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WO2025194325A1 - Adhésif optiquement transparent à base de silicone à adhérence élevée au substrat - Google Patents

Adhésif optiquement transparent à base de silicone à adhérence élevée au substrat

Info

Publication number
WO2025194325A1
WO2025194325A1 PCT/CN2024/082351 CN2024082351W WO2025194325A1 WO 2025194325 A1 WO2025194325 A1 WO 2025194325A1 CN 2024082351 W CN2024082351 W CN 2024082351W WO 2025194325 A1 WO2025194325 A1 WO 2025194325A1
Authority
WO
WIPO (PCT)
Prior art keywords
mass
hydrosilylation
less
range
component
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.)
Pending
Application number
PCT/CN2024/082351
Other languages
English (en)
Inventor
Jingui JIANG
Maki Itoh
Shi PAN
Nick Shephard
Xuedong GAO
Bin Fan
Jiayin ZHU
Chengrong ZHU
Zhihua Liu
Qing Cao
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 Toray Co Ltd
Dow Silicones Corp
Original Assignee
Dow Toray Co Ltd
Dow Silicones 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 Toray Co Ltd, Dow Silicones Corp filed Critical Dow Toray Co Ltd
Priority to PCT/CN2024/082351 priority Critical patent/WO2025194325A1/fr
Publication of WO2025194325A1 publication Critical patent/WO2025194325A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • 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
    • 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
    • C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups

Definitions

  • the present invention relates to a silicone pressure sensitive adhesive composition that produces a silicone pressure sensitive adhesive that is useful as an interlayer adhesive, and can be optically clear and can be useful as an optically clear adhesive.
  • Silicone pressure sensitive adhesives possess rheological properties and optical properties that can be especially desirable in applications such as interlayer adhesive applications benefiting from or requiring shock absorbing and dampening properties.
  • One such application is optically clear adhesives (OCAs) , but there are other interlayer adhesive applications where shock absorbance and/dampening is valuable.
  • Interlayer adhesive applications include electronic device, particularly those with light emitting diode (LED) and organic light emitting diode (OLED) devices. LED and OLED display devices can consist of many functional layers including an electrode layer and a display layer sandwiched between substrates. Interlayer adhesives are typically between functional layers to bond the functional layers together into an article. Silicone PSAs are desirable interlayer adhesives for such applications due to their shock absorbing properties, electrical insulating properties, heat resistance, cold resistance, and ability to provide optical clarity if desired.
  • silicone PSAs It would advance the art of silicone PSAs to provide a silicone PSA that has a peel strength from stainless steel at 25 °C that is at least 772 Newtons per meter (N/m) (2000 gram-force per inch (gf/in) ) , preferably 849 N/m (2200 gf/in) or more, more preferably 927 N/m (2400 gf/in) or more, and most preferably at least 1004 N/m (2600 gf/in) while at the same achieving a peel strength from stainless steel at 85 °C that is greater than 232 N/m (600 gf/in) , preferably 247 N/m (640 gf/in) or more, more preferably 270 N/m (700 gf/in) or more, and yet more preferably 309 N/m (800 gf/in) or more. It would advance the art further if such performance is obtainable from a silicone PSA composition that cures by hydrosilylation.
  • the present invention provides a solution to the challenge of providing provide a silicone PSA that has a peel strength from stainless steel at 25 °C that is at least 772 N/m (2000 gf/in) , preferably 849 N/m (2200 gf/in) or more, more preferably 927 N/m (2400 gf/in) or more, and most preferably at least 1004 N/m (2600 gf/in) while at the same achieves a peel strength from stainless steel at 85 °C that is greater than 232 N/m (600 gf/in) , preferably 247 N/m (640 gf/in) or more, more preferably 270 N/m (700 gf/in) or more, and yet more preferably 309 N/m (800 gf/in) or more.
  • the present invention provides a solution to these challenges using a silicone PSA composition that cures by hydrosilylation.
