent/FR1149563A/en not_active Expired
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2220851A (en) * | 1940-11-05 | Treatment of hydrocarbon oil | ||
| US2360623A (en) * | 1941-03-01 | 1944-10-17 | Standard Oil Dev Co | Lubricating oil composition |
| US2414263A (en) * | 1943-02-27 | 1947-01-14 | Texas Co | Phosphoric acid esters |
| US2446647A (en) * | 1946-03-27 | 1948-08-10 | Western Electric Co | Apparatus for detecting imperfections in filamentary materials |
| US2745877A (en) * | 1951-07-06 | 1956-05-15 | Geigy Ag J R | Quaternary phosphonium compounds |
| US2703814A (en) * | 1952-03-26 | 1955-03-08 | Monsanto Chemicals | Process of preparing organic phosphorus compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1025550B (en) | 1958-03-06 |
| NL99057C (en) | |
| NL206434A (en) | |
| FR1149563A (en) | 1957-12-27 |
| GB786902A (en) | 1957-11-27 |
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