GB804369A - Siloxane-oxyalkylene block copolymers - Google Patents
Siloxane-oxyalkylene block copolymersInfo
- Publication number
- GB804369A GB804369A GB6147/55A GB614755A GB804369A GB 804369 A GB804369 A GB 804369A GB 6147/55 A GB6147/55 A GB 6147/55A GB 614755 A GB614755 A GB 614755A GB 804369 A GB804369 A GB 804369A
- Authority
- GB
- United Kingdom
- Prior art keywords
- lubricants
- useful
- water
- polysiloxane
- block copolymers
- 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
- 229920001400 block copolymer Polymers 0.000 title abstract 6
- 239000000314 lubricant Substances 0.000 abstract 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Substances OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 6
- -1 polysiloxane Polymers 0.000 abstract 5
- 238000006243 chemical reaction Methods 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 abstract 3
- 239000003795 chemical substances by application Substances 0.000 abstract 3
- 229920001296 polysiloxane Polymers 0.000 abstract 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 239000002518 antifoaming agent Substances 0.000 abstract 2
- 125000004429 atom Chemical group 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 239000004205 dimethyl polysiloxane Substances 0.000 abstract 2
- 150000002009 diols Chemical class 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 abstract 2
- 229920000642 polymer Polymers 0.000 abstract 2
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 abstract 2
- 229920001451 polypropylene glycol Polymers 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- CCUWGJDGLACFQT-UHFFFAOYSA-N 2,2,3,3,4,4-hexafluoropentanedioic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)C(O)=O CCUWGJDGLACFQT-UHFFFAOYSA-N 0.000 abstract 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- 239000002202 Polyethylene glycol Substances 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 abstract 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 abstract 1
- 230000001804 emulsifying effect Effects 0.000 abstract 1
- 239000012530 fluid Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 1
- 239000004615 ingredient Substances 0.000 abstract 1
- 230000001050 lubricating effect Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- REOJLIXKJWXUGB-UHFFFAOYSA-N mofebutazone Chemical group O=C1C(CCCC)C(=O)NN1C1=CC=CC=C1 REOJLIXKJWXUGB-UHFFFAOYSA-N 0.000 abstract 1
- 238000010068 moulding (rubber) Methods 0.000 abstract 1
- 238000006386 neutralization reaction Methods 0.000 abstract 1
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 abstract 1
- YPJUNDFVDDCYIH-UHFFFAOYSA-N perfluorobutyric acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)F YPJUNDFVDDCYIH-UHFFFAOYSA-N 0.000 abstract 1
- 230000000704 physical effect Effects 0.000 abstract 1
- 229920001515 polyalkylene glycol Polymers 0.000 abstract 1
- 229920001223 polyethylene glycol Polymers 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 239000004753 textile Substances 0.000 abstract 1
- CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical compound O.CC1=CC=CC=C1 CMQCNTNASCDNGR-UHFFFAOYSA-N 0.000 abstract 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 abstract 1
- 238000005406 washing Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 239000008096 xylene Substances 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/46—Block-or graft-polymers containing polysiloxane sequences containing polyether sequences
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/022—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms containing at least two hydroxy groups
-
- 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
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
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)
- Lubricants (AREA)
Abstract
Polysiloxane-polyoxyalkylene block copolymers (see Group IV (a)) are in some cases water-soluble when they are useful as anti-foam agents or, in combination with water-soluble polyoxyethylene-polyoxypropylene diols, or their mono-or di-ethers or with ethylene or propylene glycol, as ingredients of hydrolubes. Certain of the block copolymers are also useful as metal-to-metal lubricants for moving surfaces. The particular block copolymers of Examples III, V and VIII had good emulsifying properties, especially for toluene-water systems.ALSO:A polysiloxane-polyoxyalkylene block copolymer has the general formula <FORM:0804369/IV (a)/1> wherein R1 is a low molecular weight alkyl or alkylene radical with the valence of x, R, R11 and R111 are low molecular weight alkyl radicals, x is 1 or 2, y is an integer of at least 3, n is 2, 3 or 4, a is an integer of at least 1 and not more than 3x, and z is an integer of at least 5. The polymers are formed by reacting an appropriate mono-alkyl ether of a polyalkylene glycol with a polysiloxane having 1 or 2 Si atoms bonded to carbon atoms of an alkyl or alkylene group, the remaining valencies of these Si atoms being satisfied