US3346670A - Method for the preparation of phosphate esters - Google Patents
Method for the preparation of phosphate esters Download PDFInfo
- Publication number
- US3346670A US3346670A US243721A US24372162A US3346670A US 3346670 A US3346670 A US 3346670A US 243721 A US243721 A US 243721A US 24372162 A US24372162 A US 24372162A US 3346670 A US3346670 A US 3346670A
- Authority
- US
- United States
- Prior art keywords
- surface active
- nonionic surface
- water
- active agents
- phosphate esters
- 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
Links
- 238000000034 method Methods 0.000 title claims description 47
- 150000003014 phosphoric acid esters Chemical class 0.000 title claims description 23
- 238000002360 preparation method Methods 0.000 title claims description 10
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 23
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 claims description 7
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical class C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 4
- 229920000847 nonoxynol Polymers 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 description 57
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 23
- 239000002253 acid Substances 0.000 description 15
- -1 aliphatic alcohols Chemical class 0.000 description 14
- 239000000047 product Substances 0.000 description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 229910052500 inorganic mineral Inorganic materials 0.000 description 9
- 239000011707 mineral Substances 0.000 description 9
- 229940124530 sulfonamide Drugs 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 229910019142 PO4 Inorganic materials 0.000 description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 235000021317 phosphate Nutrition 0.000 description 5
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 150000002193 fatty amides Chemical class 0.000 description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 150000003456 sulfonamides Chemical class 0.000 description 4
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 4
- BZJTUOGZUKFLQT-UHFFFAOYSA-N 1,3,5,7-tetramethylcyclooctane Chemical group CC1CC(C)CC(C)CC(C)C1 BZJTUOGZUKFLQT-UHFFFAOYSA-N 0.000 description 3
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- XEFJFCAXFQMSSY-UHFFFAOYSA-N 13-hydroxytridecanal Chemical compound OCCCCCCCCCCCCC=O XEFJFCAXFQMSSY-UHFFFAOYSA-N 0.000 description 1
- JKTAIYGNOFSMCE-UHFFFAOYSA-N 2,3-di(nonyl)phenol Chemical compound CCCCCCCCCC1=CC=CC(O)=C1CCCCCCCCC JKTAIYGNOFSMCE-UHFFFAOYSA-N 0.000 description 1
- GRUAMSTZJXJEIF-UHFFFAOYSA-N 2-dodecylbenzenesulfonamide Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(N)(=O)=O GRUAMSTZJXJEIF-UHFFFAOYSA-N 0.000 description 1
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 238000010420 art technique Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/098—Esters of polyphosphoric acids or anhydrides
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/16—Anti-static materials
Definitions
- the particular nonionics of interest in the process of the instant invention are the nonionic surface active agents having the molecular configuration of a condensation product of at least one mole of an alkylene oxide with one mole of a compound containing at least 6 carbon atoms and a reactive hydrogen atom are preferably polyoxyalkylene derivatives of alkylated and polyalkylated phenols, multi-branched chain primary aliphatic alcohols having the molecular configuration of an alcohol produced by the oxo process from a polyolefin of at least 7 carbon atoms, and straight chain aliphatic alcohols of at least carbon atoms.
- the alkylene oxide may be propylene oxide, butylene oxide or preferably ethylene oxide.
- E.O. means ethylene oxide and the number preceding same refers to the number of moles thereof reacted with one mole of the given reactive hydrogen containing compound.
- the optimum starting materials are those selected from the group consisting of phenol, alkyl phenols, alphatic alcohols, fatty acids, fatty amines, fatty amides, rosin amines, long chain sulfonamides, long chain-substituted aryl sulfonamides, and high molecular weight mercaptans.
- Nonionic surface active agents such as those of the instant invention have been previously esterified with a number of different phosphating agents, including phosphorus trichloride, PCl phosphorus oxychloride, P001 and phosphorus pentoxide, P 0 Esters produced from the chlorine-containing phosphating agents, such as the phosphorus trichloride and the phosphorus oxychloride, contain bound chlorine atoms which are undesirable in many applications.
- the perferred phosphating agent used in most instances heretofore has been phosphorus pentoxide.
- a further object of this invention is the provision of a process for the preparation of phosphate esters of nonionic surface active agents wherein a much higher percentage of the organic starting materials will be converted to phosphate esters.
- Nonionic surface active agents such as those of the instant invention have been converted heretofore to their phosphate esters by first azeotropically distilling the compounds to remove all traces of water and then reacting the dried compound with phosphorus pentoxide under anhydrous conditions.
- the removal of water prior to the phosphation process has been considered necessary to prevent the formation of phosphoric acid by reaction of the water with the phosphorus pentoxide.
