WO2000032684A1 - Improved processability of silica-filled rubber stocks - Google Patents
Improved processability of silica-filled rubber stocks Download PDFInfo
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- WO2000032684A1 WO2000032684A1 PCT/US1999/027890 US9927890W WO0032684A1 WO 2000032684 A1 WO2000032684 A1 WO 2000032684A1 US 9927890 W US9927890 W US 9927890W WO 0032684 A1 WO0032684 A1 WO 0032684A1
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- WIPO (PCT)
- Prior art keywords
- hydrogenated
- silica
- weight
- elastomer
- filler
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
- C08K5/5419—Silicon-containing compounds containing oxygen containing at least one Si—O bond containing at least one Si—C bond
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
- B60C1/0016—Compositions of the tread
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/101—Esters; Ether-esters of monocarboxylic acids
- C08K5/103—Esters; Ether-esters of monocarboxylic acids with polyalcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1535—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/12—Adsorbed ingredients, e.g. ingredients on carriers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T152/00—Resilient tires and wheels
- Y10T152/10—Tires, resilient
- Y10T152/10495—Pneumatic tire or inner tube
- Y10T152/10855—Characterized by the carcass, carcass material, or physical arrangement of the carcass materials
Definitions
- the present invention relates to the processing and vulcanization of diene polymer and copolymer elastomer-containing rubber stocks and, more particularly, silica-filled rubber stocks using processing aids with or without other reinforcing fillers.
- elastomeric compounds exhibiting reduced hysteresis when properly compounded with other ingredients such as reinforcing agents, followed by vulcanization.
- Such elastomers when compounded, fabricated and vulcanized into components for constructing articles such as tires, power belts, and the like, will manifest properties of increased rebound, decreased rolling resistance and less heat-build up when subjected to mechanical stress during normal use.
- the hysteresis of an elastomer refers to the difference between the energy applied to deform an article made from the elastomer and the energy released as the elastomer returns to its initial, undeformed state.
- lowered hysteresis properties are associated with reduced rolling resistance and heat build-up during operation of the tire. These properties, in turn, result in lower fuel consumption for vehicles using such tires.
- the property of lowered hysteresis of compounded, vulcanizable elastomer compositions is particularly significant.
- compounded elastomer systems typically include at least one elastomer (that is, a natural or synthetic polymer exhibiting elastomeric properties, such as a rubber), a reinforcing (or non- reinforcing) filler agent (such as finely divided carbon black, thermal black, or mineral fillers such as clay and the like) and a vulcanizing system such as a sulfur-containing vulcanizing (i.e.. curing) system.
- elastomer that is, a natural or synthetic polymer exhibiting elastomeric properties, such as a rubber
- a reinforcing (or non- reinforcing) filler agent such as finely divided carbon black, thermal black, or mineral fillers such as clay and the like
- a vulcanizing system such as a sulfur-containing vulcanizing (i.e.. curing) system.
- silica has been increasingly used as a reinforcing participate filler in carbon black-filled rubber components of tires and mechanical goods. While providing excellent properties, including reduced hysteresis, to the rubber stocks, these silica-loaded rubber stocks are unfortunately not easily produced, exhibiting relatively poor processability characteristics.
- the present invention provides reinforcing filler-supported additives, such as a mineral fillers, capable of improving the processability of the formulations of diene polymer elastomers reinforced with silica filler.
- the present invention also provides a process for decreasing the level of bis[3-(triethoxysilyl)propyl]tetrasulfide (Si69) in silica-filled elastomeric vulcanizable compounds.
- the present invention also provides vulcanizable silica-filled elastomeric compounds having enhanced physical properties, including decreased hysteresis and increased tear strength.
