EP0116564A1 - Epaississants polyethers pour fluides hydrauliques a base d'eau - Google Patents

Epaississants polyethers pour fluides hydrauliques a base d'eau

Info

Publication number
EP0116564A1
EP0116564A1 EP83902194A EP83902194A EP0116564A1 EP 0116564 A1 EP0116564 A1 EP 0116564A1 EP 83902194 A EP83902194 A EP 83902194A EP 83902194 A EP83902194 A EP 83902194A EP 0116564 A1 EP0116564 A1 EP 0116564A1
Authority
EP
European Patent Office
Prior art keywords
oxide
percent
copolymer
polyether polyol
weight
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.)
Withdrawn
Application number
EP83902194A
Other languages
German (de)
English (en)
Inventor
Emil J. Costagliola
Francis S. Munjat
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.)
EF Houghton and Co
Original Assignee
EF Houghton and 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 EF Houghton and Co filed Critical EF Houghton and Co
Publication of EP0116564A1 publication Critical patent/EP0116564A1/fr
Withdrawn legal-status Critical Current

Links

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
    • C10M173/00—Lubricating compositions containing more than 10% water
    • C10M173/02—Lubricating compositions containing more than 10% water not containing mineral or fatty oils
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/04—Saturated ethers
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
    • C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
    • C08G65/2609—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aliphatic hydroxyl groups
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
    • C08G65/2645—Metals or compounds thereof, e.g. salts
    • C08G65/2648—Alkali metals or compounds thereof
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
    • C08G65/2645—Metals or compounds thereof, e.g. salts
    • C08G65/2654—Aluminium or boron; Compounds thereof