- the presence of phosphoric acid during the phosphation reaction has previously been believed to be disadvantageous to a satisfactory phosphation.
- Increased conversion has been realized by adding from 0.001 to 3% by weight of water or mineral acid, based on the weight of the dried nonionic surface active agents.
- the preferred percentage of additive is between 0.1 and 0.8%
- the reaction products of the process of the instant invention are believed to be a mixture of the orthophosphates and pyrophosphates of the nonionic surface active agents starting materials.
- Phosphate esters of various nonionic surface active agents have found numerous commercial applications such as detergents, lubricants, oil additives, antistatic agents, foaming agents, corrosion inhibitors and the like.
- many of the phosphate esters have shown multiple applications when they contain higher concentration of phosphates. The importance of the discovery of the instant invention which makes possible the production of such high concentration phosphate products is readily seen.
- Example 1 Procedure A Into a two liter, electrically heated, reaction flask, fitted with an agitator, a thermometer,.and a water separator fitted to a reflux condenser, is charged 600 parts of nonylphenol containing fifteen moles of ethylene oxide (0.682 moles of the nonionic surface active agents) and 200 parts of xylene. The mixture is heated to reflux until water is completely removed from the reaction mixture. The xylene is then removed by distillation and the dried nonionic surface active agents are cooled to 50 C. The apparatus is then re-arranged so that inert gas is bubbled through the reaction mixture and a vent is kept open.
- Procedure E The same charge and procedure as in A above is employed, except that after the water is removed, there is added 2.5 parts of water to the dried nonionic surface active agents. Analysis of the product by an ion exchange procedure showed 2.34 percent of unreacted nonionic surface active agents.
- Procedure C Procedure C.-Procedure A is repeated except, after the water is removed, there is added 3 parts of phosphoric acid to the dried nonionic surface active agents.
- the unreacted nonionic surface active agents of the resulting product is 1.15 percent.
- Procedure D.Procedure A is repeated except, after the water is removed, there is added 3 parts of hydrochloric acid (chemically pure) to the dried nonionic surface active agents.
- the unreacted nonionic surface active agent in the phosphated product is 3.0 percent.
- Procedure E.Procedure A is repeated except, after the water is removed, there is added 4.8 parts of sulfuric acid (chemically pure). The resulting product is found to contain 2.5 percent of unreacted nonionic surface active agent.
- Procedure F.Procedure A is repeated except, after the water is removed, there is added 4.8 parts of water to the dried nonionic surface active agent. There is found 2.0 percent of unreacted nonionic surface active agent in the resulting product.
- Procedure G.Procedure A is repeated except, after the water is removed, there is added 0.6 part of water to the dried nonionic surface active agent. There is found 2.5 percent of unreacted nonionic surface active agent in the resulting product.
- the reaction temperature is not limited to 120130 C. as shown in Procedure A but can be as high as 200 C.
- the pressure may be atmospheric, subatmospheric or superatmospheric.
- the only limitation on the reaction conditions is that the temperature and pressure are'such that the added water or mineral acid is not driven olf during the reaction.
- a process for the preparation of phosphate esters comprising reacting phosphorus pentoxide with ethoxylated nonyl phenol or an ethoxylated aliphatic alcohol containing at least 6 carbon atoms, wherein a small amount of water is added to said ethoxylated nonyl phenol or aliphatic alcohol prior to the reaction with phosphorus pentoxide.
- a process for the preparation of phosphate esters comprising reacting one mole of phosphorus pentoxide with 0.3 to 2 moles of a nonionic surface active agent having the molecular configuration of a condensation product of at least one mole of alkylene oxide and one mole of a compound containing at least 6 carbon atoms and a reactive hydrogen atom, and selected from the group consisting of phenol, alkyl phenols, aliphatic alcohols, fatty acids, fatty amines, fatty amides, rosin amines, long chain sulfonamides, long chain-substituted aryl sulfonamides, and high molecular weight mercaptans, wherein .001% to 3% by weight of water is added to said nonproduct of at least one mole of alkylene oxide and one mole of a compound containing at least 6 carbon atoms and a reactive hydrogen atom, and selected from the group consisting of phenol, alkyl phenols, aliphatic
- a process for the preparation of phosphate esters comprising azeotropically distilling a nonionic surface active agent having the molecular configuration of a condensation product of at least one mole of alkylene oxide and one mole of a compound containing at least 6 carbon atoms and a reactive hydrogen atom and selected from the group consisting of phenol, alkyl phenols, aliphatic alcohols, fatty acids, fatty amines, fatty amides, rosin amines, long chain sulfonamides, long chain-substituted aryl sulfonamides, and high molecular weight mercaptans, to remove any water present therein, drying said nonionic surface active agent, adding to the dried nonionic surface active agent .001% to 3% by weight of water and then reacting 0.3 to 2 moles of said nonionic surface active agent with one mole of phosphorus pentoxide.
