WO2017069383A1 - Composition adhésive à base de silicone - Google Patents

Composition adhésive à base de silicone Download PDF

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Publication number
WO2017069383A1
WO2017069383A1 PCT/KR2016/007452 KR2016007452W WO2017069383A1 WO 2017069383 A1 WO2017069383 A1 WO 2017069383A1 KR 2016007452 W KR2016007452 W KR 2016007452W WO 2017069383 A1 WO2017069383 A1 WO 2017069383A1
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WO
WIPO (PCT)
Prior art keywords
group
sensitive adhesive
adhesive composition
silicone pressure
organopolysiloxane
Prior art date
Application number
PCT/KR2016/007452
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English (en)
Korean (ko)
Inventor
최한영
유병묵
Original Assignee
동우 화인켐 주식회사
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Application filed by 동우 화인켐 주식회사 filed Critical 동우 화인켐 주식회사
Publication of WO2017069383A1 publication Critical patent/WO2017069383A1/fr

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    • 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
    • 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
    • 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
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers

Definitions

  • the present invention relates to a silicone pressure-sensitive adhesive composition, and more particularly, to an organopolysiloxane including a vinylsilane group, an organopolysiloxane including a hydrosilyl group and an addition reaction catalyst, and an organopolysiloxane and hydrosilyl including the vinylsilane group.
  • an organopolysiloxane comprising a group relates to a silicone pressure sensitive adhesive composition comprising an epoxy group.
  • An adhesive is one kind of adhesive, and is often used in the form of an adhesive tape, an adhesive label, etc. which apply
  • These articles are used for various purposes, such as used for labels for identifying articles, for packing bags, or for connecting a plurality of things together.
  • Rubber-based pressure-sensitive adhesives are a general-purpose base material that has been used for a long time, and are used for products such as general-purpose tapes with low cost.
  • the acrylic pressure sensitive adhesive uses polyacrylate as a base, and can be applied to pressure sensitive adhesive products having a higher function than rubber in that chemical properties and the like are superior to rubber.
  • the silicone pressure sensitive adhesive includes high viscosity silicone raw rubber (gum) and silicone resin, and has various excellent characteristics in that the main chain has a plurality of siloxane bonds, and specifically, heat resistance, cold resistance, weather resistance, chemical resistance, electrical insulation, etc. Can be mentioned.
  • the silicone pressure-sensitive adhesive is used for high-performance tapes for industrial use such as heat-resistant tapes, process masking tapes, and mica tapes having flame retardancy by utilizing the excellent properties as described above. It is used.
  • silicone adhesives are rapidly expanding, and the cause thereof is the expansion of the product market employing a touch panel mounted on a smartphone, a tablet terminal, or the like.
  • the touch panel is bonded to a screen protection film in order to prevent contamination or scratches of the display since it is directly operated by a human finger.
  • Most of the silicone pressure sensitive adhesives used in the pressure-sensitive adhesive layer of the screen protective film are made of the characteristics of the wettability and the rework property of the excellent adherend of the silicone pressure sensitive adhesive.
  • the base material used for a screen protection film is a plastic film, and many polyester films, such as PET, which have transparency are used.
  • the plastic film is considered to be inferior to adhesiveness with an adhesive compared with a paper base material. This is considered to be because the plastic film has a flat surface and a weak anchoring effect in which the adhesive penetrates into the substrate as compared with paper having a large unevenness.
  • adhesiveness is bad, a problem may arise that an adhesive layer transfers to a to-be-adhered body when peeling after a time passes by adhering to a back surface or adhering to a to-be-adhered body when winding up with a roll.
  • Conventional silicone pressure-sensitive adhesive composition improved the cohesive force by using the MQ resin, thereby improving the cohesive force.
  • the elastic modulus is increased to harden the silicone pressure-sensitive adhesive composition, and thus, when the substrate to which the silicone pressure-sensitive adhesive composition is applied is bent, cracks may occur.
  • an object of the present invention is to provide a silicone pressure-sensitive adhesive composition excellent in adhesive strength by improving the softness and adhesion while low elastic modulus to solve the above problems.
  • an object of this invention is to provide the silicone adhesive composition excellent in peeling resistance.
  • the present invention is an organopolysiloxane comprising a vinylsilane group;
  • a silicone pressure sensitive adhesive composition comprising an organopolysiloxane comprising a hydrosilyl group and an addition reaction catalyst,
  • At least one or more of the organopolysiloxane including the vinylsilane group and the organopolysiloxane including the hydrosilyl group further provides a silicone pressure-sensitive adhesive composition comprising an epoxy group.
  • the present invention provides a silicone pressure-sensitive adhesive prepared from the silicone pressure-sensitive adhesive composition of the present invention.
  • the present invention provides a film coated with the silicone pressure-sensitive adhesive.
  • the silicone pressure-sensitive adhesive composition of the present invention has a low elastic modulus and excellent adhesive force.
  • the silicone pressure-sensitive adhesive composition of the present invention has an effect of excellent adhesion to the substrate.
  • FIG. 1 is a view showing a folding characteristic evaluation method of a substrate coated with a silicone pressure-sensitive adhesive composition.
