WO2001044416A1 - Composition lubrifiante a base de siloxane, ne degageant pas d'hydrogene, son procede de preparation et son utilisation - Google Patents
Composition lubrifiante a base de siloxane, ne degageant pas d'hydrogene, son procede de preparation et son utilisation Download PDFInfo
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- WO2001044416A1 WO2001044416A1 PCT/FR2000/003516 FR0003516W WO0144416A1 WO 2001044416 A1 WO2001044416 A1 WO 2001044416A1 FR 0003516 W FR0003516 W FR 0003516W WO 0144416 A1 WO0144416 A1 WO 0144416A1
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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
- C10M173/00—Lubricating compositions containing more than 10% water
- C10M173/02—Lubricating compositions containing more than 10% water not containing mineral or fatty oils
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C33/00—Moulds or cores; Details thereof or accessories therefor
- B29C33/56—Coatings, e.g. enameled or galvanised; Releasing, lubricating or separating agents
- B29C33/60—Releasing, lubricating or separating agents
- B29C33/62—Releasing, lubricating or separating agents based on polymers or oligomers
- B29C33/64—Silicone
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
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- 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
- C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
- C10M107/50—Lubricating compositions characterised by the base-material being a macromolecular compound containing silicon
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- 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
- C08G77/04—Polysiloxanes
- C08G77/045—Polysiloxanes containing less than 25 silicon atoms
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- 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
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups
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- C—CHEMISTRY; METALLURGY
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- 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
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
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- 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
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
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- 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
- C08G77/70—Siloxanes defined by use of the MDTQ nomenclature
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- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/02—Water
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- C10M2229/02—Unspecified siloxanes; Silicones
- C10M2229/025—Unspecified siloxanes; Silicones used as base material
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- C10M2229/04—Siloxanes with specific structure
- C10M2229/0405—Siloxanes with specific structure used as base material
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- C10M2229/041—Siloxanes with specific structure containing aliphatic substituents
- C10M2229/0415—Siloxanes with specific structure containing aliphatic substituents used as base material
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- C10M2229/042—Siloxanes with specific structure containing aromatic substituents
- C10M2229/0425—Siloxanes with specific structure containing aromatic substituents used as base material
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- C10M2229/043—Siloxanes with specific structure containing carbon-to-carbon double bonds
- C10M2229/0435—Siloxanes with specific structure containing carbon-to-carbon double bonds used as base material
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/32—Wires, ropes or cables lubricants
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- 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
- C10N2040/34—Lubricating-sealants
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- 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
- C10N2040/36—Release agents or mold release agents
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- 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
- C10N2040/38—Conveyors or chain belts
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- 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
- C10N2040/40—Generators or electric motors in oil or gas winning field
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- 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
- C10N2040/42—Flashing oils or marking oils
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- 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
- C10N2040/44—Super vacuum or supercritical use
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- 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
- C10N2040/50—Medical uses
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- 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
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/01—Emulsions, colloids, or micelles
Definitions
- Lubricant composition based on siloxane not emitting hydrogen, process for its preparation and its use
- the invention relates to a lubricant composition particularly suitable for the lubrication of vulcanization bladders used during the shaping and vulcanization of pneumatic or semi-pneumatic tires.
- the invention also relates to vulcanization bladders coated with a lubricating composition according to the invention as well as pneumatic or semi-pneumatic tires coated with said lubricating composition. According to two other of its aspects, the invention relates to a process for preparing the lubricant compositions of the invention as well as the use of said lubricant compositions for the lubrication of vulcanization bladders.
- Rubber tires for vehicles are usually manufactured by molding and vulcanizing a green casing, or unvulcanized and unshaped, in a molding press in which the green casing is pressed outward against the surface of a mold. by means of an internal fluid expandable bladder.
- the raw envelope is shaped against the external surface of the mold which defines the design of the tread of the envelope and the configuration of the sides.
- the envelope is vulcanized.
- the bladder is expanded by the internal pressure supplied by a fluid such as hot gas, hot water and / or steam, which also participates in the transfer of heat for vulcanization.
- the envelope is then allowed to cool a little in the mold, this cooling being sometimes favored by the introduction of cold or cooler water into the bladder.
- the mold is opened, the bladder is deflated by releasing the pressure of the internal fluid and the envelope is removed from the envelope mold.
- This use of shell vulcanization bladders is well known in the art.
- the bladder If adequate lubrication is not provided between the bladder and the inner surface of the envelope, the bladder generally tends to curl, which results in deformation of the envelope in the mold and also excessive wear and etching. from the surface of the bladder itself.
- the surface of the bladder also tends to stick to the inner surface of the envelope after vulcanization of the envelope and during the part of the vulcanization cycle of the envelope during which the bladder is deflated.
- air bubbles can be trapped between the surfaces of the bladder and the envelope, and favor the appearance of vulcanization defects in the envelopes resulting from an inadequate heat transfer.
- the external surface of the bladder or the internal surface of the raw or unvulcanized casing is coated with an appropriate lubricant, sometimes referred to as "jacketing cement".
- crosslinking agent with Si-H function (s) examples are methylhydrogenosilane, dimethylhydrogenosilane and polymethylhydrogenosilane.