- nonionic surface active agent is a nonylphenol containing fifteen moles of ethylene oxide.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Separation Of Suspended Particles By Flocculating Agents (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US243721A US3346670A (en) | 1962-12-11 | 1962-12-11 | Method for the preparation of phosphate esters |
| GB48718/63A GB994136A (en) | 1962-12-11 | 1963-12-10 | Method for the preparation of phosphate esters of surface active agents |
| BE641097D BE641097A (pm) | 1962-12-11 | 1963-12-11 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US243721A US3346670A (en) | 1962-12-11 | 1962-12-11 | Method for the preparation of phosphate esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3346670A true US3346670A (en) | 1967-10-10 |
Family
ID=22919857
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US243721A Expired - Lifetime US3346670A (en) | 1962-12-11 | 1962-12-11 | Method for the preparation of phosphate esters |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3346670A (pm) |
| BE (1) | BE641097A (pm) |
| GB (1) | GB994136A (pm) |
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3462365A (en) * | 1966-06-23 | 1969-08-19 | Nalco Chemical Co | Scale inhibiting compounds |
| US3488289A (en) * | 1966-06-24 | 1970-01-06 | Texaco Inc | Composition and method for treating scale |
| US3496104A (en) * | 1965-10-18 | 1970-02-17 | Yawata Seitetsu Kk | Cold rolling agent |
| US3502587A (en) * | 1966-10-06 | 1970-03-24 | Nalco Chemical Co | Scale inhibiting compositions |
| US3692884A (en) * | 1969-02-07 | 1972-09-19 | Edwin R Gaskell | Phosphate esters |
| US3963628A (en) * | 1974-06-07 | 1976-06-15 | Union Carbide Corporation | Fiber lubricant composition |
| US4118327A (en) * | 1977-03-28 | 1978-10-03 | Colgate Palmolive Company | Fabric softener and anti-static compositions |
| US4154887A (en) * | 1978-03-31 | 1979-05-15 | Gaf Corporation | Surface treatment of rigid polyvinyl chloride |
| US4215002A (en) * | 1978-07-31 | 1980-07-29 | Texaco Inc. | Water-based phosphonate lubricants |
| US4235733A (en) * | 1978-07-13 | 1980-11-25 | Kao Soap Co., Ltd. | Antibacterial soap containing trichlorohydroxy diphenyl ether bactericide and an organic phosphoric ester as a stabilizer therefor |
| US4256594A (en) * | 1979-05-04 | 1981-03-17 | The Lubrizol Corporation | Hot melt metal working lubricants containing phosphorus-containing compositions |
| US4346148A (en) * | 1979-05-04 | 1982-08-24 | The Lubrizol Corporation | Phosphorus-containing compositions, lubricants containing them and metal workpieces coated with same |
| US4358509A (en) * | 1979-05-04 | 1982-11-09 | The Lubrizol Corporation | Novel metal working additive compositions, lubricants containing them and metal workpieces coated with same |
| US4579672A (en) * | 1983-05-10 | 1986-04-01 | Exxon Research & Engineering Co. | Functional fluids and lubricants having improved water tolerance |
| US5286300A (en) * | 1991-02-13 | 1994-02-15 | Man-Gill Chemical Company | Rinse aid and lubricant |
| RU2259237C1 (ru) * | 2004-03-15 | 2005-08-27 | ФГУП "Всероссийский научно-исследовательский институт химической технологии" | Способ получения фосфорсодержащих собирателей для флотации руд |
| WO2020185513A1 (en) | 2019-03-08 | 2020-09-17 | Stepan Company | Reactive surfactants |
| WO2022195047A1 (en) | 2021-03-19 | 2022-09-22 | Nouryon Chemicals International B.V. | Agrochemical composition |
| EP4269420A1 (en) | 2022-04-26 | 2023-11-01 | Pcc Exol S.A. | Method for the preparation of phosphoric acid monoesters and diesters from alcohols |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2853471A (en) * | 1955-11-29 | 1958-09-23 | Gen Aniline & Film Corp | Making addition polymers and copolymers with phosphorus compound emulsifier |
| US3004057A (en) * | 1959-11-12 | 1961-10-10 | Gen Aniline & Film Corp | Surface active compositions |
| US3010903A (en) * | 1957-11-01 | 1961-11-28 | Exxon Research Engineering Co | Phosphate additives for hydrocarbon compositions |
