US3544614A - Complex esters produced by reacting a dicarboxylic acid,a polyhydric alcohol and boric acid - Google Patents

Complex esters produced by reacting a dicarboxylic acid,a polyhydric alcohol and boric acid Download PDF

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US3544614A
US3544614A US644497A US3544614DA US3544614A US 3544614 A US3544614 A US 3544614A US 644497 A US644497 A US 644497A US 3544614D A US3544614D A US 3544614DA US 3544614 A US3544614 A US 3544614A
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acid
boric acid
complex esters
reacting
polyhydric alcohol
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Norbert C Schwartz
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R H MILLER CO Inc
Rh Miller Co Inc
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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
    • 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
    • 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
    • C08G63/698—Polyesters containing atoms other than carbon, hydrogen and oxygen containing boron
    • C08G63/6984—Polyesters containing atoms other than carbon, hydrogen and oxygen containing boron derived from polycarboxylic acids and polyhydroxy compounds
    • 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
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
    • C10M2227/061—Esters derived from boron
    • 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
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
    • C10M2227/061—Esters derived from boron
    • C10M2227/062—Cyclic esters
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives

Definitions

  • This invention relates to the production and use of complex esters and more particularly to the production and use of complex esters which may be employed, for example, as lubricants for metallic surfaces and which lubricants have dual functions since they possess rustinhibiting characteristics.
  • the complex esters of this invention are produced by various combinations of dior polybasic carboxylic acids, polyhydric alcohols, borates and phosphates.
  • An important object of this invention is to provide lubricants for metallic surfaces containing complex esters synthesized from compositions of matter including, for example, boric acid, which lubricants actually impart rust inhibiting properties to films of the lubricants spread upon the surfaces of the metals.
  • Lubricants for metallic surfaces which lubricants in- "ice clude synthetic esters produced by the employment of some acids, sometime contain additives, which have no part in the synthesizing of the esters and have no lubrieating characteristics but are rust or corrosion inhibitors, pure and simple.
  • Another important object of this invention is to provide complex ester-containing lubricants with the dual function of inhibiting formation of rust.
  • These esters are synthesized from at least one constituent which would be regarded generally as not suitable for rust inhibiting purposes, and may actually be regarded as having corrosive properties. However, when employed as detailed herein, the resulting complex esters do inhibit formation of rust.
  • the polyhydroxylic alcohols include the glycols, triols, tetrols, and hexols, and encompass the entire general family of polyhydroxylic alcohols.
  • the concepts of (a), (b), (c), (d), and (e) in the preceding paragraphs apply to the entire family of polyhydroxylic alcohols and are not limited to these examples specifically cited.
  • the particularly suitable specific polyhydroxylic alcohols are glycerin ethylene glycol, hexylene glycol, polyethylene glycols, pentaerythritol, sorbitol, and 2,4, 7,9-tetrarnethyl-5-decyne-4, 7-diol.
  • the 60% sorbitol of Example VIII is an aqueous solution of 60% by weight sorbitol and 40% by weight water
  • the phosphoric acid of Example X is an aqueous solution of 85% by weight phosphoric acid and by weight water
  • the Surfynol 475 is an ethoxylated 2,4,7,9-tetramethyl-5-decyne-4,7 diol containing 75% by weight ethylene oxide and by weight 2,4,7,9-tetramethyl-5-decyne-4, 7-diol.
  • the present invention is in no way limited by any theory concerning the structure of the complex esters thereof and the exact nature of the over-all reactions are not entirely known; in general, the structural aspects may be tentatively summarized as follows, by referring to one fundamental monomeric unit. As the esters polymerize, a plurality of these units are joined together with each other or with incompletely formed partial units.
  • the fundamental unit is:
  • n* being the number of monomeric groups in the polymer
  • X is a boric acid or phosphoric acid radical which may contain one or two unsubstituted hydrogens.
  • Y is a polyhydroxylic alcohol radical which may contain between zero and five unreacted hydroxyl function groups. Y may also be a triethanolamine or diethanolamine radical in which there are one or two unreacted hydroxyl groups.
  • Z is a saturated or unsaturated aliphatic dicarboxylic acid radical containing four to twenty-four carbon atoms. Z may also be the phthalate radical.
  • n and n' are the number of moles of Y radicals present. It or 11' may be zero. In the present invention, the sum of n plus 11 is preferably between 0.4 and 6.0.
  • n" and n' are the number of moles of Z radicals present. 11 or 11" may be zero. In the present invention, the sum of it plus it" is preferably between 0.4 and 2.7.
  • a couple of examples of simple polymers may be represented as:
  • the first-named wire had scattered areas of slight rusting at the end of a period from mid-November to mid-December, while the second-named wire had rust areas after three days and a uniform coating of light rust at the ned of the same test period and under similar exposure conditions.
  • cold-rolled carbon steel panels were highly polished, cleaned with distilled water, alcohol and Freon TF. They were then quickly dipped into a fluidized sample of selected lubricant and allowed to drain. The samples were then placed in a humidity cabinet maintained at F. and 95% relative himidity. The samples were periodically observed and,
  • the lubricants of this invention showed no rusting of significance until an elapse of 72 hours while the panels coated with a conventional lubricant showed rusting after 48 hours.
  • the humidity cabinet maintained at 140 F. and 95% relative humidity like panels were tested.
  • the panels containing lubricants of this invention showed first rusting at 84 hours while those containing conventional lubricants, showed first corrosion at 34 hours.
  • the tests employing the humidity cabinet were carried out essentially the same as that of the American Society for Testing Materials Methods (Method No. D- 1748 Rust Preventative Evaluation in the Humidity Cabinet).

