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GB1113264A - Production and use of polyhalopolyhydropolycyclicdi-carboxylic acid-alkanolamine-phosphorus compound reaction product - Google Patents

Production and use of polyhalopolyhydropolycyclicdi-carboxylic acid-alkanolamine-phosphorus compound reaction product

Info

Publication number
GB1113264A
GB1113264A GB30246/65A GB3024665A GB1113264A GB 1113264 A GB1113264 A GB 1113264A GB 30246/65 A GB30246/65 A GB 30246/65A GB 3024665 A GB3024665 A GB 3024665A GB 1113264 A GB1113264 A GB 1113264A
Authority
GB
United Kingdom
Prior art keywords
acid
halogen
oils
orthophosphate
alkane
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
Application number
GB30246/65A
Inventor
Henryk Antoni Cyba
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Universal Oil Products Co
Original Assignee
Universal Oil Products Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Universal Oil Products Co filed Critical Universal Oil Products Co
Priority to GB30246/65A priority Critical patent/GB1113264A/en
Publication of GB1113264A publication Critical patent/GB1113264A/en
Expired legal-status Critical Current

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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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/44—Polyester-amides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
    • C08G79/02—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing phosphorus
    • C08G79/04—Phosphorus linked to oxygen or to oxygen and carbon
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    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/02—Water
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
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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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    • C10M2223/04—Phosphate esters
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    • C10M2223/041—Triaryl phosphates
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  • General Chemical & Material Sciences (AREA)