| US3033889A (en) * | 1958-10-21 | 1962-05-08 | Gen Aniline & Film Corp | Phosphate esters of branched chain alcohols |
| US3079419A (en) * | 1960-12-07 | 1963-02-26 | Stauffer Chemical Co | Process for the manufacture of trialkyl phosphates |
-
1962
- 1962-12-11 US US243721A patent/US3346670A/en not_active Expired - Lifetime
-
1963
- 1963-12-10 GB GB48718/63A patent/GB994136A/en not_active Expired
- 1963-12-11 BE BE641097D patent/BE641097A/fr unknown
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2853471A (en) * | 1955-11-29 | 1958-09-23 | Gen Aniline & Film Corp | Making addition polymers and copolymers with phosphorus compound emulsifier |
| US3010903A (en) * | 1957-11-01 | 1961-11-28 | Exxon Research Engineering Co | Phosphate additives for hydrocarbon compositions |
| US3033889A (en) * | 1958-10-21 | 1962-05-08 | Gen Aniline & Film Corp | Phosphate esters of branched chain alcohols |
| US3004057A (en) * | 1959-11-12 | 1961-10-10 | Gen Aniline & Film Corp | Surface active compositions |
| US3004056A (en) * | 1959-11-12 | 1961-10-10 | Gen Aniline & Film Corp | Surface active compositions |
| US3079419A (en) * | 1960-12-07 | 1963-02-26 | Stauffer Chemical Co | Process for the manufacture of trialkyl phosphates |
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3496104A (en) * | 1965-10-18 | 1970-02-17 | Yawata Seitetsu Kk | Cold rolling agent |
| US3462365A (en) * | 1966-06-23 | 1969-08-19 | Nalco Chemical Co | Scale inhibiting compounds |
| US3488289A (en) * | 1966-06-24 | 1970-01-06 | Texaco Inc | Composition and method for treating scale |
| US3502587A (en) * | 1966-10-06 | 1970-03-24 | Nalco Chemical Co | Scale inhibiting compositions |
| US3692884A (en) * | 1969-02-07 | 1972-09-19 | Edwin R Gaskell | Phosphate esters |
| US3963628A (en) * | 1974-06-07 | 1976-06-15 | Union Carbide Corporation | Fiber lubricant composition |
| US4118327A (en) * | 1977-03-28 | 1978-10-03 | Colgate Palmolive Company | Fabric softener and anti-static compositions |
| US4154887A (en) * | 1978-03-31 | 1979-05-15 | Gaf Corporation | Surface treatment of rigid polyvinyl chloride |
| US4235733A (en) * | 1978-07-13 | 1980-11-25 | Kao Soap Co., Ltd. | Antibacterial soap containing trichlorohydroxy diphenyl ether bactericide and an organic phosphoric ester as a stabilizer therefor |
| US4215002A (en) * | 1978-07-31 | 1980-07-29 | Texaco Inc. | Water-based phosphonate lubricants |
| US4256594A (en) * | 1979-05-04 | 1981-03-17 | The Lubrizol Corporation | Hot melt metal working lubricants containing phosphorus-containing compositions |
| US4346148A (en) * | 1979-05-04 | 1982-08-24 | The Lubrizol Corporation | Phosphorus-containing compositions, lubricants containing them and metal workpieces coated with same |
| US4358509A (en) * | 1979-05-04 | 1982-11-09 | The Lubrizol Corporation | Novel metal working additive compositions, lubricants containing them and metal workpieces coated with same |
| US4579672A (en) * | 1983-05-10 | 1986-04-01 | Exxon Research & Engineering Co. | Functional fluids and lubricants having improved water tolerance |
| US5286300A (en) * | 1991-02-13 | 1994-02-15 | Man-Gill Chemical Company | Rinse aid and lubricant |
| RU2259237C1 (ru) * | 2004-03-15 | 2005-08-27 | ФГУП "Всероссийский научно-исследовательский институт химической технологии" | Способ получения фосфорсодержащих собирателей для флотации руд |
| WO2020185513A1 (en) | 2019-03-08 | 2020-09-17 | Stepan Company | Reactive surfactants |
| EP4431532A2 (en) | 2019-03-08 | 2024-09-18 | Stepan Company | Reactive surfactants |
| WO2022195047A1 (en) | 2021-03-19 | 2022-09-22 | Nouryon Chemicals International B.V. | Agrochemical composition |
| EP4269420A1 (en) | 2022-04-26 | 2023-11-01 | Pcc Exol S.A. | Method for the preparation of phosphoric acid monoesters and diesters from alcohols |
Also Published As
| Publication number | Publication date |
|---|---|
| BE641097A (pm) | 1964-04-01 |
| GB994136A (en) | 1965-06-02 |
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