  • the present invention is at least partially a result of discovering that including hydroxyl-terminated silicone gum, and preferably but not necessarily also tetraalkoxysilane (such as tetraethoxysilane) , to silicone PSA composition at a concentration in a range for total hydroxyl-terminated silicone gum and tetraalkoxysilane of 7 to 20 weight-percent of the non-solvent components of the PSA composition can increase the peel strength of the resulting PSA to stainless steel.
  • tetraalkoxysilane such as tetraethoxysilane
  • the present invention a hydrosilylation-curable composition
  • a hydrosilylation-curable composition comprising the following components: (a) hydroxyl-functional polyorganosiloxane gum; (b) alkenyl- functional polyorganosiloxane gum; (c) optionally, tetraalkoxysilane; (d) trimethylsilyl-capped MQ resin; (e) hydrosilylation inhibitor; (f) silylhydride-functionals crosslinker at a concentration sufficient to achieve a molar SiH/alkene ratio in the hydrosilylation-curable composition that is in a range of 10 to 200; (g) platinum hydrosilylation catalyst at a concentration sufficient to provide 0.1 to 200 mass parts platinum per million mass parts of hydrosilylation-curable composition; (h) optionally, non-functional trimethylsilyl-capped polydimethylsiloxane gum; and (i) solvent; wherein the combined concentration of components (a) and (c) is in a range of 7 to
  • composition of the present invention is useful as a silicone PSA.
  • Products identified by their tradename refer to the compositions available under those tradenames on the priority date of this document.
  • Average value when referencing a value describing a molecule refers to the average value of a sample of molecules since it is generally difficult to measure the value of a single molecule.
  • Siloxane units can be characterized by the designation M, D, T or Q.
  • M refers to a siloxane unit having the formula “ (CH 3 ) 3 SiO 1/2 ” .
  • D refers to a siloxane unit having the formula “ (CH 3 ) 2 SiO 2/2 ” .
  • T refers to a siloxane unit having the formula “ (CH 3 ) SiO 3/2 ” .
  • Q refers to a siloxane unit having the formula “SiO 4/2 ” .
  • Non-oxygen groups bound to the silicon atom in M, D and T units are methyl groups unless otherwise stated or indicated.
  • an oxygen atom having a multiple of “1/2” subscript indicates that the oxygen bridges the specified atom to a second atom where the second atom is also specified with an oxygen having a multiple of “1/2” subscript.
  • ( (CH 3 ) 3 SiO 1/2 ) (SiO 4/2 ) refers to a M unit bound to a Q unit with an oxygen atom shared between the silicon atom of the M unit and a silicon atom of the Q unit.
  • the multiplier of the 1/2 subscript indicates how many oxygen atoms are in such a shared bonding configuration with the silicon atom of the siloxane unit.
  • siloxane unit designation with the suffix “-type” refers to the siloxane unit where any one or more than one methyl group is actually an R 1 group where R 1 is a hydrocarbyl containing from one to 8 carbon atoms.
  • R 1 can be methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, or octyl.
  • a siloxane unit can include as a superscript an indication of a group bound to that silicon atom in place of an alkyl group.
  • M H -type siloxane unit refers to an M-type unit with one R 1 group replaced with hydrogen: ( (R 1 ) 2 HSiO 1/2 ) .
  • M H ” siloxane unit refers to an M unit with one methyl replaced with a hydrogen atom ( (CH 3 ) 2 HSiO 1/2 ) .
  • Chemical formula designations for polysiloxanes using M, D, T, Q abbreviations typically have subscripts associated with the unit designator that can either refer to the average mole ratio of that siloxane unit relative to all siloxane units in the molecule or the average number of the associate siloxane units in the molecule.
  • the subscript associated with a siloxane unit is greater than or equal to one, then the subscript refers to the average number of those siloxane units in the molecule.
  • the subscript associated with a siloxane unit is less than one then the subscript refers to the average mole ratio of that siloxane unit relative to the number of moles of all siloxane units in the molecule.
  • An absence of a subscript implies a subscript value of one.