- One aspect of the invention is a process for the preparation of a silica-filled, vulcanized elastomeric compound comprising: (a) mixing (1) 100 parts by weight of an elastomer; (2) from about 5 to about 100 parts by weight of a reinforcing filler selected from the group consisting of silica filler or mixtures thereof with carbon black, per 100 parts of said elastomer; (3) from about 0.1 to about 150 percent by weight, based on said silica filler, of a processing aid selected from the group consisting of alkylalkoxysilanes, fatty acid esters of hydrogenated and non-hydrogenated C ⁇ and C 6 sugars; polyoxyethylene derivatives of fatty acid esters of hydrogenated and non- drogenated Cs and C 6 sugars and mixtures thereof; (4) optionally from 0 to about 40 parts by weight of a non-reinforcing filler, per 100 parts elastomer, with the provisos that if said processing aid is sorbitan
- Another aspect of the invention is a vulcanizable, silica-filled compound comprising: 100 parts by weight of an elastomer; from about 5 to about 100 parts by weight of a reinforcing filler selected from the group consisting of silica filler or mixtures thereof with carbon black, per 100 parts of said elastomer; optionally from 0 to about 20 percent by weight of bis[3- (triethoxysilyl) propyl]tetrasulfide, based upon the weight of said silica filler; from about 0.1 to about 150 percent by weight, based on said silica filler, of a processing aid selected from the group consisting of alkylalkoxysilanes, fatty acid esters of hydrogenated and non-hydrogenated C 5 and C 6 sugars; polyoxyethylene derivatives of fatty acid esters of hydrogenated and non- hydrogenated C 5 and C 6 sugars and mixtures thereof: optionally from 0 to about 40 parts by weight of a non-reinforcing filler
- Another aspect of the invention is a pneumatic tire comprising tread stock vulcanized from the above vulcanizable silica-filled compound.
- Another aspect of the invention is a pneumatic tire comprising tread stock obtainable from the above inventive process.
- the present invention provides a silica-filled, vulcanizable elastomeric compound useful as tread stocks for pneumatic tires that employs a processing aid as a replacement for Si69.
- the processing aid is selected from the group consisting of alkyl alkoxysilanes, fatty acid esters of hydrogenated and non-hydrogenated sugars, ethoxylated derivatives of fatty acid esters of hydrogenated and non-hydrogenated sugars, and mixtures thereof and wherein the processing aid is supported on the silica filler or other filler, e.g., either another reinforcing filler such as carbon black, or a non-reinforcing filler such as one of a number of mineral fillers or the like.
- from about 0.1 to about 150 percent by weight of an alkyl alkoxysilane is used in the present invention as a processing aid.
- a processing aid for silica filler, up to about 150 parts by weight of the processing aid, per 100 parts elastomer, may be used, representing a 60/40 ratio of processing aid to silica.
- a mixture of a filler and a filler-supported processing aid selected from the group consisting of alkyl alkoxysilanes, fatty acid esters of hydrogenated and non-hydrogenated sugars, ethoxylated derivatives of fatty acid esters of hydrogenated and non- hydrogenated sugars, and mixtures thereof is preferably added to the elastomer in an amount of about 5 to about 100 parts by weight per 100 parts of the elastomer. It should be stressed that when a silica-supported or carbon black- supported processing aid is used, the non-reinforcing fillers, including mineral fillers or other processing aids are not required in the elastomeric formulation.
- the processing aid is added to the silica or other filler in a mixture ratio of from about 1 :99 to about 60:40, with a 50:50 mixture being most preferred.
- certain additional fillers can be utilized according to the present invention as processing aids which include, but are not limited to, mineral fillers, such as clay (hydrous aluminum silicate), talc (hydrous magnesium silicate), and mica as well as non-mineral fillers such as urea and sodium sulfate.
- mineral fillers such as clay (hydrous aluminum silicate), talc (hydrous magnesium silicate), and mica as well as non-mineral fillers such as urea and sodium sulfate.
- Preferred micas contain principally alumina, silica and potash, although other variants are also useful, as set forth below.
- the additional fillers are also optional and can be utilized in the amount of from 0 parts to about 40 parts per 100 parts of polymer (phr), preferably in an amount from about 1 to about 20 phr. It will be understood that these mineral fillers can also be used as non-reinforcing fillers to support the processing aids of the present invention.