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Lubricants (AREA)

Description

United States Patent 3,544,614 COMPLEX ESTERS PRODUCED BY REACTING A DICARBOXYLIC ACID, A POLYHYDRIC ALCO- HOL AND BORIC ACID Norbert C. Schwartz, Homer, N.Y., assignor to R. H. Miller Company, Inc., Homer, N.Y., a corporation of New Jersey No Drawing. Filed June 8, 1967, Ser. No. 644,497 Int. Cl. C07f /04, 9/08 US. Cl. 260462 6 Claims ABSTRACT OF THE DISCLOSURE Complex esters for use as lubricants and to impart desirable rust inhibiting films on metallic surfaces, such as those of wire, rods, strips, webs and plates, by way of example, as produced by compositions of matter composed of various combinations of diand poly-basic carboxylic acids, polyhydric alcohols, borates and phosphates, particularly in the equivalent Weight ratios set out in the specification.
This invention relates to the production and use of complex esters and more particularly to the production and use of complex esters which may be employed, for example, as lubricants for metallic surfaces and which lubricants have dual functions since they possess rustinhibiting characteristics.
The complex esters of this invention are produced by various combinations of dior polybasic carboxylic acids, polyhydric alcohols, borates and phosphates.
Normal dibasic esters commonly employed as lubricants suffer from the disadvantages of lacking rust-inhibiting properties.
An important object of this invention is to provide lubricants for metallic surfaces containing complex esters synthesized from compositions of matter including, for example, boric acid, which lubricants actually impart rust inhibiting properties to films of the lubricants spread upon the surfaces of the metals.
Lubricants for metallic surfaces, which lubricants in- "ice clude synthetic esters produced by the employment of some acids, sometime contain additives, which have no part in the synthesizing of the esters and have no lubrieating characteristics but are rust or corrosion inhibitors, pure and simple.
Another important object of this invention is to provide complex ester-containing lubricants with the dual function of inhibiting formation of rust. These esters are synthesized from at least one constituent which would be regarded generally as not suitable for rust inhibiting purposes, and may actually be regarded as having corrosive properties. However, when employed as detailed herein, the resulting complex esters do inhibit formation of rust.
Other objects and advantages of the invention will be apparent during the course of the following detailed description of the invention.
In this disclosure, new, unique, and useful complex esters have been prepared by combining, for example:
(a) Boric acid, a polyhydroxylic alcohol, and a saturated or unsaturated aliphatic dicarboxylic acid or anhydride.
(b) Boric acid, a polyhydroxylic alcohol, and an aromatic dicarboxylic acid or anhydride.
(c) Boric acid, an alkylolamine, and a saturated or unsaturated aliphatic dicarboxylic acid or anhydride.
((1) Orthophosphoric acid, a polyhydroxylic alcohol, and a saturated or unsaturated aliphatic dicarboxylic acid or anhydride.
(e) Orthophosphoric acid, a polyhydroxylic alcohol, and an aromatic dicarboxylic acid or anhydride.
The polyhydroxylic alcohols include the glycols, triols, tetrols, and hexols, and encompass the entire general family of polyhydroxylic alcohols. The concepts of (a), (b), (c), (d), and (e) in the preceding paragraphs apply to the entire family of polyhydroxylic alcohols and are not limited to these examples specifically cited. Among the particularly suitable specific polyhydroxylic alcohols are glycerin ethylene glycol, hexylene glycol, polyethylene glycols, pentaerythritol, sorbitol, and 2,4, 7,9-tetrarnethyl-5-decyne-4, 7-diol.
Typical examples of formulations for the preparation of new, unique and useful complex esters of this invention are as follows:
Hours Acid Acid We1ght, Mole heated value value Example Starting ingredients grams ratio at 110 C. calc. observed Boric acid 22. 8 1. 00 I Glycerin. U.S.P 69.0 1. 96 300 200 125 Sebacic acid 146. 0 1. 89 22. 8 1. 00 II 69. 0 1. 96
136. 0 1. Boric acid. 22.8 1. In Glycerin, U.S.P 69. 0 1.
Azelaic acid, 68.0 0. 98 Phthalic acid 60.0 1. 10 Boric acid 30. 2 1. 00 IV Glycerin, U S P- 92.0 2. 05
Phthalic anhydrid 89. 0 1. 10 Be1'icacid 20.0 1.00 V Ethylene glycol. 62.0 3. 09 Azelaic acid 90. 0 1. 48 Boric acid- 20. O 1.00 VI Hexylene glycol 88. 6 3. 09 Azelaic aicd 94. 0 1. 54 Boric acid 30. 9 1. 00 VII Pentaerythritol 136.00 2.00 Sabacic acid 100.00 1.00 Boric acid 12. 5 1.00 VIII Solbitol. 85. 0 1. 62
"" Azelaic acid 50.0 1. 31
Phthalic acid 40. 0 1. 33 phosphoric acid 19. 0 1.00 IX. 200 MW polyethlcne glycol- 110. 0 3. 00 Phthalic anhydridc 46. 0 1. 50 85% phosphoric acid 43. 3 1.00 X Glycerin, U.S.P 69. 0 2.00 Azelaic acid 68.0 0.96 Plithalic anhydr 60. 0 O. 96
Hours Acid Weight, Mole heated value Example Starting ingredients grams ratio at 110 C. ealc.
Acid value observed Diethanolamine Azelaic acid Boric acid XII Triethanolamino Azolaic acid.
B oric acid XI Boric acid- XIIL Glycerin, U.S.
Maleic anhydride Boric acid XIV Surfynol 475- Sebaeic acid The above-named ingredients may be introduced to a rotary-blades mixer and thoroughly mixed together, or otherwise thoroughly mixed together in any conventional way.
The 60% sorbitol of Example VIII is an aqueous solution of 60% by weight sorbitol and 40% by weight water; the phosphoric acid of Example X is an aqueous solution of 85% by weight phosphoric acid and by weight water; and the Surfynol 475, is an ethoxylated 2,4,7,9-tetramethyl-5-decyne-4,7 diol containing 75% by weight ethylene oxide and by weight 2,4,7,9-tetramethyl-5-decyne-4, 7-diol.