  • the present invention is an organopolysiloxane comprising a vinylsilane group;
  • a silicone pressure sensitive adhesive composition comprising an organopolysiloxane comprising a hydrosilyl group and an addition reaction catalyst,
  • At least one or more of the organopolysiloxane including the vinylsilane group and the organopolysiloxane including the hydrosilyl group further relates to a silicone pressure-sensitive adhesive composition comprising an epoxy group.
  • Conventional silicone pressure-sensitive adhesive composition has increased the adhesive strength with the substrate by increasing the elastic modulus, and in order to increase the elastic modulus, MQ resin is added to the silicone pressure-sensitive adhesive composition or a technique of improving the crosslinking density is used.
  • the composition when the elastic modulus is high, the composition is hardened, so that a crack occurs when the silicone pressure-sensitive adhesive composition is applied to the substrate and the substrate is bent.
  • At least one or more of the organopolysiloxane including the vinylsilane group and the organopolysiloxane including the hydrosilyl group includes an epoxy group without adding a MQ resin or using a technique of increasing the crosslinking density.
  • coated is a board
  • a cycloolefin polymer (CycloOlefinPolymer, COP) having a carboxyl group introduced on the surface by corona treatment or triacetate cellulose (TAC) having a hydroxyl group on the surface may be used as a substrate.
  • CycloOlefinPolymer COP
  • TAC triacetate cellulose
  • the organopolysiloxane including the vinylsilane group serves as a main body of the silicone pressure sensitive adhesive composition, and the organopolysiloxane including the hydrosilyl group serves as a crosslinking agent of the silicone pressure sensitive adhesive composition.
  • the addition of the organopolysiloxane including the hydrosilyl group and the organopolysiloxane including the vinylsilane group causes an addition reaction to be connected to each other.
  • the elastic modulus is low because the epoxy group and the carboxyl group or the hydroxyl group of the substrate are connected, and thus adhesion to the substrate.
  • This very excellent silicone adhesive composition can be provided.
  • the organopolysiloxane comprising a vinylsilane group further comprises an epoxy group
  • the organopolysiloxane comprising a hydrosilyl group may or may not contain an epoxy group.
  • the organopolysiloxane containing a hydrosilyl group further contains an epoxy group
  • the organopolysiloxane including a vinylsilane group may or may not contain an epoxy group.
  • silicone pressure-sensitive adhesive composition of the present invention will be described in detail for each component.
  • the organopolysiloxane including the vinylsilane group which is one component of the silicone pressure sensitive adhesive composition of the present invention is a component that serves as a main component of the silicone pressure sensitive adhesive composition.
  • the organopolysiloxane including the vinylsilane group includes Si—CH ⁇ CH 2 groups, wherein Si—CH ⁇ CH 2 may be included in the terminal or molecule of the organopolysiloxane, and the position of the vinylsilane group and
  • the kind of organopolysiloxane containing a vinylsilane group is not specifically limited.
  • the organopolysiloxane including the vinylsilane group may preferably include one or more selected from the group consisting of the following Chemical Formulas 1 to 3.
  • N, m, p, q and r are each independently an integer of 1 to 1000,
  • the ratio of the p unit and m unit is 100: 1 to 10: 1,
  • the ratio of the q unit and the r unit is 100: 1 to 10: 1.
  • the vinyl group of the organopolysiloxane including the vinylsilane group may cause an addition reaction with the organopolysiloxane (C) including a hydrosilyl group due to the addition reaction catalyst (C) described below to connect the two compounds.
  • the organopolysiloxane including the vinylsilane group may further include an epoxy group. If the organopolysiloxane containing a hydrosilyl group does not include an epoxy group, the organopolysiloxane including the vinylsilane group must include an epoxy group, and if the organopolysiloxane including a hydrosilyl group includes an epoxy group, the vinyl The organopolysiloxane containing a silane group may or may not contain an epoxy group.
  • the silicone pressure-sensitive adhesive composition of the present invention may exhibit very excellent adhesion to the substrate.
  • the compound of Formula 5 may be included.
  • a and b are each independently an integer of 1 to 1000,
  • the ratio of the a unit and the b unit is 100: 1 to 10: 1.
  • the ratio of the a unit and the b unit is less than 10: 1, the content of the dimethylsilyl group is relatively small, there is a problem that the modulus of elasticity rises, and if it exceeds 100: 1, there is a lack of adhesion and the effect of improving adhesion It may be incomplete.
  • the organopolysiloxane including the vinylsilane group is included in 45 to 90% by weight, preferably 60 to 80% by weight relative to the total weight of the silicone pressure-sensitive adhesive composition of the present invention.
  • organopolysiloxane including the vinylsilane group is included in the range of 45 to 90% by weight, it is possible to express low modulus and high adhesion.
  • the organopolysiloxane including a hydrosilyl group as one component of the silicone pressure sensitive adhesive composition of the present invention is a component that serves as a crosslinking agent of the silicone pressure sensitive adhesive composition.
  • the organopolysiloxane including the hydrosilyl group includes a Si-H group
  • the organopolysiloxane including the hydrosilyl group is not particularly limited, but preferably, the compound of Formula 4 It may include.
  • X is an integer from 1 to 1000.
  • the organopolysiloxane including the hydrosilyl group may be reacted with the organopolysiloxane (A) including the vinylsilane group described above due to the addition reaction catalyst (C) described later to connect the two compounds.
