GB2301589A - fluorinated polysiloxane and cyclosiloxane oils - Google Patents

fluorinated polysiloxane and cyclosiloxane oils Download PDF

Info

Publication number
GB2301589A
GB2301589A GB9510866A GB9510866A GB2301589A GB 2301589 A GB2301589 A GB 2301589A GB 9510866 A GB9510866 A GB 9510866A GB 9510866 A GB9510866 A GB 9510866A GB 2301589 A GB2301589 A GB 2301589A
Authority
GB
United Kingdom
Prior art keywords
compound
formula
oil
rfzch2si
selected independently
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Withdrawn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
GB9510866A
Other versions
GB9510866D0 (en
Inventor
Dimitri Stefanovich Rondarev
Gennadii Alexandrovi Nickolaev
Gerald Richard Charl Kingsbury
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.)
WENTWORTH H K Ltd
Original Assignee
WENTWORTH H K Ltd
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 WENTWORTH H K Ltd filed Critical WENTWORTH H K Ltd
Priority to GB9510866A priority Critical patent/GB2301589A/en
Publication of GB9510866D0 publication Critical patent/GB9510866D0/en
Priority to AU58409/96A priority patent/AU5840996A/en
Priority to PCT/GB1996/001301 priority patent/WO1996038454A1/en
Publication of GB2301589A publication Critical patent/GB2301589A/en
Withdrawn legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04Polysiloxanes
    • C08G77/38Polysiloxanes modified by chemical after-treatment
    • C08G77/382Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
    • C08G77/385Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing halogens
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02Silicon compounds
    • C07F7/08Compounds having one or more C—Si linkages
    • C07F7/0834Compounds having one or more O-Si linkage
    • C07F7/0838Compounds with one or more Si-O-Si sequences
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02Silicon compounds
    • C07F7/21Cyclic compounds having at least one ring containing silicon, but no carbon in the ring
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04Polysiloxanes
    • C08G77/045Polysiloxanes containing less than 25 silicon atoms
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04Polysiloxanes
    • C08G77/22Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/24Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-containing groups
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M171/00Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
    • C10M171/001Electrorheological fluids; smart 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

Oils of formula I and II wherein at least one X is a specified polyfluoropolyether moiety and any other is H, are usable as base oils for electro-rheological fluid compositions. In (I) and II: m is 1 to 6 n is 3 to 7 X is Z - R f where Z is CH 2 , CH(CH 3 ), CH 2 CH 2 or CH 2 CH 2 -O-CO- and R f is a fluorinated polyether moiety end-stopped by CF 3 .