- the disadvantage of lubricating compositions of this type is their instability on storage. There is indeed a creaming of the emulsion following the evolution of hydrogen during transport and storage of the lubricant composition. The evolution of hydrogen responsible for the instability of the compositions of the prior art results essentially from the decomposition of the constituents with Si-H function (s).
- compositions which are the subject of EP 635 559 are lubricating compositions based on siloxane which partly meet these requirements. These compositions are in particular more stable in that they do not give off hydrogen during storage.
- compositions which are in the form of emulsions, comprise, as essential constituents, a non-reactive polydimethylsiloxane, a reactive polydimethylsiloxane, preferably with hydroxy or alkoxy termination and a crosslinking agent.
- a non-reactive polydimethylsiloxane a reactive polydimethylsiloxane, preferably with hydroxy or alkoxy termination and a crosslinking agent.
- a reactive polydimethylsiloxane preferably with hydroxy or alkoxy termination
- crosslinking agent preferably with hydroxy or alkoxy termination
- the present invention provides an improved lubricating composition which does not release hydrogen and which furthermore has excellent durability characteristics, which makes them perfectly suitable for the lubrication of bladders used during vulcanization of pneumatic and semi-pneumatic tires.
- the lubricant composition of the invention is an oil-in-water emulsion, based on siloxane which does not give off hydrogen.
- This composition more specifically includes:
- a crosslinker soluble in the silicone phase comprising at least two functions capable of reacting with the reactive polydiorganosiloxane oil (b);
- a water-soluble crosslinking agent chosen from hydroxylated silanes and / or polydiorganosiloxanes, said crosslinking agent carrying, per molecule, at least one hydroxyl group and at least one organic group with Fr function, Fr representing an optionally substituted amino function, epoxy, optionally substituted methacroyl, optionally substituted acroyl, optionally substituted ureido, optionally substituted thiol or halogen;
- a surfactant chosen from hydroxylated silanes and / or polydiorganosiloxanes, said crosslinking agent carrying, per molecule, at least one hydroxyl group and at least one organic group with Fr function, Fr representing an optionally substituted amino function, epoxy, optionally substituted methacroyl, optionally substituted acroyl, optionally substituted ureido, optionally substituted thiol or halogen;
- composition comprising:
- component (a) from 5 to 95 parts by weight of component (a);
- component (b) from 1 to 50 parts by weight of component (b);
- compositions comprising a polyorganosiloxane resin soluble in the silicone phase and carrying, before emulsification, condensable hydroxyl substituents are excluded from the subject of the invention.
- constituents (a), (b), (c), (d), (e) and (f) of the emulsion are defined with reference to their initial chemical structure, that is to say that which characterizes them before emulsification. As soon as they are in an aqueous medium, their structure is likely to be greatly modified following the hydrolysis and condensation reactions.
- dynamic viscosity in the context of the invention the Newtonian type viscosity, that is to say the dynamic viscosity, measured in a manner known per se at a given temperature, at a sufficiently low shear rate gradient so that the viscosity measured is independent of the speed gradient.
- the non-reactive polydiorganosiloxane oil (a) has a dynamic viscosity generally between 5.10 "2 and 30.10 2 Pa.s at 25 ° C. Preferably, the dynamic viscosity varies between 5.10 " 2 and 30 Pa.s, better still between 0.1 and 5 Pa.s.
- non-reactive means an oil which, under the conditions of emulsification, of preparation of the lubricant composition and of use, does not react chemically with any of the constituents of the composition.
- component (a) there may be mentioned patterned linear polydiorganosiloxanes recurring formula V ⁇ V 2 SiO 2/2, terminated at its chain ends by units V 3 VV 5 SiO ⁇ / 2, ⁇ , V 2, V 3 , V and V 5 , identical or different, representing a monovalent organic group chosen from alkyl, alkenyl, aryl, cycloalkyl, cycloalkenyl, aralkyl or alkaryl.
- alkyl denotes a saturated, linear or branched hydrocarbon group, preferably of CrC 6 (such as methyl, ethyl and propyl); alkenyl denotes a linear or branched, preferably C 2 -C 8, ethylenically unsaturated hydrocarbon group (s) (such as vinyl, allyl and butadienyl); aryl denotes an aromatic, mono- or polycyclic group, preferably C 6 -C 10 hydrocarbon (such as phenyl or naphthyie); cycloalkyl denotes a saturated, mono- or polycyclic carbocyclic group, preferably C 3 -C 8 (such as cyclohexyl); cycloalkenyl denotes a cycloalkyl group having one or more unsaturations, preferably C 6 -C 8 (such as cyclohexenyl); aralkyl denotes for example benzyl; alkaryl denotes for example benz
- component (a) is a linear, non-functionalized polydimethylsiloxane, that is to say with repeating units of formula (CH 3 ) 2 SiO 2 2 and having at its two ends units (CH 3 ) 3 SiO ⁇ / 2 .
- Component (a) is generally introduced into the composition in an amount of 5 to 95 parts by weight per 100 parts by weight of the mixture of the constituents
- composition of the invention further comprises a reactive linear polydiorganosiloxane oil (b).
- component (b) reacts with the crosslinking agent under the conditions for preparing the emulsion.
- the organic substituents of the oil (b) are aliphatic radicals, saturated or unsaturated, linear or branched, preferably having from 1 to 10 carbon atoms; saturated, unsaturated or aromatic carbocyclic, monocyclic or polycyclic radicals preferably having from 3 to 18 carbon atoms, better still from 5 to 10 carbon atoms; or radicals having both an aliphatic part and a carbocyclic part.
