US20050038188A1 - Silicones having improved chemical resistance and curable silicone compositions having improved migration resistance - Google Patents

Silicones having improved chemical resistance and curable silicone compositions having improved migration resistance Download PDF

Info

Publication number
US20050038188A1
US20050038188A1 US10/641,810 US64181003A US2005038188A1 US 20050038188 A1 US20050038188 A1 US 20050038188A1 US 64181003 A US64181003 A US 64181003A US 2005038188 A1 US2005038188 A1 US 2005038188A1
Authority
US
United States
Prior art keywords
component
composition
sio
optionally
terminated
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.)
Abandoned
Application number
US10/641,810
Other languages
English (en)
Inventor
Dongchan Ahn
Pamela Huey
Nick Shephard
Michael Watson
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dow Silicones Corp
Original Assignee
Dow Corning Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dow Corning Corp filed Critical Dow Corning Corp
Priority to US10/641,810 priority Critical patent/US20050038188A1/en
Assigned to DOW CORNING CORPORATION reassignment DOW CORNING CORPORATION ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: WATSON, MICHAEL JOHN, AHN, DONGEHAN, HUEY, PAMELA JEAN, SHEPHARD, NICK EVAN
Priority to EP04777771A priority patent/EP1664198B1/en
Priority to JP2006523187A priority patent/JP5143421B2/ja
Priority to PCT/US2004/021903 priority patent/WO2005019342A1/en
Priority to AT06076803T priority patent/ATE440914T1/de
Priority to EP06076803A priority patent/EP1741755B1/en
Priority to DE602004007016T priority patent/DE602004007016T2/de
Priority to AT04777771T priority patent/ATE364661T1/de
Priority to DE200460022873 priority patent/DE602004022873D1/de
Priority to TW93122756A priority patent/TWI350845B/zh
Publication of US20050038188A1 publication Critical patent/US20050038188A1/en
Priority to US11/180,456 priority patent/US7521124B2/en
Priority to KR20067003096A priority patent/KR101074643B1/ko
Abandoned legal-status Critical Current

Links

Images

Classifications

    • 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
    • C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
    • 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
    • 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
    • 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
    • C08L83/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D183/00—Coating compositions based on 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; Coating compositions based on derivatives of such polymers
    • C09D183/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D183/00—Coating compositions based on 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; Coating compositions based on derivatives of such polymers
    • C09D183/04—Polysiloxanes
    • C09D183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J183/00—Adhesives based on 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; Adhesives based on derivatives of such polymers
    • C09J183/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J183/00—Adhesives based on 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; Adhesives based on derivatives of such polymers
    • C09J183/04—Polysiloxanes
    • C09J183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
    • H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
    • H01L23/293—Organic, e.g. plastic
    • 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
    • C08G77/12—Polysiloxanes containing silicon bound to hydrogen
    • 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
    • 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
    • C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups
    • 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
    • C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
    • 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
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/24—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-containing groups
    • 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
    • C08G77/80—Siloxanes having aromatic substituents, e.g. phenyl side groups
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
    • H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L2224/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
    • H01L2224/31—Structure, shape, material or disposition of the layer connectors after the connecting process
    • H01L2224/32—Structure, shape, material or disposition of the layer connectors after the connecting process of an individual layer connector
    • H01L2224/321—Disposition
    • H01L2224/32135—Disposition the layer connector connecting between different semiconductor or solid-state bodies, i.e. chip-to-chip
    • H01L2224/32145—Disposition the layer connector connecting between different semiconductor or solid-state bodies, i.e. chip-to-chip the bodies being stacked
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
    • H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L2224/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
    • H01L2224/31—Structure, shape, material or disposition of the layer connectors after the connecting process
    • H01L2224/32—Structure, shape, material or disposition of the layer connectors after the connecting process of an individual layer connector
    • H01L2224/321—Disposition
    • H01L2224/32151—Disposition the layer connector connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive
    • H01L2224/32221—Disposition the layer connector connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked
    • H01L2224/32225—Disposition the layer connector connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked the item being non-metallic, e.g. insulating substrate with or without metallisation
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
    • H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L2224/42—Wire connectors; Manufacturing methods related thereto
    • H01L2224/47—Structure, shape, material or disposition of the wire connectors after the connecting process
    • H01L2224/48—Structure, shape, material or disposition of the wire connectors after the connecting process of an individual wire connector
    • H01L2224/4805—Shape
    • H01L2224/4809—Loop shape
    • H01L2224/48091—Arched
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
    • H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L2224/42—Wire connectors; Manufacturing methods related thereto
    • H01L2224/47—Structure, shape, material or disposition of the wire connectors after the connecting process
    • H01L2224/48—Structure, shape, material or disposition of the wire connectors after the connecting process of an individual wire connector
    • H01L2224/481—Disposition
    • H01L2224/48151—Connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive
    • H01L2224/48221—Connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked
    • H01L2224/48225—Connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked the item being non-metallic, e.g. insulating substrate with or without metallisation
    • H01L2224/48227—Connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked the item being non-metallic, e.g. insulating substrate with or without metallisation connecting the wire to a bond pad of the item
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
    • H01L2224/73—Means for bonding being of different types provided for in two or more of groups H01L2224/10, H01L2224/18, H01L2224/26, H01L2224/34, H01L2224/42, H01L2224/50, H01L2224/63, H01L2224/71
    • H01L2224/732—Location after the connecting process
    • H01L2224/73251—Location after the connecting process on different surfaces
    • H01L2224/73265—Layer and wire connectors
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
    • H01L23/31—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape
    • H01L23/3107—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape the device being completely enclosed
    • H01L23/3114—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape the device being completely enclosed the device being a chip scale package, e.g. CSP
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
    • H01L23/31—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape
    • H01L23/3107—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape the device being completely enclosed
    • H01L23/3121—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape the device being completely enclosed a substrate forming part of the encapsulation
    • H01L23/3128—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape the device being completely enclosed a substrate forming part of the encapsulation the substrate having spherical bumps for external connection
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L24/00—Arrangements for connecting or disconnecting semiconductor or solid-state bodies; Methods or apparatus related thereto
    • H01L24/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L24/42—Wire connectors; Manufacturing methods related thereto
    • H01L24/47—Structure, shape, material or disposition of the wire connectors after the connecting process
    • H01L24/48—Structure, shape, material or disposition of the wire connectors after the connecting process of an individual wire connector
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L24/00—Arrangements for connecting or disconnecting semiconductor or solid-state bodies; Methods or apparatus related thereto
    • H01L24/73—Means for bonding being of different types provided for in two or more of groups H01L24/10, H01L24/18, H01L24/26, H01L24/34, H01L24/42, H01L24/50, H01L24/63, H01L24/71
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/0001—Technical content checked by a classifier
    • H01L2924/00014—Technical content checked by a classifier the subject-matter covered by the group, the symbol of which is combined with the symbol of this group, being disclosed without further technical details
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/01—Chemical elements
    • H01L2924/01004—Beryllium [Be]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/01—Chemical elements
    • H01L2924/01012—Magnesium [Mg]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/01—Chemical elements
    • H01L2924/01019—Potassium [K]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/01—Chemical elements
    • H01L2924/0102—Calcium [Ca]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/01—Chemical elements
    • H01L2924/01046—Palladium [Pd]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/01—Chemical elements
    • H01L2924/01057—Lanthanum [La]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/01—Chemical elements
    • H01L2924/01077—Iridium [Ir]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/01—Chemical elements
    • H01L2924/01078—Platinum [Pt]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/01—Chemical elements
    • H01L2924/01079—Gold [Au]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/10—Details of semiconductor or other solid state devices to be connected
    • H01L2924/11—Device type
    • H01L2924/12—Passive devices, e.g. 2 terminal devices
    • H01L2924/1204—Optical Diode
    • H01L2924/12044—OLED
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/15—Details of package parts other than the semiconductor or other solid state devices to be connected
    • H01L2924/151—Die mounting substrate
    • H01L2924/153—Connection portion
    • H01L2924/1531—Connection portion the connection portion being formed only on the surface of the substrate opposite to the die mounting surface
    • H01L2924/15311—Connection portion the connection portion being formed only on the surface of the substrate opposite to the die mounting surface being a ball array, e.g. BGA
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/15—Details of package parts other than the semiconductor or other solid state devices to be connected
    • H01L2924/181—Encapsulation
    • 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