  • the organopolysiloxane including the hydrosilyl group may further include an epoxy group. If the organopolysiloxane including the vinylsilane group does not include an epoxy group, the organopolysiloxane including the hydrosilyl group must include an epoxy group, and if the organopolysiloxane including the vinylsilane group includes an epoxy group, the hydro The organopolysiloxane containing a silyl group may or may not contain an epoxy group.
  • the silicone pressure-sensitive adhesive composition of the present invention may exhibit very excellent adhesion to the substrate.
  • the organopolysiloxane including the hydrosilyl group includes an epoxy group
  • the compound of Formula 6 may be included.
  • C and d are each independently an integer of 1 to 1000,
  • the ratio of c unit and d unit is 100: 1 to 10: 1.
  • the ratio of the c unit and d unit is less than 10: 1, the content of the dimethylsilyl group is relatively small, there is a problem that the modulus of elasticity is increased, if the ratio of more than 100: 1, the adhesion strength improvement effect is insufficient due to the lack of adhesion It may be incomplete.
  • the organopolysiloxane including the hydrosilyl group is included in 5 to 50% by weight, preferably 15 to 25% by weight based on the total weight of the silicone pressure-sensitive adhesive composition of the present invention.
  • the organopolysiloxane including the hydrosilyl group is included in the range of 5 to 50% by weight, the elastic modulus is low and the adhesive force is easily expressed.
  • the effect of improving the adhesive strength is insufficient due to the decrease in the concentration of the hydrosilyl group, if more than 50% by weight may cause a problem that the release peel force is increased.
  • the addition reaction catalyst which is one component of the silicone pressure-sensitive adhesive composition of the present invention is a catalyst causing the addition reaction of the organopolysiloxane (A) including the vinylsilane group and the organopolysiloxane (B) including the hydrosilyl group.
  • the addition reaction catalyst is a platinum group metal catalyst, and is selected from the group consisting of platinum (Pt), palladium (Pd), iridium (Ir), rhodium (Rh), osmium (Os), and ruthenium (Ru) as a central metal. It contains the above, Preferably it contains platinum (Pt).
  • the addition reaction catalyst is included in an amount of 0.01 to 5% by weight, preferably 0.05 to 0.5% by weight based on the total weight of the silicone pressure-sensitive adhesive composition of the present invention.
  • the silicone pressure-sensitive adhesive composition of the present invention may further include a solvent, and the silicone pressure-sensitive adhesive composition may be dissolved in the solvent, the solution may be applied to a substrate, heated and dried to form a silicone pressure-sensitive adhesive layer.
  • An aromatic hydrocarbon type an aliphatic hydrocarbon type, a ketone type solvent, etc. can be used for the said solvent, Preferably, toluene is used also in an aromatic hydrocarbon type.
  • the present invention provides a silicone pressure-sensitive adhesive prepared from the silicone pressure-sensitive adhesive composition of the present invention.
  • the silicone pressure-sensitive adhesive composition of the present invention has a low elastic modulus and excellent adhesion, it can be said that the silicone pressure-sensitive adhesive of the present invention has the same characteristics as described above.
  • the silicone pressure-sensitive adhesive of the present invention is applied to a substrate containing a carboxyl group or a hydroxyl group on the surface, the epoxy group contained in the organopolysiloxane of the silicone pressure-sensitive adhesive composition of the present invention is connected by reacting with a carboxyl group or a hydroxyl group on the surface of the substrate, Adhesion with the substrate is very excellent, it can provide a silicone adhesive with excellent adhesion.
  • the present invention may provide a film to which the silicone pressure-sensitive adhesive of the present invention is applied, and the film has an effect of not causing cracks when bent.
  • octamethylcyclotetrasiloxane 150.0 g of octamethylcyclotetrasiloxane, 5 g of tetramethyldivinyldisiloxane, 10 g of glycidoxypropyldimethoxymethylsilane (KBM-402) are mixed, and tetramethylammonium hydroxide (TMAH; tetramethylammonium hydroxide) 0.5 as a catalyst.
  • TMAH tetramethylammonium hydroxide
  • Organopolysiloxane of Chemical Formula 6 in the form of an oil in the same manner as in Preparation Example 1, except that 20 g of tetramethyldihydrodivinylsiloxane was used instead of 5 g of tetramethyldivinyldisiloxane of Preparation Example 1. A resin was obtained.
  • Organopolysiloxanes comprising vinylsilane groups and epoxy groups:
  • Organopolysiloxanes comprising hydrosilyl groups and epoxy groups:
  • the silicone adhesive compositions of Examples 1 to 6 and Comparative Examples 1 to 4 were coated (optically clear adhesive, OCA), dried at 120 ° C. for 3 minutes, and then adhered to silicone. A layer was formed.
  • the release film was removed. Using a double-sided pressure-sensitive adhesive on the top of the release film was bonded a saponified TAC (TriAcetyl Cellulose) film fixed on the glass.
  • TAC TriAcetyl Cellulose
  • the bonded sample (TAC / OCA / PI) was left at room temperature for 24 hours, and then peeled at 180 ° using an autograph to measure the peel force, and the results are shown in Table 2 below.
  • the silicone pressure-sensitive adhesive composition of Comparative Examples 1 to 4 was relatively excellent in the occurrence of cracks, the adhesion was very weak, it was confirmed that the peeling occurs easily.
  • the silicone pressure-sensitive adhesive composition of the present invention is very excellent in adhesion, thereby exhibiting excellent peeling resistance, has a low elastic modulus has the effect of preventing the occurrence of cracking of the substrate.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

