EP1290098A1 - Composite shaped part containing polyarylene sulfide and silicon rubber - Google Patents
Composite shaped part containing polyarylene sulfide and silicon rubberInfo
- Publication number
- EP1290098A1 EP1290098A1 EP01940481A EP01940481A EP1290098A1 EP 1290098 A1 EP1290098 A1 EP 1290098A1 EP 01940481 A EP01940481 A EP 01940481A EP 01940481 A EP01940481 A EP 01940481A EP 1290098 A1 EP1290098 A1 EP 1290098A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- optionally
- parts
- composite molding
- silicone rubber
- molding according
- 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- Withdrawn
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
- C08L81/02—Polythioethers; Polythioether-ethers
-
- 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
- B29C48/00—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor
-
- 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
- B29C48/00—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor
- B29C48/03—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor characterised by the shape of the extruded material at extrusion
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
- B29K2083/00—Use of polymers having silicon, with or without sulfur, nitrogen, oxygen, or carbon only, in the main chain, as moulding material
- B29K2083/005—LSR, i.e. liquid silicone rubbers, or derivatives thereof
-
- 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
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/13—Hollow or container type article [e.g., tube, vase, etc.]
- Y10T428/1352—Polymer or resin containing [i.e., natural or synthetic]
-
- 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
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31533—Of polythioether
-
- 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
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31652—Of asbestos
- Y10T428/31663—As siloxane, silicone or silane
Definitions
- the invention relates to a composite molding containing at least one polyarylene sulfide and at least one elastomer.
- Polyarylene sulfides have a continuous operating temperature of up to 240 ° C. Polyarylene sulfides are flame-resistant and resistant to oxidation. Polyarylene sulfides are extremely hard and rigid. The absorption of water is low. The creep is low even at elevated temperatures. Due to the properties mentioned above, polyarylene sulfides are particularly suitable for the production of moldings with good mechanical properties and thermal stability. Polaraylene sulfides are characterized by chemical and heat resistance as well as rigidity.
- the high surface hardness of molded parts made of polyarylene sulfides and the low sliding friction coefficient of polyarylene sulfides can cause objects lying on top to slip and limit the operational safety of switching elements and operating elements made of polyarylene sulfides.
- seals and damping elements are provided separately and are usually mechanically anchored in an additional work step, which causes additional work and considerable additional costs.
- EP-A-0 326 712 describes improved adhesion to various plastics by means of a mixture or a reaction product from (a) a silicon-free one Compound with at least one alcoholic OH group and at least one alkylene group and (b) an organosilane with at least one alkoxy group and at least one epoxy group, but relatively long reaction times (1 h) at a temperature of 120 ° C are necessary. The long reaction times are often caused by simultaneously inhibiting adhesive additives.
- the inhibition by such additives can only be improved to a limited extent by the choice of an optimized SiH / SiVi ratio.
- Adhesion to aluminum as a substrate is only improved after a relatively long vulcanization time of 2 h (measured at 100 ° C). A possible shortening of the reaction times by increasing the temperature cannot be carried out, in particular in the case of many plastic substrates, because of the lack of temperature resistance.
- EP-A-0 493 791 describes the use of known adhesion promoters together with a tetravalent zirconium compound in order to achieve a bond between silicone rubber and PPS.
- a molded part made from a combination of polyacetal and directly molded functional elements is known.
- the functional elements consist of one or more elastomers, which contain partially or completely hydrogenated nitrile rubbers, one- and multi-component silicone rubbers or sulfur-containing rubbers.
- EP-A-0 875 536 discloses addition-crosslinking silicone rubbers and a process for the production of composite molded parts. PA and PBT are used as substrates. Usually in the production of composite molded parts between a technical polymer such as polyarylene sulfide and an elastomer
- Polymer either by surface treatment with primers or by
- the object of the present invention is to provide a composite molded part made of polyarylene sulfide with a silicone elastomer without complex pretreatment of the polyarylene sulfide during production, the adhesive strength between polyarylene sulfide and the silicone elastomer being improved.