  • This invention relates to curable silicone compositions and silicones formed by curing the curable silicone compositions. More particularly, this invention relates to hydrosilylation-curable compositions having improved resistance to Bleed. The curable silicone compositions cure to form products having improved chemical resistance and resistance to Bleed.
  • Polyorganosiloxane elastomers such as polydimethylsiloxane-based elastomers, are frequently used in the electronics industry for properties such as their thermal stability and ability to relieve stresses over a broad thermal range.
  • these polyorganosiloxane elastomers may suffer from the drawback of poor resistance to some organic chemicals, such as solvents and engine oils.
  • Fluorosilicone elastomers and organic elastomers have been used to improve chemical resistance.
  • fluorosilicone elastomers suffer from the drawback of having higher cost than polyorganosiloxane elastomers (that are non-fluorinated).
  • One proposed approach to address this is to combine fluorosilicone elastomers with polyorganosiloxane elastomers.
  • proposed approach has generally not been used due to concerns that the fluorosilicone and non-fluorinated organosilicone components would phase separate, resulting in unstable properties.
  • Silicone compositions that cure to form elastomers may also suffer from the drawback of poor resistance to Bleed.
  • Bleed can be problematic in applications in which the composition is applied to a portion of a substrate before curing.
  • the species that Bleed (out of the silicone composition) may contaminate the substrate. This tends to be particularly problematic for adhesives, such as die attach adhesives used in electronics applications, because the addition of adhesion promoters to hydrosilylation-reaction curable polyorganosiloxane elastomer compositions has been found to increase Bleed.
  • Organic elastomers may suffer from the drawback of having insufficient flexibility or bulk thermal properties. Therefore, there is a need in the electronics industry for curable silicone compositions having improved resistance to Bleed, where the curable silicone compositions cure to form elastomers having improved chemical resistance and resistance to Bleed, while retaining flexibility and bulk thermal properties.
  • This invention relates to a composition prepared by mixing components comprising:
  • Component (I) is free of fluorine atoms.
  • Component (II) is free of fluorine atoms.
  • Component (IV) has at least one functional group reactive with component (I), component (II), or both. When component (II) is not present, the component (IV) has an average of at least two silicon-bonded hydrogen atoms per molecule. Components (IV) and (V) are present in amounts sufficient to improve resistance to Bleed.
  • “Bleed” means an undesirable tendency for species to move across the interface of a silicone composition or cured product thereof. Bleed includes movement of species out of the silicone composition, or cured product thereof, onto, for example, a substrate on which the silicone composition, or cured product thereof, is applied. Bleed further includes movement of species into the silicone composition, or cured product thereof, from outside of the silicone composition, or cured product thereof.
  • Silicone resistance means reduced tendency of a silicone to swell, or degrade, or both, when exposed to solvents and oils.
  • centipoise centipoise
  • IR infrared
  • “Migration” means the tendency of fluorine-containing species to move toward the interface of a silicone composition or a cured product thereof, without crossing the interface, thereby enriching the content of fluorine-containing species at the interface as compared to the bulk.
  • mm means millimeters.
  • Pascal seconds Pascal seconds
  • This invention relates to a composition prepared by mixing components comprising:
  • Component (I) is a polyorganosiloxane having an average of at least two unsaturated organic groups per molecule.
  • Component (I) may have a linear, branched, or resinous structure.
  • Component (I) may be a homopolymer or a copolymer.
  • the unsaturated organic groups may be alkenyl groups having from 2 to 12 carbon atoms and are exemplified by, but not limited to, vinyl, allyl, butenyl, and hexenyl.
  • the unsaturated organic groups may be alkynyl groups having 2 to 12 carbon atoms, and are exemplified by, but not limited to, ethynyl, propynyl, and butynyl.
  • the unsaturated organic groups may contain acrylate-functional or methacrylate-functional groups and are exemplified by, but not limited to, acryloyloxyalkyl such as acryloyloxypropyl and methacryloyloxyalkyl such as methacryloyloxypropyl.
  • the unsaturated organic groups in component (I) may be located at terminal, pendant, or both terminal and pendant positions.
  • the remaining silicon-bonded organic groups in component (I) may be monovalent organic groups free of aliphatic unsaturation. These monovalent organic groups may have 1 to 20 carbon atoms, alternatively 1 to 10 carbon atoms, and are exemplified by, but not limited to alkyl such as methyl, ethyl, propyl, pentyl, octyl, undecyl, and octadecyl; cycloalkyl such as cyclohexyl; aryl such as phenyl, tolyl, xylyl, benzyl, and 2-phenylethyl; and cyano-functional groups such as cyanoalkyl groups exemplified by cyanoethyl and cyanopropyl.
  • Component (I) is free of fluorine atoms.
  • component (I) is not specifically restricted, however, component (I) may have a viscosity of 0.05 to 500 Pa ⁇ s at 25° C., alternatively 0.1 to 200 Pa ⁇ s at 25° C. Component (I) is added to the composition in an amount of 100 weight parts.
  • Component (I) may comprise a polyorganosiloxane of the formula
  • ⁇ has an average value of 0 to 2000, and ⁇ has an average value of 2 to 2000.
  • Each R 1 is independently a monovalent organic group. Suitable monovalent organic groups include, but are not limited to, acrylic functional groups such as acryloyloxypropyl and methacryloyloxypropyl; alkyl groups such as methyl, ethyl, propyl, and butyl; alkenyl groups such as vinyl, allyl, and butenyl; alkynyl groups such as ethynyl and propynyl; aromatic groups such as phenyl, tolyl, and xylyl; and cyanoalkyl groups such as cyanoethyl and cyanopropyl.
  • R 2 is independently an unsaturated monovalent organic group.
  • R 2 is exemplified by alkenyl groups such as vinyl, allyl, and butenyl and alkynyl groups such as ethynyl and propynyl, and acrylic functional groups such as acryloyloxypropyl and methacryloyloxypropyl.
  • ⁇ has an average value of 0 to 2000
  • ⁇ has an average value of 0 to 2000
  • Each R 3 is independently a monovalent organic group.
  • Suitable monovalent organic groups include, but are not limited to, acrylic functional groups such as acryloyloxypropyl and methacryloyloxypropyl; alkyl groups such as methyl, ethyl, propyl, and butyl; alkenyl groups such as vinyl, allyl, and butenyl; alkynyl groups such as ethynyl and propynyl; aromatic groups such as phenyl, tolyl, and xylyl; and cyanoalkyl groups such as cyanoethyl and cyanopropyl.
  • R 4 is independently an unsaturated organic hydrocarbon group.
  • R 4 is exemplified by alkenyl groups such as vinyl, allyl, and butenyl; alkynyl groups such as ethynyl and propynyl; and acrylic functional groups such as acryloyloxypropyl and methacryloyloxypropyl.
  • Component (I) may comprise polydiorganosiloxanes such as
  • component (I) Methods of preparing polydiorganosiloxanes suitable for use as component (I), such as hydrolysis and condensation of the corresponding organohalosilanes or equilibration of cyclic polydiorganosiloxanes, are well known in the art.
  • Component (I) may comprise resins such as an MQ resin consisting essentially of R 5 3 SiO 1/2 units and SiO 4/2 units, a TD resin consisting essentially of R 5 SiO 3/2 units and R 5 2 SiO 2/2 units, an MT resin consisting essentially of R 5 3 SiO 1/2 units and R 5 SiO 3/2 units, an MTD resin consisting essentially of R 5 3 SiO 1/2 units, R 5 SiO 3/2 units, and R 5 2 SiO 2/2 units, or a combination thereof.
  • resins such as an MQ resin consisting essentially of R 5 3 SiO 1/2 units and SiO 4/2 units, a TD resin consisting essentially of R 5 SiO 3/2 units and R 5 2 SiO 2/2 units, an MT resin consisting essentially of R 5 3 SiO 1/2 units and R 5 SiO 3/2 units, an MTD resin consisting essentially of R 5 3 SiO 1/2 units, R 5 SiO 3/2 units, and R 5 2 SiO 2/2 units, or a combination thereof.
  • Each R 5 is a monovalent organic group.
  • the monovalent organic groups represented by R 5 may have 1 to 20 carbon atoms, alternatively 1 to 10 carbon atoms.
  • Examples of monovalent organic groups include, but are not limited to, acrylate functional groups such as acryloxyalkyl groups, methacrylate functional groups such as methacryloxyalkyl groups, cyano-functional groups, and monovalent hydrocarbon groups.
  • Monovalent hydrocarbon groups include, but are not limited to, alkyl such as methyl, ethyl, propyl, pentyl, octyl, undecyl, and octadecyl; cycloalkyl such as cyclohexyl; alkenyl such as vinyl, allyl, butenyl, and hexenyl; alkynyl such as ethynyl, propynyl, and butynyl; and aryl such as phenyl, tolyl, xylyl, benzyl, and 2-phenylethyl.
  • Cyano-functional groups include, but are not limited to cyanoalkyl groups such as cyanoethyl and cyanopropyl.
  • the resin may contain an average of 3 to 30 mole percent of unsaturated organic groups.
  • the unsaturated organic groups may be alkenyl groups, alkynyl groups, acrylate-functional groups, methacrylate-functional groups, or combinations thereof.
  • the mole percent of unsaturated organic groups in the resin is the ratio of the number of moles of unsaturated group-containing siloxane units in the resin to the total number of moles of siloxane units in the resin, multiplied by 100.
  • resin may be prepared by treating a resin copolymer produced by the silica hydrosol capping process of Daudt et al. with at least an alkenyl-containing endblocking reagent.
  • the method of Daudt et al. is disclosed in U.S. Pat. No. 2,676,182.
  • the method of Daudt et al. involves reacting a silica hydrosol under acidic conditions with a hydrolyzable triorganosilane such as trimethylchlorosilane, a siloxane such as hexamethyldisiloxane, or mixtures thereof, and recovering a copolymer having M and Q units.
  • a hydrolyzable triorganosilane such as trimethylchlorosilane, a siloxane such as hexamethyldisiloxane, or mixtures thereof.
  • the resulting copolymers generally contain from 2 to 5 percent by weight of hydroxyl groups.
  • the resin which typically contains less than 2 percent by weight of silicon-bonded hydroxyl groups, may be prepared by reacting the product of Daudt et al. with an unsaturated organic group-containing endblocking agent and an endblocking agent free of aliphatic unsaturation, in an amount sufficient to provide from 3 to 30 mole percent of unsaturated organic groups in the final product.
  • endblocking agents include, but are not limited to, silazanes, siloxanes, and silanes. Suitable endblocking agents are known in the art and exemplified in U.S. Pat. Nos. 4,584,355; 4,591,622; and 4,585,836. A single endblocking agent or a mixture of such agents may be used to prepare the resin.
  • Component (I) can be a single polyorganosiloxane or a combination comprising two or more polyorganosiloxanes that differ in at least one of the following properties: structure, viscosity, average molecular weight, siloxane units, and sequence.
  • Component (II) is an organohydrogenpolysiloxane having an average of at least two silicon-bonded hydrogen atoms per molecule.
  • Component (II) can be can be a homopolymer or a copolymer.
  • Component (II) can have a linear, branched, cyclic, or resinous structure.
  • the silicon-bonded hydrogen atoms in the component (II) can be located at terminal, pendant, or at both terminal and pendant positions.
  • Component (II) is free of fluorine atoms.
  • Component (II) can comprise siloxane units including, but not limited to, HR 6 2 SiO 1/2 , R 6 3 SiO 1/2 , HR 6 SiO 2/2 , R 6 2 SiO 2/2 , R 6 SiO 3/2 , and SiO 4/2 units.
  • each R 6 is independently selected from monovalent organic groups free of aliphatic unsaturation.
  • Component (II) may comprise a compound of the formula
  • ⁇ has an average value of 0 to 2000, and ⁇ has an average value of 2 to 2000.
  • Each R 7 is independently a monovalent organic group free of aliphatic unsaturation. Suitable monovalent organic groups free of aliphatic unsaturation include alkyl groups such as methyl, ethyl, propyl, and butyl; aromatic groups such as phenyl, tolyl, and xylyl; and cyano-functional groups exemplified by cyanoalkyl groups such as cyanoethyl and cyanopropyl.
  • ⁇ has an average value of 0 to 2000
  • ⁇ has an average value of 0 to 2000
  • Each R 8 is independently a monovalent organic group free of aliphatic unsaturation. Suitable monovalent organic groups free of aliphatic unsaturation include alkyl groups such as methyl, ethyl, propyl, and butyl; aromatic groups such as phenyl, tolyl, and xylyl; and cyano-functional groups exemplified by cyanoalkyl groups such as cyanoethyl and cyanopropyl.
  • Component (II) is exemplified by
  • Component (II) can be a combination of two or more organohydrogenpolysiloxanes that differ in at least one of the following properties: structure, average molecular weight, viscosity, siloxane units, and sequence.
  • organohydrogenpolysiloxanes suitable for use as component (II) such as hydrolysis and condensation of organohalosilanes, are well known in the art.
  • Methods of preparing organohydrogenpolysiloxane resins suitable for use as component (II) are also well known as exemplified in U.S. Pat. Nos. 5,310,843; 4,370,358; and 4,707,531.
  • the molar ratio of silicon-bonded hydrogen atoms in component (II) to aliphatically unsaturated groups in component (I) is not critical.
  • Component (III) is a hydrosilylation catalyst.
  • Component (III) is added to the composition in an amount of 0.1 to 1000 ppm of platinum group metal, alternatively 1 to 500 ppm, alternatively 2 to 200, alternatively 5 to 150 ppm, based on the weight of the composition.
  • Suitable hydrosilylation catalysts are known in the art and commercially available.
  • Component (III) may comprise a platinum group metal selected from platinum, rhodium, ruthenium, palladium, osmium or iridium metal or organometallic compound thereof, or a combination thereof.
  • Component (III) is exemplified by compounds such as chloroplatinic acid, chloroplatinic acid hexahydrate, platinum dichloride, and complexes of said compounds with low molecular weight organopolysiloxanes or platinum compounds microencapsulated in a matrix or coreshell type structure.
  • Complexes of platinum with low molecular weight organopolysiloxanes include 1,3-diethenyl-1,1,3,3-tetramethyldisiloxane complexes with platinum. These complexes may be microencapsulated in a resin matrix.
  • Suitable hydrosilylation catalysts for component (III) are described in, for example, U.S. Pat. Nos. 3,159,601; 3,220,972; 3,296,291; 3,419,593; 3,516,946; 3,814,730; 3,989,668; 4,784,879; 5,036,117; and 5,175,325 and EP 0 347 895 B.
  • Microencapsulated hydrosilylation catalysts and methods of preparing them are known in the art, as exemplified in U.S. Pat. No. 4,766,176 and the references cited therein; and U.S. Pat. No. 5,017,654.
  • Component (IV) is a fluoroorganosilicone having at least one functional group reactive with component (I), component (II), or both. When component (II) is not present in the composition, the component (IV) has an average of at least two silicon-bonded hydrogen atoms per molecule.
  • the viscosity of component (IV) is not specifically restricted, however, component (IV) may have a viscosity of 0.0001 to 500 Pa ⁇ s at 25° C.
  • Component (IV) may comprise a compound of the formula:
  • ⁇ has an average value of 0 to 2000, and ⁇ has an average value of 1 to 500.
  • Each R 9 is independently a hydrogen atom or a monovalent organic group.
  • Suitable monovalent organic groups include monovalent hydrocarbon groups that are free of aliphatic unsaturation such as alkyl groups such as methyl, ethyl, propyl, and butyl; aromatic groups such as phenyl, tolyl, and xylyl; and cyano-functional groups exemplified by cyanoalkyl groups such as cyanoethyl and cyanopropyl.
  • Suitable monovalent organic groups also include unsaturated monovalent organic groups exemplified by acrylate functional groups; methacrylate functional groups; alkenyl groups such as vinyl, allyl, and butenyl; and alkynyl groups such as ethynyl, propynyl, and butynyl.
  • at least one R 9 is a hydrogen atom or an unsaturated monovalent organic group.
  • Each R 10 is independently a fluoro-functional organic group.
  • Suitable fluoro-functional organic groups include, but are not limited to, fluorinated alkyl groups such as 3,3,3-trifluoropropyl, 4,4,4,3,3-pentafluorobutyl, 5,5,5,4,4,3,3-heptafluoropentyl, and 6,6,6,5,5,4,4,3,3-nonafluorohexyl.
  • ⁇ has an average value of 0 to 2000, and ⁇ has an average value of 0 to 500.
  • Each R 11 is independently a hydrogen atom or a monovalent organic group.
  • Suitable monovalent organic groups include cyano-functional groups exemplified by cyanoalkyl groups such as cyanoethyl and cyanopropyl; and monovalent hydrocarbon groups free of aliphatic unsaturation, exemplified by alkyl groups such as methyl, ethyl, propyl, and butyl; and aromatic groups such as phenyl, tolyl, and xylyl.
  • Suitable monovalent organic groups also include unsaturated monovalent organic groups exemplified by acrylate functional groups; methacrylate functional groups; alkenyl groups such as vinyl, allyl, and butenyl; and alkynyl groups such as ethynyl, propynyl, and butynyl.
  • at least one R 11 is a hydrogen atom or an unsaturated monovalent organic group.
  • Each R 12 is independently a fluoro-functional organic group.
  • Suitable fluoro-functional organic groups include fluorinated alkyl groups such as 3,3,3-trifluoropropyl, 4,4,4,3,3-pentafluorobutyl, 5,5,5,4,4,3,3-heptafluoropentyl, and 6,6,6,5,5,4,4,3,3-nonafluorohexyl.
  • Each R 13 is independently a divalent organic group such as a divalent hydrocarbon group. Suitable divalent organic groups for R 13 may have at least 2 carbon atoms, alternatively, 2 to 20 carbon atoms, alternatively 2 to 10 carbon atoms. Examples of suitable divalent hydrocarbon groups for R 13 include alkylene groups such as methylene, ethylene, propylene, and butylene. Each R 14 is independently a monovalent hydrocarbon group free of aliphatic unsaturation.
  • R 14 is exemplified by alkyl such as methyl, ethyl, propyl, pentyl, octyl, undecyl, and octadecyl; cycloalkyl such as cyclohexyl; and aryl such as phenyl, tolyl, xylyl, benzyl, and 2-phenylethyl.
  • Each R 15 is independently a hydrogen atom or an aliphatically unsaturated hydrocarbon group exemplified by alkenyl such as vinyl, allyl, butenyl, and hexenyl; and alkynyl such as ethynyl, propynyl, and butynyl.
  • R 15 is an aliphatically unsaturated hydrocarbon group, then all R 15 in the molecule may be the same or different aliphatically unsaturated hydrocarbon group. If one R 15 in a molecule is a hydrogen atom, then all R 15 may be hydrogen atoms.
  • Component (IV) is exemplified by
  • Component (IV) is added to the composition in an amount sufficient to provide resistance to Bleed and chemical resistance to a cured silicone prepare by curing the composition.
  • Component (IV) may be added to the composition an amount of 0.01 to 100 parts by weight based on the weight of component (I). Without wishing to be bound by theory, it is thought that the halogenated portion of component (IV) migrates to the surface of the composition when cured. It is thought that sufficient chemical resistance and resistance to Bleed for many applications can be obtained without adding a higher amount of component (IV), which would dramatically increase the cost of the composition.
  • Component (IV) can be a combination of two or more fluoroorganosilicones that differ in at least one of the following properties: structure, average molecular weight, viscosity, siloxane units, and sequence.
  • Fluoroorganosilicones suitable for use as component (IV) are known in the art. Fluoroorganosilicones may be prepared by those methods disclosed above for components (I) and (II), by varying appropriate starting materials. One skilled in the art would be able to manufacture suitable fluoroorganosilicones for component (IV) without undue experimentation.
  • Component (V) is an adhesion promoter.
  • Component (V) is added to the composition in an amount sufficient to impart adhesion to a cured silicone prepared by curing the composition.
  • Component (IV) and component (V) are added to the composition in combination in amounts sufficient to provide resistance to Bleed to a cured silicone prepared by curing the composition.
  • Component (V) may be added to the composition in an amount of 0.01 to 50 weight parts based on the weight of the composition, alternatively 0.05 to 2 weight parts, alternatively 0.5 to 1.5 weight parts.
  • Component (V) may comprise a transition metal chelate, an alkoxysilane, a combination of an alkoxysilane and a hydroxy-functional polyorganosiloxane, or a combination thereof.
  • Component (V) can be an unsaturated or epoxy-functional compound. Suitable epoxy-functional compounds are known in the art and commercially available, see for example, U.S. Pat. Nos. 4,087,585; 5,194,649; 5,248,715; and 5,744,507 col. 4-5.
  • Component (VI) may comprise an unsaturated or epoxy-functional alkoxysilane.
  • the functional alkoxysilane can have the formula R 28 ⁇ Si(OR 29 ) (4- ⁇ ) , where ⁇ is 1, 2, or 3, alternatively ⁇ is 1.
  • Each R 28 is independently a monovalent organic group with the proviso that at least one R 28 is an unsaturated organic group or an epoxy-functional organic group.
  • Epoxy-functional organic groups for R 28 are exemplified by 3-glycidoxypropyl and (epoxycyclohexyl)ethyl.
  • Unsaturated organic groups for R 28 are exemplified by 3-methacryloyloxypropyl, 3-acryloyloxypropyl, and unsaturated monovalent hydrocarbon groups such as vinyl, allyl, hexenyl, undecylenyl.
  • Each R 29 is independently an unsubstituted, saturated hydrocarbon group of at least 1 carbon atom.
  • R 29 may have up to 4 carbon atoms, alternatively up to 2 carbon atoms.
  • R 29 is exemplified by methyl, ethyl, propyl, and butyl.
  • suitable epoxy-functional alkoxysilanes include 3-glycidoxypropyltrimethoxysilane, 3 -glycidoxypropyltriethoxysilane, (epoxycyclohexyl)ethyldimethoxysilane, (epoxycyclohexyl)ethyldiethoxysilane and combinations thereof.
  • Suitable unsaturated alkoxysilanes include vinyltrimethoxysilane, allyltrimethoxysilane, allyltriethoxysilane, hexenyltrimethoxysilane, undecylenyltrimethoxysilane, 3-methacryloyloxypropyl trimethoxysilane, 3-methacryloyloxypropyl triethoxysilane, 3-acryloyloxypropyl trimethoxysilane, 3-acryloyloxypropyl triethoxysilane, and combinations thereof.
  • Component (V) may comprise an epoxy-functional siloxane such as a reaction product of a hydroxy-terminated polyorganosiloxane with an epoxy-functional alkoxysilane, as described above, or a physical blend of the hydroxy-terminated polyorganosiloxane with the epoxy-functional alkoxysilane.
  • Component (V) may comprise a combination of an epoxy-functional alkoxysilane and an epoxy-functional siloxane.
  • component (V) is exemplified by a mixture of 3-glycidoxypropyltrimethoxysilane and a reaction product of hydroxy-terminated methylvinylsiloxane with 3-glycidoxypropyltrimethoxysilane, or a mixture of 3-glycidoxypropyltrimethoxysilane and a hydroxy-terminated methylvinylsiloxane, or a mixture of 3-glycidoxypropyltrimethoxysilane and a hydroxy-terminated methyvinyl/dimethylsiloxane copolymer.
  • these components may be stored separately in multiple-part kits.
  • Suitable transition metal chelates include titanates, zirconates such as zirconium acetylacetonate, aluminum chelates such as aluminum acetylacetonate, and combinations thereof. Transition metal chelates and methods for their preparation are known in the art, see for example, U.S. Pat. No. 5,248,715, EP 0 493 791 A1, and EP 0 497 349 B1.
  • An optional component may be added to the composition in addition to components (I)-(V).
  • Suitable optional components include (VI) an unsaturated ester-functional compound, (VII) a void reducing agent, (VIII) a pigment, (IX) a filler, (X) a cure modifier, (XI) a rheology modifier, and combinations thereof.
  • Component (VI) is an unsaturated ester-functional compound, i.e., an organic compound having at least one ester group per molecule and at least one unsaturated group per molecule capable of undergoing hydrosilylation.
  • Component (VI) may comprise: vi) a combination thereof.
  • each R 16 is independently a hydrogen atom, a monovalent hydrocarbon group of 1 to 4 carbon atoms, or CF 3 .
  • monovalent hydrocarbon groups for R 16 include alkyl groups such as methyl, ethyl, propyl, and butyl.
  • Each R 17 is independently a hydrogen atom, a monovalent organic group, with the proviso that not all R 17 are hydrogen atoms, or a metal ion.
  • Examples of monovalent organic groups for R 17 include monovalent hydrocarbon groups, fluoroalkyl groups, epoxy functional groups, and polyether groups.
  • Examples of monovalent hydrocarbon groups include, but are not limited to, alkyl such as methyl, ethyl, propyl, pentyl, octyl, undecyl, dodecyl, and octadecyl; cycloalkyl such as cyclohexyl; alkenyl such as vinyl, allyl, butenyl, and hexenyl; alkynyl such as ethynyl, propynyl, and butynyl; and aryl such as phenyl, tolyl, xylyl, benzyl, and 2-phenylethyl.
  • Examples of epoxy-functional groups for R 17 include 3-glycidoxypropyl.
  • fluoroalkyl groups for R 17 include but are not limited to —(CH 2 ) x (CF 2 ) y CF 3 where x has an average value of 0 to 20 and y has an average value of 0 to 20, branched fluoroalkyl groups such as perfluoro t-butyl, and cyclic fluoroalkyl groups such as perfluorocyclohexyl, and fluoroaryl groups such as perfluorophenyl.
  • polyether groups for R 17 include, but are not limited to, —(CH 2 CH 2 O) z CH 2 CH 3 , —(CH(CH 3 )CH 2 O) z CH(CH 3 )CH 3 , —(CH2CH 2 O) z CH 2 CH ⁇ CH 2 , —(CH(CH 3 )CH 2 O) z CH 2 CH ⁇ CH 2 , —(CH 2 CH 2 CH 2 CH 2 O) z CH 2 CH 3 , —(CH 2 CH 2 CH 2 O) z CH ⁇ CH 2 , —(CH 2 CH 2 O) z CH 2 CH 2 OH, —(CH(CH 3 )CH 2 O) z CH(CH 3 )CH 2 —OH, —(CH 2 CH 2 O) z CH 2 CH 2 OCH 3 , and —(CH(CH 3 )CH 2 O) z CH(CH 3 )CH 2 —OCH 3 where z has an average value of 1 to 20, and cyclic ethers such
  • fluoropolyether groups for R 17 include, but are not limited to, —(CF 2 —CF 2 —O) z H, —(CF(CF 3 )CF 2 O) z H, —(CF 2 CF 2 O) z CF 3 , —(CF(CF 3 )CF 2 O) z CF 3 , where z is as defined above, —(CH 2 ) i (CF(CF 3 )) j —(O—CF(CF 3 ) k —F where i has an average value of 0 to 10, j has an average value of 0 to 10 and k has an average value of 1 to 20.
  • metal ions for R 17 include, but are not limited to, positive ions such as Zn, Al, Ca, Na, Mg and K.
  • each R 18 is independently a hydrogen atom, a monovalent hydrocarbon group of 1 to 4 carbon atoms, or CF 3 .
  • monovalent hydrocarbon groups for R 18 include alkyl such as methyl, ethyl, propyl, and butyl.
  • Each R 19 is independently a divalent organic group of 1 to 20 carbon atoms.
  • Examples of divalent organic groups for R 19 include, but are not limited to, alkylene such as methylene, ethylene, propylene, pentylene, neo-pentylene, octylene, undecylene, and octadecylene; cycloalkylene such as cylcohexylene; alkenylene such as vinylene, allylene, butenylene, and hexenylene; alkynylene such as ethynylene, propynylene, and butynylene; arylene such as phenylene, tolylene, xylylene, benzylene, and 2-phenylethylene; ether diol derivatives such as —(CH 2 CH 2 O) z —CH 2 CH 2 — and —(CH(CH 3 )CH 2 O) z —CH(CH 3 )CH 2 where z is as defined above for R 19 ; alkylene/arylene combinations such as 4,4′
  • Examples of divalent fluorinated organic groups for R 19 include, but are not limited to, —(CH 2 ) x (CH(F)) y (CF 2 ) z —, —(CF 2 CF 2 O) z —, —(CF(CF 3 )CF 2 O) z — where x, y, and z are as defined above, perfluorocyclohexyl-1,4-dimethyl, and 4,4′-hexafluoroisopropylidene diphenyl (derived from hexafluoro Bisphenol “A”).
  • Each R 20 is independently a hydrogen atom or a monovalent hydrocarbon group of 1 to 20 carbon atoms.
  • Examples of monovalent hydrocarbon groups for R 20 include, but are not limited to, alkyl such as methyl, ethyl, propyl, pentyl, octyl, undecyl, and octadecyl; cycloalkyl such as cyclohexyl; alkenyl such as vinyl, allyl, butenyl, and hexenyl; alkynyl such as ethynyl, propynyl, and butynyl; and aryl such as phenyl, tolyl, xylyl, benzyl, and 2-phenylethyl.
  • alkyl such as methyl, ethyl, propyl, pentyl, octyl, undecyl, and octadecyl
  • cycloalkyl such as cyclohexyl
  • alkenyl such as vinyl, allyl, butenyl, and he
  • Each R 21 is independently a hydrogen atom, a monovalent hydrocarbon group of 1 to 20 carbon atoms, a hydroxyl group, or CF 3 .
  • Examples of monovalent hydrocarbon groups for R 21 include, but are not limited to, alkyl such as methyl, ethyl, propyl, pentyl, octyl, undecyl, and octadecyl; cycloalkyl such as cyclohexyl; alkenyl such as vinyl, allyl, butenyl, and hexenyl; alkynyl such as ethynyl, propynyl, and butynyl; and aryl such as phenyl, tolyl, xylyl, benzyl, and 2-phenylethyl.
  • alkyl such as methyl, ethyl, propyl, pentyl, octyl, undecyl, and octadecyl
  • cycloalkyl such as cyclohexyl
  • alkenyl such as vinyl, allyl, butenyl, and he