- a process for the preparation of a silica-filled, vulcanized elastomeric compound according to the present invention comprises mixing an elastomer with from about 5 to about 100 parts by weight of a reinforcing filler selected from the group consisting of silica filler and mixtures thereof with carbon black, from 0 to about 20 percent by weight, based on said silica filler, of bis[3-(triethoxysilyl)propyl]tetrasulfide, from 0.1 to about 150 percent by weight, based on said silica filler, of an alkylalkoxysilane, and a cure agent; and, effecting vulcanization.
- a reinforcing filler selected from the group consisting of silica filler and mixtures thereof with carbon black
- the present invention also includes a vulcanizable silica- filled compound comprising an elastomer, a silica filler, from 0 to about 20 percent by weight, based on said silica filler, of bis[3- (triethoxysilyl)propyl]tetrasulf ⁇ de, from about 0.1 to about 150 percent by weight, based on said silica filler, of an alkylalkoxysilane, and a cure agent.
- the compound further contains a natural rubber.
- the present invention also includes a pneumatic tire comprising tread stock vulcanized from the above compound made from the above process.
- the elastomer can be a diene monomer homopolymer or a copolymer of a diene monomer and a monomer selected from the group consisting of monovinyl aromatic monomers and triene monomers.
- the alkylalkoxysilane can be represented by the formula (Rl) 2 Si(OR 2 )2 or RjSi(OR 2 ) 3 , wherein each Rj independently is selected from the group consisting of Cj to about Cj 8 aliphatic, about C 5 to about Cj 2 cyclo- aliphatic, and about C 6 to about C 18 aromatic; and wherein the alkoxy groups are the same or are different, each R 2 independently containing from one to about 6 carbon atoms.
- the alkylalkoxysilane can be selected from the group consisting of octyltriethoxy silane, octyltrimethyloxy silane, (3- glycidoxypropyl)trimethoxy silane, (3-glycidoxypropyl)triethoxy silane, hexyltrimethoxy silane, ethyltrimethyoxy silane, propyltriethoxy silane, phenyltrimethoxy silane, cyclohexyltrimethoxy silane, cyclohexyltriethyoxy silane, dimethyldimethyoxy silane, 3-chloropropyltriethoxy silane, methacroyltrimethoxy silane, and i-butyltriethoxy silane.
- the alkylalkoxysilane is octyltriethoxy silane.
- that processing aid is selected from the group consisting of at least one sorbitan ester of an oleate, laurate, palmitate and stearate fatty acids, polyoxyethylene derivatives thereof, at least one ester of a polyhydroxy compound, and mixtures thereof. More preferably, that processing aid is sorbitan monooleate.
- the elastomer is a styrene butadiene rubber. More preferably, the elastomer is a copolymer of styrene butadiene rubber and butyl rubber. Even more preferably, the elastomer is mixed with carbon black.
- the process also optionally includes mixing insoluble sulfur prior to the vulcanizing step.
- the present invention also includes a first alternative process for the preparation of a silica-filled, vulcanized elastomeric compound comprising the steps of mixing an elastomer with from about 5 to about 100 parts by weight of a reinforcing filler per 100 parts of elastomer, wherein said reinforcing fillers are selected from the group consisting of silica filler and mixtures thereof with carbon black; from 0 to about 20 percent by weight of bis [3- (triethoxysilyl)propyl]tetrasulfide, based upon the weight of said silica filler; from about 0.1 to about 150 percent by weight of a processing aid selected from the group consisting of fatty acid esters of hydrogenated and non-hydrogenated C 5 and C 6 sugars, polyoxyethylene derivatives of fatty acid esters of hydrogenated and non-hydrogenated C 5 and C sugars, and mixtures thereof; from about 0 to about
- the first alternative process utilizes a vulcanizable silica-filled compound which comprises 100 parts by weight of an elastomer; from about 5 to about 100 parts by weight of a reinforcing filler per 100 parts of elastomer, wherein said reinforcing fillers are selected from the group consisting of silica filler and mixtures thereof with carbon black; from 0 to about 20 percent by weight of bis [3 -(triethoxysilyl) propyljtetrasulfide.