As for the complex esters of this invention, the present invention is in no way limited by any theory concerning the structure of the complex esters thereof and the exact nature of the over-all reactions are not entirely known; in general, the structural aspects may be tentatively summarized as follows, by referring to one fundamental monomeric unit. As the esters polymerize, a plurality of these units are joined together with each other or with incompletely formed partial units. The fundamental unit is:
n* being the number of monomeric groups in the polymer, in which:
X is a boric acid or phosphoric acid radical which may contain one or two unsubstituted hydrogens.
Y is a polyhydroxylic alcohol radical which may contain between zero and five unreacted hydroxyl function groups. Y may also be a triethanolamine or diethanolamine radical in which there are one or two unreacted hydroxyl groups.
Z is a saturated or unsaturated aliphatic dicarboxylic acid radical containing four to twenty-four carbon atoms. Z may also be the phthalate radical.
n and n' are the number of moles of Y radicals present. It or 11' may be zero. In the present invention, the sum of n plus 11 is preferably between 0.4 and 6.0.
n" and n' are the number of moles of Z radicals present. 11 or 11" may be zero. In the present invention, the sum of it plus it" is preferably between 0.4 and 2.7.
A couple of examples of simple polymers may be represented as:
(The symbols m, m, and m" are used to indicate that the quantities may be diflerent from n, n, and n.)
With the above tentative summary in view, a generalized structural composition and mole ratios of examples as above are summarized in the following table:
Numb er of equivalents of carboxylic acid These concepts encompass the complete family of dicarboxylic acids and the concepts are not limited to these examples specifically cited.
In addition to the acids named in the above examples, I have experimented with other related acids such as: oxalic, malonic, succinic, glutaric, adipic, pimelic and suberic.
A number of tests were run in connection with the rust-inhibiting characteristics of the lubricants of this invention. These included outdoor exposure of 1 /2 x 2 inch cold rolled l8-gauge mild steel panels coated with a solution of 0.05% ester of this invention in isopropyl alcohol. Exposure to air and rain disclosed only slight rusting over a period of a months exposure, while a like panel, similarly exposed, but uncoated, typically started rusting in one day and was badly rusted in about four days. As a further test, a lubricant of this invention was used as a wire-drawing lubricant to draw bright basic wire in two holes from inch rod down to 0.2437 inch. Exposed to the air, snow and rain, and compared with a like sample containing a lubricating film of approximately 20% potassium oleate, 5% lime and the balance water, the first-named wire had scattered areas of slight rusting at the end of a period from mid-November to mid-December, while the second-named wire had rust areas after three days and a uniform coating of light rust at the ned of the same test period and under similar exposure conditions. In another test, cold-rolled carbon steel panels were highly polished, cleaned with distilled water, alcohol and Freon TF. They were then quickly dipped into a fluidized sample of selected lubricant and allowed to drain. The samples were then placed in a humidity cabinet maintained at F. and 95% relative himidity. The samples were periodically observed and,
when significant corrosion appeared, they were removed. The lubricants of this invention showed no rusting of significance until an elapse of 72 hours while the panels coated with a conventional lubricant showed rusting after 48 hours. With the humidity cabinet maintained at 140 F. and 95% relative humidity like panels were tested. The panels containing lubricants of this invention showed first rusting at 84 hours while those containing conventional lubricants, showed first corrosion at 34 hours. The tests employing the humidity cabinet were carried out essentially the same as that of the American Society for Testing Materials Methods (Method No. D- 1748 Rust Preventative Evaluation in the Humidity Cabinet).
What is claimed is:
1. Complex esters obtained by reacting at at least about 110 C. for about 150 to about 300 hours, an aliphatic dibasic carboxylic acid or its anhydride, a polyhydric alcohol, and boric acid, said dibasic acid being an acid or anhydride selected from the group consisting of sebacic, azelaic, phthalic, maleic, oxalic, malonic, succinic, glutaric, adipic, pimelic, and suberic, said polyhydric alcohol being selected from the group consisting of glycerin, ethylene glycol, hexylene glycol, pentaaerythritol, sorbitol, polyethylene glycol, having a molecular weight of about 200, and ethoxylated 2,4,7,9-tetramethyl-S-decyne-4,7-diol containing about 75% by weight ethylene oxide and 25% by weight 2,4,7,9-tetramethyl-5-decyne-4,7-diol, said mole ratio of acid and alcohol per mole of boric acid being from about 1.0 to 2.6 and 0.6 to 3.0, respectively.
2. The composition of claim 1 where the acid is sebacic and the alcohol is glycerin.
3. The composition of claim 1 where the acid is azelaic and the alcohol is glycerin.
4. The composition of claim 1 where the acid is a mixture of azelaic and phthalic and the alcohol is glycerin.
5. The composition of claim 1 where the acid is azelaic and the alcohol is ethylene glycol.
6. The composition of claim 1 where the acid is maleic and the alcohol is glycerin.
References Cited UNITED STATES PATENTS 2,189,833 2/1940 Rosenblum 260-462 X 3,202,693 8/1965 Gaertner 260-978 X CHARLES B. PARKER, Primary Examiner A. H. SUTTO, Assistant Examiner U.S. Cl. X.R.
US644497A 1967-06-08 1967-06-08 Complex esters produced by reacting a dicarboxylic acid,a polyhydric alcohol and boric acid Expired - Lifetime US3544614A (en)