  • Each R 22 is independently a hydrogen atom, a monovalent hydrocarbon group of 1 to 4 carbon atoms, or CF 3 .
  • monovalent hydrocarbon groups for R 22 include, but are not limited to, alkyl such as methyl, ethyl, propyl, pentyl, octyl, undecyl, and octadecyl; cycloalkyl such as cyclohexyl; alkenyl such as vinyl, allyl, butenyl, and hexenyl; alkynyl such as ethynyl, propynyl, and butynyl; and aryl such as phenyl, tolyl, xylyl, benzyl, and 2-phenylethyl.
  • Each R 23 is independently a hydrogen atom or a monovalent hydrocarbon group of 1 to 20 carbon atoms.
  • monovalent hydrocarbon groups for R 23 include, but are not limited to, alkyl such as methyl, ethyl, propyl, pentyl, octyl, undecyl, and octadecyl; cycloalkyl such as cyclohexyl; alkenyl such as vinyl, allyl, butenyl, and hexenyl; alkynyl such as ethynyl, propynyl, and butynyl; and aryl such as phenyl, tolyl, xylyl, benzyl, and 2-phenylethyl.
  • each R 24 and each R 25 are independently a monovalent organic group or a hydrogen atom with the proviso that at least one of R 24 or R 25 is unsaturated.
  • monovalent organic groups for R 24 include monovalent hydrocarbon groups, fluoroalkyl groups, epoxy functional groups, and polyether groups, all exemplified by those listed for R 17 .
  • Examples of monovalent organic groups for R 25 include monovalent hydrocarbon groups, fluoroalkyl groups, epoxy functional groups, and polyether groups, all exemplified, but not limited, by those listed for R 17 . Additional examples of monovalent organic groups for R 25 include oxygen-bridged monovalent organic groups such as —O—C(O)O—(CH 2 ) o CH ⁇ CH 2 where o has an average value of 0 to 20 and carbon-bridged carbonyl groups such as —CH 2 —C(O)—CH 3 .
  • each R 26 is independently a monovalent organic group or a hydrogen atom, with the proviso that at least one R 26 is an aliphatically unsaturated monovalent organic group or a hydrogen atom.
  • monovalent organic groups for R 26 include monovalent hydrocarbon groups, fluoroalkyl groups, epoxy functional groups, and polyether groups, all exemplified by those listed for R 17 .
  • Each R 27 is independently an oxygen atom or a divalent organic group.
  • divalent organic groups for R 27 include divalent hydrocarbon groups, fluoroalkylene groups, epoxy functional groups, and polyether functional groups, all exemplified, but not limited, by those listed for R 19 .
  • Component (VI) is exemplified by 2-ethylhexylacrylate, 2-ethylhexylmethacrylate, methylacrylate, methylmethacrylate, neopentylglycol diacrylate, neopentylglycoldimethacrylate, glycidyl acrylate, glycidyl methacrylate, allyl acrylate, allyl methacrylate strearyl acrylate, tetrahydrofurfuryl methacrylate, caprolactone acrylate perfluorobutyl acrylate, perfluorobutyl methacrylate, tetrahydroperfluoroacrylate, phenoxyethyl acrylate, phenoxyethyl methacrylate, Bisphenol “A” acrylate, Bisphenol “A” dimethacrylate, ethoxylated Bisphenol “A” acrylate, ethoxylated Bisphenol “A” methacryl
  • Component (VI) is added to the composition in an amount of 0.01 to 50 weight parts based on the weight of the composition. Without wishing to be bound by theory, it is thought that component (VI) improves both chemical resistance and the adhesive property of the cured product of the composition.
  • Unsaturated ester-functional compounds suitable for component (VI) are known in the art and commercially available from, for example, Sartomer Company and Aldrich Chemical Company. One skilled in the art would be able to obtain unsaturated ester-functional compounds without undue experimentation.
  • Component (VII) is a void reducing agent.
  • Component (VII) is added to the composition in an amount sufficient to reduce voids.
  • Suitable void reducing agents are known in the art and commercially available, see for example, EP 0 850 997 A2 and U.S. Pat. Nos. 4,273,902 and 5,684,060.
  • Suitable void reducing agents can comprise zeolites, anhydrous aluminum sulfate, molecular sieves (preferably with a pore diameter of 10 ⁇ or less), kieselguhr, silica gel, activated carbon, palladium compounds such as palladium metal, palladium metal supported on a substrate exemplified by carbon or alumina, and organopalladium compounds.
  • Component (VIII) is a pigment.
  • the amount of component (VIII) added to the composition depends on the type of pigment selected.
  • Component (VIII) may be added to the composition in an amount of 0.001% to 30% based on the weight of the composition.
  • Pigments are known in the art and commercially available. Suitable pigments include carbon blacks, such as LB-1011C carbon black from Williams, chromium oxide pigments, such as Harcros G-6099, titanium dioxides such as those available from DuPont, and UV-active dyes such as (thiophenediyl)bis(t-butylbenzoxazole) which is commercially available under the name UVITEX OB from Ciba Specialty Chemicals.
  • Component (IX) is a filler.
  • the amount of component (IX) added to the composition depends on the type of filler selected.
  • Component (IX) may be added to the composition in an amount of 0.1% to 90% based on the weight of the compositions.
  • Suitable fillers include reinforcing fillers such silica, titania, and combinations thereof. Suitable reinforcing fillers are known in the art and commercially available, such as a ground silica sold under the name MIN-U-SIL by U.S. Silica of Berkeley Springs, W. Va. or fumed silica sold under the name CAB-O-SIL by Cabot Corporation of Massachusetts.
  • Conductive fillers may also be used as component (IX).
  • Suitable conductive fillers include metal particles, metal oxide particles, and a combination thereof.
  • Suitable thermally conductive fillers are exemplified by aluminum nitride; aluminum oxide; barium titinate; beryllium oxide; boron nitride; diamond; graphite; magnesium oxide; metal particulate such as copper, gold, nickel, or silver; silicon carbide; tungsten carbide; zinc oxide, and a combination thereof.
  • Conductive fillers are known in the art and commercially available, see for example, U.S. Pat. No. 6,169,142 (col. 4, lines 7-33).
  • CB-A20S and Al-43-Me are aluminum oxide fillers of differing particle sizes commercially available from Showa-Denko, and AA-04, AA-2, and AA18 are aluminum oxide fillers commercially available from Sumitomo Chemical Company.
  • Silver filler is commercially available from Metalor Technologies U.S.A. Corp. of Attleboro, Mass., U.S.A. Boron nitride filler is commercially available from Advanced Ceramics Corporation, Cleveland, Ohio, U.S.A.
  • the shape of the conductive filler particles is not specifically restricted, however, rounded or spherical particles may prevent viscosity increase to an undesirable level upon high loading of the thermally conductive filler in the composition.
  • thermally conductive fillers having differing particle sizes and different particle size distributions may be used. For example, it may be desirable to combine a first conductive filler having a larger average particle size with a second conductive filler having a smaller average particle size in a proportion meeting the closest packing theory distribution curve. This improves packing efficiency and may reduce viscosity and enhance heat transfer.
  • the thermally conductive filler may optionally be surface treated with a treating agent. Treating agents and treating methods are known in the art, see for example, U.S. Pat. No. 6,169,142 (col. 4, line 42 to col. 5, line 2).
  • the thermally conductive filler may be treated with the treating agent prior to combining the thermally conductive filler with the other components of the composition, or the thermally conductive filler may be treated in situ.
  • the treating agent can be an alkoxysilane having the formula: R 30 p Si(OR 31 ) (4-p) , where p is 1, 2, or 3; alternatively p is 3.
  • R 30 is a substituted or unsubstituted monovalent hydrocarbon group of at least 1 carbon atom, alternatively at least 8 carbon atoms.
  • R 30 has up to 50 carbon atoms, alternatively up to 30 carbon atoms, alternatively up to 18 carbon atoms.
  • R 30 is exemplified by alkyl groups such as hexyl, octyl, dodecyl, tetradecyl, hexadecyl, and octadecyl; and aromatic groups such as benzyl, phenyl and phenylethyl.
  • R 30 can be saturated or unsaturated, branched or unbranched, and unsubstituted.
  • R 30 can be saturated, unbranched, and unsubstituted.
  • R 31 is an unsubstituted, saturated hydrocarbon group of at least 1 carbon atom.
  • R 31 may have up to 4 carbon atoms, alternatively up to 2 carbon atoms.
  • the treating agent is exemplified by hexyltrimethoxysilane, octyltriethoxysilane, decyltrimethoxysilane, dodecyltrimethyoxysilane, tetradecyltrimethoxysilane, phenyltrimethoxysilane, phenylethyltrimethoxysilane, octadecyltrimethoxysilane, octadecyltriethoxysilane, and a combination thereof.
  • Alkoxy-functional oligosiloxanes can also be used as treatment agents. Alkoxy-functional oligosiloxanes and methods for their preparation are known in the art, see for example, EP 1 101 167 A2.
  • suitable alkoxy-functional oligosiloxanes include those of the formula (R 32 O) d Si(OSiR 33 2 R 34 ) 4-d . In this formula, d is 1, 2, or 3, alternatively d is 3.
  • Each R 32 can be an alkyl group.
  • Each R 33 can be independently selected from saturated and unsaturated monovalent hydrocarbon groups of 1 to 10 carbon atoms.
  • Each R 34 can be a saturated or unsaturated monovalent hydrocarbon group having at least 11 carbon atoms.
  • Metal fillers can be treated with alkylthiols such as octadecyl mercaptan and others, and fatty acids such as oleic acid, stearic acid, titanates, titanate coupling agents, zirconate coupling agents, and a combination thereof.
  • alkylthiols such as octadecyl mercaptan and others
  • fatty acids such as oleic acid, stearic acid, titanates, titanate coupling agents, zirconate coupling agents, and a combination thereof.
  • Treatment agents for alumina or passivated aluminum nitride could include alkoxysilyl functional alkylmethyl polysiloxanes (e.g., partial hydrolysis condensate of R 35 b R 36 c Si(OR 37 ) (4-b-c) or cohydrolysis condensates or mixtures), similar materials where the hydrolyzable group would be silazane, acyloxy or oximo.
  • a group tethered to Si such as R 35 in the formula above, is a long chain unsaturated monovalent hydrocarbon or monovalent aromatic-functional hydrocarbon.
  • R 36 is a monovalent hydrocarbon group
  • R 37 is a monovalent hydrocarbon group of 1 to 4 carbon atoms.
  • b is 1, 2, or 3 and c is 0, 1, or 2, with the proviso that b+c is 1, 2, or 3.
  • One skilled in the art could optimize a specific treatment to aid dispersion of the filler without undue experimentation.
  • Component (X) is a cure modifier.
  • Component (X) can be added to extend the shelf life or working time, or both, of the composition of this invention.
  • Component (X) can be added to raise the curing temperature of the composition.
  • Suitable cure modifiers are known in the art and are commercially available.
  • Component (X) is exemplified by acetylenic alcohols such as methyl butynol, ethynyl cyclohexanol, dimethyl hexynol, and combinations thereof; cycloalkenylsiloxanes such as methylvinylcyclosiloxanes exemplified by 1,3,5,7-tetramethyl-1,3,5,7-tetravinylcyclotetrasiloxane, 1,3,5,7-tetramethyl-1,3,5,7-tetrahexenylcyclotetrasiloxane, and combinations thereof; ene-yne compounds such as 3-methyl-3-penten-1-yne, 3,5-dimethyl-3-hexen-1-yne; triazoles such as benzotriazole; phosphines; mercaptans; hydrazines; amines such as tetramethyl ethylenediamine, dialkyl fumarates, dialken
  • Suitable cure modifiers are disclosed by, for example, U.S. Pat. Nos. 3,445,420; 3,989,667; 4,584,361; and 5,036,117.
  • component (X) added to the composition will depend on the particular cure modifier used, the nature and amount of component (III), and the composition of component (II). However, the amount of component (X) may be 0.001% to 10% based on the weight of the composition.
  • Component (XI) is a rheology modifier. Rheology modifiers can be added to change the thixotropic properties of the composition.
  • Component (XI) is exemplified by flow control additives; reactive diluents; anti-settling agents; alpha-olefins; hydroxyl-terminated silicone-organic copolymers, including but not limited to hydroxyl-terminated polypropyleneoxide-dimethylsiloxane copolymers; and combinations thereof.
  • Component (XII) is a spacer.
  • Spacers can comprise organic particles, inorganic particles, or a combination thereof. Spacers can be thermally conductive, electrically conductive, or both. Spacers can have a particle size of 25 micrometers to 250 micrometers. Spacers can comprise monodisperse beads.
  • the amount of component (XII) depends on various factors including the distribution of particles, pressure to be applied during placement of the composition, temperature of placement, and others.
  • the composition can contain up to 15%, alternatively up to 5% of component (XII) added in addition to, or instead of, a portion of component (IX).
  • optional components may be added in addition to, or instead of, all or a portion of those described above, provided the optional component does not prevent the composition from curing to form a silicone product having improved chemical resistance, as described above.
  • optional components include, but are not limited to, acid acceptors; anti-oxidants; stabilizers such as magnesium oxide, calcium hydroxide, metal salt additives such as those disclosed in EP 0 950 685 A1, heat stabilizers, and ultra-violet (UV) stabilizers; flame retardants; silylating agents, such as 4-(trimethylsilyloxy)-3-penten-2-one and N-(t-butyl dimethylsilyl)-N-methyltrifluoroacetamide; desiccants, such as zeolites, anhydrous aluminum sulfate, molecular sieves (preferably with a pore diameter of 10 ⁇ or less), kieselguhr, silica gel, and activated carbon; and blowing agents, such as water, methanol, ethanol, iso
  • the components in the composition may be selected such that the molar ratio of the total amount of silicon-bonded hydrogen atoms to aliphatically unsaturated groups in the composition (SiH tot /Vi tot ) is at least 0.3, alternatively at least 0.5, alternatively at least 0.9, and alternatively at least 1.0.
  • SiH tot /Vi tot may be up to 5.0, alternatively up to 3.0, and alternatively up to 2.0. Without wishing to be bound by theory, it is thought that if SiH tot /Vi tot is too low, then the composition may not cure or may not adhere to some substrates.
  • the composition may be a one-part composition or a multiple-part composition such as a two-part composition.
  • components (II) and (III) are stored in separate parts. Any of components (I) and (IV)-(XII) can be added to either or both parts.
  • One skilled in the art would know how to select components for each part without undue experimentation.
  • kit When a multiple part composition is prepared, it may be marketed as a kit.
  • the kit may further comprise information or instructions or both as how to use the kit, how to combine the parts, or how to cure the resulting combination, or combinations thereof.
  • a kit comprising Part A and Part B can be prepared as follows.
  • Part A comprises:
  • Part A and Part B can be mixed together in a ratio of Part A:Part B (A:B) of 0.05:1 to 20:1, alternatively 0.1:1 to 10:1, alternatively 1:1 to 5:1.
  • compositions described above can be prepared by mixing the components by any convenient means.
  • the composition can be prepared by mixing all components at ambient temperature.
  • component (X) may be added before component (III).
  • the mixer used is not specifically restricted and will be determined by the viscosity of the components and the composition.
  • Suitable mixers include but are not limited to paddle type mixers, kneader type mixers, non-intrusive mixers such as those reliant on centrifugal motion, and two- and three-roll rubber mills.
  • paddle type mixers kneader type mixers
  • non-intrusive mixers such as those reliant on centrifugal motion
  • two- and three-roll rubber mills two- and three-roll rubber mills.
  • composition of this invention is useful for a range of applications where modified surface or interface properties, or both, are desired.
  • the compositions described above cure to form a part that can be used as an adhesive; protective coating for electronic circuitry, planar surfaces, fibers or small particles; or gasketing materials.
  • Exposed surfaces of the fully cured or partially cured products of this composition may also be useful as substrates for bonding by another adhesive or for secondary bonding to another substrate (as exemplified by a dry film adhesive).
  • the composition of this invention cures to form a cured silicone that can be used as an adhesive, such as a die attach adhesive for use in electronics applications.
  • the composition can be cured at ambient or elevated temperature.
  • the composition may be applied to a substrate before or during curing. Exposed surfaces of the fully cured or partially cured products of this invention may also be useful as a substrate for bonding by another adhesive.
  • Cured products prepared using the compositions of this invention can vary in properties from rigid resins to elastomers to gels, depending upon the types and concentrations of components (I) and (II) and any optional components that are added to the composition.
  • Cured products prepared using the compositons are useful in a variety of end-use applications, for example, as coatings or as molded or extruded articles.
  • the compositions can be applied to substrates by spraying, dipping, pouring, screen printing, extrusion or by the use of a brush, roller or coating bar. The selection of a particular application method will be determined at least in part by the viscosity of the curable composition.
  • Suitable substrates to which the composition, or cured product thereof, may be applied and which are useful in electronics applications include epoxies, polycarbonates, poly(butylene terephthalate) resins, polyamide resins and blends thereof, such as blends of polyamide resins with syndiotactic polystyrene such as those commercially available from the Dow Chemical Company, of Midland, Mich., U.S.A., acrylonitrile-butadiene-styrenes, styrene-modified poly(phenylene oxides), poly(phenylene sulfides), vinyl esters, polyphthalamides, polyimides, silicon, aluminum, stainless steel alloys, titanium, copper, nickel, silver, gold, and combinations thereof.
  • composition of this invention can be used, for adhering two surfaces, such as in lid seal applications.
  • the composition can be used for gluing a plastic lid onto a plastic housing for electronic circuitry in an assembly process by a method comprising:
  • composition can be used, for example, to coat an electronic circuit board, by method comprising:
  • composition can be used, for example, for die attach applications, in a method comprising:
  • the method may further comprise one or more optional steps such as (4) repeating steps (1) to (3) to attach one or more additional semiconductor dice to the semiconductor die, (5) wire bonding the semiconductor die or semiconductor dice, (6) cleaning, for example by exposure to plasma, (7) overmolding the semiconductor die or semiconductor dice with a molding compound, and (8) attaching solder balls to form a finished package.
  • the electronic substrate may be, for example, a circuit board, a TAB tape, or other substrate known in the art, or the electronic substrate may be a semiconductor die.
  • FIG. 1 shows an example of a package 100 prepared according to this method.
  • the package 100 includes a semiconductor die 101 bonded to a substrate 102 shown as a polyimide TAB tape flexible circuit through a die attach adhesive 103 prepared from the composition of this invention.
  • the semiconductor die 101 is electrically connected to the substrate 102 through lead bonds 104 .
  • the shapes of the lead bonds 104 are dependent on the height of the semiconductor die 101 from the substrate 102 .
  • Encapsulant 105 is used to protect the lead bonds 104 .
  • FIG. 1 also shows the solder balls 106 , which provide the connection mechanism to the substrate (not shown) on which the package 100 will be mounted.
  • composition of this invention may be printed or dispensed on the substrate 402 .
  • the semiconductor die 401 may then be placed with pressure and heat onto the composition to prepare the die attach adhesive 403 .
  • FIG. 2 shows an example of a package 200 prepared according to this method.
  • the package includes a first semiconductor die 201 stacked on top of a second semiconductor die 202 and attached through a first die attach adhesive 203 .
  • the second semiconductor die 202 is mounted to a substrate 204 shown in FIG. 2 as a circuit board through a second die attach adhesive 205 .
  • the first die attach adhesive 203 and the second die attach adhesive 205 are prepared by curing the composition of this invention.
  • the first die attach adhesive 203 and the second die attach adhesive 205 may be the same or different.
  • the package 200 may be assembled, for example, by applying a composition according to this invention to the substrate 204 .
  • the second semiconductor die 202 may be heated and placed onto the composition with enough pressure to spread the composition uniformly under the second semiconductor die 202 .
  • the heat of the die may partially or fully cure the composition to form the second die attach adhesive 205 .
  • a composition according to this invention may then be applied to the top of the second semiconductor die 202 and the first semiconductor die 201 may be applied hot to the composition with sufficient pressure, as described above.
  • the composition partially or fully cures to form the first die attach adhesive 203 .
  • the first semiconductor die 201 is electrically connected to the substrate through bonding wires 206 and the second semiconductor die 202 is electrically connected to the substrate through bonding wires 207 .
  • An overmolding 208 may then be applied to protect the semiconductor dice 201 , 202 and the bonding wires 206 , 207 .
  • Solder balls 209 may then be added to the substrate 204 .
  • Filler 1 is fumed silica treated with hexamethyldisilazane.
  • Filler 2 is spherical fused silica.
  • Catalyst 1 is a combination of 55% dimethylvinylsiloxy terminated polydimethyl siloxane having a viscosity of 2200 centiStokes (cSt), 45% encapsulated platinum catalyst, and 5% fumed silica treated with hexamethyldisilazane.
  • Catalyst 2 is polycarbonate encapsulated platinum catalyst.
  • Cure Modifier is phenyl butynol.
  • Pigment is Shawnigan Black.
  • Polymer 1 is a combination of 69% dimethylvinylsiloxy terminated polydimethyl siloxane having a degree of polymerization of 300 and 31% of an MQ resin containing vinyl groups.
  • Polymer 2 is dimethylvinylsiloxy terminated polydimethyl siloxane having a viscosity of 2200 centiStokes (cSt).
  • Spacer is styrenedivinylbenzene crosslinked spherical particles having 90% of their diameters being 38 to 45 micrometers.
  • Organohydrogenpolysiloxane 1 is a trimethylsiloxy-terminated poly(dimethylsiloxane/methylhydrogensiloxane) having a degree of polymerization of 12, and a ratio of dimethylsiloxane units/methyl hydrogensiloxane units of 0.6.
  • Fluoroorganosilicone 1 is trimethylsiloxy-terminated poly(methylhydrogensiloxane/methyl-6,6,6,5,5,4,4,3,3-nonafluorohexylsiloxane) having an average of 28 methylhydrogensiloxane units and 12 methyl-6,6,6,5,5,4,4,3,3-nonafluorohexyl siloxane units per molecule.
  • Adhesion Promoter is a reaction product of hydroxy-terminated poly(dimethylsiloxane/methyvinlysiloxane) with (glycidoxypropyl)trimethoxysilane.
  • Phenylsiloxane 1 is phenylmethylvinylsiloxy terminated polydimethylsiloxane.
  • Phenylsiloxane 2 is PhSi(O(CH 3 ) 2 H), where Ph represents a phenyl group.
  • a base is prepared by milling the following components in a 1 quart Ross mixer: Filler 1, Filler 2, Pigment, and the Polymer or Polymers selected for each example.
  • a blend is prepared by blending Cure Modifier and Organohydrogenpolysiloxane or Fluoroorganosilicone, or both, and heating for at least 30 minutes at 70 ° C.
  • the base, the blend, and any additional Polymer or Polymers are combined in a 20 gram dental mixer cup and are mixed at 3,500 revolutions per minute for 30 seconds.
  • the resulting mixture is allowed to cool and Catalyst is added and is hand mixed for 10 seconds.
  • the resulting mixture is again mixed at 3,500 revolutions per minute for 10 seconds with the dental mixer.
  • Rate of Bleed is measured as follows. A sample is allowed to equilibrate to room temperature. A 9 mm (length) piece of Continuous Au/Cu PI TAB tape purchased from Hitachi Cable is cut and taped to the middle section of a stainless steel print frame that fits in a vacuum plate on the printer. The two edges of this plate will have holes exposed that need to be covered with PI cut to the same geometry as the Hitachi TAB tape. This will effectively seal the SS frame so that the vacuum plate can hold the frame and tape in place. This frame is then loaded into the vacuum plate attached to the printer.
  • the sample is screen-printed using the “bleed study” stencil. As soon as the print is made and the carriage is unloaded from the printer, the tab edge of the Hitachi TAB tape is taped to the SS frame. This will prevent any flow of material from being affected by the tape's tendency to curl at the edges.
  • a time of print is noted on the frame, and if an initial photograph is needed, the frame is transferred directly to the TEFLON stage used with the SPOT Microscope.
  • a tilt of 25-35 degrees will enhance the halo of the bleeding layer on the image captured.
  • the microscope zoom is adjusted from 1 to 4.9X, with the latter giving the best optical reference to measure or quantify the bleed from a nubbin. Once focused on a nubbin at the correct zoom, a picture is taken and the image saved to a file. This process is then repeated after 24 hours.
  • nubbin diameter is measured followed by the diameter of the halo of bleeding material and a percent increase from initial nubbin diameter is calculated.
  • Comparative example 1 shows that Bleed occurs in a composition that contains no fluoroorganosilicone and no adhesion promoter. Comparative example 1 and comparative examples 2-6 show that as the amount of adhesion promoter in the composition increases, Bleed also increases, even though the ratio of silicon-bonded hydrogen to aliphatically unsaturated organic groups is constant. Comparative examples 1 -7 show that when a fluoroorganosilicone is added to the composition of comparative example 1, Bleed decreases. Example 1 and comparative examples 1-7 show that even though adhesion promoter is present, Bleed does not increase when both fluoroorganosilicone and adhesion promoter are present.
  • Examples 1-6 and comparative examples 1-6 show that when both fluoroorganosilicone and adhesion promoter are present, Bleed is reduced as compared to when both fluoroorganosilicone and adhesion promoter are absent and when fluoroorganosilicone is absent and adhesion promoter is present the composition.
  • compositions Containing Component (II) Containing Component (II)
  • compositions containing adhesion promoters but no fluoroorganosilicones exhibit greater Bleed than the compositions that contain neither adhesion promoters nor fluoroorganosilicones and the compositions that contain fluoroorganosilicones but no adhesion promoters.
  • the compositions containing both adhesion promoters and fluoroorganosilicones exhibit less Bleed than the compositions containing fluoroorganosilicones and no adhesion promoters.
  • Samples are prepared by combining Polymer 2, Pigment, Spacer, filler 2, Crosslinker 1, Adhesion Promoter, Catalyst 2, Adhesion Promoter, and any Phenylsiloxanes and Crosslinkers.
  • Bleed is measured as the percent increase in diameter of a dot of sample placed on an electronic circuit tape.
  • the circuit tape is Hitachi polyimide TAB Tape LC-TAB ⁇ BGA 220A14, which consists of gold plated copper circuit traces with Tomoegawa X epoxy laminate adhesive between the traces. Dots of sample with diameters ranging from 0.914 mm to 1.953 mm are placed on to the epoxy surface on this circuit tape. Immediately after the dots are applied to the epoxy surface, pictures of the dots are taken and the time of placement is recorded along with the picture.
  • the growth in the size of the diameter in relation to the diameter of the original dot is an indication of the relative amount of Bleed for a given formulation.
  • Comparative examples 8-15 show that when a phenylsiloxane is used instead of a fluoroorganosilicone, Bleed increases.
  • FIG. 1 shows an example of a package in which the composition of this invention is used as a die attach adhesive.
  • FIG. 2 shows an example of a package in which the composition of this invention is used as a die attach adhesive.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Physics & Mathematics (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • General Physics & Mathematics (AREA)
  • Computer Hardware Design (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Power Engineering (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Paints Or Removers (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Silicon Polymers (AREA)
US10/641,810 2003-08-14 2003-08-14 Silicones having improved chemical resistance and curable silicone compositions having improved migration resistance Abandoned US20050038188A1 (en)