- silica filler based upon the weight of said silica filler; from about 0.1 to about 150 percent by weight of a processing aid selected from the group consisting of fatty acid esters of hydrogenated and non-hydrogenated C and C 6 sugars, polyoxyethylene derivatives of fatty acid esters of hydrogenated and non-hydrogenated C 5 and C 6 sugars, and mixtures thereof; from about 0 to about 40 parts by weight of an additional filler other than silica or carbon black; and a cure agent; with the provisos that if said processing aid is sorbitan monooleate, then at least one of said polyoxyethylene derivatives or said additional fillers is also present and, that the minimal amount for each said processing aid and said additional filler, if present, is about one part by weight.
- a processing aid selected from the group consisting of fatty acid esters of hydrogenated and non-hydrogenated C and C 6 sugars, polyoxyethylene derivatives of fatty acid esters of hydrogenated and non-hydrogenated C 5 and C 6 sugars
- the present invention also includes a pneumatic tire comprising tread stock vulcanized from the above alternative compound made from the above alternative process.
- the alternative process can include an additional step of adding a natural rubber.
- silica filler used in the alternative process and compound has a surface area of about 32 to about 400 m2/g and a pH of about 5.5 to about 7.
- the alternative process and compound has an amount of said carbon black reinforcing filler ranging from about 0 to about 50 parts by weight, per 100 parts by weight of elastomer, and an amount of said reinforcing silica filler ranging from about 1 to 100 parts, per 100 parts of elastomer, with the proviso that where carbon is 0, at least 30 phr of silica is employed.
- the fatty acid esters of hydrogenated and non- hydrogenated C and C 6 sugars are selected from the group consisting of sorbitan monooleate, sorbitan dioleate, sorbitan trioleate. sorbitan sesquioleate, sorbitan laurate. sorbitan palmitate and sorbitan stearate.
- the polyoxyethylene derivatives of fatty acid esters of hydrogenated and non- hydrogenated Cs and C 6 sugars are selected from the group consisting of POE (20) sorbitan stearate; POE (20) sorbitan oleate; POE (20) sorbitan tri-oleate; POE (20) sorbitan sesquioleate; POE (20) sorbitan laurate and POE (20) sorbitan palmitate.
- the processing aid comprises a mixture of at least one fatty acid ester of hydrogenated and non-hydrogenated C 5 and C 6 sugars and at least one polyoxyethylene derivative of a fatty acid ester of hydrogenated and non-hydrogenated C 5 and C 6 sugars.
- the additional filler is selected from the group consisting of mica, talc, urea, clay, sodium sulfate and mixtures thereof and more preferably, is included with the mixture of at least one fatty acid ester of hydrogenated and non-hydrogenated C 5 and C 6 sugars.
- the present invention provides a second alternative process for the preparation of a silica-filled, vulcanized elastomeric compound comprising mixing 100 parts by weight of an elastomer with from about 5 to about 100 parts by weight of a reinforcing filler selected from the group consisting of silica filler or mixtures thereof with carbon black, per 100 parts of said elastomer; from about 0.1 to about 150 percent by weight, based on said silica filler, of a processing aid selected from the group consisting of alkylalkoxysilanes, fatty acid esters of hydrogenated and non-hydrogenated C5 and C6 sugars; polyoxyethylene derivatives of fatty acid esters of hydrogenated and non-hydrogenated C5 and C6 sugars and mixtures thereof; from 0 to about 40 parts by weight of a non-reinforcing filler, per 100 parts elastomer; and a cure agent: wherein said processing aid is first mixed with and supported on at least some of either said reinforcing filler
- the second alternative process utilizes a vulcanizable, silica- filled compound comprising 100 parts by weight of an elastomer; from about 5 to about 100 parts by weight of a reinforcing filler selected from the group consisting of silica filler or mixtures thereof with carbon black, per 100 parts of said elastomer; from about 0.1 to about 150 percent by weight, based on said silica filler, of a processing aid selected from the group consisting of alkylalkoxysilanes, fatty acid esters of hydrogenated and non-hydrogenated C5 and C6 sugars; polyoxyethylene derivatives of fatty acid esters of hydrogenated and non-hydrogenated C5 and C6 sugars and mixtures thereof; from 0 to about 40 parts by weight of a non-reinforcing filler, per 100 parts elastomer; and a cure agent; wherein said processing aid is supported on at least some of either said reinforcing filler or said non-reinforcing filler.