Description

OTLS This invention relates to electro-rheological fluid (ERF) compositions, to base oils for use in such compositions, to fluorinated polysiloxane compounds for use as or in such base oils, and to the preparation of such compounds.
ERF compositions have been known and used for many years.
They comprise fine dielectric particles suspended in electrically non-conductive base oil, the viscosity of the composition changing markedly, rapidly and reversibly in response to changes of applied electric field. These properties have led to ERF compositions being used in various electro-mechanical devices, including clutches, shock absorbers, propeller shafts, vibrators, dampers etc. Numerous materials have been used as the particulate dielectric solid phase, including zeolites, silica gel, starches, and various polymers and ionomers. A number of different materials have been used or proposed as base oil, e.g. fluorosilicones these are compounds which have the fluorine in propyl (or higher alkyl) chains attached to silicon atoms of polysiloxane backbones, for example as in
where x is 2 or ore.
Evidence on the usefulness of fluorosilicone compounds as base oils for -R fluids is widely known from, for example, EP-A-0284268, and GB-A-2210893.
We have found it extremely difficult to manufacture such compounds, wherein simple fluorinated alkyl groups are attached to a silicone chain or ring, of the density and low viscosity acknowledged in this prior art to be necessary for useful ER fluid base materials. EP-A-0284268 establishes a useful limit of molecular weight of such a polymer as being 200 to 700; we find that these fluorosilicones are of too low density unless the alkyl chains are longer than propyl, and in the latter case the viscosity can become too high to be ideal as an ER fluid base oil usable at working temperature.
The current invention teaches the attachment of perfluoropolyether chains, instead of the more usual simple fluoroalkyl chains, to the silicone chain or cyclic ring.
Such novel perfluoropolyether silicone compounds can be manufactured that have a molecular weight of above 600 (normally in the 700 to 2000 range or higher) whilst having low viscosity at 20 C of around 15 cps and achieving a density of around 1.40; in ERF compositions it is important to match fluid density with that of the solid materials - such as lithium salt of polymethacrylic acid, which is taught in prior documents mentioned above as being useful as the particulate component in ERF compositions.
As the manufacturing process will produce a mixture of various compounds of varying chain length and ring size which are controllable by adjustments to the manufacturing process, a feature of the invention is that both viscosity and density can be varied within quite wide ranges without the need to add other liquids, e.g. heavy perfluorocarbon or CTFE compounds or lighter alkyl siloxanes. Variations of viscosity and density can also be achieved by appropriate choice of molecular weight for the perfluoropolyether side chains.
The invention provides at least one compound selected from those of formulae I and II
wherein each X is selected independently from H and ZRf but in each formula at least one X is not H, and wherein m is an integer of 1 to 6; n is an integer of 3 to 7; the or each Z is selected independently from -CH2-, -CH(CH3)-, -CH2CH2-, and
the or each Rf is selected independently from CF3O(CF2O)p (CF2CF2O)q CF2- and CF3O(CF2O)p(CF2CF(CF3)O)qCF2- and CF30 (CFO)p(CF(CF2)CF2O)qCF-; p is an integer of 1 to 7; and q is zero, 1 or 2.
Preferably, in formula I, each X is selected independently from H and CF3 (CF2O)pCF2CH (CH3) - and at least one X is not H; p can for example be 5.
The present invention also provides a base oil for an ERF composition, which base oil comprises at least one compound selected from perfluoropolyether derivatives of linear and cyclic polysiloxanes. The base oil preferably comprises at least one perfluoropolyether derivative of a cyclic polysiloxane and at least one perfluoropolyether derivative of a linear polysiloxane. The invention also provides an ERF composition containing base oil according to the invention.
The base oil of the invention preferably has a density of from 1.3 to 1.6 g/cm and a viscosity less than 25 cps. Preferred base oils of the invention comprise at least one compound selected from those of formulae I and II above, most preferably a combination of at least one compound of formula I and at least one compound of formula II.
The base oil according to the invention may include a minor amount (preferably less than 5 vol.%) of cyclic and/or linear polysiloxane of low molecular weight to reduce the overall viscosity to the required value. Such polysiloxane may for example be of sufficiently short chain or small ring as to have a viscosity below 10 cps at 20 C. The base oil may additionally or instead include high density non-conducting liquid (e.g. chlorotrifluoroethylene) to increase overall density. The density of the base oil should ideally be the same as that of the solid dielectric particles with which it is to be used in an ERF composition.
The preferred particulate dielectric solid phase for use in ERF compositions according to the invention is polymethylacrylic acid lithium salt, but others (including those mentioned above) could be used additionally or instead.
The dielectric particles are suitably of particle size in the 1-50 micron ran, and may be present in an amount of 5 to 60 volume % of the ERr composition; minimum amount is preferably 20 volume ; and the maximum amount is preferably 40 volume The perfLloropolyether compounds according to the invention can be obtained by the following procedures.