Priority Applications (12)

Application Number Priority Date Filing Date Title
US10/641,810 US20050038188A1 (en) 2003-08-14 2003-08-14 Silicones having improved chemical resistance and curable silicone compositions having improved migration resistance
DE200460022873 DE602004022873D1 (de) 2003-08-14 2004-07-09 Beschichtungsverfahren wobei silikonezusammensetzungen mit erhöhtem chemischem widerstand und verbessertem migrationswiderstand verwendet werden.
DE602004007016T DE602004007016T2 (de) 2003-08-14 2004-07-09 Silikone mit verbesserter chemikalienbeständigkeit und härtbare silikonzusammensetzungen mit verbesserter migrationsbeständigkeit
JP2006523187A JP5143421B2 (ja) 2003-08-14 2004-07-09 電子構成部品の製造方法
PCT/US2004/021903 WO2005019342A1 (en) 2003-08-14 2004-07-09 Silicones having improved chemical resistance and curable silicone compositions having improved migration resistance
AT06076803T ATE440914T1 (de) 2003-08-14 2004-07-09 Beschichtungsverfahren wobei silikonezusammensetzungen mit erhíhtem chemischem widerstand und verbessertem migrationswiderstand verwendet werden.
EP06076803A EP1741755B1 (en) 2003-08-14 2004-07-09 Method of coating using curable silicone compositions having improved chemical resistance and migration resistance
EP04777771A EP1664198B1 (en) 2003-08-14 2004-07-09 Silicones having improved chemical resistance and curable silicone compositions having improved migration resistance
AT04777771T ATE364661T1 (de) 2003-08-14 2004-07-09 Silikone mit verbesserter chemikalienbeständigkeit und härtbare silikonzusammensetzungen mit verbesserter migrationsbeständigkeit
TW93122756A TWI350845B (en) 2003-08-14 2004-07-29 Silicones having improved chemical resistance and curable silicone compositions having improved migration resistance
US11/180,456 US7521124B2 (en) 2003-08-14 2005-07-13 Silicones having improved chemical resistance and curable silicone compositions having improved migration resistance
KR20067003096A KR101074643B1 (ko) 2003-08-14 2006-02-14 내약품성이 개선된 실리콘 및 이동 저항이 개선된 경화성실리콘 조성물