- aliphatic and / or carbocyclic radicals are optionally substituted by -OH and / or amino (optionally substituted) and / or halogen and / or cyano radicals.
- the substituent of the amino group can be an aliphatic radical, a carbocyclic radical, or comprise both an aliphatic part and a carbocyclic part, the aliphatic and carbocyclic radicals being as defined above. Mention may be made, as halogen, of chlorine, fluorine, bromine or iodine, fluorine being more specifically suitable.
- the organic groups of the oil (b) are alkyl groups, preferably C ⁇ -C 6 ; cycloalkyl, preferably C 3 -C 8 , aryl, preferably C ⁇ -Cio (and for example phenyl); or C 2 -C 6 alkenyl (for example allyl or vinyl); said groups being optionally substituted by hydroxyl and / or amino (optionally substituted), and / or halo, and / or cyano.
- the substituents of the amino group are for example alkyl, such as (Cr C 10 ) alkyl; alkenyl, such as (C 2 -C 8 ) alkenyl; aryl, such as (C 6 -C ⁇ 0 ) aryl; cycloalkyl, such as (C 3 -C 8 ) cycloalkyl.
- a preferred group of components (b) consists of oils of formula:
- R and R 2 which are identical or different represent -OH; alkyl, especially (C ⁇ -C ⁇ ) alkyl; cycloalkyl, in particular (C 3 -C 8 ) cycloalkyl; alkenyl, especially (C 2 -C 6 ) alkenyl; cycloalkenyl, especially (C 5 -C 8 ) cycloalkenyl; or amino.
- Ri and R 2 are independently chosen from (d-
- C 6 alkyl (such as methyl); (C6-C- ⁇ 0 ) aryl, and for example phenyl; (C 2 - C 8 ) alkenyl (such as vinyl); or alternatively amino; (C ⁇ -C 6 ) alkylamino; or di (d-
- oils (b) most used, because of their availability in industrial products, are those for which R 1 and R 2 are independently chosen from methyl, ethyl, propyl, phenyl, vinyl and 3,3,3-trifluoropropyl. Very preferably, 80% by number of these radicals are methyl radicals.
- oil (b) to the ⁇ , ⁇ -dihydroxypolydimethylsiloxanes bearing at the ends of (CH 3 ) 2 (OH) SiO 1/2 units .
- Component (b) is preferably used in an amount of 5 to 40 parts by weight, better still in an amount of 10 to 30 parts by weight per 100 parts by weight of the mixture of components (a) + (b) + (c) + (d) + (f).
- the crosslinker (c) soluble in the silicone phase comprises at least two functions capable of reacting with the oil (b) so as to cause the crosslinking of the oil.
- said reactive functions of the crosslinker (c) react with the oil (b) under the conditions for preparing the emulsion.
- the crosslinker (c) preferably has the formula:
- a represents 1, so that the crosslinker (c) has the formula: YSi (Zi) 3 .
- a preferred group of crosslinker (c) is formed by all of the organotrialcoxysilanes, organotriacyloxysilanes, organotrioximosilanes and tetraalkylsilicates.
- organic monovalent group includes in particular aliphatic radicals, saturated or unsaturated, linear or branched in C- ⁇ -C 30 ; saturated, unsaturated or aromatic C 6 -C 30 carbocyclic, mono- or polycyclic radicals; as well as the radicals having both an aliphatic part as defined above and a carbocyclic part as defined above; each of these radicals being optionally substituted with an amino, epoxy, thiol or ester function.
- groups Y are more particularly the radicals (Cr
- CioJalkylcarbonyloxy optionally substituted by epoxy (C 2 -C 10 ) alkenylcarbonyloxy optionally substituted by epoxy; (C 3 -C 8 ) cycloalkylcarbonyloxy optionally substituted by epoxy; (C 6 -C ⁇ o) arylcarbonyloxy; • -R a -NR' ⁇ R ' 2 in which
- R a represents nothing or represents a divalent aliphatic hydrocarbon radical, linear or branched, saturated or unsaturated in C ⁇ -C 20 , preferably in C1-C10, and for example (CrC ⁇ o) alkylene;
- R'i and R ' 2 independently represent H, a (C ⁇ -C 20 ) alkyl group, preferably (C- ⁇ -C ⁇ o) alkyl; a (C 3 -C 8 ) cycloalkyl group; or an (C 6 -C ⁇ 0 ) aryl group, preferably phenyl;
- R b and R c identical or different, are as defined for R a above; and R'i and R ' 2 are as defined above;
- R 3 represents C ⁇ -C 20 alkyl
- C ⁇ -C ⁇ o alkyl
- C- ⁇ -C 3 alkyl and in particular methyl
- C 6 -C 20 aryl, better still (C 6 -C ⁇ o) aryl, for example phenyl; or arylalkyl in which the aryl and alkyl parts are as defined above;
- R represents a hydrogen atom; alkyl -C 20, more preferably (C ⁇ -C ⁇ 2) alkyl, for example methyl; C 2 -C 2 alkylcarbonyl ⁇ , better still (C 2 -C ⁇ 3 ) alkylcarbonyl; (C 6 -C 20 ) aryl, better still (C 6 - C ⁇ o) aryl, for example phenyl; or arylalkyl and preferably (C 6 - C ⁇ o) aryl- (C- ⁇ -C- ⁇ 2 ) alkyl; or alternatively R 4 represents O;
- R 3 represents methyl, phenyl or benzyl and R represents H or methyl.