- the present invention also includes a pneumatic tire comprising tread stock vulcanized from the above second alternative compound made from the above second alternative process.
- the alkyl alkoxysilanes are selected from the group consisting of octyltriethoxy silane, octyltrimethyloxy silane, (3-glycidoxypropyl)trimethoxy silane, (3-glycidoxypropyl)triethoxy silane, hexyltrimethoxy silane, ethyltrimethyoxy silane, propyltriethoxy silane, phenyltrimethoxy silane, cyclohexyltrimethoxy silane, cyclohexyltnethyoxy silane, dimethyldimethyoxy silane, 3-chloropropyltriethoxy silane, methacroyltrimethoxy silane, and i- butyltriethoxy
- the silica or carbon black-support processing aid is provided as a 50/50 mixture of processing aid to support.
- Example Nos. 2-6 indicated a Mooney viscosities (ML l+4/100°C) comparable to the control, C-DD, with 3 phr of Si69 processing aid.
- Tensile properties of the cured elastomeric stocks, containing processing aids comprising octyl triethoxy silane and sorbitan oleate supported on silica are comparable to the tensile properties of the control elastomeric stock formulation, C-DD, containing 3 phr of Si69 processing aid. Curing at 171°C for 20 minutes was used to obtain the physical properties set forth below.
- silica-filled vulcanizable elastomeric stock formulations was conducted to determine the effects of the silica and carbon black-supported processing aids on the physical properties and processability of the elastomeric formulations after six months of ambient storage.
- the elastomeric stock formulations were prepared according to Table III, below, and the physical properties were evaluated after curing at 170°C for 20 minutes, followed by six months of ambient aging.
- the data for the physical properties and processability of the elastomeric formulations for the ambient aging study are shown in Table IV, below.
- elastomeric formulations containing a silica-supported or carbon black-supported processing aid selected from the group consisting of an alkyl alkoxysilane, fatty acid ester of hydrogenated or non-hydrogenated C5 and C ⁇ sugars, e.g., sorbitan, and ethoxylated derivatives of fatty acid esters of these sugars provide physical properties, after six months of ambient aging, comparable to the control elastomeric formulation containing 3 phr of Si69 as a processing aid (C-DD).
- a silica-supported or carbon black-supported processing aid selected from the group consisting of an alkyl alkoxysilane, fatty acid ester of hydrogenated or non-hydrogenated C5 and C ⁇ sugars, e.g., sorbitan, and ethoxylated derivatives of fatty acid esters of these sugars
- the process of the present invention is useful in improving the processability of formulations of diene polymer elastomers containing silica filler by reducing the viscosity of silica-filled elastomeric vulcanizable compounds. It is further demonstrated that the present invention provides vulcanizable silica-filled elastomeric compounds having enhanced physical properties.
- Practice of the present invention allows a reduction of Si69 which is added to vulcanizable rubber compositions containing silica fillers. The reduction can be effected by the addition of the processing aids described herein, mineral and non-mineral fillers as well as combinations of more than one.