  • Polyorganosiloxane gum refers to a linear polyorganosiloxane having a number-average molecular weight (Mn) that is greater than 200,000 grams per mole (g/mol) and that is typically less than 1 million g/mol. Determine Mn for a polyorganosiloxane gum
  • the present invention is a composition
  • a composition comprising the following components: (a) hydroxyl-functional polyorganosiloxane gum; (b) alkenyl-functional polyorganosiloxane gum; (c) tetraalkoxysilane (tetraalkylorthosilicate) ; (d) non-functional MQ resin; (e) a hydrosilylation inhibitor; (f) a silylhydride-functional crosslinker; (g) a hydrosilylation catalyst; (h) optionally, non-functional trimethylsilyl-capped polydimethylsiloxane gum; and (i) a solvent.
  • the hydroxyl-functional polyorganosiloxane gum is preferably a linear polyorganosiloxane gum.
  • the hydroxyl functionalities on the linear polyorganosiloxane gum are terminal, typically with one hydroxyl on either end of the linear polyorganosiloxane gum.
  • the hydroxyl-functional polyorganosiloxane gum can have an average chemical structure (I) : HOMe 2 SiO (Me 2 SiO) d SiMe 2 OH (I)
  • subscript d indicates the average number of (Me 2 SiO) groups per molecule and has an average value in a range of 2000 to 5000.
  • Subscript d can have a have an average value of 2000 or more, 2500 or more, 3000 or more, 3500 or more, even 4000 or more, while at the same time is typically 5000 or less, 4500 or less, or eve 3000 or less.
  • the hydroxyl-functional polyorganosiloxane gum is typically present at a concentration in a range of 5-20 mass%, and can be 5 mass%or more, 7 mass%or more, 10 mass%or more, 11 mass%or more, 12 mass%or more, 13 mass%or more, 14 mass%or more, even 15 mass%or more, while at the same time is typically 20 mass%or less, 19 mass%or less, 18 mass%or less, 17 mass%or less, 16 mass%or less, 15 mass%or less, 14 mass%or less, 12 mass%or less, 11 mass%or less, or even 10 mass%or less, with mass%relative to the combined mass of the composition components other than solvent (that is, the combined mass of components (a) - (h) ) .
  • the hydroxyl-functional polyorganosiloxane gum can be free of alkenyl groups.
  • the alkenyl-functional polyorganosiloxane gum can be one or more than one alkenyl-functional polyorganosiloxane gum.
  • Alkenyl-functional polyorganosiloxane gum is a polyorganosiloxane gum that comprises alkenyl functionality.
  • the alkenyl-functional polyorganosiloxane contains and average of 2 or more alkenyl groups per molecule.
  • the alkenyl-functional polyorganosiloxane gum has terminal alkenyl-functionality and at the same time can comprise or be free of pendant alkenyl-functionality.
  • the alkenyl-functional polysiloxane gum can be free of functional groups other than the alkenyl groups.
  • the alkenyl-functionality contains from two to 6 carbon atoms.
  • the alkenyl functionality is a vinyl (Vi) group.
  • the alkenyl-functional polyorganosiloxane gum has a Mn that is in a range of 200,000 to 1,500,000 grams per mole (g/mol) .
  • the non-functional trimethyl silyl-terminated polyorganosiloxane gum has a Mn that is 200,000 g/mol or more, and can be 300,000 g/mol or more, 400,000 g/mol or more, 450,000 g/mol or more, 500,000 g/mol or more, 600,000 g/mol or more, 700,000 g/mol or more, 800,000 g/mol or more, while at the same time is typically 1,500,000 g/mol or less, and can be 1,000,000 g/mol or less, 900,000 g/mol or less, 800,000 g/mol or less, 700,000 g/mol or less, 600,000 g/mol or less, even 500,000 g/mol or less.
  • the hydrosilylation-curable composition of the present invention is free of alkenyl-functional polyorganosiloxane having a MN below 150,000 g/mol.
  • Styragel is a trademark of Waters Technologies Corporation.
