WO2020013461A1 - Oligomère de siloxane comprenant un métal organique, procédé de production d'oligomère de siloxane, composition de revêtement dur comprenant l'oligomère de siloxane, film de revêtement dur et dispositif d'affichage - Google Patents

Oligomère de siloxane comprenant un métal organique, procédé de production d'oligomère de siloxane, composition de revêtement dur comprenant l'oligomère de siloxane, film de revêtement dur et dispositif d'affichage Download PDF

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Publication number
WO2020013461A1
WO2020013461A1 PCT/KR2019/007125 KR2019007125W WO2020013461A1 WO 2020013461 A1 WO2020013461 A1 WO 2020013461A1 KR 2019007125 W KR2019007125 W KR 2019007125W WO 2020013461 A1 WO2020013461 A1 WO 2020013461A1
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WO
WIPO (PCT)
Prior art keywords
group
formula
hard coating
bis
siloxane oligomer
Prior art date
Application number
PCT/KR2019/007125
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English (en)
Korean (ko)
Inventor
신수철
백성균
홍지현
Original Assignee
㈜켐텍인터내셔날
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Publication date
Application filed by ㈜켐텍인터내셔날 filed Critical ㈜켐텍인터내셔날
Publication of WO2020013461A1 publication Critical patent/WO2020013461A1/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
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0016—Plasticisers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/15—Heterocyclic compounds having oxygen in the ring
    • C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
    • C08K5/1515—Three-membered rings
    • 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
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • 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
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/63—Additives non-macromolecular organic
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors

Definitions

  • a touch type display device commonly touches the outermost surface of the display device using a user's finger or touch pen. Therefore, the outermost surface of the touch type display device needs to have some degree of hardness while controlling the light incident on the display device. Accordingly, it is common to adopt an optical film such as a hard coating film to the outside of the display panel constituting the flat panel display device including a touch type display.
  • the tempered glass may be damaged even with slight bending because the tempered glass has a very low elasticity.
  • the problem of breaking the hard coating film made of tempered glass becomes more serious.
  • the tempered glass instead of the tempered glass, it is made of plastic materials such as polyethylene terephthalate (PET), polyethylene naphthalate (PEN), and polyimide (PI).
  • PET polyethylene terephthalate
  • PEN polyethylene naphthalate
  • PI polyimide
  • the present invention is a substrate; It is formed on the substrate, and provides a hard coating film comprising a hard coating layer made of a cured product of the above-described hard coating composition.
  • the coating layer of the film was measured by the JIS K5400 method using a pencil hardness tester (Heidon).
  • Heidon pencil hardness tester
  • the pencil used the pencil of 6B-9H by Mitsubishi.
  • the load of the pencil on the coating layer was 0.75 kg
  • the angle at which the pencil was drawn was 45 °
  • the speed at which the pencil was drawn was 60 mm / min.
  • the pencil hardness was measured using a pencil of the step below, and the maximum pencil hardness value when there is no scratch in all five evaluations are shown in Table 3 and Table 4.

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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)
  • Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Nonlinear Science (AREA)
  • Manufacturing & Machinery (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Mathematical Physics (AREA)
  • Silicon Polymers (AREA)
  • Paints Or Removers (AREA)

Abstract

La présente invention concerne un oligomère de siloxane obtenu en faisant réagir deux types de monomères de siloxane différents avec un métal organique, son procédé de production, une composition de revêtement dur comprenant l'oligomère de siloxane, un film de revêtement dur qui est un produit durci issu de la composition de revêtement dur, et un dispositif d'affichage. Le film de revêtement dur composé du produit durci de l'oligomère de siloxane, selon la présente invention, présente d'excellentes propriétés physiques telles qu'une résistance aux rayures. Ainsi, grâce à l'application du film de revêtement dur dérivé de l'oligomère de siloxane selon la présente invention à un film optique, par exemple, un film de fenêtre tel qu'une fenêtre de couverture, il est possible d'obtenir un dispositif d'affichage présentant d'excellentes propriétés physiques.
PCT/KR2019/007125 2018-07-12 2019-06-13 Oligomère de siloxane comprenant un métal organique, procédé de production d'oligomère de siloxane, composition de revêtement dur comprenant l'oligomère de siloxane, film de revêtement dur et dispositif d'affichage WO2020013461A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020180081052A KR101930729B1 (ko) 2018-07-12 2018-07-12 유기 금속을 가지는 실록산 올리고머, 실록산 올리고머의 제조 방법, 실록산 올리고머를 포함하는 하드 코팅 조성물, 하드 코팅 필름 및 디스플레이 장치
KR10-2018-0081052 2018-07-12