Abstract
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Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP99965889A EP1135433B1 (en) | 1998-12-01 | 1999-11-24 | Improved processability of silica-filled rubber stocks |
DE69925861T DE69925861T2 (en) | 1998-12-01 | 1999-11-24 | IMPROVED PROCESSABILITY OF SILICA-FILLED RUBBER COMPOSITIONS |
JP2000585321A JP2002531617A (en) | 1998-12-01 | 1999-11-24 | Improved processability of silica-filled rubber raw materials |
CA002353503A CA2353503C (en) | 1998-12-01 | 1999-11-24 | Improved processability of silica-filled rubber stocks |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/203,438 US6384117B1 (en) | 1997-07-11 | 1998-12-01 | Processability of silica-filled rubber stocks |
US09/203,438 | 1998-12-01 |
Publications (1)
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WO2000032684A1 true WO2000032684A1 (en) | 2000-06-08 |
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Application Number | Title | Priority Date | Filing Date |
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PCT/US1999/027890 WO2000032684A1 (en) | 1998-12-01 | 1999-11-24 | Improved processability of silica-filled rubber stocks |
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US (3) | US6384117B1 (en) |
EP (1) | EP1135433B1 (en) |
JP (1) | JP2002531617A (en) |
CA (1) | CA2353503C (en) |
DE (1) | DE69925861T2 (en) |
WO (1) | WO2000032684A1 (en) |
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US9034962B2 (en) | 2004-04-27 | 2015-05-19 | Bridgestone Corporation | Method of producing a tire composition having improved silica reinforcement |
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US7879958B2 (en) | 2007-08-07 | 2011-02-01 | Bridgestone Corporation | Polyhydroxy compounds as polymerization quenching agents |
US8324329B2 (en) | 2007-08-07 | 2012-12-04 | Bridgestone Corporation | Process for producing functionalized polymers |
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Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2002010267A2 (en) * | 2000-07-31 | 2002-02-07 | Bridgestone Corporation | Silica-reinforced rubber compounds containing moisture stabilized polymers |
WO2002010267A3 (en) * | 2000-07-31 | 2002-06-06 | Bridgestone Corp | Silica-reinforced rubber compounds containing moisture stabilized polymers |
US6433065B1 (en) | 2000-10-13 | 2002-08-13 | Bridgestone Corporation | Silica-reinforced rubber compounded with mercaptosilanes and alkyl alkoxysilanes |
US6608145B1 (en) | 2000-10-13 | 2003-08-19 | Bridgestone Corporation | Silica-reinforced rubber compounded with an organosilane tetrasulfide silica coupling agent at high mixing temperature |
EP1394198A1 (en) * | 2002-07-25 | 2004-03-03 | Wacker Polymer Systems GmbH & Co. KG | Hydrophobically modified polymers |
US7183358B2 (en) * | 2002-07-25 | 2007-02-27 | Wacker Polymer Systems Gmbh & Co. Kg | Hydrophobically modified polymers |
US9034962B2 (en) | 2004-04-27 | 2015-05-19 | Bridgestone Corporation | Method of producing a tire composition having improved silica reinforcement |
EP3266818A4 (en) * | 2015-03-05 | 2018-03-14 | Bridgestone Corporation | Rubber composition and tire |
WO2016147089A1 (en) * | 2015-03-13 | 2016-09-22 | Bridgestone Corporation | Method to prepare rubber compounds containing silicon dioxide for the production of tyres |
US10233266B2 (en) | 2015-03-13 | 2019-03-19 | Bridgestone Corporation | Method to prepare rubber compounds containing silicon dioxide for the production of tyres |
Also Published As
Publication number | Publication date |
---|---|
DE69925861D1 (en) | 2005-07-21 |
JP2002531617A (en) | 2002-09-24 |
DE69925861T2 (en) | 2006-05-11 |
US20030022972A1 (en) | 2003-01-30 |
EP1135433B1 (en) | 2005-06-15 |
CA2353503A1 (en) | 2000-06-08 |
US6384117B1 (en) | 2002-05-07 |
CA2353503C (en) | 2009-03-17 |
US6790889B2 (en) | 2004-09-14 |
EP1135433A1 (en) | 2001-09-26 |
US6342552B1 (en) | 2002-01-29 |
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