  • the alkenyl-functional polyorganosiloxane gum can have an average chemical structure (II) : [Vi (CH 3 ) 2 SiO] [ (CH 3 ) 2 SiO] d’ [Vi (CH 3 ) 2 Si] (II)
  • Vi refers to a vinyl group and subscript d’ refers to the average number of [ (CH 3 ) 2 SiO] siloxane units in the molecule and has a value in a range of 2,400 to 16,400, and can be 2,400 or more, 2,500 or more, 3,000 or more, 4,000 or more, 5,000 or more, 5,400 or more, even 6,000 or more while at the same time is typically 16,400 or less, and can be 16,000 or less, 15,000 or less, 14,000 or less, 13,000 or less, 12,000 or less, 10,000 or less, 8,000 or less, even 6,000 or less.
  • the concentration of alkenyl-functional polyorganosiloxane can be in a range of 5.0 to 30 mass%and is typically 5.0 mass%or more, and can be 6.0 or more, 7.0 or more, 8.0 or more, 9.0 or more, 10.0 or more, 11.0 or more, 12.0 or more, 13.0 or more, even 14.0 or more while at the same time is typically 30 mass%or less, and can be 25 mass%or less, 23 mass%or less, 20 mass%or less, 19 mass%or less, 18 mass%or less, 17 mass%or less, 16 mass%or less, 15 mass%or less, 14 mass%or less, 10 mass%or less, even 8 mass%or less, where mass%of alkenyl-functional polyorganosiloxane is relative to the combined mass of the composition components other than solvent (that is, the combined mass of components (a) - (h) ) .
  • An additional discovery of the present invention is that if tetraalkoxysilane is include with the hydroxyl-functional polyorganosiloxane gum, then the 25 C and 85 °C peel strengths of the resulting PSA from stainless steel further increases relative to use of hydroxyl-functional polyorganosiloxane gum alone.
  • Tetraalkoxysilane also known as tetraalkyl orthosilicate, has the general chemical structure: (R 1 O) 4 Si, where each R 1 is an alkyl group.
  • R 1 is selected from alkyl group having one or more, two or more, three or more four or more, five or more, even 6 or more carbon atoms while at the same time typically having 8 or fewer, 7 or fewer, 6 or fewer, 5 or fewer, 4 or fewer, 3 or fewer, even 2 or fewer carbon atoms.
  • the tetraalkoxysilane is one or both tetraalkoxysilane selected from tetramethoxysilane (tetramethyl orthosilicate) and tetraethoxysilane (tetraethyl orthosilicate) .
  • the tetraalkoxysilane can be a single tetraalkoxysilane or a combination of more than one tetraalkoxysilane.
  • the concentration of tetraalkoxysilane is in a range of zero to 6.0 mass%, preferably 1.0 to 6.0 mass%, and more preferably 2.0 to 6.0 mass%.
  • the concentration of tetraalkoxysilane is zero mass%or more, and can be 1.0 mass%or more, 2.0 mass%or more, 3.0 mass%or more, 3.5 mass%or more, even 4.0 mass%or more while at the same time is typically 6.0 mass%or less, 5.0 mass%or less, 4.0 mass%or less, even 3.5 mass%or less.
  • Mass%of tetraalkoxysilane is relative to the combined mass of the composition components other than solvent (that is, the combined mass of components (a) - (h) ) .
  • the mass ratio of tetraalkoxysilane to hydroxyl-functional polyorganosiloxane gum can be zero or more, but is desirably in a range of 0.15 to 0.70 and can be zero or more, 0.15 or more, 0.20 or more, 0.25 or more, 0.30 or more, 0.35 or more, 0.40 or more, 0.45 or more, even 0.50 or more, while at the same time is typically 0.70 or less, 0.65 or less, 0.60 or less, or 0.55 or less.