- the object is achieved by a composite molded part containing at least one polyarylene sulfide and at least one one- or more-component silicone rubber, as described in EP-A-0 875 536 or US Pat. No. 5,998,515.
- Polyarylene sulfides can be prepared via dihalogenated aromatic compounds.
- Preferred dihalogenated aromatic compounds are p-dichlorobenzene, m-dichlorobenzene, 2,5-dichlorotoluene, p-dibromobenzene, 1,4-dichloronaphthalene, 1-methoxy-2,5-dichlorobenzene, 4,4'-dichlorobiphenyl, 3,5- Dichlorobenzoic acid, 4,4'-dichlorodiphenyl ether, 4,4'-dichlodiphenyl sulfone, 4,4'-dichlorodiphenyl sulfoxide and 4,4'-dichlorodiphenyl ketone.
- the polyarylene sulfide is obtained as described in EP-A-0 259 984 in a two-stage polymerization process for prepolymerization and main polymerization, a dihalogenated aromatic compound being polymerized with an alkali metal sulfide in an aprotic organic polar solvent to give polyarylene sulfide.
- polyphenylene sulfide is preferably used as the polyarylene sulfide for the production of composite molded parts.
- Polyphenylene sulfide (PPS) is a linear partially crystalline polymer with the general formula: where n> 1.
- housings are also made from polyphenylene sulfide.
- Polyphenylene sulfides have a low mechanical damping factor, which in some applications requires the use of soft damping elements.
- a seal is often required at connection points.
- silicone rubbers such as those described in EP-A-0 875 536 or US Pat. No. 5,998,515, have very good adhesive strength to the polyphenylene sulfide of the molded part, without the polyphenylene sulfide being adhesive-modified or after injection molding is pretreated.
- Addition-crosslinking mixtures which have at least one hydrogen siloxane with at least 2 SiH groups and an alkoxysilane or alkoxysiloxane with at least one epoxy group and optionally a peroxide have good adhesion to substrates and low reactivity.
- the mixture can be processed without a variety of additional components.
- Addition-crosslinking silicone rubber mixtures contain a) 100 parts of at least one alkenyl group-containing linear or branched organopolysiloxane with at least 2 alkenyl groups with a viscosity of 0.01 to 30,000 Pas, b) at least one hydrogen siloxane with at least 2 SiH functions per molecule in an amount so that the molar ratio of the SiH group to the total amount of Si-bonded alkenyl groups is at least 1.5, c) at least one Pt or Rh catalyst and optionally an inhibitor, d) 0.1 to 10 parts of at least one alkoxysilane with at least one epoxy group and / or alkoxysiloxane at least one epoxy group or silanes as described in EP 902059, US 3730932 and US 5998515, and optionally e) 0 to 200, preferably 5 to 200 parts of at least one, optionally surface-modified filler and optionally f) further auxiliaries, such as phenyl silicone oils for self-lub
- organopolysiloxane (a) encompasses all polysiloxanes previously used in crosslinkable organopolysiloxane compositions.
- (A) is preferably a siloxane composed of units of the general formula (I)
- R 1 is a monovalent aliphatic radical having 1 to 8 carbon atoms, preferably methyl
- R 2 is an akenyl radical having 2 to 8 carbon atoms, preferably vinyl
- a 0, 1, 2 or 3
- b 0, 1 or 2
- the sum a + b 0, 1, 2 or 3, with the proviso that on average there are at least two radicals R 2 per molecule.
- dimethylvinylsiloxane is stopped.
- Organopolysiloxanes (a) preferably have viscosities from 0.01 to 200 Pas, very particularly preferably from 0.2 to 200 Pas. The viscosities are determined according to DIN 53 019 at 20 ° C.
- Hydrogen siloxanes (b) are preferably linear, cyclic or branched organopolysiloxanes composed of units of the general formula (II) (R 3 ) c (H) d SiO (4. C. D) / 2 (II),
- R 3 is a monovalent aliphatic radical having 1 to 8 carbon atoms, preferably
- the hydrogen siloxanes (b) preferably have a viscosity of 0.01 to 5 Pas.