- Y is (C 2 -C ⁇ 0 ) unsubstituted alkenyl; or (C- ⁇ -C- ⁇ o) alkyl optionally substituted by a group chosen from:
- R ' T , R' 2 independently represent H, (C 3 -C 8 ) cycloalkyl or (C 6 -
- Y represents aminopropyl, ethylaminopropyl, n-butylaminoethyl, cyclohexylaminopropyl, phenylaminoethyl,
- N-aminoethylaminopropyl dimethylaminopropyl, glycidyloxypropyl
- Zi represents methoxy, ethoxy, propoxy, methoxyethoxy, acetoxy or an oxime group
- a particularly preferred group of constituents (c) is formed by the alkyltnalcoxysilanes of formula YSi (Zi) 3 in which Y is alkyl, in particular (C ⁇ -C 30 ) alkyl (preferably (C1-C1 0 ) alkyl) and Zi is alkoxy , especially (CC 20 ) alkoxy, preferably (C1-C10) alkoxy.
- methyltrimethoxysilane and methylt ⁇ ethoxysilane are described in US 4,889,770, such as beta-aminoethyltrimethoxysilane, beta-aminoethyltriethoxysilane, beta-aminoethylt ⁇ isopropoxysilane, gamma-aminopropyltrimethoxysilane, gamma-aminopropyltriethoxysilane, gamma-am ⁇ nopropyltriane) am ⁇ nopropyl (n-butoxy) silane, delta-aminobutylt ⁇ methoxysilane, epsilon-aminohexyltriethoxysilane, 4-am ⁇ nocyclohexyltriethoxysilane,
- the lubricating composition comprises from 0.1 to 20 parts by weight, per hundred parts by weight of the sum of the constituents (a) + (b) + (c) + (d) + (f), of the crosslinker (c), preferably 0.2 to 10 parts by weight, more preferably 0.5 to 5.
- water-solubility should be understood to mean the ability of a product to dissolve in water at a temperature of 25 ° C, at least 5% by weight.
- the organic substituents of the crosslinker (d) other than the organic group (s) having a Fr function are aliphatic radicals, saturated or unsaturated, linear or branched, preferably having from 1 to 10 carbon atoms; saturated, unsaturated or aromatic carbocyclic, monocyclic or polycyclic radicals preferably having from 3 to 18 carbon atoms, better still from 5 to 10 carbon atoms; or radicals having both an aliphatic part and a carbocyclic part.
- Fr is an amino function
- a preferred organic group with a Fr function is a group
- the water-soluble crosslinking agent has the formula: in which R a , R'i and R ' 2 are as defined above. More preferably, R a represents alkylene, in particular (CrC 6 ) alkylene, and R'1 and R ' 2 independently represent a hydrogen atom or an alkyl group, in particular (CC 6 ) alkyl.
- the water-soluble crosslinking agent can be a linear and / or cyclic hydroxyl polydiorganosiloxane, with MD and / or D siloxyl units, and / or a hydroxylated polydiorganosiloxane resin having, in its structure, T siloxyl units optionally associated with M and / or D and / or Q, or alternatively Q siloxyl units associated with M and / or D units.
- This linear, cyclic or network polydiorganosiloxane is not substituted by hydrolysable organic functions such as alkoxy functions.
- G is alkyl, in particular (C ⁇ -C 6 ) alkyl (for example methyl, ethyl, isopropyl, tert-butyl and n-hexyl), hydroxyl, alkenyl (for example vinyl or allyl) or else a function Fr, the preferred Fr functions being as defined above
- linear hydroxyl polydiorganosiloxane usable as crosslinking agent (d)
- Fr This constituent (d) is used at a rate of 0.5 to 15 parts by weight per hundred parts by weight of the sum of the constituents (a) + (b) + (c) + (d) + (f), preferably at a rate of 0.6 at 5 parts by weight, and better at 0.8 to 3 parts by weight
- Anionic, cationic, nonionic and zwittenonic surfactants can be used alone or as a mixture
- anionic surfactant mention may be made of the alkali metal salts of aromatic sulfonic hydrocarbon acids or the alkali metal salts of alkyl sulfonic acids
- Non-ionic surfactants are more particularly preferred in the context of the invention.
- poly (alkylene oxide) aryl ether polyoxyethylenated alkylphenols may be mentioned.
- poly (alkylene oxide) alkyl ether polyethylene glycol isodecyl ether and polyethylene glycol methyl ethyl ether containing 3 to 15 units of ethylene oxide per molecule can be mentioned.
- the amount of surfactant (e) depends on the type of each of the constituents present as well as on the very nature of the surfactant used. Generally, the composition comprises from 0.5 to 10% by weight of surfactant (better still
- the lubricant composition of the invention further comprises a condensation catalyst (f) chosen from those conventionally used in the art for catalyzing the crosslinking of oils of type (b) using crosslinking agents of type (c) and / or (d) defined above.
- a condensation catalyst (f) chosen from those conventionally used in the art for catalyzing the crosslinking of oils of type (b) using crosslinking agents of type (c) and / or (d) defined above.