A first method comprises rydrolysing a mixture of dichlorodimethylsilane and dichlorosilane of formula RfZCH2Si(CH3)CI2, blocking of end groups using hexamethyldisilazane (CH3)3SiNHSi(CH3)3 as chain terminator, and distilling the product with catalytic depolymerisation to obtain a compound or mixture of compounds of formula I/II.
Suitably the RfZCH2Si(CH3)Cl2 starting material for the above method is prepared by catalytic reaction of CH3SiHCl2 with olefinic compound RfZ1=CH2 where Z'= is -CH=, -C(CH3)= or -CH2CH=. Olefin RfZl=CH2 can be prepared by several routes.
When -Z' is C(CH3)=, RfC(CH3)=CH2 olefin can be prepared by dehydration of alcohol of formula RfC(CH3)2OH. The alcohol RfC(CH3)2OH can be prepared by reacting ester of formula RfCOOCH3 with Grignard reagent CH3MgBr. In general, the RfZCH2Si(CH3)Cl starting material is suitably made using fluoroorganic compound RfCOY where Y is F, Cl, OH, OCH3, OC2Hs. For example, if z is -CH(CH3)- a suitable route is
-RfCH (CH3) CH2Si (OH3) C.
if Z is -CH2-, a suitable route is
-RfCH2CH2Si (CH3) CQ2; if Z is -CH2CH2-, a suitable route is
RfCH2-CH=CH2-RfCH2CH2CH2Si (CM3) CQ2; This first method produces predominantly cyclic polysiloxanes of general formula I.
A second method comprises preparing at least one compound selected from those of formulae III and IV
wherein B is selected independently from H and -CH2CH2CX but in each formula at least one B is not H, and m and n are as defined hereinbefore, by co-hydrolysis of dimethyldichlorosilane (CH3)2SiCÇ2 with methyl-ychloropropyl dichlorosilane CH2ClCH2CH2Si(CH3)Cl2, reacting said chlorosiloxane(s) with perfluoro compound RfCOOM where M is Li, Na or K, and separating out resultant compound or mixture of compounds of formula I/II.
Compound RfCOOM may be obtained from compound RfCOY above.
This method produces predominantly linear polysiloxanes of general formula II.
In these methods, Rf is of course as defined hereinbefore. RfCO- is suitably CF30(CF20)sCF2CO-, with Y being for example OCH3 (especially in the first method above) or OH (especially in the second method).
An Example of the above first method for obtaining a perfluoroether compound according to the invention will now be described in detail: E X A M P L E (a) Synthesis of chlorosilane RfZCH2Si(CH3)Cl2 using fluoroorganic polymer RfCOY where Y is OCH3, Rf is CF30(CF2O)sCF2-, and Z is -CH(CH3)-.
[i] Alcohol RfC (CH3)2OH is synthesised by adding 2253 g (4.3 mol) of RfCOOCH3 to 3 liters of 3M Grignard reagent CH3MgBr solution in THF at 5-10 C while stirring intensively for 3 hours,neutralising excess CH3MgBr with n-butanol (50 ml),removal of THF by vaccuum distillation and neutralisation of any THF residue by 10% HCl up to pH=3 while cooling; followed by separation of the organic layer from the water-salt fraction, washing it with water and drying using anhydrous Na2SO4, and extraction of alcohol of formula RfC (CH3)2OH by distillation.
Yield - 2028 g (90%); b.p. @ 5 mm Hg - 80 to 8100 IR spectrum - [OH] - 3400 cm-1; [CH3] - 3000 cm-1 [ii] synthesis of olefin RfC(CH3)=CH2 by reacting 1572 g of the alcohol obtained in [i] above with 470 g of P2Os at 100-140 C using an oil bath and stirring until the exothermic reaction is completed, and extraction of the olefin RfC(CH,)=CH2 by distillation at 0 to -1 atm. The olefin is further purified using a column of not less than 20 theoretical plates to take the 460C fraction.
Yield - 1290 g (85%), b.p. - 46 C at 10 mm Hg; IRspectrum: [OH3 - OH2] - 3000 2900 cm-1; [C=C] - 1760 cm-1 [iii] synthesis of chlorosilane RfZCN2S (OH3) Cl3 by catalytic reaction of the olefin obtained in [ii] above with methyldichlorosilane OH3SiHCl2; 316 g of methyldichlorosilane CH3SiHCl2 is placed into a reactor fitted with a stirrer and reverse refrigeration facilities and 5.5 ml of catalyst [0.1M solution of H2PtCl6 in (CH3)2CHOH] is added dropwise to secure stable boiling of the methyldichlorosilane. In two hours 1265 g of RfC(CH3)=CH2 is added gradually, resulting in the chlorosilane RfZCH2Si(CH3)Cl2 being obtained by rectification at 900C and 11 mm Hg. Yield - 1382 g (89%).
(b) Co-hydrolysis of the chlorosilane obtained in (a) above with dimethyldichlorosilane (CH3)2SiCl2 is effected by adding gradually 932 g (1.5 mol) of RfZCH2Si(CH3)Cl2 and 1072 g (0.83 mol) of (CH3)2SiCl2 to 460 ml of water with stirring over one hour at below 400C leaving, the mixture still for 2 hours until two layers separate; isolating the lower layer and washing it with water until the pH is between 7 and 6, and drying over CaCl2. Yield - 940 g.
(c) Blockage of end groups with hexamethyldisilazane is effected by mixing 900 g of the co-hydrolysate obtained in (b) above with 36 g (0.22 mol) of hexamethyldisilazane at 1000C, and removal of ammonia and excess hexamethyldisilazane by vaccuum evaporation.
(d) Distillation combined with catalytic depolymerisation is performed by heating the mixture obtained in (c) above gradually to 250-320 C over 4-5 hours in the presence of catalyst (KOH) at 2 to 5 mm Hg, distillation to separate the fraction with b.p. of 180 to 230 C at 1 to 2 mm Hg, treating the distillate with Al203 (1% by weight) over 48 hours, and filtering through a dense ashless filter.
The product compound was of density 1.385 - 1.395, viscosity 15 cps, and average molecular weight 2000.
This product was a mixture of formula I (majority) and formula II (minority) compounds wherein X is CF30 (CF2Q)5CF2CH(CH3) -.