  • the combined mass of hydroxyl-functional polyorganosiloxane gum (component (a) ) and tetraalkoxysilane (component (c) ) is in a range of 7 to 20 mass%, and can be 7 mass%or more, 8 mass%or more, 9 mass%or more, 10 mass%or more, 11 mass%or more, 12 mass%or more, 13 mass%or more, 14 mass%or more, 15 mass%or more, 16 mass%or more, 17 mass%or more, 18 mass%or more, even 19 mass%or more, while at the same time is typically 20 mass%or less, 19 mass%or less, 18 mass%or less, 17 mass%or less, 16 mass%or less, 15 mass%or less, 14 mass%or less, 13 mass%or less, 12 mass%or less, 11 mass%or less, 10 mass%or less, 9 mass%or less, or even 8 mass%or less.
  • Trimethylsilyl-capped MQ resin contains predominately, preferably exclusively, two types of siloxane units.
  • the first siloxane unit has the general formula R 3 SiO 1/2 (an “M” siloxane unit) where each R is a methyl ( “Me” ) group.
  • the second siloxane unit has the general formula SiO 4/2 (a “Q” siloxane unit) .
  • Each O 1/2 refers to an oxygen atom bound to the identified silicon atom and also bound to (thereby shared with) another silicon atom, a hydrogen or an hydrocarbyl group but where the vast majority of the O 1/2 oxygen atoms are shared between two silicon atoms.
  • the trimethylsilyl-capped MQ resin can comprise some T OZ siloxane units, which have a general formula ZOSiO 3/2 , where OZ refers to a group consisting of OH and OR functionality and R refers to an alkyl group.
  • the amount of T OZ siloxane units in the trimethylsilyl-capped MQ resin is typically in a range of zero to 10 mass%, preferably zero to 8 mass%, zero to 6 mass%, zero to 4 mass%, zero to 2 mass%and can be zero mass%, with mass%of T OZ siloxane units relative to the mass of trimethylsilyl-capped MQ resin
  • the trimethylsilyl-capped MQ resin can be a single trimethylsilyl-capped MQ resin or a combination of more than one trimethylsilyl-capped MQ resin.
  • the trimethylsilyl-capped MQ resin typically has an weight-average molecular weight (Mw) that is 5,000 g/mol or higher and that can be 6,000 g/mol or higher, 7,000 g/mol or higher, 8,000 or higher, 9,000 g/mol or higher, 10,000 g/mol or higher, 11,000 g/mol or higher, 12,000 g/mol or higher, 13,000 g/mol or higher, even 14,000 g/mol or higher while at the same time is typically 16,000 g/mol or less, and can be 15,000 g/mol or less, 14,000 g/mol or less, 13,000 g/mol or less, 12,000 g/mol or less, 11,000 g/mol or less, 10,00 g/mol or less, 9,000 g/mol or less, 8,000 g/mol or less, even 7,000 g/mol or less.
  • Mw weight-average molecular weight
  • the trimethylsilyl-capped MQ resin typically has a Mn of 2,000 g/mol or more, and can be 2, 500 g/mol or more, 3,000 g/mol or more, 4,000 g/mol or more, 4, 500 g/mol or more, even 5,000 g/mol or more, while at the same time is typically 7,000 g/mol or less, and can be 6,000 g/mol or less, even 5,000 g/mol or less. Determine Mn in like manner as described above for component (b) .
  • the trimethylsilyl-capped MQ resin is introduced into the composition as a solution or dispersion in a solvent such as an organic solvent.
  • a solvent such as an organic solvent.
  • the concentration of trimethylsilyl-capped MQ resin is typically in a range of 30 to 70 mass%, and generally is 30 mass%or more, and can be 40 mass%or more, 50 mass%or more, even 55 mass%or more while at the same time is typically 70 mass%or less, and can be 65 mass%or less, even 60 mass%or less, with mass%relative to the combined mass of the composition components other than solvent (that is, the combined mass of components (a) - (h) ) .
  • the mass ratio of trimethylsilyl-capped MQ resin (mass of component (d) ) to the mass of polysiloxane gum components (sum of the masses of components (a) , (b) and (h) ) is in a range of 1.5 to 2.0, and can be 1.5 or more, 1.6 or more, 1.7 or more, 1.8 or more, even 1.9 or more, while at the same time is typically 2.0 or less, 1.9 or less, 1.8 or less, 1.7 or less, or even 1.6 or less.
