GB1081285A - Esters of phosphorus acids and lubricating compositions comprising them - Google Patents
Esters of phosphorus acids and lubricating compositions comprising themInfo
- Publication number
- GB1081285A GB1081285A GB42861/64A GB4286164A GB1081285A GB 1081285 A GB1081285 A GB 1081285A GB 42861/64 A GB42861/64 A GB 42861/64A GB 4286164 A GB4286164 A GB 4286164A GB 1081285 A GB1081285 A GB 1081285A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbon atoms
- alkyl
- integer
- phenyl
- compounds
- 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
Links
- 150000002148 esters Chemical class 0.000 title abstract 6
- 239000000203 mixture Substances 0.000 title abstract 6
- 230000001050 lubricating effect Effects 0.000 title abstract 4
- 150000003017 phosphorus Chemical class 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 30
- 125000000217 alkyl group Chemical group 0.000 abstract 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 15
- 125000005037 alkyl phenyl group Chemical group 0.000 abstract 14
- 150000001875 compounds Chemical class 0.000 abstract 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 12
- -1 aryl phosphate esters Chemical class 0.000 abstract 10
- 239000002253 acid Substances 0.000 abstract 9
- 229910052739 hydrogen Inorganic materials 0.000 abstract 9
- 239000001257 hydrogen Substances 0.000 abstract 9
- 229910019142 PO4 Inorganic materials 0.000 abstract 8
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 8
- 235000021317 phosphate Nutrition 0.000 abstract 8
- 239000010452 phosphate Substances 0.000 abstract 7
- 125000003342 alkenyl group Chemical group 0.000 abstract 6
- 150000002431 hydrogen Chemical group 0.000 abstract 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 3
- 238000001816 cooling Methods 0.000 abstract 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 3
- 229910052698 phosphorus Inorganic materials 0.000 abstract 3
- 239000011574 phosphorus Substances 0.000 abstract 3
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 230000007935 neutral effect Effects 0.000 abstract 2
- 125000000963 oxybis(methylene) group Chemical group [H]C([H])(*)OC([H])([H])* 0.000 abstract 2
- 150000003014 phosphoric acid esters Chemical class 0.000 abstract 2
- 239000000376 reactant Substances 0.000 abstract 2
- 229940035044 sorbitan monolaurate Drugs 0.000 abstract 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 238000005097 cold rolling Methods 0.000 abstract 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 abstract 1
Classifications
-
- 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
- C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
-
- 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
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- 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
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/02—Water
-
- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
-
- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/042—Metal salts thereof
-
- 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
- C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
-
- 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
- C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2225/02—Macromolecular compounds from phosphorus-containg monomers, obtained by reactions involving only carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
- C10N2040/24—Metal working without essential removal of material, e.g. forming, gorging, drawing, pressing, stamping, rolling or extruding; Punching metal
-
- C—CHEMISTRY; METALLURGY
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
- C10N2040/241—Manufacturing joint-less pipes
-
- C—CHEMISTRY; METALLURGY
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
- C10N2040/242—Hot working
-
- C—CHEMISTRY; METALLURGY
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
- C10N2040/243—Cold working
-
- C—CHEMISTRY; METALLURGY
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
- C10N2040/244—Metal working of specific metals