by O linked either directly or via (-Si(R2)O-) units or chains of such units to alkyl radicals. Typical copolymers have the formul <FORM:0804369/IV (a)/2> in which p+q+r=y (above), <FORM:0804369/IV (a)/3> in which p+q=y, or <FORM:0804369/IV (a)/4> in which p+q+r+s+t+u=y, which in this case has a minimum value of 6. The general reaction for the preparation of these polymers may be written <FORM:0804369/IV (a)/5> <FORM:0804369/IV (a)/6> The polysiloxanes used as staring materials may have mol. wts. of 300-10,000 and may be prepared by reacting a polysiloxane, e.g. a trimeric or tetrameric cyclic siloxane, with a trialkoxysilane or a bis-(trialkoxysilyl) ethane, e.g. as described in Specification 792,470. Suitable polyoxyalkylene monoethers for the as starting materials are described in U.S.A. Specification 2,448,664 and in British Specification 616,256. The reaction is preferably performed in presence of a mutual solvent, e.g. toluene, xylene. The alcohol removed in the reaction may pass off as an azeotrope with the solvent. Suitable catalysts for the reaction are trifluoroacetic, perfluorobutyric, perfluoroglutaric, monochloroacetic or acetic acid, or alkali metal hydroxides. The latter form silanolates with the siloxane. Removal or neutralization of catalyst may be necessary for stability of the products. In Example (1), monobutyl - poly - (oxyethylene - oxy - 1,2 - propylene) glycol, monobutyl-polypropylene glycol, or monomethyl-polyethylene glycol is condensed by refluxing in toluene and trifluoroacetic acid with a triethoxy-polydimethylsiloxane obtained by heating a cyclic dimethyl polysiloxane with ethyltriethoxysilane in presence of alkali. The physical properties and solubilities of the products are tabulated. Examples (2)-(9) are basically similar, illustrating variations of molecular weight and starting materials within the general field. Example (10) describes the condensation of monobutyl-polypropylene glycol with a hexaethoxydimethylsiloxane obtained by equilibrating hexaethoxydisilylethane and dimethylsiloxane cyclic tetramer. Some of the products are water-soluble, and useful as antifoam agents, rubber lubricants especially for type moulds, or textile lubricants. They are miscible with water-soluble polyoxyethylene-polyoxypropylene diols or their mono- or di-ethers, or with ethylene or propylene glycol to form useful lubricants or hydraulic fluids. Certain products are good metal-to-metal lubricants for moving surfaces. Their lubricating properties are compared in the Specification with those of conventional lubricants.ALSO:Polysilonare-polyonyathylen block copolymers (see Group IVa) when water soluble or useful as rubber lubricants especially for tyre moulds, when they may be applied from aqueous solutions and excess is readily removable by washing. The particular product of Ex 1(a) was useful as a release-agent in rubber moulding.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US804369XA | 1954-03-22 | 1954-03-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB804369A true GB804369A (en) | 1958-11-12 |
Family
ID=22157372
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB6147/55A Expired GB804369A (en) | 1954-03-22 | 1955-03-02 | Siloxane-oxyalkylene block copolymers |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB804369A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3445276A (en) * | 1965-08-04 | 1969-05-20 | Union Carbide Corp | Textile materials coated with hydrolytically stable siloxane-oxyalkylene block copolymers containing sih |
| US4207071A (en) * | 1979-02-01 | 1980-06-10 | Dow Corning Corporation | Durable modification of fibrous substrates using a polyoxyethylene-containing silane and articles therefrom |
| WO1985004891A1 (en) * | 1984-04-24 | 1985-11-07 | Bp Chemicals Limited | Preparation of polymer polyols |
| US4784844A (en) * | 1979-12-03 | 1988-11-15 | General Electric Company | Volatile silicone-water emulsions and methods of preparation and use |
-
1955
- 1955-03-02 GB GB6147/55A patent/GB804369A/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3445276A (en) * | 1965-08-04 | 1969-05-20 | Union Carbide Corp | Textile materials coated with hydrolytically stable siloxane-oxyalkylene block copolymers containing sih |
| US4207071A (en) * | 1979-02-01 | 1980-06-10 | Dow Corning Corporation | Durable modification of fibrous substrates using a polyoxyethylene-containing silane and articles therefrom |
| US4784844A (en) * | 1979-12-03 | 1988-11-15 | General Electric Company | Volatile silicone-water emulsions and methods of preparation and use |
| WO1985004891A1 (en) * | 1984-04-24 | 1985-11-07 | Bp Chemicals Limited | Preparation of polymer polyols |
| EP0162589A1 (en) * | 1984-04-24 | 1985-11-27 | BP Chemicals Limited | Preparation of polymer polyols |
| AU576581B2 (en) * | 1984-04-24 | 1988-09-01 | Polyol International B.V. | Preparation of polymer polyols |
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