Claims (20)

CLAIMS:
1. At least one compound selected from those of formulae I and II
wherein each X is selected independently from H and ZRf but in each formula at least one X is not H, and wherein m is an integer of 1 to 6; n is an integer of 3 to 7; the or each Z is selected independently from -CH2-, -CH(CH3)-, -CH2CH2-, and
the or each Rf is selected independently from CF30(CF20)p(CF2CF20)q CF2 CF30(CF20)p(CF2CF(CF3)0)q CF2- and CF3O(CF2O)p(CF(CF3)CF2O)qCF2-; p is an integer of 1 to 7; and q is zero, 1 or 2.
2. At least one compound according to claim 1 selected from those of formula I wherein each X is selected independently from H and CF3(CF20)pCF2CH(CH3) and at least one X is not H.
3. At least one compound according to claim 1 or 2 of average molecular weight of at least 700.
4. An oil for use as the liquid component of an electro-rheological fluid, the oil comprising at least one compound selected from perfluoropolyether derivatives of linear and cyclic polysiloxanes.
5. An oil according to claim 4 comprising at least one perfluoropolyether derivative of a cyclic polysiloxane and at least one perfluoropolyether derivative of a linear polysiloxane.
6. An oil according to claim 4 comprising at least one compound according to claim 1 or 2 or 3.
7. An oil according to claim 6 comprising at least one compound of formula I and at least one compound of formula II.
8. An oil according to any of claims 4 to 7 having at 200C a density of from 1.3 to 1.6 g/cm3 and a viscosity less than 25 cps.
9. An oil according to any of claims 4 to 8 containing [a] linear and/or cyclic polysiloxane to reduce overall viscosity, and/or [b] high density liquid to increase overall density.
10. An electro-rheological fluid having a liquid component according to any of claims 4 to 9.
11. A fluid according to claim 10 wherein the solid phase is selected from polymers, starches, zeolites, acrylamides and aminosilicone sulphate ionomers.
12. A fluid according to claim 10 wherein the solid phase is lithium salt of polymethacrylic acid.
13. A method of preparing a compound or compounds according to claim 1 which comprises hydrolysing a mixture of dimethyldichlorosilane and dichlorosilane of formula RfZCH2Si(CH3)Ct2, by blockage of end groups with hexamethyldisilazane as chain terminator, and distilling the product combined with catalytic depolymerisation to obtain a compound or mixture of compounds according to claim 1, Rf and Z being as defined in claim 1.
14. A method according to claim 13 wherein the RfZCH2Si(CH3)Ct2 is prepared by catalytic reaction of CH3SiHCB2 with olefinic compound RfZl=CH2 where Z'= is -CH=, -C(CH;)=, or -CH2CH=.
15. A method according to claim 14 wherein the olefin RfC (CH3) =CH2 is prepared by dehydration of alcohol of formula RO(CH3)OH.
16. A method according to claim 15 wherein the alcohol RfC (CH3) 2OH is prepared by reacting ester of formula RfCOOCH3 with Grignard reagent CH3MgBr.
17. A method of preparing a compound or compounds according to claim 1 where Z is -CH2-CH2-O-C- which 0 comprises preparing at least one compound selected from those of formulae III and IV
wherein B is -CH2CH2Cf and m and n are as defined in claim 1, reacting said chlorosiloxane(s) with perfluoro compound RfCOOM where M is Li, Na or K and Rf is as defined in claim 1, and separating out resultant compound or mixture of compounds according to claim 1.
18. Use of a compound of formula RfCOY wherein Rf is as defined in claim 1 and Y is F, C, OH, OCH3,OC2Hs in making a compound of formula RfZCH2Si(CH3)C22 wherein Z is as defined in claim 1.
19. Use of a compound of formula RfCOY wherein Rf is as defined in claim 1 and Y is F, CQ, OH, OCH3,OC2Hs, OLi, ONa or OK in making a compound according to claim 1, 2 or 3.
20. A compound of formula RfCOY wherein Rf is as defined in claim 1 and Y is Ct, OH, OCH3,OC2Hs, OLi, ONa, OK.
GB9510866A 1995-05-30 1995-05-30 fluorinated polysiloxane and cyclosiloxane oils Withdrawn GB2301589A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
GB9510866A GB2301589A (en) 1995-05-30 1995-05-30 fluorinated polysiloxane and cyclosiloxane oils
AU58409/96A AU5840996A (en) 1995-05-30 1996-05-30 Fluorinated polysiloxanes, their preparation and use in elec tro-rheological fluids
PCT/GB1996/001301 WO1996038454A1 (en) 1995-05-30 1996-05-30 Fluorinated polysiloxanes, their preparation and use in electro-rheological fluids