  • the mass ratio of trimethylsilyl-capped MQ resin (mass of component (d) ) to the mass of alkenyl-functional polysiloxane gum (mass of component (b) ) is 2.6 or higher.
  • the mass of component (d) to the mass of component (b) is 2.6 or higher, and can be 2.7 or higher, 2.8 or higher, 2.9 or higher, 3.0 or higher, 4.0 or higher, 5.0 or higher, 6.0 or higher, 7.0 or higher, even 8.0 or higher, while at the same time is typically 10.0 or lower, and can be 9.0 or lower, 8.0 or lower, 7.0 or lower, 6.0 or lower, 5.0 or lower, 4.0 or lower, even 3.0 or lower.
  • the concentration of hydrosilylation inhibitor is typically greater than zero mass%, and is desirably 0.10 mass%or more, 0.20 mass%or more, even 0.30 mass%or more while at the same time is typically 1.0 mass%or less, and can be 0.90 mass%or less, 0.80 mass%or less, 0.70 mass%or less, 0.60 mass%or less, 0.50 mass%or less, 0.40 mass%or less, even 0.35 mass%or less, with mass%relative to the combined mass of the composition components other than solvent (that is, the combined mass of components (a) - (h) ) .
  • the silylhydride-functional crosslinker is typically a siloxane that contains 2 or more silylhydride (SiH) functional groups.
  • the silylhydride-functional crosslinker is desirably a linear siloxane with pendant SiH functional groups that either includes or is free of terminal SiH functional groups.
  • the silylhydride-functional crosslinker can be a linear silylhydride-functional polydimethyl siloxane with pendant SiH functionality.
  • the silylhydride- functional crosslinker can have an average chemical structure (III) : [ (CH 3 ) 3 SiO] [ (CH 3 ) 2 SiO] m [H (CH 3 ) SiO] n [ (CH 3 ) 3 Si] (III)
  • subscript m is the average number of [ (CH 3 ) 2 SiO] siloxane units and has a value in a range of 2 to 10
  • subscript n is the average number of [H (CH 3 ) SiO] siloxane units and has a value in a range of 2 to 10.
  • Subscript m can be 2 or more, 3 or more, 4 or more, even 5 or more, while at the same time is typically 10 or less, 9 or less, 8 or less, 7 or less, 6 or less, 5 or less, even 4 or less.
  • Subscript n can be 2 or more, 3 or more, 4 or more, 5 or more, even 6 or more, while at the same time is typically 10 or less, 9 or less, 8 or less, even 7 or less.
  • the concentration of silylhydride-functional crosslinker is often in a range of 0.50 to 1.00 mass%, and can be 0.50 mass%or more, 0.60 mass%or more, 0.70 mass%or more, 0.80 mass%or more, even 0.90 mass%or more while at the same time is 1.00 mass%or less, 0.90 mass%or less, 0.80 mass%or less, 0.70 mass%or less, even 0.65 mass%or less, with mass%relative to the combined mass of the composition components other than solvent (that is, the combined mass of components (a) - (h) ) .
  • the hydrosilylation catalyst can be any catalyst that facilitates hydrosilylation reactions.
  • the hydrosilylation catalyst is a platinum-based hydrosilylation catalyst.
  • Platinum-based hydrosilylation catalysts include compounds and complexes such as platinum (0) -1, 3-divinyl-1, 1, 3, 3-tetramethyldisiloxane (Karstedt’s catalyst) , platinum-carbonyl complexes, platinum cyclovinylmethylsiloxane complexes, platinum acetylacetonate (acac) , cyclopentadienyl alky platinum, platinum black, platinum compounds such as chloroplatinic acid, chloroplatinic acid hexahydrate, a reaction product of chloroplatinic acid and a monohydric alcohol, platinum bis (ethylacetoacetate) , platinum bis (acetylacetonate) , platinum dichloride, and complexes of the platinum compounds with olefins or low molecular
  • the catalyst can be a supported Pt catalysts with Pt metal particles or compounds adsorbed onto or absorbed into a support material such as carbon or alumina.