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US10/641,810 US20050038188A1 (en) 2003-08-14 2003-08-14 Silicones having improved chemical resistance and curable silicone compositions having improved migration resistance

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US11/180,456 Continuation-In-Part US7521124B2 (en) 2003-08-14 2005-07-13 Silicones having improved chemical resistance and curable silicone compositions having improved migration resistance

Publications (1)

Publication Number Publication Date
US20050038188A1 true US20050038188A1 (en) 2005-02-17

Family

ID=34136444

Family Applications (2)

Application Number Title Priority Date Filing Date
US10/641,810 Abandoned US20050038188A1 (en) 2003-08-14 2003-08-14 Silicones having improved chemical resistance and curable silicone compositions having improved migration resistance
US11/180,456 Expired - Fee Related US7521124B2 (en) 2003-08-14 2005-07-13 Silicones having improved chemical resistance and curable silicone compositions having improved migration resistance

Family Applications After (1)

Application Number Title Priority Date Filing Date
US11/180,456 Expired - Fee Related US7521124B2 (en) 2003-08-14 2005-07-13 Silicones having improved chemical resistance and curable silicone compositions having improved migration resistance

Country Status (8)

Country Link
US (2) US20050038188A1 (ja)
EP (2) EP1741755B1 (ja)
JP (1) JP5143421B2 (ja)
KR (1) KR101074643B1 (ja)
AT (2) ATE440914T1 (ja)
DE (2) DE602004022873D1 (ja)
TW (1) TWI350845B (ja)
WO (1) WO2005019342A1 (ja)

