WO2021153607A1 - ポリオルガノシロキサン化合物およびその製造方法、ハードコート組成物、ならびにハードコーフィルムおよびその製造方法 - Google Patents

ポリオルガノシロキサン化合物およびその製造方法、ハードコート組成物、ならびにハードコーフィルムおよびその製造方法 Download PDF

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Publication number
WO2021153607A1
WO2021153607A1 PCT/JP2021/002818 JP2021002818W WO2021153607A1 WO 2021153607 A1 WO2021153607 A1 WO 2021153607A1 JP 2021002818 W JP2021002818 W JP 2021002818W WO 2021153607 A1 WO2021153607 A1 WO 2021153607A1
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WO
WIPO (PCT)
Prior art keywords
hard coat
group
general formula
polyorganosiloxane compound
compound
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.)
Ceased
Application number
PCT/JP2021/002818
Other languages
English (en)
French (fr)
Japanese (ja)
Inventor
寛人 高麗
祐介 田口
里香 森
聡子 小松
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.)
Kaneka Corp
Original Assignee
Kaneka 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 Kaneka Corp filed Critical Kaneka Corp
Priority to JP2021574069A priority Critical patent/JP7699063B2/ja
Publication of WO2021153607A1 publication Critical patent/WO2021153607A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/02Polycondensates containing more than one epoxy group per molecule
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04Polysiloxanes
    • C08G77/14Polysiloxanes containing silicon bound to oxygen-containing groups
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04Coating
    • C08J7/046Forming abrasion-resistant coatings; Forming surface-hardening coatings
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING 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
    • C09D163/00Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING 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
    • C09D183/00Coating 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
    • C09D183/04Polysiloxanes
    • C09D183/06Polysiloxanes containing silicon bound to oxygen-containing groups
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING 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
    • C09D7/00Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40Additives
    • C09D7/60Additives non-macromolecular
    • C09D7/63Additives non-macromolecular organic

Definitions

  • a polyorganosiloxane compound obtained by condensing a silane compound having a hydrocarbon group having a specific chain length between a Si atom and an epoxy group has excellent transparency and surface after photocuring. It has been found that it has hardness and is also excellent in bending resistance.
  • the ratio of the number of structures (5) to the total number of Si atoms of the polyorganosiloxane compound is preferably 30% or more, more preferably 50% or more, further preferably 60% or more, particularly preferably 70% or more, and particularly preferably 80% or more. , 85% or more, 90% or more, or 95% or more.
  • the silane compound represented by the general formula (A) has one Si per molecule
  • the polyorganosiloxane compound produced by condensing the silane compound of N molecules contains N Si atoms.
  • the epoxy group remains unreacted during the hydrolysis and condensation reactions, n structures (5) are formed from n silane compounds (1). Therefore, in the polyorganosiloxane compound obtained by condensing the silane compound, the ratio (molar ratio: n / N) of the silane compound (1) to the silane compound used as a raw material is the structure with respect to the number of Si atoms in the polyorganosiloxane compound. It is approximately equal to the ratio of (5).
  • Examples of particles having a reactive functional group on the surface include surface-modified inorganic particles and core-shell polymer particles.
  • the thickness of the hard coat layer is preferably 0.5 ⁇ m or more, more preferably 2 ⁇ m or more, further preferably 3 ⁇ m or more, particularly preferably 5 ⁇ m or more, and may be 10 ⁇ m or more, 20 ⁇ m or more, or 30 ⁇ m or more.
  • the thickness of the hard coat layer is preferably 100 ⁇ m or less, more preferably 80 ⁇ m or less, and may be 70 ⁇ m or less.
  • Total light transmittance and haze> It was measured by the method described in JIS K7361-1: 1999 and JIS K7136: 2000 using a haze meter "HZ-V3" manufactured by Suga Test Instruments. A D65 light source was used for the measurement, and the total light transmittance was calculated as the ratio of the total transmitted light flux (parallel light component and diffused light component) to the parallel incident light flux on the hard coat film.
  • the hard coat layer forming surface is on the upper side (in the hard coat film 6, the hard coat layer formed by using the hard coat composition 1 is on the upper side), and the hard coat film is placed on a horizontal desk and placed on the hard coat layer.
  • a PET film having a thickness of 75 ⁇ m was placed and pressed for 1 second with a load of 10 N / cm 2. After unloading, visually check the presence or absence of sticking (blocking) between the hard coat layer and the PET film, and if there is no sticking at all, A, sticking occurs, but the area is loaded. The area within 30% of the area was designated as B, and the area larger than 30% was designated as C.
  • the hard coat film 13 is a polyorganosiloxane which is a condensate of a silane compound (2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane) in which a Si atom and an alicyclic epoxy group are bonded via an ethylene group.
  • a hard coat layer is formed using compound 6.
  • the hard coat film 8 in which the hard coat layer was formed using the composition 10 using the antimony-based photocationic polymerization initiator exhibited a mandrel diameter (flexibility) equivalent to that of the hard coat film 3, but the hard coat The surface hardness was lower than that of the film 3, and an increase in haze was observed after the moist heat test. From these results, the hardness and moist heat resistance (transparency after the moist heat test) of the hard coat layer can be improved by using the non-antimony-based photocationic polymerization initiator as compared with the case of using the antimony-based photopolymerization initiator. It can be seen that there is a tendency to improve.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Silicon Polymers (AREA)
  • Paints Or Removers (AREA)
PCT/JP2021/002818 2020-01-30 2021-01-27 ポリオルガノシロキサン化合物およびその製造方法、ハードコート組成物、ならびにハードコーフィルムおよびその製造方法 Ceased WO2021153607A1 (ja)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2021574069A JP7699063B2 (ja) 2020-01-30 2021-01-27 ハードコーフィルムおよびその製造方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2020014038 2020-01-30
JP2020-014038 2020-01-30