- the hydrogen siloxanes (b) can additionally also contain organopolysiloxanes whose number of SiH groups is x 2 ⁇ x ⁇ 20.
- Catalysts (c) for the crosslinking reaction are preferably Pt (O) complexes with alkenylsiloxanes as ligands in catalytic amounts of 1 to 100 ppm.
- Inhibitors are all common compounds that have hitherto been used for this purpose, such as alkylols or vinylsiloxanes in amounts of 50 to 10,000 ppm.
- Preferred alkoxyisilanes or alkoxysiloxanes which have at least one epoxy group (d) are those which have a maximum of 5 carbon atoms in the alkoxy function in amounts of 0.1 to 10 parts, based on the sum of all components, cf. EP-A-0 691 364.
- a composite molded part is also provided, the silicone rubber being an addition-crosslinked silicone rubber mixture comprising a) 100 parts of at least one linear or branched organopolysiloxane containing alkenyl groups with at least 2 alkenyl groups with a viscosity of 0.01 to 30,000 Pas, b) at least one hydrogen siloxane with at least 2 SiH functions per molecule in an amount such that the molar ratio of the SiH group to the total amount of Si-bonded alkenyl groups is at least 1.5, c) at least one Pt or Rh catalyst and optionally one
- Inhibitor d) 0.1 to 10 parts of at least one alkoxysilane with at least one epoxy group and / or alkoxysiloxane with at least one epoxy group, and optionally, e) 0 to 200, preferably 5 to 200 parts of at least one, optionally surface-modified filler and optionally, f) further auxiliaries, such as phenyl silicone oils for self-lubricating mixtures or color pastes, such as silicone oils containing 10 to 70% by weight of pigments, and g) optionally a peroxide.
- auxiliaries such as phenyl silicone oils for self-lubricating mixtures or color pastes, such as silicone oils containing 10 to 70% by weight of pigments, and g) optionally a peroxide.
- Fillers (e) are preferably reinforcing fillers, such as pyrogenic or precipitated silica with BET surface areas between 50 and 400 m 2 / g, which can also be treated on the surface, in amounts of preferably 10 to 50 parts, and / or extender fillers, like quartz flour, diatomaceous earth.
- the surface treatment of the fillers can also be carried out in situ by adding silazanes, such as hexamethylsilazane and / or divinyltetramethyldisilazane, and vinylalkoxysilanes, such as vinyltrimethoxysilane and water, or other customary filler treatment agents, such as alkoxysilanes or siloxane diols.
- the mixture can contain other auxiliaries (f), such as phenyl silicones, which provide self-lubricating vulcanizates, such as copolymers of dimethylsiloxy and diphenylsiloxy or methylphenylsiloxy groups, and polysiloxanes with methylphenylsiloxy groups with a viscosity of preferably 0.1 to 10 Pas or color pastes.
- auxiliaries such as phenyl silicones, which provide self-lubricating vulcanizates, such as copolymers of dimethylsiloxy and diphenylsiloxy or methylphenylsiloxy groups, and polysiloxanes with methylphenylsiloxy groups with a viscosity of preferably 0.1 to 10 Pas or color pastes.
- the amount of auxiliaries is preferably 0 to 10, preferably 0.05 to 10 parts by weight.
- the silicone rubber mixture can additionally contain at least one peroxide (g) in amounts of 0.1 to 2 parts, based on the total mixture.
- Aroyl peroxides are preferred as peroxides (g).
- the amount of peroxide is preferably 0 to 1% by weight, preferably 0.1 to 0.5% by weight.
- the composite molded parts are sealing and / or damping elements and areas for
- the composite molded parts made of polyphenylene sulfide and a silicone elastomer are preferably produced in a one-step process by inserting technology or in a multi-component injection molding process or by coextrusion, casting, calendering or the like. manufactured.