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB9510866A GB2301589A (en) 1995-05-30 1995-05-30 fluorinated polysiloxane and cyclosiloxane oils

Publications (2)

Publication Number Publication Date
GB9510866D0 GB9510866D0 (en) 1995-07-26
GB2301589A true GB2301589A (en) 1996-12-11

Family

ID=10775219

Family Applications (1)

Application Number Title Priority Date Filing Date
GB9510866A Withdrawn GB2301589A (en) 1995-05-30 1995-05-30 fluorinated polysiloxane and cyclosiloxane oils

Country Status (3)

Country Link
AU (1) AU5840996A (en)
GB (1) GB2301589A (en)
WO (1) WO1996038454A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107667125A (en) * 2015-06-18 2018-02-06 陶氏环球技术有限责任公司 Method for ERF to be made

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0384730A2 (en) * 1989-02-21 1990-08-29 Shin-Etsu Chemical Co., Ltd. Process for preparing a fluoroorganopolysiloxane

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1537922A (en) * 1966-07-11 1968-08-30 Montedison Spa Derivatives of perfluorinated ethers and polyethers
FR1545639A (en) * 1966-07-12 1968-11-15 Montedison Spa Polyoxyperfluoromethylene compounds and method of preparation
JPH0662647B2 (en) * 1988-02-12 1994-08-17 信越化学工業株式会社 Fluorine-containing organosilicon compound
GB9114102D0 (en) * 1991-06-29 1991-08-14 Dow Corning Electrorheological fluid containing a fluorohexylalkyl functional polysiloxane copolymer
DE69311241T2 (en) * 1992-09-21 1998-01-15 Dow Corning Improved electrorheological liquid preparations containing organosiloxanes

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0384730A2 (en) * 1989-02-21 1990-08-29 Shin-Etsu Chemical Co., Ltd. Process for preparing a fluoroorganopolysiloxane

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107667125A (en) * 2015-06-18 2018-02-06 陶氏环球技术有限责任公司 Method for ERF to be made

Also Published As

Publication number Publication date
WO1996038454A1 (en) 1996-12-05
GB9510866D0 (en) 1995-07-26
AU5840996A (en) 1996-12-18

Similar Documents

Publication Publication Date Title
EP0384699B1 (en) Process for preparing a fluororganopolysiloxane
CN1164597C (en) Preparation of amino-functional silicone
Lang et al. Siloxane and carbosiloxane based dendrimers: synthesis, reaction chemistry, and potential applications
EP0824102B1 (en) Alkyl substituted siloxanes and alkyl substituted polyether fluids
US5041588A (en) Chemically reactive fluorinated organosilicon compounds and their polymers
JPH01207294A (en) Fluorine-containing organo-silicic compound
JPS5910374B2 (en) Fluorosilicone manufacturing method
US3719696A (en) Organosilicon polymers containing silacyclobutane structures
US3168543A (en) Organosiloxane-polyoxyalkylene ether copolymers
Ameduri et al. Hybrid organic–inorganic gels containing perfluoro-alkyl moieties
US3183254A (en) Organic silicone compounds and method for producing same
CA2210586A1 (en) Cyclic silane esters and solvolysis products thereof, and processes for the preparation of the cyclic silane esters and the solvolysis products
GB2301589A (en) fluorinated polysiloxane and cyclosiloxane oils
EP0384730B1 (en) Process for preparing a fluoroorganopolysiloxane
US3567753A (en) Polysiloxane-polyoxyalkylene copolymers
KR970010592B1 (en) Cyclic and linear polysiloxane silicone fluids and preparation thereof
Allcock et al. Hybrid phosphazene-organosilicon polymers: II. High-polymer and materials synthesis and properties
US4049676A (en) Sulfolanyloxyalkyl cyclic polysiloxanes
US3350350A (en) Method for preparing polysilarylene-polysiloxane copolymers
EP0556780A2 (en) Organic silicon compounds
CN113336945A (en) Siloxane polymer with phenylene (phenylene) main chain and preparation method thereof
US5527933A (en) Method for preparing a hybrid organodisilanol and polymers thereof
JPH0578491A (en) Branched fluoralkyl group-containing polysiloxane and its production
RU2422473C1 (en) Carbosilane-siloxane dendrimers
US3576020A (en) Fluoroaromatic silicone compounds

Legal Events

Date Code Title Description
WAP Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1)