Definitions

  • This invention pertains to novel alpha oiefin oxide-capped polyether polyols which are particularly suitable for use as thickeners for aqueous systems, such as water-based hydraulic fluids.
  • Water-soluble or water-dispersible thickeners of a variety of chemical types are used in aqueous liquids to increase their viscosity.
  • efforts have been made to provide water-based hydraulic fluids of acceptable properties.
  • polyether polyols have been suggested for used therein as thickeners.
  • SUS Sabolt Universal Seconds
  • the thickeners are polyether polyols which have been capped with an aliphatic alpha oiefin oxide containing from about 10 to about 30 carbon atoms.
  • the polyether polyols which are capped are obtained by reacting ethylene oxide and a lower alkylene oxide having 3 to 4 carbon atoms with an active hydrogen compound which is a polyhydric alcohol to form a heteric or block copolymer.
  • the reaction by which such copolymers may be capped may be illustrated as follows:
  • the polyether polyols are first prepared by reacting ethylene oxide, at least one lower alkylene oxide having 3 to 4 carbon atoms, and an active hydrogen compound which is a polyhydric alcohol.
  • OMPI Methods for preparing these polyether polyols are well known, and good results may be obtained by bringing a mixture containing the ethylene oxide and the lower alkylene oxide into intimate contact with the aliphatic polyhydric alcohol active hydrogen compound in the liquid phase, throughout which a suitable catalyst is uniformly dispersed.
  • a suitable catalyst sodium and potassium hydroxide are preferred.
  • the reaction is carried out at temperatures on the order of 50° to 160° C, under a pressure of from about 20 to about 100 psig.
  • the concentration of the catalyst may vary from about 0.1 to about 5 percent by weight of the active hydrogen compound.
  • the lower alkylene oxides used in the reaction include 1,2-propylene oxide, and butylene oxide.
  • the percentages by weight of these components vary from about 10 to about 90 percent of ethylene oxide, to from about 90 to 10 percent of another lower alkylene oxide or mixture thereof.
  • the copolymers which may be either heteric or block, contain about 65 to about 85 percent ethylene oxide and about 35 to about 15 percent lower alkylene oxide containing 3 to 4 carbon atoms.
  • a particularly preferred polyether polyol is a block copolymer comprising 75 percent ethylene oxide and 25 percent 1,2-propylene oxide.
  • the reactive hydrogen compounds or initiators employed in preparing the polyether polyols which are then capped with -an aliphatic alpha oiefin oxide are selected from the group consisting of alkane polyols, alkene polyols, alkyne polyols and oxyalkylene polyols.
  • the alkane polyols should contain from about 2 to about 10 carbon atoms from about 2 to about 6 hydroxyl groups.
  • alkane polyols are ethylene glycol, diethylene glycol, propylene glycol, 1,4-butanediol, trimethylol propane, pentaerythritol and the like.
  • the alkene polyols, like the alkane polyols may have from 2 to 10 carbon atoms and 2 to 6 hydroxyl groups.
  • Useful alkene polyols include 2-butene-l,4-diol, 2-hexene-l,4,6-triol, l,5-hexadiene-3,4-diol, and the like.
  • alkyne polyols which may also contain the same number of carbon atoms and hydroxyl groups as the alkane and alkene polyols, are 2-butyne-l,4-diol, 2-hexyne-l,4,6-triol and 4-octyne-l,2,7,8-tetrol.
  • oxyalkylene polyols ethylene glycol, diethylene glycol, triethylene glycol, dipropylene glycol and tripropyle ⁇ e glycol are preferred active hydrogen compounds.
  • a relatively minor amount of initiator or active hydrogen compound e.g.
  • the polyether polyols which are to be capped generally will have a molecular weight of about 5000 to about 75,000, preferably from about 10,000 to about 15,000.
  • the aliphatic alpha oiefin oxides which are used to cap the polyether polyols described hereinabove are those containing on the order of from about 10 to about 30 carbon atoms, preferably from about 12 to about 18 carbon atoms.
  • the amount of alpha oiefin oxide required to obtain the improved thickeners of this invention is generally from about 1 to about 20 percent, preferably from about 1 to about 10 percent, by weight of the capped polyether polyol.
  • Examples of preferred alpha oiefin oxides are 1,2-epoxy hexadecane, 1,2-epoxy heptadecane, 1,2-epoxy octadecane, and mixtures thereof.
  • such reactant first be rendered substantially anhydrous. This may be accomplished by heating the polyether polyol in the presence of an organic solvent, such as toluene or xylene, under reflux conditions for several hours, following which the solvent is stripped to remove water.
  • BF3 catalyst preferably in ether, is added to the reaction vessel under a blanket of an inert gas such as nitrogen.
  • an alkaline catalyst such as sodium hydroxide, sodium methoxide or potassium hydroxide may be used in place of BF3.
  • Such alkaline catalyst may be an anhydrous solid or in the form of a concentrated aqueous solution.
  • the catalyst is in the form of an aqueous solution
  • the catalyst and polyol should be combined following which water is removed to provide anhydrous reactants as hereinabove described.
  • the alpha oiefin oxide is then added and the reaction takes place over a period of several hours in the absence of heat.
  • reaction temperatures should be maintained in the range of from about 45 to about 50° C, although such temperatures may be as high as 155° C, particularly where an alkaline catalyst is employed.
  • a hydraulic fluid was prepared by combining the following constituents:
  • Vapor phase corrosion inhibitor* 2. 0
  • the hydraulic fluid which had a hazy opaque appearance, had a viscosity of 420 SUS at 100°F. , a pH of 9.2 and a specific gravity of about 1.07 at 60° F.
  • a hydraulic fluid was prepared by combining the following constituents: TABLE III
  • the hydraulic fluid which had a hazy opaque color, had a viscosity of 152 SUS at 100° F., a pH of 9.0-9.4 and a specific gravity of about 1.07.
  • Example V To a 3 liter, 3 neck flask prepared for heating and agitation were added 120 g. of a block copolymer comprising about 75 percent by weight of ethylene oxide and 25 percent of 1,2-propylene oxide and having a molecular weight of about 2000 (Ucon 75H 1400, Union Carbide Corp.), 25 g. of a mixture of aliphatic alpha oiefin oxides having from 16 ot 18 carbon atoms, and 1 ml. of a mixture comprising BF3 (47%) in ether were added, and the reaction mixture was heated for a period of approximately 25 minutes. A capped polyether polyol thickener for aqueous systems was obtained.
  • Example VI To a 3 liter, 3 neck flask prepared for heating and agitation were added 120 g. of a block copolymer comprising about 75 percent by weight of ethylene oxide and 25 percent of 1,2-propylene oxide and having a molecular weight of about 2000 (Ucon 75H 1400, Union