- organometallic salt there may be mentioned zirconium naphthenate and zirconium octylate.
- Said catalyst is preferably a tin catalytic compound, generally an organotin salt.
- organotin salts which can be used are described in particular in the work of NOLL, Chemistry and Technology of Silicones Academy Press (1968), page 337. It is also possible to define, as tin catalytic compound, either distannoxanes or polyorganostannoxanes , or the reaction product of a tin salt, in particular of a tin dicarboxylate on ethyl polysilicate, as described in US Pat. No. 3,862,919.
- the reaction product of a silicate of alkyl or an alkyltrialkoxysilane on dibutyltin diacetate as described in Belgian patent BE 842 305 may also be suitable.
- the catalyst is the tin salt of an organic acid, such as dibutyltin diacetate, dibutyltin dilaurate, dioctyltin dilaurate, dibutyltin dioctate, zinc naphthenate, zinc naphthenate cobalt, zinc octylate, cobalt octylate and dioctyltin di (isomercaptoacetate).
- an organic acid such as dibutyltin diacetate, dibutyltin dilaurate, dioctyltin dilaurate, dibutyltin dioctate, zinc naphthenate, zinc naphthenate cobalt, zinc octylate, cobalt octylate and dioctyltin di (isomercaptoacetate).
- the preferred tin salts are the tin bischelates (EP 147 323 and EP 235 049), the diorgano-tin dicarboxylates and, in particular, the dibutyi- or dioctyltin diversatates (British patent GB 1,289,900, the diacetate of dibutyl- or dioctyltin, dibutyi- or dioctyltin dilaurate or the hydrolysis products of the precipitated species (for example diorgano and polystannoxanes).
- the catalyst (f) is introduced into the lubricating composition in an amount of 0.05 to 10 parts by weight, per hundred parts by weight of the sum of the constituents (a) + (b) + (c) + (d) + ( f), preferably in an amount of 0.08 to 5 parts by weight, and better still from 0.1 to 2 parts by weight.
- Dioctyltin dilaurate is most particularly preferred.
- the lubricant composition according to the present invention can also contain one or more additional ingredients such as film-forming polymers, complementary lubricants and anti-friction agents, coalescing agents, wetting or dispersing agents, air, anti-foaming agents, thickeners, stabilizers, preservatives such as biocides, antifungals in amounts which can vary considerably, for example, between 0.2 and 50% by weight of the composition.
- additional ingredients such as film-forming polymers, complementary lubricants and anti-friction agents, coalescing agents, wetting or dispersing agents, air, anti-foaming agents, thickeners, stabilizers, preservatives such as biocides, antifungals in amounts which can vary considerably, for example, between 0.2 and 50% by weight of the composition.
- thickeners are cellulosic thickeners (carboxymethylcellulose), acrylic thickeners, polyurethane, hydrocolloid gums (xanthan gum) and their mixtures.
- glycols and / or aliphatic petroleum fractions may be used as a coalescing agent.
- Wetting or dispersible agents which can be used in the context of the invention are, for example, phosphates and / or polyacrylics, such as for example sodium hexametaphosphate and sodium polyacrylates.
- the compositions of the invention can be prepared in a conventional manner by using conventional methods of the prior art.
- An advantageous method consists in emulsifying in water (g) a mixture of the lipophilic constituents (a), (b), (c) and (f), in the presence of the surfactant (e), these constituents being involved in the state where they are found naturally. Then, the missing constituent (s), namely the constituent (d) and possibly the additional ingredient (s), is (are) added (s), either directly to the emulsion (case of water-soluble constituents, like (d)), or in the form of aqueous emulsion (case of constituents soluble in the silicone phase, like for example a film-forming polymer).
- an aqueous emulsion of the lipophilic constituents (a), (b) and (c) is prepared as indicated above, in the presence of the surfactant (e), then the missing constituents, in particular the constituents (d) and (f ) are added either directly to the emulsion (case of component (d)), or in the form of an aqueous emulsion (case of component (f) and possibly, for example, of the film-forming polymer).
- an aqueous emulsion of the lipophilic constituents (a) and (c) is prepared as indicated above, in the presence of the surfactant (e), then the missing constituents, in particular the constituents (b), (d) and ( f) are added, either directly to the emulsion (case of component (d)), or in the form of an aqueous emulsion (case of components (b), (f) and possibly, for example, of the film-forming polymer).
- the emulsification can be direct or proceed by inversion.
- the possible emulsion of the reactive oil (b), when one is used, is preferably prepared in the presence of the same surfactant (e) as that used in the initial emulsification process.
- Possible catalyst emulsion (f) or the additional ingredient is preferably prepared in the presence of another type of surfactant, such as for example a polyvinyl alcohol
- the process of the invention is carried out at room temperature
- the process of the invention can also comprise an additional step of heating the resulting emulsion. This step makes it possible to accelerate the crosslinking processes.
- the temperature can be increased up to 40 ° C. so as to accelerate the crosslinking of the constituents present
- This heating step can be replaced by a step of storing the emulsion at room temperature until complete crosslinking.
- the lubricating properties of the composition of the invention are significantly improved in the event of complete crosslinking of the crosslinkable constituents of the composition.