- the sealing or damping elements can be molded directly onto molded parts made of polyphenylene sulfide without the need for further assembly steps.
- the sealing or damping elements can be molded directly onto molded parts made of polyphenylene sulfide without the need for further assembly steps.
- Fields of application for the composite molded parts according to the invention are, for example, housings in automobile construction, such as resonators, valve covers, valve pistons, air mass meters or sanitary parts.
- polyphenylene sulfone or polyphenylene sulfoxide are also suitable as industrial polymers for the purposes of the invention.
- the adhesive strength is determined either qualitatively on the molded part or quantitatively via the peeling force in accordance with DIN 53 289.
- Example 1a A plate of Fortron® 1140 L4 polyphenylene sulfide was placed in a tool. The LIM 9070 silicone rubber mixture was applied to the plate. The tool was then heated to a temperature of 175 ° C. and the housing was pressed in a press for 15 minutes. Bad adhesion is found.
- Example 1a A plate of Fortron® 1140 L4 polyphenylene sulfide was placed in a tool. The LIM 9070 silicone rubber mixture was applied to the plate. The tool was then heated to a temperature of 175 ° C. and the housing was pressed in a press for 15 minutes. Bad adhesion is found.
- Example 1a A plate of Fortron® 1140 L4 polyphenylene sulfide was placed in a tool. The LIM 9070 silicone rubber mixture was applied to the plate. The tool was then heated to a temperature of 175 ° C. and the housing was pressed in a press for 15 minutes. Bad adhesion is found.
- Example 1a A plate of Fortron
- a plate of Fortron® 4332 L6 polyphenylene sulfide was placed in a tool.
- the LIM 9070 silicone rubber mixture was applied to the plate.
- the tool was then heated to a temperature of 175 ° C. and the housing was pressed in a press for 15 minutes. Bad adhesion is found.
- a plate of Fortron® 1140 L4 polyphenylene sulfide was placed in a tool.
- the silicone rubber mixture LSR 2040 + 2% VP AI 3662 was applied to the plate.
- the tool was then heated to a temperature of 175 ° C. and the housing was pressed in a press for 15 minutes. One finds cohesion.
- a plate of Fortron® 4332 L6 polyphenylene sulfide was placed in a tool.
- the silicone rubber mixture LSR 2040 + 2% VP AI 3662 was applied to the plate.
- the tool was then heated to a temperature of 175 ° C. and the housing was pressed in a press for 15 minutes. One finds cohesion.
- Example 3a Plates (2 test specimens) made of Fortron® 4332 L6 polyphenylene sulfide were placed on top
- the composite molded parts were produced from the following examples (mold temperature 150 ° C) on an injection molding machine with a turntable mold, a polyphenylene molded part being produced in the first step and a silicone seal being injection molded onto the first molded part in parallel with the production of a further polyphenylene molded part ).
- Fortron® 1140 L4 was used as polyphenylene sulfide and LIM 9070 was used as silicone rubber. One finds cohesion.