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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS54142462A (en) * 1978-04-28 1979-11-06 Ishihara Yakuhin Kk Lubricant for plastic processing
US4226734A (en) * 1977-12-22 1980-10-07 Dietrich Schuster Cooling, lubricating, and cleaning agent
US4258448A (en) * 1977-06-15 1981-03-31 Bayer Aktiengesellschaft Method of dispersing, emulsifying materials with phosphoric acid esters
US4265664A (en) * 1978-05-12 1981-05-05 Chemie Linz Aktiengesellschaft Spirocyclic boron compounds, a process for their manufacture and their use as a flame-retardant additive
EP0036708A1 (en) * 1980-03-24 1981-09-30 Mobil Oil Corporation Friction reducing additives
EP0037631A1 (en) * 1980-03-10 1981-10-14 Mobil Oil Corporation Friction reducing additives and compositions thereof
US4301026A (en) * 1978-12-02 1981-11-17 Teruhisa Kondo Antioxidant for carbonaceous material and method
US4370248A (en) * 1980-03-20 1983-01-25 Mobil Oil Corporation Borated hydroxyl-containing acid esters and lubricants containing same
US4376712A (en) * 1980-03-10 1983-03-15 Mobil Oil Corporation Friction reducing additives and compositions thereof
US4406802A (en) * 1981-04-30 1983-09-27 Mobil Oil Corporation Friction reducing additives and compositions thereof
US4530771A (en) * 1982-08-03 1985-07-23 Karonite Chemical Co., Ltd. Lubricating oil compositions
US4533481A (en) * 1983-04-20 1985-08-06 The Lubrizol Corporation Polycarboxylic acid/boric acid/amine salts and aqueous systems containing same
US5064545A (en) * 1986-12-17 1991-11-12 The Lubrizol Corporation Process for overbasing via metal borate formation
US5242608A (en) * 1986-12-17 1993-09-07 The Lubrizol Corporation Process for overbasing via metal borate formation