Abstract

A phosphorus-containing polycondensate is obtained by reacting (i) an acid ester of orthophosphoric, pyrophosporic or thiophosphoric acid; or a mono- or dialkane or mono- or diaromatic phosphinic acid; or an alkane or aromatic phosphonic acid or acid ester thereof, with (ii) a polymer derived from (a) a polyhalopolyhydropolycycli dicarboxylic acid of the formula <FORM:1113264/C3/1> or <FORM:1113264/C3/2> wherein X is halogen, hydrogen or a C1-10 alkyl group, at least two X's being halogen; Y is halogen, hydrogen or a C1-10 alkyl group; m is 1-4, p is 0 or 1, and n is 1-4, or an anhydride or ester thereof, and (b) an alkanolamine having at least two hydroxy groups or at least two amino groups. Preferred compounds (i) include acid orthophosphates, pyrophosphates and dithiophosphates of C6-20 alkanols or of oxyethylenated alcohols or alkylphenols. Suitable acids (a) may be obtained by Diels-Alder reaction between e.g. maleic, fumaric, itaconic, citraconic or glutaconic acid and e.g. hexachlorocyclopentadiene or the 1:2-, 1:5-, 1:2:3-, 1:2:3:4 and 1:2:3:4:5 polychlorocyclopentadienes or any conjugated diene followed by a second Diels-Alder reaction with a polyhalocycloalkadiene. Suitable alkanolamines (b) include N-alkyl-dialkanolamines. In examples the reactants used are: bis-(pentaoxyethylenated nonyl phenol) orthophosphate, bis-(octaoxyethylenated nonyl phenol) orthophosphate, a mixed mono- and di-tridecyl orthophosphate, bis-(trioxypropylenated octylphenol) orthophosphate, bis - (pentaoxypropylenated dodecanol) orthophosphate, O-capryl-O-hexyl dithiophosphate, benzene phosphonic acid and monobenzene phosphonic acid; 5:6:7:8:9: 9 - hexachloro - 1:2:3:4:4a:5:8:8a-octahydro octahydro - 5:8 - methano - 2:3 - naphthalene dicarboxylic anhydride, chlorendic anhydride and the octyl ester of 5:6:7:8:9:9-hexachloro - 1:2:3:4:4a:5:8:8a - octahydro - 1:4:5:8 - dimethano - 2:3 - naphthalene dicarboxylic acid; and N-tallow-diethanolamine, N:N1 - dioctyl - N - hydroxyethylaminoethylethanolamine, N - decylaminopropyl - propanolamine and N - soya - diethanolamine. Uses: Lubricant additives, acting as extreme pressure additives, viscosity index improvers, pour point depressants, detergents, dispersants, peroxide decomposers, corrosion inhibitors; fire-resistant additives, anti-fouling paint additives, and oxidative and thermal stabilizers for organic compounds, including natural and synthetic oils and greases, plastics, coatings, paints, drying oils and textiles; insecticides.ALSO:Oils, fuels and greases may contain 0.01-20 wt. per cent of an additive obtained by reacting (i) an acid ester of orthophosphoric, pyrophosphoric or thiophosphoric acid, or a mono- or di-alkane- or aromatic phosphinic acid, or an alkane- or aromatic phosphonic acid or acid ester thereof with (ii) a polycondensate of (a) a polyhalopolyhydropolycyclic dicarboxylic acid of the formula <FORM:1113264/C4-C5/1> or <FORM:1113264/C4-C5/2> wherein each X and Y is halogen, hydrogen or a Cl-10 alkyl group, at least 2 X's being halogen. m is 1-4, p is 0 or 1 and n is 1-4 and (b) an alkanolamine having at least two hydroxy groups and/or at least two amino groups (see Division C3). The additive functions as an extreme pressure additive, oxidation and corrosion inhibitor, antiwear agent, viscosity index improver, pour point depressant and dispersant. Suitable substrates include mineral, animal, marine and vegetable oils and synthetic oils, e.g. gasoline, naphtha, kerosene, jet fuel, diesel fuel, fuel oil, mineral lubricating oil, aliphatic esters, polyalkylene oxides, silicones, phosphoric and silicic acid esters and fluorocarbons, and also greases, e.g. metal base synthetic greases, whale grease, wool grease and greases from inedible fats, tallow and butchers' waste. The product compositions may be lubricating oils, transmission, hydraulic or industrial fluids, cutting, rolling, soluble or slushing oils, or drawing compounds. In examples such additives are incorporated into a transmission oil, dioctyl sebacate lubricating oil, a white mineral lubricating oil, and a grease containing lithium stearate in a Mid-Continent lubricating oil.ALSO:Insecticide compositions contain as the active ingredient a reaction product of (i) an acid ester of orthophosphoric, pyrophosphoric or thiophosphoric acid, or a mono- or di-alkane- or aromatic phosphinic acid, or an alkane- or aromatic phosphomic acid or acid ester thereof with (ii) a polycondensate derived from (a) a polyhalopolyhydropolycyclic dicarboxylic acid of the formula <FORM:1113264/A5-A6/1> or <FORM:1113264/A5-A6/2> wherein each X and Y is halogen, hydrogen or a C1-10 alkyl group, at least 2 X's being halogen, m is 1-4, p is 0 or 1 and n is 1-4 and (b) an alkanolamine having at least 2 hydroxy groups and/or at least 2 amino groups.
GB30246/65A 1965-07-16 1965-07-16 Production and use of polyhalopolyhydropolycyclicdi-carboxylic acid-alkanolamine-phosphorus compound reaction product Expired GB1113264A (en)

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GB30246/65A GB1113264A (en) 1965-07-16 1965-07-16 Production and use of polyhalopolyhydropolycyclicdi-carboxylic acid-alkanolamine-phosphorus compound reaction product

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GB30246/65A GB1113264A (en) 1965-07-16 1965-07-16 Production and use of polyhalopolyhydropolycyclicdi-carboxylic acid-alkanolamine-phosphorus compound reaction product

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4115370A (en) * 1975-02-21 1978-09-19 Snia Viscosa Societa' Nazionale Industria Applicazioni Viscosa S.P.A. Unsaturated polyesteramides, method for their production and hardenable resins produced from the said polyesteramides

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4115370A (en) * 1975-02-21 1978-09-19 Snia Viscosa Societa' Nazionale Industria Applicazioni Viscosa S.P.A. Unsaturated polyesteramides, method for their production and hardenable resins produced from the said polyesteramides

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