- Example 6 Fortron® 1140 L4 was used as polyphenylene sulfide and LSR as silicone rubber
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Injection Moulding Of Plastics Or The Like (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Laminated Bodies (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Abstract
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10025257A DE10025257A1 (en) | 2000-05-22 | 2000-05-22 | Composite molded parts containing polyarylene sulfide and silicone rubber |
DE10025257 | 2000-05-22 | ||
PCT/EP2001/005549 WO2001090266A1 (en) | 2000-05-22 | 2001-05-16 | Composite shaped part containing polyarylene sulfide and silicon rubber |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1290098A1 true EP1290098A1 (en) | 2003-03-12 |
Family
ID=7643087
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP01940481A Withdrawn EP1290098A1 (en) | 2000-05-22 | 2001-05-16 | Composite shaped part containing polyarylene sulfide and silicon rubber |
Country Status (8)
Country | Link |
---|---|
US (1) | US6875517B2 (en) |
EP (1) | EP1290098A1 (en) |
JP (1) | JP2003534438A (en) |
CN (1) | CN1328342C (en) |
AU (1) | AU2001274040A1 (en) |
DE (1) | DE10025257A1 (en) |
TW (1) | TW593600B (en) |
WO (1) | WO2001090266A1 (en) |
Families Citing this family (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002293935A (en) * | 2001-03-30 | 2002-10-09 | Petroleum Energy Center | Method for baking polyarylene sulfide by-product salt |
DE10308742A1 (en) * | 2003-02-28 | 2004-09-16 | Krauss-Maffei Kunststofftechnik Gmbh | Process for the production of multi-component molded plastic parts |
US8877306B2 (en) * | 2006-03-09 | 2014-11-04 | Manoj Ajbani | Compatibalized blends of polyphenylene sulfide and thermoplastic vulcanizate |
US7981981B2 (en) * | 2006-03-09 | 2011-07-19 | Ticona Llc | Flexible, hydrocarbon-resistant polyarylenesulfide compounds and articles |
DE102007007569A1 (en) * | 2007-02-15 | 2008-08-21 | Wacker Chemie Ag | Addition-crosslinkable silicone compositions with low coefficients of friction |
KR20140063838A (en) | 2011-09-20 | 2014-05-27 | 티코나 엘엘씨 | Overmolded composite structure for an electronic device |
WO2013043565A1 (en) | 2011-09-20 | 2013-03-28 | Ticona Llc | Polyarylene sulfide/liquid crystal polymer alloy and compositions including same |
CN103987758B (en) | 2011-09-20 | 2016-06-08 | 提克纳有限责任公司 | The housing of portable electric appts |
WO2013101315A1 (en) | 2011-09-20 | 2013-07-04 | Ticona Llc | Low halogen content disulfide washed polyarylene sulfide |
CN108102370A (en) | 2011-09-20 | 2018-06-01 | 提克纳有限责任公司 | The polyarylene sulfide composition of the melt-processed of low chlorine filling |
US9394430B2 (en) | 2012-04-13 | 2016-07-19 | Ticona Llc | Continuous fiber reinforced polyarylene sulfide |
US9493646B2 (en) | 2012-04-13 | 2016-11-15 | Ticona Llc | Blow molded thermoplastic composition |
US9494260B2 (en) | 2012-04-13 | 2016-11-15 | Ticona Llc | Dynamically vulcanized polyarylene sulfide composition |
US9765219B2 (en) | 2012-04-13 | 2017-09-19 | Ticona Llc | Polyarylene sulfide components for heavy duty trucks |
US9494262B2 (en) | 2012-04-13 | 2016-11-15 | Ticona Llc | Automotive fuel lines including a polyarylene sulfide |
US9758674B2 (en) | 2012-04-13 | 2017-09-12 | Ticona Llc | Polyarylene sulfide for oil and gas flowlines |
EP2969566A4 (en) * | 2013-03-12 | 2016-11-23 | Ansell Ltd | Breach or contamination indicating article |
WO2015031233A1 (en) | 2013-08-27 | 2015-03-05 | Ticona Llc | Heat resistant toughened thermoplastic composition for injection molding |
US9757892B2 (en) | 2013-08-27 | 2017-09-12 | Ticona Llc | Thermoplastic composition with low hydrocarbon uptake |
CN103965642A (en) * | 2014-05-12 | 2014-08-06 | 四川大学 | Polyphenylene sulfide/silicone rubber thermoplastic elastomer as well as preparation method and application thereof |