Publications (1)

Publication Number Publication Date
WO2021153607A1 true WO2021153607A1 (ja) 2021-08-05

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PCT/JP2021/002818 Ceased WO2021153607A1 (ja) 2020-01-30 2021-01-27 ポリオルガノシロキサン化合物およびその製造方法、ハードコート組成物、ならびにハードコーフィルムおよびその製造方法

Country Status (2)

Country Link
JP (1) JP7699063B2 (https=)
WO (1) WO2021153607A1 (https=)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPWO2021172200A1 (https=) * 2020-02-25 2021-09-02
CN116529661A (zh) * 2021-10-08 2023-08-01 株式会社Lg化学 用于显示装置的无基底型覆盖窗、包括其的显示装置和用于制造其的方法
WO2025206154A1 (ja) * 2024-03-27 2025-10-02 住友ベークライト株式会社 ポリカーボネート積層体

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2016193956A (ja) * 2015-03-31 2016-11-17 株式会社カネカ 光または熱硬化性樹脂組成物からなる積層体
WO2017110522A1 (ja) * 2015-12-25 2017-06-29 株式会社ニコン・エシロール ハードコート層形成用組成物、および、光学部材
JP2019056106A (ja) * 2017-09-19 2019-04-11 三洋化成工業株式会社 活性エネルギー線硬化性組成物

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2016193956A (ja) * 2015-03-31 2016-11-17 株式会社カネカ 光または熱硬化性樹脂組成物からなる積層体
WO2017110522A1 (ja) * 2015-12-25 2017-06-29 株式会社ニコン・エシロール ハードコート層形成用組成物、および、光学部材
JP2019056106A (ja) * 2017-09-19 2019-04-11 三洋化成工業株式会社 活性エネルギー線硬化性組成物

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPWO2021172200A1 (https=) * 2020-02-25 2021-09-02
JP7851239B2 (ja) 2020-02-25 2026-04-24 株式会社カネカ ハードコーフィルムおよびその製造方法
CN116529661A (zh) * 2021-10-08 2023-08-01 株式会社Lg化学 用于显示装置的无基底型覆盖窗、包括其的显示装置和用于制造其的方法
WO2025206154A1 (ja) * 2024-03-27 2025-10-02 住友ベークライト株式会社 ポリカーボネート積層体

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JP7699063B2 (ja) 2025-06-26
JPWO2021153607A1 (https=) 2021-08-05

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