La présente invention concerne une composition adhésive à base de silicone contenant : un organopolysiloxane comprenant un groupe vinylsilane ; un organopolysiloxane comprenant un groupe hydrosilyle ; et un catalyseur de réaction d'addition, caractérisée en ce que l'organopolysiloxane comprenant un groupe vinylsilane et/ou l'organopolysiloxane comprenant un groupe hydrosilyle comprennent un groupe époxy. La composition adhésive à base de silicone selon l'invention a un bas module d'élasticité et une excellente force d'adhérence.
PCT/KR2016/007452 2015-10-23 2016-07-08 Composition adhésive à base de silicone WO2017069383A1 (fr)

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KR1020150147771A KR20170047540A (ko) 2015-10-23 2015-10-23 실리콘 점착제 조성물
KR10-2015-0147771 2015-10-23

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WO2017069383A1 true WO2017069383A1 (fr) 2017-04-27

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Publication number Priority date Publication date Assignee Title
KR102240003B1 (ko) 2019-11-22 2021-04-14 한국신발피혁연구원 응집성과 기재 밀착성이 우수한 실리콘 점착제 조성물 및 이를 이용하여 제조되는 실리콘 점착시트
KR102512239B1 (ko) * 2020-12-28 2023-03-21 주식회사 에이치알에스 실리콘 점착 코팅용 조성물 및 이를 포함하는 점착 필름

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4721764A (en) * 1986-04-02 1988-01-26 Shin Etsu Chemical Co., Ltd. Curable organopolysiloxane composition
KR20110084601A (ko) * 2010-01-18 2011-07-26 한국과학기술원 엘이디 봉지재용 실록산 수지 조성물
KR101080156B1 (ko) * 2011-07-27 2011-11-07 (주)에버텍엔터프라이즈 반도체 장치용 폴리유기실리콘 조성물
KR101136888B1 (ko) * 2011-07-27 2012-04-20 (주)에버텍엔터프라이즈 발광 다이오드용 폴리유기실리콘 조성물
KR20150105636A (ko) * 2013-01-29 2015-09-17 주식회사 케이씨씨 반도체칩 접착용 실리콘 고무 조성물

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4721764A (en) * 1986-04-02 1988-01-26 Shin Etsu Chemical Co., Ltd. Curable organopolysiloxane composition
KR20110084601A (ko) * 2010-01-18 2011-07-26 한국과학기술원 엘이디 봉지재용 실록산 수지 조성물
KR101080156B1 (ko) * 2011-07-27 2011-11-07 (주)에버텍엔터프라이즈 반도체 장치용 폴리유기실리콘 조성물
KR101136888B1 (ko) * 2011-07-27 2012-04-20 (주)에버텍엔터프라이즈 발광 다이오드용 폴리유기실리콘 조성물
KR20150105636A (ko) * 2013-01-29 2015-09-17 주식회사 케이씨씨 반도체칩 접착용 실리콘 고무 조성물

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