[go: up one dir, main page]

WO2025155450A1 - Revêtement antiadhésif à base de silicone contenant de la silicone tris(triméthylsiloxy) à fonction alcène - Google Patents

Revêtement antiadhésif à base de silicone contenant de la silicone tris(triméthylsiloxy) à fonction alcène

Info

Publication number
WO2025155450A1
WO2025155450A1 PCT/US2025/010541 US2025010541W WO2025155450A1 WO 2025155450 A1 WO2025155450 A1 WO 2025155450A1 US 2025010541 W US2025010541 W US 2025010541W WO 2025155450 A1 WO2025155450 A1 WO 2025155450A1
Authority
WO
WIPO (PCT)
Prior art keywords
coating composition
functional
alkene
release coating
silicone
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/US2025/010541
Other languages
English (en)
Inventor
Gunn JO
Bokyung Kim
Yeong Gwang KIM
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 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 Silicones Corp filed Critical Dow Silicones Corp
Publication of WO2025155450A1 publication Critical patent/WO2025155450A1/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
    • 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
    • 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
    • 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
    • C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups

Definitions

  • Silicone release coatings are a popular choice in the industry due to their low surface energy. Silicone release coatings are typically formed by crosslinking (curing) a curable silicone release composition. Continual development of higher quality adherences such as optically clear adhesives (OCA) and multi-layer ceramic capacitors (MLCC) continue to drive a need for release coating with lower release force, even in silicone release coatings, to increase productivity with faster release speed without hindering adherend quality.
  • OCA optically clear adhesives
  • MLCC multi-layer ceramic capacitors
  • Some current approaches to reducing release force for release coatings include increasing surface roughness of the coating through inclusion of silica particle and addition of monofunctional polymers to control the modulus of the release coating composition. These approaches tend to unfavorably increase cost efficiency and reduce stability of product quality.
  • the present invention is a curable silicone release coating composition
  • a curable silicone release coating composition comprising: (a) an alkene-functional silicone gum having an average of at least 2 alkenyl groups per molecule; (b) an SiH-functional silicone having an average of at least 2 SiH groups per molecule at a concentration such that the molar ratio of SiH groups relative to alkenyl groups from the alkene-functional silicone gum is greater than 1.00; (c) greater than zero to 10 weight- percent relative to curable silicone release coating composition weight of an alkene-functional siloxane release additive having an average chemical formula: [(CHs ⁇ SiOhSiR, where R is a terminally unsaturated hydrocarbyl group containing from 2 to 20 carbon atoms; (d) hydrosilylation catalyst; and (e) optionally, one or any combination of more than one component selected from solvent, additional release agents, hydrosilylation inhibitors, adhesion promoters, fumed silica and MQ resins.
  • 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.
  • the alkene-functional silicone gum component contains an average of at least 2 alkenyl groups per molecule.
  • the alkenyl groups are desirably terminally unsaturated.
  • the alkenyl groups contain 2 or more, and can contain 3 or more, 4 or more 5 or more, 6 or more, even 7 or more carbon atoms while at the same time typically contain 8 or fewer, and can contain 7 or fewer, 6 or fewer, 5 or fewer, 4 or fewer, even 3 or fewer carbon atoms.
  • the alkenyl groups are selected from vinyl and allyl groups.
  • the alkene-functional silicone gum can be free of SiH groups.
  • the alkene-functional silicone gum is desirably one or any combination of more than one linear alkene- functional silicone polymer.
  • the alkene-functional silicone gum can be any one or any combination of more than one silicone gums having an average chemical formula (I):
  • R’ is a hydrocarbyl group with 2 or more, 3 or more, 4 or more, 5 or more, 6 or more, even 7 or more while at the same time 8 or fewer, 7 or fewer, 6 or fewer, 5 or fewer, 4 or fewer, even 3 or fewer carbon atoms; subscript m has an average value in a range of 20 to 10,000 and can be 20 or more 40 or more, 50 or more 100 or more, 250 or more, 500 or more, 750 or more, 1000 or more, 2000 or more, 3000 or more, 4000 or more, 5000 or more, 6000 or more, even 70000 or more while at the same time is typically 10,000 or less, 9000 or less, 8000 or less, 8000 or less, 6000 or less, 5000 or less, 1000 or less, 750 or less, even 500 or less;
  • the hydrosilylation catalyst (d) can be any known in the art.
  • the hydrosilylation catalyst can be selected from the group consisting of: (d-1) a metal selected from platinum, rhodium, ruthenium, palladium, osmium, and iridium; (d-2) a compound of the metal (d-1), (d-3). a complex of the compound (d-2) with an organopolysiloxane , and (d-4) the compound (d-2) microencapsulated in a matrix or core/shell type structure.
  • the concentration of hydrosilylation catalyst is sufficient to catalyze the curing reaction of the curable silicone release coating.
  • the concentration of hydrosilylation catalyst is one mass-part to 500 mass parts, and can be one mass part or more, 5 mass parts or more, 10 mass parts or more even 20 mass parts or more while at the same time is typically 500 mass parts or less and can be 300 mass parts or less, even 100 mass parts or less, with mass parts relative to one million mass parts of the combination of alkene-functional silicone gum (a) and SiH-functional silicone (b).
  • hydrosilylation inhibitors include those selected from the group consisting of : acetylenic alcohols; silylated acetylenic compounds; cycloalkenylsiloxanes; ene- yne compounds; triazoles; phosphines; mercaptans; hydrazines; amines; fumarates such as dialkyl fumarates, dialkenyl fumarates, and dialkoxyalkyl fumarates; maleates, nitriles, ethers, and combinations of two or more of the aforementioned materials.
  • Suitable acetylenic alcohols include dimethyl hexynol, and 3,5-dimethyl-l-hexyn-3- ol, methyl butynol such as l-butyn-3-ol, l-propyn-3-ol, 2-methyl 3-butyn-2-ol, 3-methyl-l-butyn-3-ol, 3-methyl-l-pentyn-3-ol, 3- phenyl-l-butyn-3-ol, 4-ethyl-l-octyn-3-ol , 3,5 dimethyl- l-hexyn-3-ol , and 1-ethynyl-l- cyclohexanol, and a combination thereof .
  • Suitable cycloalkenylsiloxanes include methylvinylcyclosiloxanes exemplified by 1,3, 5, 7 tetramethyl- 1 , 3,5,7- tetravinylcyclotetrasiloxane, l,3,5,7-tetramethyl-l,3,5,7-tetrahexenylcyclotetrasiloxane, combination thereof.
  • Suitable ene-yne compounds include 3-methyl-3-penten- 1-yne, 3,5- dimethyl-3-hexen-l-yne .
  • Suitable triazoles include benzotriazole .
  • Suitable amines include tetramethyl ethylenediamine.
  • MQ resins refer to resinous silicones comprising SiO.4/2 siloxane units and R’3SiOi/2 siloxane units where R’ is as defined herein above.
  • the present invention also include a method for using the curable silicone release coating composition of the present invention, wherein the method comprises applying a coating of the curable silicone release coating composition onto a substrate and then heating the coating to cure the curable silicone release coating composition.
  • the coating is applied at a temperature below 100 degrees Celsius (°C), more typically at a temperature of 80 °C or lower, 70 °C or lower, 60 °C or lower, 50 °C or lower, 40 °C or lower, even 30 °C or lower while at the same time at a temperature of greater than 0°C, typically 10 °C or higher, 20 °C or higher, even
  • Table 1 lists the materials for use in the following Samples.
  • “Hex” refers to a hexenyl group.
  • Me refers to a methyl group.
  • Vi refers to a vinyl group.
  • PFBE refers to a perfluorobutylethyl group (CF3CF2CF2CF2CH2CH2-).
  • DOWSIL is a trademark of The Dow Chemical Company.
  • S YL-OFF is a trademark of Dow Silicones Corporation.
  • TDCC refers to The Dow Chemical Company.
  • Fluorinated release agents are common in the market place. These samples compare performance of fluorinated release agents to the alkene-functional siloxane release agent of the present invention.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Paints Or Removers (AREA)