- oils (a) and (b) as well as the crosslinkers (c) and (d) are commercially available or easily accessible to those skilled in the art by implementing conventional methods described in the prior art
- the functionalization is easily carried out by appropriate substitution or addition reaction
- the crosslinker (d) represents a water-soluble silicone resin equipped with hydroxyl group (s) and group (s) Fr, this can be obtained ⁇ by cohydrolysis
- hydrolysable organofunctional substituents capable of generating in situ volatile organic compounds (VOCs) during crosslinking by condensation are, for example, alkoxy, acetoxy, ketiminoxy, enoxy.
- the heterocondensation mechanisms involved are of the OH / OH and OH / OR d type , these OH or OR d being carried by the hydrolysates derived from silanes Si and S 2 .
- the hydrolysates derived from Sofh are alcohols, in this case.
- the silane Si is advantageously a trialcoxysilane, preferably a trimethoxysilane, a triethoxysilane, a methyldimethoxysilane or a methyldiethoxysilane, carrying an amino amino function of the type: 3-aminopropyl; N-methyl-3-aminopropyl: N-aminoethyl-3-aminopropyl; C 6 H 5 CH 2 NH (CH 2 ) 2 NH- (CH 2 ) 3 -; • 3-ureidopropyl;
- the Sofh that it comprises are preferably alkoxy radicals, advantageously C ⁇ -C 6 , for example: methoxy, ethoxy or propoxy.
- This silane S 2 preferably an alkoxysilane, can also contain at least one alkyl substituent, advantageously C 1 -C 6 , for example: methyl, ethyl, propyl.
- the crosslinker (d) is a resin obtained: ⁇ by hydrolysis of a silane S 3 substituted with Fr and Sofh, ⁇ by homocondensation of the hydrolyzed silanes S 3 , ⁇ and by "stripping" steam entrainment of the hydrolysates derived from Sofh
- the silane S 3 is preferably a substituted alkoxysilane Fr. It may be, for example, a trialcoxysilane making it possible to obtain a hydroxylated resin with T units, also called T (OH) resin.
- This silane S 3 can be of the same type as the silane Si as defined above.
- the functions Fr substituting S 3 correspond to the same definition as that given above.
- a cross-linking agent (d) of the water-soluble polydiorganosiloxane resin type mention may be made of that obtained from ⁇ -aminopropyltriethoxysilane hydrolyzed and subjected to a "stripping" of the ethanol formed by hydrolysis.
- the present invention also relates to articles lubricated using the lubricant composition of the invention as well as the use of the lubricant composition of the invention for the lubrication of various articles. More particularly, the invention relates to:
- an expandable rubber bladder obtainable by heating the expandable bladder defined above, in particular at 80-150 ° C (preferably 100-
- a raw pneumatic or semi-pneumatic tire comprising elements which will constitute its external tread intended to come into contact with the ground, coated on its internal surface with a composition according to the invention;
- the lubricant composition of the invention can be applied in any way, and for example by spraying, brushing or even using a sponge or a brush. It is preferable to operate so as to cover the article to be coated with an even layer of coating.
- the lubrication of the vulcanization bladder used during the vulcanization of pneumatic or semi-pneumatic tires can be carried out in two different ways.
- a raw tire is placed in a tire mold, an expandable bladder is placed in the mold, the mold is closed and the bladder is expanded by applying internal fluid pressure. hot, so that the bandage is pressed against the mold, shaped and vulcanized.
- the mold is then opened, the bladder is deflated and the bandage is recovered, shaped and vulcanized.
- the same bladder is used to manufacture a thousand bandages.
- the expandable rubber bladder used during the manufacture of the bandages is initially coated with a composition according to the invention.
- the lubrication of the bladder is direct. Then there is an exhaustion of the lubricating effect of this bladder. In this subsequent phase, it is the internal surface of the bandage (that which comes into contact with the bladder) which is coated with the lubricating composition. There is regeneration of the lubrication of the rubber bladder by transfer from the tire.
- the mold pressing / bladder release cycles implemented during the manufacture of the tires follow one another as follows: the bladder initially coated with the lubricating composition (direct lubrication) and heated to 80-150 ° C. is used without subsequent coating for 5 to 10 cycles (each cycle leading to the production of a different tire), then
- the lubricant composition of the invention does not comprise any Si-H bonded component so that the risk of evolution of hydrogen during storage or transport is zero
- the lubricant composition of the invention also has excellent durability, the lubricating properties being exerted for a long time.
- This example illustrates a lubricating composition according to the invention.
- the formulation of this composition which is an oil in water emulsion, is given in the table below.
- Reactive oil ⁇ , ⁇ -dihydroxypolydimethylsiloxane having a dynamic viscosity of 0.75 Pa.s at 25 ° C.
- the lubricant composition of Table 1 was prepared as indicated below.
- a mixture composed of non-reactive low viscosity polydimethylsiloxane (a), reactive oil (b), methyltriethoxysilane (c), surfactant (e) and of a part of distilled water (according to a water / surfactant ratio of 1, 2) is homogenized beforehand with moderate stirring for 15 minutes at room temperature.
- the mixture thus obtained is treated by grinding until phase inversion using a Moritz ® mill, to pass a fluid phase water / oil to a thick oil phase / water.
- the dilution of the thick phase obtained is carried out with average stirring in 40 minutes, using the amount of distilled water remaining to obtain an emulsion whose dry matter is 50% by weight.
- the bactericidal agent and the antioxidant agent are added during dilution.