Publications (1)

Publication Number Publication Date
WO2020013461A1 true WO2020013461A1 (fr) 2020-01-16

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PCT/KR2019/007125 WO2020013461A1 (fr) 2018-07-12 2019-06-13 Oligomère de siloxane comprenant un métal organique, procédé de production d'oligomère de siloxane, composition de revêtement dur comprenant l'oligomère de siloxane, film de revêtement dur et dispositif d'affichage

Country Status (2)

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KR (1) KR101930729B1 (fr)
WO (1) WO2020013461A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023205123A1 (fr) * 2022-04-21 2023-10-26 Meta Platforms Technologies, Llc Additif pour loca à faible contrainte et traitement d'un loca pour coller des substrats optiques

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101930729B1 (ko) * 2018-07-12 2018-12-19 (주)켐텍인터내셔날 유기 금속을 가지는 실록산 올리고머, 실록산 올리고머의 제조 방법, 실록산 올리고머를 포함하는 하드 코팅 조성물, 하드 코팅 필름 및 디스플레이 장치
KR102606416B1 (ko) 2019-04-25 2023-11-28 삼성디스플레이 주식회사 하드 코팅층을 갖는 보호 윈도우 및 이를 포함하는 플렉서블 표시 장치

Citations (6)

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KR100831238B1 (ko) * 2005-12-01 2008-05-22 주식회사 엘지화학 중굴절 및 고굴절 실록산계 피복 조성물, 이의 제조방법,및 이로부터 제조되는 광학 렌즈
KR100882153B1 (ko) * 2001-06-29 2009-02-06 다우 코닝 도레이 캄파니 리미티드 액상 알콕시실릴-관능성 실리콘 수지, 이의 제조방법 및경화성 실리콘 수지 조성물
JP5386314B2 (ja) * 2009-01-13 2014-01-15 コリア アドバンスト インスティテュート オブ サイエンス アンド テクノロジー 透明複合体組成物
KR20170128438A (ko) * 2015-03-17 2017-11-22 바스프 에스이 신규 실록산 중합체 조성물 및 그의 용도
KR101798160B1 (ko) * 2017-05-16 2017-12-13 한국생산기술연구원 하드코팅 수지 조성물
KR101930729B1 (ko) * 2018-07-12 2018-12-19 (주)켐텍인터내셔날 유기 금속을 가지는 실록산 올리고머, 실록산 올리고머의 제조 방법, 실록산 올리고머를 포함하는 하드 코팅 조성물, 하드 코팅 필름 및 디스플레이 장치

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100882153B1 (ko) * 2001-06-29 2009-02-06 다우 코닝 도레이 캄파니 리미티드 액상 알콕시실릴-관능성 실리콘 수지, 이의 제조방법 및경화성 실리콘 수지 조성물
KR100831238B1 (ko) * 2005-12-01 2008-05-22 주식회사 엘지화학 중굴절 및 고굴절 실록산계 피복 조성물, 이의 제조방법,및 이로부터 제조되는 광학 렌즈
JP5386314B2 (ja) * 2009-01-13 2014-01-15 コリア アドバンスト インスティテュート オブ サイエンス アンド テクノロジー 透明複合体組成物
KR20170128438A (ko) * 2015-03-17 2017-11-22 바스프 에스이 신규 실록산 중합체 조성물 및 그의 용도
KR101798160B1 (ko) * 2017-05-16 2017-12-13 한국생산기술연구원 하드코팅 수지 조성물
KR101930729B1 (ko) * 2018-07-12 2018-12-19 (주)켐텍인터내셔날 유기 금속을 가지는 실록산 올리고머, 실록산 올리고머의 제조 방법, 실록산 올리고머를 포함하는 하드 코팅 조성물, 하드 코팅 필름 및 디스플레이 장치

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023205123A1 (fr) * 2022-04-21 2023-10-26 Meta Platforms Technologies, Llc Additif pour loca à faible contrainte et traitement d'un loca pour coller des substrats optiques

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