  • the hydrosilylation catalyst can be part of a solution that includes complexes of platinum with low molecular weight organopolysiloxanes that include 1, 3-diethenyl-1, 1, 3, 3-tetramethyldisiloxane complexes with platinum. These complexes may be microencapsulated in resin.
  • Other transition or noble metal compounds can also be used as hydrosilylation catalysts, for example, di- ⁇ . -carbonyl di-. ⁇ . -cyclopentadienyl dinickel.
  • Typical hydrosilylation catalyst to obtain a platinum concentration in the composition that is in a range of 10 to 200 mass parts per million mass parts composition.
  • the non-functional trimethyl silyl-terminated polyorganosiloxane gum desirably has a number-average molecular weight (Mn) that is in a range of 200,000 to 1,500,000 grams per mol (g/mol) .
  • Mn number-average molecular weight
  • the non-functional trimethyl silyl-terminated polyorganosiloxane gum has a Mn that is 200,000 g/mol or more, and can be 300,000 g/mol or more, 400,000 g/mol or more, 500,000 g/mol or more, 600,000 g/mol or more, 700,000 g/mol or more, 750,000 g/mol or more, 800,000 g/mol or more, while at the same time is typically 1,500,000 g/mol or less, and can be 1,000,000 g/mol or less, 900,000 g/mol or less, 800,000 g/mol or less, even 700,000 g/mol or less.
  • Component (h) can have an average chemical structure (IV) : [ (CH 3 ) 3 SiO] [ (CH 3 ) 2 SiO] d [ (CH 3 ) 3 Si] (IV)
  • subscript d is the average number of [ (CH 3 ) 2 SiO] siloxane units in the molecule and has a value in a range of 9,000 to 10,000, and can be 9,000 or more, even 9,500 or more while at the same time is typically 10,000 or less, and can be 9,750 or less.
  • Component (h) is optional, which means the concentration of component (h) in the composition can be zero mass-percent (mass%) .
  • the concentration of component (h) is typically in a range of 0 to 25 mass%and can be 5 mass%or more, even 10 mass%or more, while at the same time is typically 25 mass%or less, and can be 20 mass%or less, where mass%of component (h) is relative to the combined mass of the composition components other than solvent (that is, the combined mass of components (a) - (h) ) .
  • the solvent is a carrier for the other components of the composition and desirably dissolves components (a) and (b) .
  • Suitable solvents include polysiloxane solvents and, preferably organic solvents.
  • the solvent is an organic solvent.
  • Exemplary organic solvents include: aromatic hydrocarbon-based solvents such as toluene, xylene and benzene; aliphatic hydrocarbon-based solvents such as heptane, hexane, octane and isoparaffin; ester-based solvents such as ethyl acetate and isobutyl acetate; ether-based solvents such as diisopropyl ether and 1, 4-dioxane; and chlorinated aliphatic hydrocarbon-based solvents such as trichloroethylene, perchloroethylene and methylene chloride.
  • the concentration of solvent is typically in a range of 30 to 70 mass%of the mass of the composition.
  • the concentration of solvent can be 30 mass%or more, 35 mass%or more, 40 mass%or more, 45 mass%or more, 50 mass%or more, even 55 mass%or more, while at the same time is typically 75 mass%or less, 70 mass%or less, 65 mass%or less, or even 60 mass%or less, with mass%of solvent relative to the mass of the composition.
  • Table 1 lists the materials for preparing the samples below. “Me” refers to “methyl” . “Vi” refers to “vinyl” . DOWSIL is a trademark of The Dow Chemical Company. SYL-OFF is a trademark of Dow Silicones Corporation.
  • compositions according to the formulations listed in Tables 2a and 2b, where amounts of the components are listed in grams (g) .
  • Ex 1 is a composition of the present invention.