- the silane (d) and the catalyst (f) in the form of an emulsion are added at the end of dilution, homogenization with moderate stirring is carried out for 10 minutes, followed by filtration.
- the emulsion obtained is characterized by an average particle size of 0.485 ⁇ m and a proportion of dry matter (60 min, 120 ° C.) of 49.4% by weight.
- This example illustrates a composition which does not contain the water-soluble crosslinker (d) and is therefore not therefore in accordance with the invention.
- This composition is prepared as in Example 1, except that the step of adding the silane (d) is omitted.
- the emulsion obtained is characterized by an average particle size of 0.485 ⁇ m and a proportion of dry matter (60 min, 120 ° C.) of 49.4% by weight.
- EXAMPLE 2 In this example, the durability of the lubricating properties of the compositions of example 1 according to the invention and of the comparative example are compared.
- the durability of a lubricating composition corresponds to the number of tires produced without degrading the surface of the inflatable bladder.
- An inflatable bladder film previously treated with the lubricating composition to be evaluated, is pressed in contact with an unvulcanized tire casing film, according to a series of pressure and temperature cycles simulating the stages of manufacturing a pneumatic on the industrial tool.
- the tire cover film is replaced with each mold.
- the test is finished when the two surfaces in contact remain bonded.
- the lubricating composition on the surface of the film of the inflatable bladder is exhausted and no longer acts as a lubricating interface.
- Table 3 reports the durability of the compositions of Examples 1 and comparative.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Lubricants (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP00985434A EP1250405A1 (fr) | 1999-12-17 | 2000-12-14 | Composition lubrifiante a base de siloxane, ne degageant pas d'hydrogene, son procede de preparation et son utilisation |
CA002394135A CA2394135C (fr) | 1999-12-17 | 2000-12-14 | Composition lubrifiante a base de siloxane, ne degageant pas d'hydrogene, son procede de preparation et son utilisation |
AU21855/01A AU2185501A (en) | 1999-12-17 | 2000-12-14 | Siloxane-based lubricating composition, not releasing hydrogen, preparation method and use thereof |
US10/149,584 US6846780B2 (en) | 1999-12-17 | 2000-12-14 | Siloxane-based lubricant composition, not releasing hydrogen, preparation method and use thereof |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9916006A FR2802546B1 (fr) | 1999-12-17 | 1999-12-17 | Composition lubrifiante a base de siloxane, ne degageant pas d'hydrogene, son procede de preparation et son utilisation |
FR99/16006 | 1999-12-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2001044416A1 true WO2001044416A1 (fr) | 2001-06-21 |
Family
ID=9553432
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR2000/003516 WO2001044416A1 (fr) | 1999-12-17 | 2000-12-14 | Composition lubrifiante a base de siloxane, ne degageant pas d'hydrogene, son procede de preparation et son utilisation |
Country Status (6)
Country | Link |
---|---|
US (1) | US6846780B2 (fr) |
EP (1) | EP1250405A1 (fr) |
AU (1) | AU2185501A (fr) |
CA (1) | CA2394135C (fr) |
FR (1) | FR2802546B1 (fr) |
WO (1) | WO2001044416A1 (fr) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2833623A1 (fr) * | 2001-12-14 | 2003-06-20 | Rhodia Chimie Sa | Composition pour le traitement de fibres textiles |
FR2838449A1 (fr) * | 2002-04-12 | 2003-10-17 | Rhodia Chimie Sa | Composition lubrifiante a base de siloxane, ne degageant pas d'hydrogene, son procede de preparation et son utilisation |
FR2838447A1 (fr) * | 2002-04-12 | 2003-10-17 | Rhodia Chimie Sa | Composition a base de siloxane, ne degageant pas d'hydrogene, destinee au moulage-demoulage de pneumatiques |
CN114127195A (zh) * | 2019-07-29 | 2022-03-01 | 米其林集团总公司 | 用于硫化胶囊涂层的硅酮橡胶组合物 |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2825099B1 (fr) * | 2001-05-23 | 2003-07-18 | Rhodia Chimie Sa | Procede de preparation d'une composition lubrifiante a base de polysiloxanes ne degageant pas d'hydrogene |
US20050266166A1 (en) * | 2004-05-26 | 2005-12-01 | Halsey Glenn T | Method for coating paper machines |
FR2902438A1 (fr) * | 2006-06-20 | 2007-12-21 | Rhodia Recherches & Tech | Composition lubrifiante a base de siloxane, ne degageant pas d'hydrogene, son procede de preparation et son utilisation |