Cited By (51)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030168731A1 (en) * 2002-03-11 2003-09-11 Matayabas James Christopher Thermal interface material and method of fabricating the same
WO2008019953A1 (en) * 2006-08-14 2008-02-21 Dow Corning Corporation Silicone release coating compositions
US7521125B2 (en) 2003-08-14 2009-04-21 Dow Corning Corporation Adhesives having improved chemical resistance and curable silicone compositions for preparing the adhesives
WO2010015837A1 (en) * 2008-08-07 2010-02-11 Pyroban Limited Coating for reducing explosion hazard
US20100059171A1 (en) * 2006-01-18 2010-03-11 Lg Chem.Ltd. Pressure Sensitive Adhesive For Transporting Flexible Substrate
CN102516870A (zh) * 2011-12-21 2012-06-27 天津灯塔涂料工业发展有限公司 铝色环氧有机硅耐热漆及制备方法
CN102977606A (zh) * 2012-12-12 2013-03-20 黄山市强路新材料有限公司 一种阻燃高抗撕液态硅树脂的制备方法
US20130082369A1 (en) * 2010-04-02 2013-04-04 Kaneka Corporation Curable resin composition, curable resin composition tablet, molded body, semiconductor package, semiconductor component and light emitting diode
US20140194019A1 (en) * 2010-12-22 2014-07-10 Dow Corning Corporation Silicone Composition, Silicone Adhesive, Coated and Laminated Substrates
WO2014160067A1 (en) * 2013-03-14 2014-10-02 Dow Corning Corporation Thermally curable silicone compositions as temporary bonding adhesives
US8927026B2 (en) 2011-04-07 2015-01-06 The Procter & Gamble Company Shampoo compositions with increased deposition of polyacrylate microcapsules
US8980292B2 (en) 2011-04-07 2015-03-17 The Procter & Gamble Company Conditioner compositions with increased deposition of polyacrylate microcapsules
WO2015059258A1 (en) * 2013-10-24 2015-04-30 Wacker Chemie Ag Led encapsulant
US9162085B2 (en) 2011-04-07 2015-10-20 The Procter & Gamble Company Personal cleansing compositions with increased deposition of polyacrylate microcapsules
US9186642B2 (en) 2010-04-28 2015-11-17 The Procter & Gamble Company Delivery particle
GB2530388A (en) * 2014-07-25 2016-03-23 Dow Corning Fluoro-silicone compositions as temporary bonding adhesives field of the invention
CN107001803A (zh) * 2014-12-18 2017-08-01 迈图高新材料日本合同公司 阻燃性聚有机硅氧烷组合物、阻燃性固化物、光学用部件、光源用透镜或盖子以及成型方法
US9993793B2 (en) 2010-04-28 2018-06-12 The Procter & Gamble Company Delivery particles
WO2018112911A1 (en) 2016-12-23 2018-06-28 Dow (Shanghai) Holding Co., Ltd. Polyorganosiloxane release coating and method for its preparation and use
US10147631B2 (en) 2016-09-26 2018-12-04 Dow Silicones Corporation Fluoro-silicone compositions as temporary bonding adhesives
WO2019079365A1 (en) 2017-10-19 2019-04-25 Dow Silicones Corporation POLYORGANOSILOXANE COMPOSITIONS CONTAINING 2-SUBSTITUTED 1-ALKYNYL-1-CYCLOHEXANOL USEFUL AS HYDROSILYLATION REACTION INHIBITOR
CN111057242A (zh) * 2019-12-31 2020-04-24 惠州市安品新材料有限公司 有机硅锚固剂的制备方法和应用
WO2020131367A1 (en) 2018-12-21 2020-06-25 Dow Silicones Corporation Polyfunctional organosiloxanes, compositions containing same, and methods for the preparation thereof
WO2020131369A1 (en) 2018-12-21 2020-06-25 Dow Silicones Corporation Methods for making polyfunctional organosiloxanes and compositions containing same
WO2020131366A1 (en) 2018-12-21 2020-06-25 Dow Silicones Corporation Polyfunctional organosiloxanes, compositions containing same, and methods for the preparation thereof
WO2020231644A1 (en) 2019-05-16 2020-11-19 Dow Silicones Corporation Polysiloxane controlled release additive, method for the preparation thereof, and release coating composition
WO2021031185A1 (en) 2019-08-22 2021-02-25 Dow Silicones Corporation Polyorganosiloxane release coating composition
WO2021061417A1 (en) 2019-09-26 2021-04-01 Dow Silicones Corporation Silicone release coating composition and methods for the preparation and use of same
WO2021081863A1 (en) 2019-10-31 2021-05-06 Dow Silicones Corporation Silicone pressure sensitive adhesive composition and methods for the preparation and use thereof
WO2021113058A1 (en) 2019-12-02 2021-06-10 Dow Silicones Corporation Composition for preparing a release coating
WO2021113321A1 (en) 2019-12-02 2021-06-10 Dow Silicones Corporation Composition for preparing a release coating
WO2021113318A1 (en) 2019-12-02 2021-06-10 Dow Silicones Corporation Composition for preparing a release coating
WO2021113317A1 (en) 2019-12-02 2021-06-10 Dow Silicones Corporation Composition for preparing a release coating
WO2021138151A1 (en) 2019-12-30 2021-07-08 Dow Silicones Corporation Pressure sensitive adhesive composition
WO2021138152A1 (en) 2019-12-30 2021-07-08 Dow Silicones Corporation Composition for preparing a release coating, release coating composition, and related methods
WO2021138150A1 (en) 2019-12-30 2021-07-08 Dow Silicones Corporation Composition for preparing a release coating, release coating composition, and related methods
WO2021142653A1 (en) 2020-01-15 2021-07-22 Dow Silicones Corporation Silicone pressure sensitive adhesive composition and methods for the preparation and use thereof
WO2021262494A1 (en) 2020-06-24 2021-12-30 Dow Silicones Corporation Methods for making polyfunctional organosiloxanes and compositions containing same
WO2021262337A1 (en) 2020-06-22 2021-12-30 Dow Silicones Corporation Low intensity radiation curable silicone release coating composition and method for its preparation and use
WO2022061795A1 (en) 2020-09-27 2022-03-31 Dow Silicones Corporation Additive organopolysiloxane composition, curable composition, and film
WO2022216367A1 (en) 2021-04-09 2022-10-13 Dow Silicones Corporation Pressure sensitive adhesive composition and methods for its preparation and use in flexible organic light emitting diode applications
WO2022246594A1 (en) 2021-05-24 2022-12-01 Dow Silicones Corporation Composition for preparing a release coating and method of preparing coated substrate
US11549039B2 (en) 2017-10-19 2023-01-10 Dow Silicones Corporation Pressure sensitive adhesive composition and methods for its preparation and use in flexible organic light emitting diode applications
CN115746699A (zh) * 2022-11-24 2023-03-07 杭州之江有机硅化工有限公司 一种透明有机硅涂覆胶组合物及其制备方法和应用
WO2023115340A1 (en) 2021-12-21 2023-06-29 Dow Silicones Corporation Release coating composition
WO2023146692A1 (en) 2022-01-26 2023-08-03 Dow Silicones Corporation Pressure sensitive adhesive composition and methods for its preparation and use in flexible organic light emitting diode applications
WO2023184222A1 (en) 2022-03-30 2023-10-05 Dow Silicones Corporation Curable composition for silicone pressure sensitive adhesives
US11781050B2 (en) 2021-07-21 2023-10-10 Dow Global Technologies Llc Aqueous dispersion of a silicone pressure sensitive adhesive base and methods for preparation and use of the dispersion
WO2024006430A1 (en) 2022-06-30 2024-01-04 Dow Silicones Corporation Composition for preparing a release coating
WO2024108429A1 (en) 2022-11-23 2024-05-30 Dow Silicones Corporation Composition for preparing a release coating and method of preparing coated substrate
US12116511B2 (en) 2021-04-09 2024-10-15 Dow Silicones Corporation Process for preparing a solventless polyorganosiloxane pellet and a waterborne dispersion of a silicone pressure sensitive adhesive base

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050038183A1 (en) * 2003-08-14 2005-02-17 Dongchan Ahn Silicones having improved surface properties and curable silicone compositions for preparing the silicones
US20050038188A1 (en) 2003-08-14 2005-02-17 Dongchan Ahn Silicones having improved chemical resistance and curable silicone compositions having improved migration resistance
CA2596490A1 (en) * 2005-02-09 2006-08-17 Angiodynamics, Inc. Reinforced balloon for a catheter
US7834083B2 (en) * 2006-10-11 2010-11-16 Samsung Electro-Mechanics Co., Ltd. Nanocomposite composition comprising transparent nanoparticles
JP5355423B2 (ja) * 2007-02-22 2013-11-27 ダウ コーニング コーポレーション 伝導性フィルムを調製するためのプロセスおよびそのプロセスを用いて調製した物品
DE102008000517B4 (de) * 2008-03-05 2018-04-26 Robert Bosch Automotive Steering Gmbh Verfahren zum druckdichten Fügen eines metallischen Lenkgetriebegehäuses mit einem Kunststoffgehäusedeckel
DE102009002231A1 (de) * 2009-04-06 2010-10-07 Wacker Chemie Ag Bei Raumtemperatur selbsthaftende Pt-katalysierte additions-vernetzende Siliconzusammensetzungen
CN101811890B (zh) * 2009-12-28 2012-09-05 河北理工大学 耐酸复相陶瓷涂层及其制备方法
US20140342625A1 (en) 2011-12-06 2014-11-20 Dow Corning Corporation Curable Silicone Composition, Cured Material, Manufactured Articles, Methods And Uses
CN102977607B (zh) * 2012-12-12 2015-09-30 黄山市强路新材料有限公司 一种阻燃高抗撕液态硅树脂
CN104981510B (zh) 2012-12-28 2017-12-15 道康宁公司 用于换能器的可固化有机聚硅氧烷组合物和此类可固化有机硅组合物在换能器方面的应用
CN104981518B (zh) * 2012-12-28 2019-01-29 美国陶氏有机硅公司 用于换能器的可固化有机聚硅氧烷组合物和此类可固化有机硅组合物在换能器方面的应用
DE102015101748A1 (de) * 2015-02-06 2016-08-11 Osram Opto Semiconductors Gmbh Elektronisches Bauelement mit einem Werkstoff umfassend Epoxysilan-modifiziertes Polyorganosiloxan
CN108586747B (zh) * 2018-04-11 2020-11-06 杭州师范大学 一种中高苯基含量甲基苯基硅油的制备方法
CN109439274B (zh) * 2018-11-02 2020-11-10 烟台德邦科技有限公司 一种耐油密封胶的制备方法
EP3994225B1 (en) * 2019-07-03 2024-03-06 Dow Silicones Corporation Silicone pressure sensitive adhesive composition containing a fluorosilicone additive and methods for the preparation and use thereof
CN110408031A (zh) * 2019-07-12 2019-11-05 湖北大学 具有多端官能团的活性支化碳硅烷及其制备方法
RU2727373C1 (ru) * 2020-01-30 2020-07-21 Общество с ограниченной ответственностью "ВЛАДСИЛАН" (ООО "ВЛАДСИЛАН") Композиция на основе линейно-лестничного силоксанового блок-сополимера для получения защитных покрытий
TW202407051A (zh) * 2022-08-01 2024-02-16 日商陶氏東麗股份有限公司 光擴散性聚矽氧組成物以及光擴散材

Citations (53)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2676182A (en) * 1950-09-13 1954-04-20 Dow Corning Copolymeric siloxanes and methods of preparing them
US3159601A (en) * 1962-07-02 1964-12-01 Gen Electric Platinum-olefin complex catalyzed addition of hydrogen- and alkenyl-substituted siloxanes
US3220972A (en) * 1962-07-02 1965-11-30 Gen Electric Organosilicon process using a chloroplatinic acid reaction product as the catalyst
US3296291A (en) * 1962-07-02 1967-01-03 Gen Electric Reaction of silanes with unsaturated olefinic compounds
US3419593A (en) * 1965-05-17 1968-12-31 Dow Corning Catalysts for the reaction of = sih with organic compounds containing aliphatic unsaturation
US3445420A (en) * 1966-06-23 1969-05-20 Dow Corning Acetylenic inhibited platinum catalyzed organopolysiloxane composition
US3516946A (en) * 1967-09-29 1970-06-23 Gen Electric Platinum catalyst composition for hydrosilation reactions
US3814730A (en) * 1970-08-06 1974-06-04 Gen Electric Platinum complexes of unsaturated siloxanes and platinum containing organopolysiloxanes
US3975362A (en) * 1975-04-28 1976-08-17 Dow Corning Corporation Low temperature reversion resistant organosilicon polymers
US3989667A (en) * 1974-12-02 1976-11-02 Dow Corning Corporation Olefinic siloxanes as platinum inhibitors
US3989668A (en) * 1975-07-14 1976-11-02 Dow Corning Corporation Method of making a silicone elastomer and the elastomer prepared thereby
US4087585A (en) * 1977-05-23 1978-05-02 Dow Corning Corporation Self-adhering silicone compositions and preparations thereof
US4273902A (en) * 1978-06-30 1981-06-16 G-C Dental Industrial Corp. Dental silicone compositions and the method of using the same
US4348454A (en) * 1981-03-02 1982-09-07 General Electric Company Ultraviolet light curable acrylic functional silicone compositions
US4355121A (en) * 1981-04-09 1982-10-19 General Electric Company Heat strength curable silicone rubber compositions
US4360610A (en) * 1981-03-23 1982-11-23 Dow Corning Corporation Method of improving silicone rubber composition
US4370358A (en) * 1980-09-22 1983-01-25 General Electric Company Ultraviolet curable silicone adhesives
US4386170A (en) * 1980-10-31 1983-05-31 Dow Corning Corporation Curable fluorinated silicone elastomer
US4492786A (en) * 1983-08-26 1985-01-08 General Electric Company Modified organopolysiloxane composition
US4500447A (en) * 1982-09-08 1985-02-19 Toray Silicone Company, Inc. Electrically conductive silicone rubber compositions
US4584355A (en) * 1984-10-29 1986-04-22 Dow Corning Corporation Silicone pressure-sensitive adhesive process and product with improved lap-shear stability-I
US4584361A (en) * 1985-06-03 1986-04-22 Dow Corning Corporation Storage stable, one part polyorganosiloxane compositions
US5091135A (en) * 1987-09-11 1992-02-25 Polyplastic Co., Ltd. Improvements in the encapsulation of electronic components employing low stress encapsulant composition
US5194649A (en) * 1991-01-29 1993-03-16 Dow Corning Toray Silicone Co., Ltd. Organopentasiloxane and method for its preparation
US5204436A (en) * 1990-08-03 1993-04-20 Shin-Etsu Chemical Co., Ltd. Curable silicone composition and its cured product
US5248715A (en) * 1992-07-30 1993-09-28 Dow Corning Corporation Self-adhering silicone rubber with low compression set
US5254623A (en) * 1992-09-25 1993-10-19 Dow Corning Corporation Curable fluorinated organosiloxane compositions exhibiting improved adhesion
US5302632A (en) * 1991-04-22 1994-04-12 Dow Corning Corporation High consistency organosiloxane compositions comprising fluorinated and non-fluorinated polyorganosiloxanes
US5310843A (en) * 1991-10-17 1994-05-10 Dow Corning Toray Silicone Co., Ltd. Organopolysiloxane and method for the preparation thereof
US5349037A (en) * 1992-03-03 1994-09-20 Shin-Etsu Chemical Co., Ltd. Adhesive composition
US5399602A (en) * 1992-09-28 1995-03-21 Dow Corning Toray Silicone, Co. Ltd. Oil-resistant silicone rubber composition
US5405929A (en) * 1993-06-30 1995-04-11 Dow Corning Toray Silicone Co., Ltd. Curable silicone composition
US5447987A (en) * 1993-12-24 1995-09-05 Shin-Etsu Chemical Co., Ltd. Organopolysiloxane compositions
US5482775A (en) * 1989-02-02 1996-01-09 Canon Kabushiki Kaisha Silicon composition and elastic roller using the composition
US5578381A (en) * 1994-08-31 1996-11-26 Dow Corning Toray Silicone Co., Ltd. Release coating compositions
US5595826A (en) * 1995-10-11 1997-01-21 Dow Corning Corporation Curable organopolysiloxane compositions with improved adhesion
US5616403A (en) * 1994-07-11 1997-04-01 General Electric Company Fluorosilicone coatings
US5665794A (en) * 1996-05-20 1997-09-09 Dow Corning Corporation Method for controlling cure initiation and curing times of platinum group metal curing fluorosilicone compositions
US5684060A (en) * 1996-04-09 1997-11-04 Minnesota Mining And Manufacturing Company Compositions containing inorganic, organic and organometallic palladium hydrogen scavengers
US5696211A (en) * 1995-12-23 1997-12-09 Dow Corning Corporation Silicone release coating compositions
US5744507A (en) * 1996-12-30 1998-04-28 Dow Corning Corporation Foamable organosiloxane compositions curable to silicone foams having improved adhesion
US5756598A (en) * 1996-12-30 1998-05-26 Dow Corning Corporation Resin-containing organosiloxane compositions curable to silicone elastomers having low weep
US5777047A (en) * 1996-12-30 1998-07-07 Dow Corning Corporation Organosiloxane compositions with fluorinated resins curable to silicone elastomers having low weep
US5824736A (en) * 1992-09-21 1998-10-20 Dow Corning Toray Silicone Co., Ltd. Fluorosilicone rubber composition
US5989719A (en) * 1998-10-13 1999-11-23 Dow Corning Corporation Oil resistant liquid silicone rubber compositions
US6056976A (en) * 1998-11-12 2000-05-02 Leiras Oy Elastomer, its preparation and use
US6169142B1 (en) * 1998-06-17 2001-01-02 Shin Etsu Chemical Co., Ltd. Thermal conductive silicone rubber compositions and method of making
US20020032270A1 (en) * 2000-07-11 2002-03-14 Syuuichi Azechi Silicone rubber adhesive composition and integrally molded article thereof
US6362554B1 (en) * 1999-07-29 2002-03-26 Encap Motor Corporation Stator assembly
US20020148100A1 (en) * 2001-01-09 2002-10-17 Du Hung T. Electric motor having armature coated with a thermally conductive plastic
US20030071382A1 (en) * 2001-10-17 2003-04-17 Neal Griffith D. Method of encapsulating hard disc drive and other electrical components
US6685855B1 (en) * 2003-06-11 2004-02-03 Cool Options, Inc. Method of making thermally-conductive casings for optical heads in optical disc players
US6794035B2 (en) * 2001-10-02 2004-09-21 Polymatech Co., Ltd. Graphitized carbon fiber powder and thermally conductive composition