Abstract

L'invention concerne une composition de revêtement antiadhésif à base de silicone qui contient : (a) une gomme de silicone à fonction alcène ayant en moyenne au moins 2 groupes alcényle par molécule ; (b) une silicone à fonction SiH ayant en moyenne au moins 2 groupes SiH par molécule à une concentration telle que le rapport molaire des groupes SiH aux groupes alcényle de la gomme de silicone à fonction alcène est supérieur à 1,00 ; (c) plus de zéro à 10 pour cent en poids par rapport au poids de la composition de revêtement antiadhésif à base de silicone durcissable d'un additif antiadhésif à base de siloxane à fonction alcène ayant la formule chimique moyenne suivante : [(CH3)3SiO]3SiR, où R est un groupe hydrocarbyle à insaturation terminale contenant 2 à 20 atomes de carbone ; (d) un catalyseur d'hydrosilylation ; et (e) facultativement, un ou toute combinaison de plusieurs composants choisis parmi un solvant, des agents antiadhésifs supplémentaires, des inhibiteurs d'hydrosilylation, des promoteurs d'adhésion, de la silice pyrogénée et des résines MQ.
PCT/US2025/010541 2024-01-16 2025-01-07 Revêtement antiadhésif à base de silicone contenant de la silicone tris(triméthylsiloxy) à fonction alcène Pending WO2025155450A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US202463621160P 2024-01-16 2024-01-16
US63/621,160 2024-01-16