-
- C—CHEMISTRY; METALLURGY
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
- C10N2040/244—Metal working of specific metals
- C10N2040/245—Soft metals, e.g. aluminum
-
- C—CHEMISTRY; METALLURGY
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
- C10N2040/244—Metal working of specific metals
- C10N2040/246—Iron or steel
-
- C—CHEMISTRY; METALLURGY
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
- C10N2040/244—Metal working of specific metals
- C10N2040/247—Stainless steel
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)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Lubricants (AREA)
Abstract
A lubricating and cooling composition for cold rolling comprises an aqueous solution containing from 0.1 to 15% by weight of an ester of an acid of phosphorus having the formula <FORM:1081285/C4-C5/1> wherein x is an integer from 1 to 500, y is 0 or an integer from 1 to 500, x plus y is an integer of more than 14 and y/x has a value of 0 to 15, n is 1 or 2, m is 0 or 1 and n plus m equals 2, z is an integer from 1 to 3, R represents (a) hydrogen, (b) alkyl containing from 1 to 18 carbon atoms, (c) alkenyl containing from 1 to 18 carbon atoms, (d) phenyl, (e) alkylphenyl containing up to 15 carbon atoms, (f) sorbitan monolaurate, (g) <FORM:1081285/C4-C5/2> wherein R111 is alkyl or alkenyl containing from 1 to 18 carbon atoms, (h) <FORM:1081285/C4-C5/3> wherein n1 is an integer from 1 to 500 or (i) <FORM:1081285/C4-C5/4> wherein X is -(C2H4O)n11H wherein n11 is an integer from 1 to 500, R1 is hydrogen, alkyl containing from 1 to 18 carbon atoms, phenyl, alkylphenyl containing up to 15 carbon atoms or <FORM:1081285/C4-C5/5> wherein Y is hydrogen, alkyl containing from 1 to 18 carbon atoms, phenyl, alkylphenyl containing up to 15 carbon atoms or <FORM:1081285/C4-C5/6> wherein R, x and y are as stated above and R11 is alkyl containing up to 18 carbon atoms, phenyl or alkylphenyl containing up to 15 carbon atoms.ALSO:The invention comprises esters of acids of phosphorus having the formula <FORM:1081285/C3/1> wherein x is an integer from 1 to 500, y is 0 or an integer from 1 to 500, x plus y is an integer of more than 14 and y/x has a value of 0 to 15, n is 1 or 2, m is 0 or 1 and n plus m equals 2, z is an integer from 1 to 3, R represents (a) hydrogen, (b) alkyl containing from 1 to 18 carbon atoms, (c) alkenyl containing from 1 to 18 carbon atoms, (d) phenyl, (e) alkyl phenyl containing up to 15 carbon atoms, (f) sorbitan monolaurate, (g) <FORM:1081285/C3/2> wherein R111 is alkyl or alkenyl containing from 1 to 18 carbon atoms, (h) <FORM:1081285/C3/3> wherein n1 is an integer from 1 to 500 or (i) <FORM:1081285/C3/4> wherein X is -(C2H4O)n11H wherein n11 is an integer from 1 to 500, R1 is hydrogen, alkyl containing from 1 to 18 carbon atoms, phenyl, alkylphenyl containing up to 15 carbon atoms or <FORM:1081285/C3/5> wherein Y is hydrogen, alkyl containing from 1 to 18 carbon atoms, phenyl, alkylphenyl containing up to 15 carbon atoms or RO[(C2H4O)x(C3H6O)y] wherein R, x and y are as stated above and R1 is alkyl containing up to 18 carbon atoms, phenyl or alkyl phenyl containing up to 15 carbon atoms. The compounds may conveniently be divided into three categories, namely, (I) acid and neutral hydroxy polyoxyalkylene alkyl and aryl phosphate esters, (II) esters of Group (I) where the terminal hydroxy group of the polyoxyalkyl radical has been replaced by an end group -OR and (III) polymeric phosphate esters. Compounds of category (I) may be prepared by reacting a mono- or dialkyl acid phosphate or mixtures thereof (or similar alkylphenyl acid phosphates) with a polyoxyalkylene glycol of the formula [HO(C2H4O)x(C3H6O)y]H at temperatures of 130 DEG to 225 DEG C., the mole ratio of glycol to phosphate ester being less than 1. Compounds of category (II) may be produced in the same manner as category (I) except that in the glycol reactant one of the hydroxy groups will be replaced by the group -OR. The compounds of category (III) may be prepared in the same