WO2016094381A1 (en) | 2014-12-11 | 2016-06-16 | Ticona Llc | Stabilized flexible thermoplastic composition and products formed therefrom |
EP3231844B1 (en) * | 2014-12-12 | 2019-11-27 | DIC Corporation | Polyarylene sulfide resin composition, molded article, composite molded article, and method for producing composite molded article |
US20230323154A1 (en) * | 2022-04-12 | 2023-10-12 | Comotomo 2022 Inc. | Adhesion between base material and resilient material layer |
Family Cites Families (14)
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US4087585A (en) | 1977-05-23 | 1978-05-02 | Dow Corning Corporation | Self-adhering silicone compositions and preparations thereof |
JPH0813887B2 (en) | 1986-08-13 | 1996-02-14 | 呉羽化学工業株式会社 | Process for producing poly (arylene sulfide) having excellent handling property |
JP2614472B2 (en) | 1987-12-29 | 1997-05-28 | 東レ・ダウコーニング・シリコーン株式会社 | Curable organopolysiloxane composition |
DE69002295T2 (en) * | 1989-09-25 | 1993-11-04 | Schneider Usa Inc | MULTILAYER EXTRUSION AS A METHOD FOR PRODUCING BALLOONS FOR VESSEL PLASTICS. |
JPH04222871A (en) | 1990-12-25 | 1992-08-12 | Toray Dow Corning Silicone Co Ltd | Curable organopolysiloxane composition |
US5164461A (en) | 1991-03-14 | 1992-11-17 | General Electric Company | Addition-curable silicone adhesive compositions |
JP2734302B2 (en) * | 1992-01-21 | 1998-03-30 | 信越化学工業株式会社 | Silicone rubber adhesive composition |
US5416144A (en) * | 1993-12-20 | 1995-05-16 | General Electric Company | Addition-curable silicone adhesive compositions and bis (trialkoxysilyalkylene) urea adhesion promoters |
DE4424105A1 (en) | 1994-07-08 | 1996-01-11 | Bayer Ag | Siloxanes containing epoxy groups and their mixtures with polycarbonates |
DE4439766C1 (en) | 1994-11-07 | 1996-04-04 | Hoechst Ag | Molded parts made of polyacetal with directly molded functional elements |
TW296401B (en) * | 1994-12-26 | 1997-01-21 | Shinetsu Chem Ind Co | |
CA2236391A1 (en) * | 1997-05-02 | 1998-11-02 | Bayer Aktiengesellschaft | Addition crosslinking silicone rubber mixtures, a process for the preparation thereof, a process for the preparation of composite molded parts and the use thereof |
US5998515A (en) | 1997-12-29 | 1999-12-07 | General Electric Company | Liquid injection molding silicone elastomers having primerless adhesion |
DE19943666A1 (en) * | 1999-09-13 | 2001-03-15 | Ge Bayer Silicones Gmbh & Co | Addition-crosslinking silicone rubber mixtures, a process for their production, process for the production of composite molded parts and use of the silicone rubber mixtures |
-
2000
- 2000-05-22 DE DE10025257A patent/DE10025257A1/en not_active Withdrawn
-
2001
- 2001-05-16 US US10/296,133 patent/US6875517B2/en not_active Expired - Fee Related
- 2001-05-16 CN CNB018113532A patent/CN1328342C/en not_active Expired - Fee Related
- 2001-05-16 WO PCT/EP2001/005549 patent/WO2001090266A1/en not_active Application Discontinuation
- 2001-05-16 JP JP2001587067A patent/JP2003534438A/en active Pending
- 2001-05-16 EP EP01940481A patent/EP1290098A1/en not_active Withdrawn
- 2001-05-16 AU AU2001274040A patent/AU2001274040A1/en not_active Abandoned
- 2001-05-18 TW TW090111986A patent/TW593600B/en not_active IP Right Cessation
Non-Patent Citations (1)
Title |
---|
See references of WO0190266A1 * |
Also Published As
Publication number | Publication date |
---|---|
WO2001090266A1 (en) | 2001-11-29 |
US6875517B2 (en) | 2005-04-05 |
JP2003534438A (en) | 2003-11-18 |
TW593600B (en) | 2004-06-21 |
CN1437641A (en) | 2003-08-20 |
CN1328342C (en) | 2007-07-25 |
US20040028854A1 (en) | 2004-02-12 |
DE10025257A1 (en) | 2001-12-06 |
AU2001274040A1 (en) | 2001-12-03 |
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