Publications (1)

Publication Number Publication Date
WO2025155450A1 true WO2025155450A1 (fr) 2025-07-24

Family

ID=94536199

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2025/010541 Pending WO2025155450A1 (fr) 2024-01-16 2025-01-07 Revêtement antiadhésif à base de silicone contenant de la silicone tris(triméthylsiloxy) à fonction alcène

Country Status (1)

Country Link
WO (1) WO2025155450A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0559575A1 (fr) * 1992-03-06 1993-09-08 Minnesota Mining And Manufacturing Company Compositions d'organosilicones
EP1603988A2 (fr) * 2003-03-17 2005-12-14 Dow Corning Corporation Adhesifs sensibles a la pression sans solvant presentant une force de cohesion amelioree a temperature elevee
US20070289495A1 (en) * 2004-11-18 2007-12-20 Dow Corning Corporation Silicone Release Coating Compositions
WO2012166870A1 (fr) * 2011-06-02 2012-12-06 Dow Corning Corporation Adhésif sensible à la pression en film épais et structure stratifiée faite de celui-ci

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0559575A1 (fr) * 1992-03-06 1993-09-08 Minnesota Mining And Manufacturing Company Compositions d'organosilicones
EP1603988A2 (fr) * 2003-03-17 2005-12-14 Dow Corning Corporation Adhesifs sensibles a la pression sans solvant presentant une force de cohesion amelioree a temperature elevee
US20070289495A1 (en) * 2004-11-18 2007-12-20 Dow Corning Corporation Silicone Release Coating Compositions
WO2012166870A1 (fr) * 2011-06-02 2012-12-06 Dow Corning Corporation Adhésif sensible à la pression en film épais et structure stratifiée faite de celui-ci

Similar Documents

Publication Publication Date Title
JP7332576B2 (ja) 感圧性接着剤ならびにその調製および使用
US6121368A (en) Silicone composition and silicone pressure sensitive adhesive formed therefrom
JP5343911B2 (ja) 無溶剤型シリコーン粘着剤用離型剤組成物及び剥離シート
TWI755447B (zh) 聚有機矽氧烷剝離型塗料及其製備和使用方法
CN111032800B (zh) 加成性有机聚硅氧烷组合物、可固化组合物和薄膜
JP7263616B2 (ja) 二重硬化性組成物
CN113874454B (zh) 聚有机硅氧烷防粘涂层及其制备和用途
EP0273705B1 (fr) Composition réticulable de silicone pour la protection anticorrosion
JP2021500417A (ja) 感圧接着剤組成物およびその調製方法ならびにフレキシブル有機発光ダイオード用途での使用
JP2508891B2 (ja) シリコ―ンゴム組成物及びその硬化物
TW202311458A (zh) 抗靜電聚矽氧離型塗層及其製備方法及用途
JPS6328931B2 (fr)
CN117412860A (zh) 含有多氟聚醚硅烷添加剂的有机硅压敏粘合剂组合物以及所述组合物的制备方法和用途
US12091548B2 (en) Curable composition for silicone pressure sensitive adhesives
JPH07166066A (ja) 一液型の無溶剤コンフォーマルコーティング
US11859111B2 (en) Silicone pressure sensitive adhesive and methods for the preparation and use thereof
JP7256286B2 (ja) 添加剤オルガノポリシロキサン組成物、硬化性組成物、及びフィルム
WO2025155450A1 (fr) Revêtement antiadhésif à base de silicone contenant de la silicone tris(triméthylsiloxy) à fonction alcène
WO2022226797A1 (fr) Adhésif silicone sensible à la pression durci par réaction d'hydrosilylation, composition et procédé pour sa préparation et son utilisation dans un dispositif d'affichage flexible
CN117321160A (zh) 包含含氟聚有机氢硅氧烷交联剂的有机硅压敏粘合剂组合物以及所述组合物的制备方法和用途
EP4010406B1 (fr) Polymère organopolysiloxane en grappes pour durcissement rapide à l'air
TWI837387B (zh) 加成硬化型聚矽氧塗佈組成物、聚矽氧硬化物及光半導體裝置
JP7742422B2 (ja) シリコーン感圧接着剤及び組成物、並びにその調製方法及びフレキシブル表示装置における使用方法
KR20220131948A (ko) 이중 경화 조성물
KR100535439B1 (ko) 실리콘 디스퍼젼 이형제 조성물

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 25704367

Country of ref document: EP

Kind code of ref document: A1