way as category (I) compounds except that the mole ratio of glycol to phosphate ester should be greater than 1. The compounds may be used in lubricating and cooling compositions (See Division )ALSO:The invention comprises esters of acids of phosphorus having the formula <FORM:1081285/C2/1> wherein x is an integer from 1 to 500, y is 0 or an integer from 1 to 500, x plus y is an integer of more than 14 and y/x has a value of 0 to 15, n is 1 or 2, m is 0 or 1 and n plus m equals 2, z is an integer from 1 to 3, R represents (a) hydrogen, (b) alkyl containing from 1 to 18 carbon atoms, (c) alkenyl containing from 1 to 18 carbon atoms, (d) phenyl, (e) alkyl phenyl containing up to 15 carbon atoms, (f) sorbitan monolenate, (g) <FORM:1081285/C2/2> wherein R111 is alkyl or alkenyl containing from 1 to 18 carbon atoms, (h): <FORM:1081285/C2/3> wherein n1 is an integer from 1 to 500 or (i) <FORM:1081285/C2/4> wherein X is -(C2H4O)n H, wherein n11 is an n11 is an integer from 1 to 500, R1 is hydrogen, alkyl containing from 1 to 18 carbon atoms, phenyl, alkyl phenyl containing up to 15 carbon atoms or <FORM:1081285/C2/5> wherein Y is hydrogen, alkyl containing from 1 to 18 carbon atoms, phenyl, alkylphenyl containing up to 15 carbon atoms or RO[C2H4O)x(C3H6O)y] wherein R, x and y are as stated above, and R11 is alkyl containing up to 18 carbon atoms, phenyl or alkyl phenyl containing up to 15 carbon atoms. The compounds may conveniently be divided into three categories, namely, (I) acid and neutral hydroxy polyoxy-alkylene alkyl and aryl phosphate esters, (II) esters of group (I) where the terminal hydroxyl group of the polyoxyalkyl radical has been replaced by an end group RO and (III) polymeric phosphate esters. Compounds of category (I) may be prepared by reacting a mono- or dialkyl acid phosphate or mixtures thereof (or similar alkylphenyl acid phosphate) with a polyoxy-alkylene glycol of the formula [HO(C2H4O)x(C3H6O)y]H at temperatures of 130 DEG to 225 DEG C., the mole ratio of glycol to phosphate ester being less than 1. Compounds of category (II) may be produced in the same manner as category (I) except that in the glycol reactant one of the hydroxyl groups will be replaced by the group -OR. The compounds of category (III) may be prepared in the same way as category (I) compounds except that the mole ratio of glycol to phosphate ester should be greater than 1. The compounds may be used in lubricating and cooling compositions (see Division C5).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31807963A | 1963-10-22 | 1963-10-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1081285A true GB1081285A (en) | 1967-08-31 |
Family
ID=23236546
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB42861/64A Expired GB1081285A (en) | 1963-10-22 | 1964-10-21 | Esters of phosphorus acids and lubricating compositions comprising them |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1081285A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0010012A1 (en) * | 1978-09-29 | 1980-04-16 | P C U K Produits Chimiques Ugine Kuhlmann | Cleaning agent for dispersing hydrocarbons in a marine environment |
| GB2196632A (en) * | 1986-10-27 | 1988-05-05 | Sandoz Ltd | Phosphoric acid esters of polyethers |
-
1964
- 1964-10-21 GB GB42861/64A patent/GB1081285A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0010012A1 (en) * | 1978-09-29 | 1980-04-16 | P C U K Produits Chimiques Ugine Kuhlmann | Cleaning agent for dispersing hydrocarbons in a marine environment |
| FR2437241A1 (en) * | 1978-09-29 | 1980-04-25 | Ugine Kuhlmann | CLEANING AGENT DISPERSING HYDROCARBONS IN THE MARINE ENVIRONMENT |
| GB2196632A (en) * | 1986-10-27 | 1988-05-05 | Sandoz Ltd | Phosphoric acid esters of polyethers |
| US4830764A (en) * | 1986-10-27 | 1989-05-16 | Sandoz Ltd. | Polyoxyalkylene-containing phosphoric acid esters |
| GB2196632B (en) * | 1986-10-27 | 1990-06-20 | Sandoz Ltd | Phosphoric acid esters of polyethers, their production and use. |
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