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Polyethers (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

Polyols polyéthers coiffés d'un oxyde d'alpha oléfine sont préparés en faisant réagir un copolymère hétérique ou bloc pratiquement anhydre d'oxyde d'éthylène et un oxyde d'alkylène avec un oxyde d'alpha oléfine en présence d'un catalyseur. Les polyols polyéthers coiffés sont utiles en tant qu'épaississants pour systèmes aqueux, comme des fluides hydrauliques à base d'eau.
EP83902194A 1982-07-08 1983-06-03 Epaississants polyethers pour fluides hydrauliques a base d'eau Withdrawn EP0116564A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US39630182A 1982-07-08 1982-07-08
US396301 2003-03-25

Publications (1)

Publication Number Publication Date
EP0116564A1 true EP0116564A1 (fr) 1984-08-29

Family

ID=23566688

Family Applications (1)

Application Number Title Priority Date Filing Date
EP83902194A Withdrawn EP0116564A1 (fr) 1982-07-08 1983-06-03 Epaississants polyethers pour fluides hydrauliques a base d'eau

Country Status (5)

Country Link
EP (1) EP0116564A1 (fr)
KR (1) KR840005420A (fr)
CA (1) CA1333811C (fr)
IT (1) IT8348649A0 (fr)
WO (1) WO1984000361A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3531915A1 (de) * 1985-09-07 1987-03-19 Bayer Ag Verdickungssysteme fuer hoch wasserhaltige funktionelle fluessigkeiten und die diese verdickungssysteme enthaltenden hoch wasserhaltigen funktionellen fluessigkeiten
DE3807235A1 (de) * 1988-03-05 1989-09-14 Basf Ag Fliesenklebstoff
DE4017687A1 (de) * 1990-06-01 1991-12-05 Bayer Ag Verbesserte funktionelle fluessigkeiten
DE4017688A1 (de) * 1990-06-01 1991-12-05 Bayer Ag Verbesserte funktionelle fluessigkeiten und neue polyoxyalkylenpolymere
CN105934502B (zh) * 2014-01-28 2020-03-13 巴斯夫欧洲公司 烷氧基化聚乙二醇在润滑油组合物中的用途

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3829506A (en) * 1971-06-01 1974-08-13 Basf Wyandotte Corp Biodegradable surface active agents having good foam properties and foam stabilizing characteristics
US3748276A (en) * 1971-07-19 1973-07-24 Basf Wyandotte Corp Aqueous gel composition containing polyether polyol gelling agents
US4310436A (en) * 1979-10-22 1982-01-12 Basf Wyandotte Polyether-based thickeners with additives for increased efficiency in aqueous systems
US4312775A (en) * 1979-10-22 1982-01-26 Basf Wyandotte Corporation Polyether thickeners for aqueous systems containing additives for increased thickening efficiency
US4312768A (en) * 1979-10-22 1982-01-26 Basf Wyandotte Corporation Synergistic polyether thickeners for water-based hydraulic fluids
US4381205A (en) * 1982-04-05 1983-04-26 E. F. Houghton & Company Metal quenching process

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO8400361A1 *

Also Published As

Publication number Publication date
CA1333811C (fr) 1995-01-03
WO1984000361A1 (fr) 1984-02-02
KR840005420A (ko) 1984-11-12
IT8348649A0 (it) 1983-07-08

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Legal Events

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PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

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STAA Information on the status of an ep patent application or granted ep patent

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Effective date: 19840613

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Inventor name: COSTAGLIOLA, EMIL, J.

Inventor name: MUNJAT, FRANCIS S.