Family Cites Families (53)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4329273A (en) 1978-03-07 1982-05-11 General Electric Company Self-bonding silicone rubber compositions
US4591622A (en) 1984-10-29 1986-05-27 Dow Corning Corporation Silicone pressure-sensitive adhesive process and product thereof
US4585836A (en) 1984-10-29 1986-04-29 Dow Corning Corporation Silicone pressure-sensitive adhesive process and product with improved lap-shear stability-II
JPS61195129A (ja) 1985-02-22 1986-08-29 Toray Silicone Co Ltd 有機けい素重合体の製造方法
JPS6348901A (ja) 1986-08-19 1988-03-01 Mitsubishi Electric Corp マイクロ波デバイス
JPS63205359A (ja) 1987-02-20 1988-08-24 Shin Etsu Chem Co Ltd 硬化性フツ素シリコ−ン組成物
US4766176A (en) 1987-07-20 1988-08-23 Dow Corning Corporation Storage stable heat curable organosiloxane compositions containing microencapsulated platinum-containing catalysts
US4784879A (en) 1987-07-20 1988-11-15 Dow Corning Corporation Method for preparing a microencapsulated compound of a platinum group metal
JP2630993B2 (ja) 1988-06-23 1997-07-16 東レ・ダウコーニング・シリコーン株式会社 ヒドロシリル化反応用白金系触媒含有粒状物およびその製造方法
JPH0214244A (ja) 1988-06-30 1990-01-18 Toray Dow Corning Silicone Co Ltd 加熱硬化性オルガノポリシロキサン組成物
US5082706A (en) * 1988-11-23 1992-01-21 Dow Corning Corporation Pressure sensitive adhesive/release liner laminate
JP2502714B2 (ja) * 1988-12-05 1996-05-29 東芝シリコーン株式会社 室温硬化性ポリオルガノシロキサン組成物
JPH02218755A (ja) 1989-02-20 1990-08-31 Toray Dow Corning Silicone Co Ltd 硬化性オルガノポリシロキサン組成物
JPH02298549A (ja) 1989-05-12 1990-12-10 Shin Etsu Chem Co Ltd 接着性組成物
US5036117A (en) 1989-11-03 1991-07-30 Dow Corning Corporation Heat-curable silicone compositions having improved bath life
US4946878A (en) * 1990-01-29 1990-08-07 Dow Corning Corporation Rapidly curable extrudable organosiloxane compositions
US5082894A (en) * 1990-03-19 1992-01-21 Dow Corning Corporation Storage stable one-part organosiloxane compositions
US5858468A (en) * 1990-10-29 1999-01-12 Mcdonnell Douglas Corporation Chemical resistant coatings
US5110845A (en) * 1990-12-03 1992-05-05 Dow Corning Corporation Extrudable curable organosiloxane compositions
JPH04222871A (ja) 1990-12-25 1992-08-12 Toray Dow Corning Silicone Co Ltd 硬化性オルガノポリシロキサン組成物
JP3270489B2 (ja) 1991-01-30 2002-04-02 東レ・ダウコーニング・シリコーン株式会社 硬化性オルガノポリシロキサン組成物
GB9103191D0 (en) 1991-02-14 1991-04-03 Dow Corning Platinum complexes and use thereof
US5164461A (en) 1991-03-14 1992-11-17 General Electric Company Addition-curable silicone adhesive compositions
US6004679A (en) * 1991-03-14 1999-12-21 General Electric Company Laminates containing addition-curable silicone adhesive compositions
JPH06145525A (ja) 1992-11-05 1994-05-24 Toray Dow Corning Silicone Co Ltd 硬化性オルガノポリシロキサン組成物
US5270425A (en) * 1992-11-23 1993-12-14 Dow Corning Corporation One-part curable organosiloxane compositions
JP3024445B2 (ja) * 1993-06-30 2000-03-21 信越化学工業株式会社 剥離剤用シリコーン組成物及び剥離紙
US5373078A (en) * 1993-10-29 1994-12-13 Dow Corning Corporation Low viscosity curable organosiloxane compositions
JPH07150044A (ja) * 1993-11-25 1995-06-13 Toray Dow Corning Silicone Co Ltd 硬化性ポリマー組成物
JPH07145322A (ja) * 1993-11-25 1995-06-06 Toray Dow Corning Silicone Co Ltd 硬化性オルガノポリシロキサン組成物
JP3153089B2 (ja) * 1993-12-24 2001-04-03 信越化学工業株式会社 オルガノポリシロキサン組成物
EP0661335A1 (en) 1993-12-27 1995-07-05 Dow Corning Corporation Organosiloxane compositions capable of curing against acid-containing solder fluxes
DE19526300A1 (de) 1995-05-19 1996-11-21 Gen Electric Silicon-Haftkleber hohen Feststoffgehaltes mit verbesserter Überlapp-Scherfestigkeit
JPH0925415A (ja) * 1995-07-10 1997-01-28 Nitto Denko Corp 硬化性含フッ素シリコーン組成物
JPH09286919A (ja) * 1996-04-18 1997-11-04 Toray Dow Corning Silicone Co Ltd 硬化性オルガノポリシロキサン組成物およびその硬化物
JPH09286971A (ja) 1996-04-19 1997-11-04 Toray Dow Corning Silicone Co Ltd シリコーン系ダイボンディング剤、半導体装置の製造方法および半導体装置
EP0850997A3 (en) 1996-12-24 2001-03-14 Dow Corning Corporation Filled addition curable compositions having reduced gassing and increased shelf stability
EP0850999A3 (en) * 1996-12-30 1998-12-02 Dow Corning Corporation Silicone release coating compositions
JPH115902A (ja) 1997-06-17 1999-01-12 Shin Etsu Chem Co Ltd 硬化性シリコーンゴム組成物
JP3454095B2 (ja) 1997-07-14 2003-10-06 信越化学工業株式会社 液状硬化性組成物
JP3885843B2 (ja) * 1997-11-28 2007-02-28 東レ・ダウコーニング株式会社 シリコーン系剥離剤用消泡剤
DE69903675T2 (de) 1998-02-04 2003-07-03 Shin-Etsu Chemical Co., Ltd. Additionshärbare Silikonmischungen
JP2000078679A (ja) 1998-08-27 2000-03-14 Nec Home Electronics Ltd ワイヤレスマイクロフォン装置
US6297305B1 (en) 1998-09-02 2001-10-02 Dow Corning Toray Silicone Company, Ltd. Curable silicone composition
DE69905542T2 (de) 1998-11-30 2003-12-11 Shin-Etsu Chemical Co., Ltd. Additionshärtbare Silikonelastomermischung
DE10019599A1 (de) 2000-04-20 2001-10-31 Wacker Chemie Gmbh Selbsthaftende additionsvernetzende Siliconzusammensetzungen
JP2001352768A (ja) 2000-06-05 2001-12-21 Canon Inc 積層電気−機械エネルギー変換素子および振動波駆動装置
JP2002020719A (ja) 2000-07-11 2002-01-23 Shin Etsu Chem Co Ltd シリコーンゴム接着剤組成物及び該接着剤組成物と熱可塑性樹脂との一体成形体
JP2002194201A (ja) 2000-12-22 2002-07-10 Shin Etsu Chem Co Ltd 硬化性フルオロポリエーテル系ゴム組成物
US6512037B1 (en) * 2001-06-06 2003-01-28 Dow Corning Corporation Silicone composition and cured silicone product
US7045586B2 (en) * 2003-08-14 2006-05-16 Dow Corning Corporation Adhesives having improved chemical resistance and curable silicone compositions for preparing the adhesives
US20050038188A1 (en) 2003-08-14 2005-02-17 Dongchan Ahn Silicones having improved chemical resistance and curable silicone compositions having improved migration resistance
US20050038183A1 (en) 2003-08-14 2005-02-17 Dongchan Ahn Silicones having improved surface properties and curable silicone compositions for preparing the silicones

Patent Citations (54)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2676182A (en) * 1950-09-13 1954-04-20 Dow Corning Copolymeric siloxanes and methods of preparing them
US3159601A (en) * 1962-07-02 1964-12-01 Gen Electric Platinum-olefin complex catalyzed addition of hydrogen- and alkenyl-substituted siloxanes
US3220972A (en) * 1962-07-02 1965-11-30 Gen Electric Organosilicon process using a chloroplatinic acid reaction product as the catalyst
US3296291A (en) * 1962-07-02 1967-01-03 Gen Electric Reaction of silanes with unsaturated olefinic compounds
US3419593A (en) * 1965-05-17 1968-12-31 Dow Corning Catalysts for the reaction of = sih with organic compounds containing aliphatic unsaturation
US3445420A (en) * 1966-06-23 1969-05-20 Dow Corning Acetylenic inhibited platinum catalyzed organopolysiloxane composition
US3516946A (en) * 1967-09-29 1970-06-23 Gen Electric Platinum catalyst composition for hydrosilation reactions
US3814730A (en) * 1970-08-06 1974-06-04 Gen Electric Platinum complexes of unsaturated siloxanes and platinum containing organopolysiloxanes
US3989667A (en) * 1974-12-02 1976-11-02 Dow Corning Corporation Olefinic siloxanes as platinum inhibitors
US3975362A (en) * 1975-04-28 1976-08-17 Dow Corning Corporation Low temperature reversion resistant organosilicon polymers
US3989668A (en) * 1975-07-14 1976-11-02 Dow Corning Corporation Method of making a silicone elastomer and the elastomer prepared thereby
US4087585A (en) * 1977-05-23 1978-05-02 Dow Corning Corporation Self-adhering silicone compositions and preparations thereof
US4273902A (en) * 1978-06-30 1981-06-16 G-C Dental Industrial Corp. Dental silicone compositions and the method of using the same
US4370358A (en) * 1980-09-22 1983-01-25 General Electric Company Ultraviolet curable silicone adhesives
US4386170A (en) * 1980-10-31 1983-05-31 Dow Corning Corporation Curable fluorinated silicone elastomer
US4348454A (en) * 1981-03-02 1982-09-07 General Electric Company Ultraviolet light curable acrylic functional silicone compositions
US4360610A (en) * 1981-03-23 1982-11-23 Dow Corning Corporation Method of improving silicone rubber composition
US4355121A (en) * 1981-04-09 1982-10-19 General Electric Company Heat strength curable silicone rubber compositions
US4500447A (en) * 1982-09-08 1985-02-19 Toray Silicone Company, Inc. Electrically conductive silicone rubber compositions
US4492786A (en) * 1983-08-26 1985-01-08 General Electric Company Modified organopolysiloxane composition
US4584355A (en) * 1984-10-29 1986-04-22 Dow Corning Corporation Silicone pressure-sensitive adhesive process and product with improved lap-shear stability-I
US4584361A (en) * 1985-06-03 1986-04-22 Dow Corning Corporation Storage stable, one part polyorganosiloxane compositions
US5091135A (en) * 1987-09-11 1992-02-25 Polyplastic Co., Ltd. Improvements in the encapsulation of electronic components employing low stress encapsulant composition
US5482775A (en) * 1989-02-02 1996-01-09 Canon Kabushiki Kaisha Silicon composition and elastic roller using the composition
US5204436A (en) * 1990-08-03 1993-04-20 Shin-Etsu Chemical Co., Ltd. Curable silicone composition and its cured product
US5194649A (en) * 1991-01-29 1993-03-16 Dow Corning Toray Silicone Co., Ltd. Organopentasiloxane and method for its preparation
US5302632A (en) * 1991-04-22 1994-04-12 Dow Corning Corporation High consistency organosiloxane compositions comprising fluorinated and non-fluorinated polyorganosiloxanes
US5310843A (en) * 1991-10-17 1994-05-10 Dow Corning Toray Silicone Co., Ltd. Organopolysiloxane and method for the preparation thereof
US5349037A (en) * 1992-03-03 1994-09-20 Shin-Etsu Chemical Co., Ltd. Adhesive composition
US5248715A (en) * 1992-07-30 1993-09-28 Dow Corning Corporation Self-adhering silicone rubber with low compression set
US5824736A (en) * 1992-09-21 1998-10-20 Dow Corning Toray Silicone Co., Ltd. Fluorosilicone rubber composition
US5254623A (en) * 1992-09-25 1993-10-19 Dow Corning Corporation Curable fluorinated organosiloxane compositions exhibiting improved adhesion
US5399602A (en) * 1992-09-28 1995-03-21 Dow Corning Toray Silicone, Co. Ltd. Oil-resistant silicone rubber composition
US5405929A (en) * 1993-06-30 1995-04-11 Dow Corning Toray Silicone Co., Ltd. Curable silicone composition
US5447987A (en) * 1993-12-24 1995-09-05 Shin-Etsu Chemical Co., Ltd. Organopolysiloxane compositions
US5616403A (en) * 1994-07-11 1997-04-01 General Electric Company Fluorosilicone coatings
US6074703A (en) * 1994-07-11 2000-06-13 General Electric Company Fluorosilicone coatings
US5578381A (en) * 1994-08-31 1996-11-26 Dow Corning Toray Silicone Co., Ltd. Release coating compositions
US5595826A (en) * 1995-10-11 1997-01-21 Dow Corning Corporation Curable organopolysiloxane compositions with improved adhesion
US5696211A (en) * 1995-12-23 1997-12-09 Dow Corning Corporation Silicone release coating compositions
US5684060A (en) * 1996-04-09 1997-11-04 Minnesota Mining And Manufacturing Company Compositions containing inorganic, organic and organometallic palladium hydrogen scavengers
US5665794A (en) * 1996-05-20 1997-09-09 Dow Corning Corporation Method for controlling cure initiation and curing times of platinum group metal curing fluorosilicone compositions
US5777047A (en) * 1996-12-30 1998-07-07 Dow Corning Corporation Organosiloxane compositions with fluorinated resins curable to silicone elastomers having low weep
US5756598A (en) * 1996-12-30 1998-05-26 Dow Corning Corporation Resin-containing organosiloxane compositions curable to silicone elastomers having low weep
US5744507A (en) * 1996-12-30 1998-04-28 Dow Corning Corporation Foamable organosiloxane compositions curable to silicone foams having improved adhesion
US6169142B1 (en) * 1998-06-17 2001-01-02 Shin Etsu Chemical Co., Ltd. Thermal conductive silicone rubber compositions and method of making
US5989719A (en) * 1998-10-13 1999-11-23 Dow Corning Corporation Oil resistant liquid silicone rubber compositions
US6056976A (en) * 1998-11-12 2000-05-02 Leiras Oy Elastomer, its preparation and use
US6362554B1 (en) * 1999-07-29 2002-03-26 Encap Motor Corporation Stator assembly
US20020032270A1 (en) * 2000-07-11 2002-03-14 Syuuichi Azechi Silicone rubber adhesive composition and integrally molded article thereof
US20020148100A1 (en) * 2001-01-09 2002-10-17 Du Hung T. Electric motor having armature coated with a thermally conductive plastic
US6794035B2 (en) * 2001-10-02 2004-09-21 Polymatech Co., Ltd. Graphitized carbon fiber powder and thermally conductive composition
US20030071382A1 (en) * 2001-10-17 2003-04-17 Neal Griffith D. Method of encapsulating hard disc drive and other electrical components
US6685855B1 (en) * 2003-06-11 2004-02-03 Cool Options, Inc. Method of making thermally-conductive casings for optical heads in optical disc players