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2189833A (en) * 1930-03-25 1940-02-13 Rosenblum Israel Resinous condensation products and method of producing same
US3202693A (en) * 1962-10-11 1965-08-24 Monsanto Co Succinate half-esters of alkylene glycol phosphate

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2189833A (en) * 1930-03-25 1940-02-13 Rosenblum Israel Resinous condensation products and method of producing same
US3202693A (en) * 1962-10-11 1965-08-24 Monsanto Co Succinate half-esters of alkylene glycol phosphate

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4258448A (en) * 1977-06-15 1981-03-31 Bayer Aktiengesellschaft Method of dispersing, emulsifying materials with phosphoric acid esters
US4226734A (en) * 1977-12-22 1980-10-07 Dietrich Schuster Cooling, lubricating, and cleaning agent
US4303540A (en) * 1977-12-22 1981-12-01 Dietrich Schuster Cooling, lubricating and cleaning agent
JPS54142462A (en) * 1978-04-28 1979-11-06 Ishihara Yakuhin Kk Lubricant for plastic processing
JPS5757118B2 (en) * 1978-04-28 1982-12-02 Ishihara Yakuhin Kk
US4265664A (en) * 1978-05-12 1981-05-05 Chemie Linz Aktiengesellschaft Spirocyclic boron compounds, a process for their manufacture and their use as a flame-retardant additive
US4301026A (en) * 1978-12-02 1981-11-17 Teruhisa Kondo Antioxidant for carbonaceous material and method
EP0037631A1 (en) * 1980-03-10 1981-10-14 Mobil Oil Corporation Friction reducing additives and compositions thereof
US4376712A (en) * 1980-03-10 1983-03-15 Mobil Oil Corporation Friction reducing additives and compositions thereof
US4370248A (en) * 1980-03-20 1983-01-25 Mobil Oil Corporation Borated hydroxyl-containing acid esters and lubricants containing same
EP0036708A1 (en) * 1980-03-24 1981-09-30 Mobil Oil Corporation Friction reducing additives
JPS56150097A (en) * 1980-03-24 1981-11-20 Mobil Oil Corp Friction reducing additive,lubricant composition and internal combustion engine fuel consumption reduction method
US4406802A (en) * 1981-04-30 1983-09-27 Mobil Oil Corporation Friction reducing additives and compositions thereof
US4530771A (en) * 1982-08-03 1985-07-23 Karonite Chemical Co., Ltd. Lubricating oil compositions
US4533481A (en) * 1983-04-20 1985-08-06 The Lubrizol Corporation Polycarboxylic acid/boric acid/amine salts and aqueous systems containing same
US5064545A (en) * 1986-12-17 1991-11-12 The Lubrizol Corporation Process for overbasing via metal borate formation
US5242608A (en) * 1986-12-17 1993-09-07 The Lubrizol Corporation Process for overbasing via metal borate formation
US6090757A (en) * 1986-12-17 2000-07-18 The Lubrizol Corporation Process for overbasing via metal borate formation

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