  • Comp Ex A is Ex 1 without either hydroxyl-functional polyorganosiloxane gum (component (a) ) or tettraalkoxysilane (component (c) ) .
  • Comp Ex B is Ex 1 without the hydroxyl-functional polyorganosiloxane gum (component (a) ) but with tetraalkoxysilane (component (c) .
  • These three samples illustrate the need for the hydroxyl-functional polyorganosiloxane gum to achieve the target peel strengths from stainless steel at both 25 °C and 85 °C.
  • Ex 7 A comparison of Ex 1 with Ex 7 illustrates the advantage of including both hydroxyl-functional gum and tetraalkoxysilane to achieve highest Peel Force from stainless steel.
  • Ex 7 is equivalent to Ex 1, except without the tetraalkoxy silane.
  • Ex 7 shows a lower Peel Force from stainless steel at both 25 °C and 85 °C than Ex 1, but still demonstrates a Peel Force from stainless steel that is both 772 N/m or more at 25 °C and 232 N/m or more at 85 °C.
  • Ex 8 is equivalent to Ex 5, except without the tetraalkoxy silane.
  • Ex 8 shows a lower Peel Force from stainless steel at both 25 °C and 85 °C than Ex 5, but still demonstrates a Peel Force from stainless steel that is both 772 N/m or more at 25 °C and 232 N/m or more at 85 °C.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

Une composition durcissable par hydrosilylation selon l'invention contient les composants suivants : (a) une gomme de polyorganosiloxane à fonctionnalité hydroxyle ; (b) une gomme de polyorganosiloxane à fonctionnalité alcényle ; (c) facultativement, du tétraalcoxysilane ; (d) une résine MQ coiffée par triméthylsilyle ; (e) un inhibiteur d'hydrosilylation ; (f) un agent de réticulation à fonctionnalité hydrure de silyle à une concentration suffisante pour obtenir un rapport molaire SiH/alcène dans la composition durcissable par hydrosilylation qui est dans une plage de 10 à 200 ; (g) un catalyseur d'hydrosilylation au platine à une concentration suffisante pour fournir 0,1 à 200 parties en masse de platine par million de parties en masse de composition durcissable par hydrosilylation ; (h) facultativement, une gomme de polydiméthylsiloxane coiffée par triméthylsilyle non fonctionnelle ; et (i) un solvant ; la concentration combinée des composants (a) et (c) étant dans une plage de 7 à 20 pour cent en masse par rapport à la concentration combinée des composants (a) à (h).
PCT/CN2024/082351 2024-03-19 2024-03-19 Adhésif optiquement transparent à base de silicone à adhérence élevée au substrat Pending WO2025194325A1 (fr)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4985525A (en) * 1989-03-13 1991-01-15 Dow Corning Corporation Clear organosiloxane compositions
US5059484A (en) * 1989-03-13 1991-10-22 Dow Corning Corporation Optically clear composites comprising two layer of organic polymers and an organosiloxane adhesive
US11702575B2 (en) * 2017-08-03 2023-07-18 Henkel Ag & Co., Kgaa Curable silicone optically clear adhesives and uses thereof
US11732169B2 (en) * 2017-11-02 2023-08-22 Shin-Etsu Chemical Co., Ltd. Silicone adhesive composition, adhesive tape, adhesive sheet and double-sided adhesive sheet

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4985525A (en) * 1989-03-13 1991-01-15 Dow Corning Corporation Clear organosiloxane compositions
US5059484A (en) * 1989-03-13 1991-10-22 Dow Corning Corporation Optically clear composites comprising two layer of organic polymers and an organosiloxane adhesive
US11702575B2 (en) * 2017-08-03 2023-07-18 Henkel Ag & Co., Kgaa Curable silicone optically clear adhesives and uses thereof
US11732169B2 (en) * 2017-11-02 2023-08-22 Shin-Etsu Chemical Co., Ltd. Silicone adhesive composition, adhesive tape, adhesive sheet and double-sided adhesive sheet

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