US8030267B2 (en) * | 2006-09-11 | 2011-10-04 | Shiseido Company Ltd. | Silica composite capsules obtained by blending water-soluble silane derivative, composition containing the same, and transparent gel-form composition |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2494294A1 (fr) * | 1980-11-20 | 1982-05-21 | Goodyear Tire & Rubber | Nouvelle vessie de vulcanisation d'enveloppes ou bandages pneumatiques ou semi-pneumatiques, traitee en surface, composition de traitement pour celle-ci et procede de vulcanisation des enveloppes |
US4554122A (en) * | 1980-03-25 | 1985-11-19 | Releasomers, Inc. | Method for air bladder release during tire production |
EP0206314A2 (fr) * | 1985-06-27 | 1986-12-30 | Wacker Silicones Corporation | Emulsions aqueuses de silicones comme lubrifiant pour vessies de vulcanisation |
EP0279372A2 (fr) * | 1987-02-13 | 1988-08-24 | Wacker-Chemie Gmbh | Emulsions contenant des silicones et leur emploi comme lubrifiant de bag de galbage |
EP0635559A2 (fr) * | 1993-07-23 | 1995-01-25 | Rhone-Poulenc Specialty Chemicals Co. | Composition lubrifiante à base siloxane ne dégageant pas d'hydrogène |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4533305A (en) * | 1980-11-20 | 1985-08-06 | The Goodyear Tire & Rubber Company | Surface treated tire curing bladder, treatment composition therefor and method for curing tires |
USRE32318E (en) * | 1980-11-20 | 1986-12-30 | The Goodyear Tire & Rubber Company | Tire curing bladder lubricant |
EP0111100B1 (fr) * | 1982-10-16 | 1990-08-22 | Grace Service Chemicals GmbH | Utilisation d'une couche de séparation dans la vulcanisation d'articles en caoutchouc |
JPH02311564A (ja) * | 1989-05-25 | 1990-12-27 | Toray Dow Corning Silicone Co Ltd | タイヤ成形用ブラダー潤滑剤組成物 |
US5321075A (en) * | 1989-09-25 | 1994-06-14 | Dow Corning Corporation | Precured silicone emulsion |
-
1999
- 1999-12-17 FR FR9916006A patent/FR2802546B1/fr not_active Expired - Fee Related
-
2000
- 2000-12-14 CA CA002394135A patent/CA2394135C/fr not_active Expired - Fee Related
- 2000-12-14 WO PCT/FR2000/003516 patent/WO2001044416A1/fr active Application Filing
- 2000-12-14 US US10/149,584 patent/US6846780B2/en not_active Expired - Fee Related
- 2000-12-14 AU AU21855/01A patent/AU2185501A/en not_active Abandoned
- 2000-12-14 EP EP00985434A patent/EP1250405A1/fr not_active Withdrawn
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4554122A (en) * | 1980-03-25 | 1985-11-19 | Releasomers, Inc. | Method for air bladder release during tire production |
FR2494294A1 (fr) * | 1980-11-20 | 1982-05-21 | Goodyear Tire & Rubber | Nouvelle vessie de vulcanisation d'enveloppes ou bandages pneumatiques ou semi-pneumatiques, traitee en surface, composition de traitement pour celle-ci et procede de vulcanisation des enveloppes |
EP0206314A2 (fr) * | 1985-06-27 | 1986-12-30 | Wacker Silicones Corporation | Emulsions aqueuses de silicones comme lubrifiant pour vessies de vulcanisation |
EP0279372A2 (fr) * | 1987-02-13 | 1988-08-24 | Wacker-Chemie Gmbh | Emulsions contenant des silicones et leur emploi comme lubrifiant de bag de galbage |
EP0635559A2 (fr) * | 1993-07-23 | 1995-01-25 | Rhone-Poulenc Specialty Chemicals Co. | Composition lubrifiante à base siloxane ne dégageant pas d'hydrogène |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2833623A1 (fr) * | 2001-12-14 | 2003-06-20 | Rhodia Chimie Sa | Composition pour le traitement de fibres textiles |
WO2003054285A2 (fr) * | 2001-12-14 | 2003-07-03 | Rhodia Chimie | Composition pour le traitement de fibres textiles |
WO2003054285A3 (fr) * | 2001-12-14 | 2003-12-18 | Rhodia Chimie Sa | Composition pour le traitement de fibres textiles |
FR2838449A1 (fr) * | 2002-04-12 | 2003-10-17 | Rhodia Chimie Sa | Composition lubrifiante a base de siloxane, ne degageant pas d'hydrogene, son procede de preparation et son utilisation |
FR2838447A1 (fr) * | 2002-04-12 | 2003-10-17 | Rhodia Chimie Sa | Composition a base de siloxane, ne degageant pas d'hydrogene, destinee au moulage-demoulage de pneumatiques |
WO2003087227A1 (fr) * | 2002-04-12 | 2003-10-23 | Rhodia Chimie | Composition a base de siloxane, ne degageant pas d'hydrogene, destinee au moulage-demoulage de pneumatiques |
US8101279B2 (en) | 2002-04-12 | 2012-01-24 | Bluestar Silicones France Sas | Siloxane-based composition, which does not emit hydrogen, intended for molding/mold-release of pneumatic tires |
CN114127195A (zh) * | 2019-07-29 | 2022-03-01 | 米其林集团总公司 | 用于硫化胶囊涂层的硅酮橡胶组合物 |
CN114127195B (zh) * | 2019-07-29 | 2023-05-16 | 米其林集团总公司 | 用于硫化胶囊涂层的硅酮橡胶组合物 |
Also Published As
Publication number | Publication date |
---|---|
AU2185501A (en) | 2001-06-25 |
US20030109386A1 (en) | 2003-06-12 |
FR2802546A1 (fr) | 2001-06-22 |
FR2802546B1 (fr) | 2002-03-29 |
US6846780B2 (en) | 2005-01-25 |
CA2394135C (fr) | 2007-01-30 |
CA2394135A1 (fr) | 2001-06-21 |
EP1250405A1 (fr) | 2002-10-23 |
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