Cited By (70)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030168731A1 (en) * 2002-03-11 2003-09-11 Matayabas James Christopher Thermal interface material and method of fabricating the same
US7521125B2 (en) 2003-08-14 2009-04-21 Dow Corning Corporation Adhesives having improved chemical resistance and curable silicone compositions for preparing the adhesives
US20100059171A1 (en) * 2006-01-18 2010-03-11 Lg Chem.Ltd. Pressure Sensitive Adhesive For Transporting Flexible Substrate
US8128773B2 (en) * 2006-01-18 2012-03-06 Lg Chem, Ltd. Pressure sensitive adhesive for transporting flexible substrate
US20100255205A1 (en) * 2006-08-14 2010-10-07 Stephen Cray Silicone Release Coating Compositions
WO2008019953A1 (en) * 2006-08-14 2008-02-21 Dow Corning Corporation Silicone release coating compositions
US9562149B2 (en) 2006-08-14 2017-02-07 Dow Corning Corporation Silicone release coating compositions
US20110183137A1 (en) * 2008-08-07 2011-07-28 Lee Spraggon Coating for reducing explosion hazard
WO2010015837A1 (en) * 2008-08-07 2010-02-11 Pyroban Limited Coating for reducing explosion hazard
US20130082369A1 (en) * 2010-04-02 2013-04-04 Kaneka Corporation Curable resin composition, curable resin composition tablet, molded body, semiconductor package, semiconductor component and light emitting diode
US9178120B2 (en) * 2010-04-02 2015-11-03 Kaneka Corporation Curable resin composition, curable resin composition tablet, molded body, semiconductor package, semiconductor component and light emitting diode
US11096875B2 (en) 2010-04-28 2021-08-24 The Procter & Gamble Company Delivery particle
US9186642B2 (en) 2010-04-28 2015-11-17 The Procter & Gamble Company Delivery particle
US9993793B2 (en) 2010-04-28 2018-06-12 The Procter & Gamble Company Delivery particles
US20140194019A1 (en) * 2010-12-22 2014-07-10 Dow Corning Corporation Silicone Composition, Silicone Adhesive, Coated and Laminated Substrates
US8927026B2 (en) 2011-04-07 2015-01-06 The Procter & Gamble Company Shampoo compositions with increased deposition of polyacrylate microcapsules
US9162085B2 (en) 2011-04-07 2015-10-20 The Procter & Gamble Company Personal cleansing compositions with increased deposition of polyacrylate microcapsules
US8980292B2 (en) 2011-04-07 2015-03-17 The Procter & Gamble Company Conditioner compositions with increased deposition of polyacrylate microcapsules
US10143632B2 (en) 2011-04-07 2018-12-04 The Procter And Gamble Company Shampoo compositions with increased deposition of polyacrylate microcapsules
US9561169B2 (en) 2011-04-07 2017-02-07 The Procter & Gamble Company Conditioner compositions with increased deposition of polyacrylate microcapsules
CN102516870A (zh) * 2011-12-21 2012-06-27 天津灯塔涂料工业发展有限公司 铝色环氧有机硅耐热漆及制备方法
CN102977606A (zh) * 2012-12-12 2013-03-20 黄山市强路新材料有限公司 一种阻燃高抗撕液态硅树脂的制备方法
WO2014160067A1 (en) * 2013-03-14 2014-10-02 Dow Corning Corporation Thermally curable silicone compositions as temporary bonding adhesives
CN105917479A (zh) * 2013-10-24 2016-08-31 瓦克化学股份公司 Led封装材料
WO2015059258A1 (en) * 2013-10-24 2015-04-30 Wacker Chemie Ag Led encapsulant
GB2530388A (en) * 2014-07-25 2016-03-23 Dow Corning Fluoro-silicone compositions as temporary bonding adhesives field of the invention
CN107001803A (zh) * 2014-12-18 2017-08-01 迈图高新材料日本合同公司 阻燃性聚有机硅氧烷组合物、阻燃性固化物、光学用部件、光源用透镜或盖子以及成型方法
US10147631B2 (en) 2016-09-26 2018-12-04 Dow Silicones Corporation Fluoro-silicone compositions as temporary bonding adhesives
WO2018112911A1 (en) 2016-12-23 2018-06-28 Dow (Shanghai) Holding Co., Ltd. Polyorganosiloxane release coating and method for its preparation and use
US11008480B2 (en) 2016-12-23 2021-05-18 Dow (Shanghai) Holding Co., Ltd Polyorganosiloxane release coating and method for its preparation and use
WO2019079365A1 (en) 2017-10-19 2019-04-25 Dow Silicones Corporation POLYORGANOSILOXANE COMPOSITIONS CONTAINING 2-SUBSTITUTED 1-ALKYNYL-1-CYCLOHEXANOL USEFUL AS HYDROSILYLATION REACTION INHIBITOR
US11549039B2 (en) 2017-10-19 2023-01-10 Dow Silicones Corporation Pressure sensitive adhesive composition and methods for its preparation and use in flexible organic light emitting diode applications
US10876019B2 (en) 2017-10-19 2020-12-29 Dow Silicones Corporation Polyorganosiloxane compositions containing a 2-substituted-1-alkynyl-1-cyclohexanol useful as a hydrosilylation reaction inhibitor
WO2020131366A1 (en) 2018-12-21 2020-06-25 Dow Silicones Corporation Polyfunctional organosiloxanes, compositions containing same, and methods for the preparation thereof
WO2020131369A1 (en) 2018-12-21 2020-06-25 Dow Silicones Corporation Methods for making polyfunctional organosiloxanes and compositions containing same
US11787908B2 (en) 2018-12-21 2023-10-17 Dow Silicones Corporation Methods for making polyfunctional organosiloxanes and compositions containing same
EP4212575A1 (en) 2018-12-21 2023-07-19 Dow Silicones Corporation Methods for making polyfunctional organosiloxanes and compositions containing same
US11643506B2 (en) 2018-12-21 2023-05-09 Dow Silicones Corporation Polyfunctional organosiloxanes, compositions containing same, and methods for the preparation thereof
WO2020131367A1 (en) 2018-12-21 2020-06-25 Dow Silicones Corporation Polyfunctional organosiloxanes, compositions containing same, and methods for the preparation thereof
US11905375B2 (en) 2018-12-21 2024-02-20 Dow Silicones Corporation Polyfunctional organosiloxanes, compositions containing same, and methods for the preparation thereof
WO2020231644A1 (en) 2019-05-16 2020-11-19 Dow Silicones Corporation Polysiloxane controlled release additive, method for the preparation thereof, and release coating composition
US11685844B2 (en) 2019-05-16 2023-06-27 Dow Silicones Corporation Polysiloxane controlled release additive, method for the preparation thereof, and release coating composition
WO2021031185A1 (en) 2019-08-22 2021-02-25 Dow Silicones Corporation Polyorganosiloxane release coating composition
WO2021061417A1 (en) 2019-09-26 2021-04-01 Dow Silicones Corporation Silicone release coating composition and methods for the preparation and use of same
WO2021081863A1 (en) 2019-10-31 2021-05-06 Dow Silicones Corporation Silicone pressure sensitive adhesive composition and methods for the preparation and use thereof
WO2021113058A1 (en) 2019-12-02 2021-06-10 Dow Silicones Corporation Composition for preparing a release coating
WO2021113317A1 (en) 2019-12-02 2021-06-10 Dow Silicones Corporation Composition for preparing a release coating
WO2021113318A1 (en) 2019-12-02 2021-06-10 Dow Silicones Corporation Composition for preparing a release coating
WO2021113321A1 (en) 2019-12-02 2021-06-10 Dow Silicones Corporation Composition for preparing a release coating
WO2021138151A1 (en) 2019-12-30 2021-07-08 Dow Silicones Corporation Pressure sensitive adhesive composition
WO2021138152A1 (en) 2019-12-30 2021-07-08 Dow Silicones Corporation Composition for preparing a release coating, release coating composition, and related methods
WO2021138150A1 (en) 2019-12-30 2021-07-08 Dow Silicones Corporation Composition for preparing a release coating, release coating composition, and related methods
CN111057242A (zh) * 2019-12-31 2020-04-24 惠州市安品新材料有限公司 有机硅锚固剂的制备方法和应用
WO2021142653A1 (en) 2020-01-15 2021-07-22 Dow Silicones Corporation Silicone pressure sensitive adhesive composition and methods for the preparation and use thereof
US11174420B2 (en) 2020-01-15 2021-11-16 Dow Silicones Corporation Silicone pressure sensitive adhesive composition and methods for the preparation and use thereof
WO2021262337A1 (en) 2020-06-22 2021-12-30 Dow Silicones Corporation Low intensity radiation curable silicone release coating composition and method for its preparation and use
WO2021262494A1 (en) 2020-06-24 2021-12-30 Dow Silicones Corporation Methods for making polyfunctional organosiloxanes and compositions containing same
WO2022061795A1 (en) 2020-09-27 2022-03-31 Dow Silicones Corporation Additive organopolysiloxane composition, curable composition, and film
US12037459B2 (en) 2020-09-27 2024-07-16 Dow Silicones Corporation Additive organopolysiloxane composition, curable composition, and film
US12116511B2 (en) 2021-04-09 2024-10-15 Dow Silicones Corporation Process for preparing a solventless polyorganosiloxane pellet and a waterborne dispersion of a silicone pressure sensitive adhesive base
WO2022216367A1 (en) 2021-04-09 2022-10-13 Dow Silicones Corporation Pressure sensitive adhesive composition and methods for its preparation and use in flexible organic light emitting diode applications
WO2022246594A1 (en) 2021-05-24 2022-12-01 Dow Silicones Corporation Composition for preparing a release coating and method of preparing coated substrate
US11781050B2 (en) 2021-07-21 2023-10-10 Dow Global Technologies Llc Aqueous dispersion of a silicone pressure sensitive adhesive base and methods for preparation and use of the dispersion
WO2023115340A1 (en) 2021-12-21 2023-06-29 Dow Silicones Corporation Release coating composition
WO2023146692A1 (en) 2022-01-26 2023-08-03 Dow Silicones Corporation Pressure sensitive adhesive composition and methods for its preparation and use in flexible organic light emitting diode applications
WO2023184222A1 (en) 2022-03-30 2023-10-05 Dow Silicones Corporation Curable composition for silicone pressure sensitive adhesives
US12091548B2 (en) 2022-03-30 2024-09-17 Dow Silicones Corpo ation Curable composition for silicone pressure sensitive adhesives
WO2024006430A1 (en) 2022-06-30 2024-01-04 Dow Silicones Corporation Composition for preparing a release coating
WO2024108429A1 (en) 2022-11-23 2024-05-30 Dow Silicones Corporation Composition for preparing a release coating and method of preparing coated substrate
CN115746699A (zh) * 2022-11-24 2023-03-07 杭州之江有机硅化工有限公司 一种透明有机硅涂覆胶组合物及其制备方法和应用

Also Published As

Publication number Publication date
ATE440914T1 (de) 2009-09-15
TWI350845B (en) 2011-10-21
US7521124B2 (en) 2009-04-21
JP5143421B2 (ja) 2013-02-13
WO2005019342A1 (en) 2005-03-03
DE602004022873D1 (de) 2009-10-08
EP1741755B1 (en) 2009-08-26
TW200510483A (en) 2005-03-16
EP1664198B1 (en) 2007-06-13
DE602004007016T2 (de) 2008-02-07
ATE364661T1 (de) 2007-07-15
EP1741755A3 (en) 2007-01-24
KR20060080177A (ko) 2006-07-07
EP1741755A2 (en) 2007-01-10
EP1664198A1 (en) 2006-06-07
US20050271884A1 (en) 2005-12-08
DE602004007016D1 (de) 2007-07-26
JP2007502344A (ja) 2007-02-08
KR101074643B1 (ko) 2011-10-19

Similar Documents

Publication Publication Date Title
US7521124B2 (en) Silicones having improved chemical resistance and curable silicone compositions having improved migration resistance
US7045586B2 (en) Adhesives having improved chemical resistance and curable silicone compositions for preparing the adhesives
US20050038183A1 (en) Silicones having improved surface properties and curable silicone compositions for preparing the silicones
JP3950493B2 (ja) 導電性シリコーンゴム組成物、半導体装置の製造方法およびその半導体装置
EP0757080A2 (en) Curable organosiloxane compositions and semiconductor devices
JPH03170581A (ja) 導電性接着剤
TW202134350A (zh) 固化性有機聚矽氧烷組成物及其固化物、保護劑或黏合劑以及電氣電子設備
JP3207929B2 (ja) 半導体素子被覆剤および半導体装置
US7485202B2 (en) Method for making a flat-top pad
KR100490186B1 (ko) 전기전도성실리콘조성물,이를사용하는반도체장치의제조방법및반도체장치
JP3691587B2 (ja) 硬化性オルガノポリシロキサン組成物および半導体装置
JP2002265786A (ja) 硬化性オルガノポリシロキサン組成物、および半導体装置の製造方法
JP3479815B2 (ja) エポキシ樹脂組成物及び半導体装置

Legal Events

Date Code Title Description
AS Assignment

Owner name: DOW CORNING CORPORATION, MICHIGAN

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:AHN, DONGEHAN;HUEY, PAMELA JEAN;SHEPHARD, NICK EVAN;AND OTHERS;REEL/FRAME:014764/0468;SIGNING DATES FROM 20030909 TO 20031008

STCB Information on status: application discontinuation

Free format text: EXPRESSLY ABANDONED -- DURING EXAMINATION