WO2023008492A1 - ハードコートフィルムおよびその製造方法、ならびにディスプレイ - Google Patents

ハードコートフィルムおよびその製造方法、ならびにディスプレイ Download PDF

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Publication number
WO2023008492A1
WO2023008492A1 PCT/JP2022/028985 JP2022028985W WO2023008492A1 WO 2023008492 A1 WO2023008492 A1 WO 2023008492A1 JP 2022028985 W JP2022028985 W JP 2022028985W WO 2023008492 A1 WO2023008492 A1 WO 2023008492A1
Authority
WO
WIPO (PCT)
Prior art keywords
hard coat
general formula
group
coat layer
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/JP2022/028985
Other languages
English (en)
French (fr)
Japanese (ja)
Inventor
文康 石黒
祐介 田口
寛人 高麗
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 JP2023538603A priority Critical patent/JPWO2023008492A1/ja
Publication of WO2023008492A1 publication Critical patent/WO2023008492A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D1/00—Processes for applying liquids or other fluent materials
    • B05D1/40—Distributing applied liquids or other fluent materials by members moving relatively to surface
    • B05D1/42—Distributing applied liquids or other fluent materials by members moving relatively to surface by non-rotary members
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
    • B05D3/02—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by baking
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
    • B05D3/04—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to gases
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
    • B05D3/06—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D5/00—Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
    • B05D7/02—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials to macromolecular substances, e.g. rubber
    • B05D7/04—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials to macromolecular substances, e.g. rubber to surfaces of films or sheets
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
    • B05D7/24—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials for applying particular liquids or other fluent materials
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/34—Layered products comprising a layer of synthetic resin comprising polyamides
    • 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
    • C08G59/00—Polycondensates 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
    • C08G59/02—Polycondensates containing more than one epoxy group per molecule
    • 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
    • C08G59/00—Polycondensates 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
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/32—Epoxy compounds containing three or more epoxy 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
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
    • G02B1/14—Protective coatings, e.g. hard coatings

Definitions

  • the hard coat film may have hard coat layers on both sides of the resin film.
  • the hard coat layer on at least one side should contain the above cured silsesquioxane compound.
  • silane compound The silane compounds represented by general formula (A) and general formulas (1) and (2) have 1 to 3 (—OR 2 ) in one molecule, and Si—OR 2 is hydrolyzed. have sex. Therefore, a silsesquioxane compound is obtained by condensation of the silane compound.
  • R 3 in general formula (A), general formula (1) and general formula (2) is preferably a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 25 carbon atoms and 7 carbon atoms.
  • a monovalent hydrocarbon group selected from the group consisting of 1 to 12 aralkyl groups. Specific examples of hydrocarbon groups include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, isopropyl, isobutyl, cyclohexyl, and ethylhexyl groups. , benzyl group, phenyl group, tolyl group, xylyl group, naphthyl group, phenethyl group and the like.
  • the silsesquioxane compound obtained by condensation of the silane compound represented by the general formula (2) has an organic group R4 having a specific chain length between the epoxy group, which is a polymerizable functional group, and the Si atom. Due to the presence of , the molecular structure has flexibility even after curing due to the reaction of epoxy groups. Therefore, the hard coat layer composed of the cured product of the silsesquioxane compound exhibits excellent flexibility (flexibility).
  • the ratio of the structure represented by general formula (5) to the total of the structure represented by general formula (5) and the structure represented by general formula (6) is higher than 0.4. Large is preferred.
  • the ratio of the structure of general formula (5) to the sum of the structure of general formula (5) and the structure of general formula (6) is more preferably 0.45 or more, more preferably 0.5 or more. As the ratio of the structure represented by formula (5) increases, the hardness of the hard coat layer 3 tends to increase, and curling of the hard coat film tends to be suppressed.
  • the total ratio of the silane compound represented by the general formula (1) and the silane compound represented by the general formula (2) to the total amount of the silane compound represented by the general formula (A) is preferably 0.4 or more. , is more preferably 0.6 or more, more preferably 0.8 or more, and may be 0.9 or more, 0.95 or more, or 1.
  • the content of the particles in the hard coat composition is preferably 100 parts by weight or less, more preferably 50 parts by weight or less, relative to 100 parts by weight of the silsesquioxane compound.
  • the hard coat composition may contain additives such as inorganic pigments, organic pigments, surface conditioners, surface modifiers, plasticizers, dispersants, wetting agents, thickeners, antifoaming agents, and UV stabilizers. good.
  • the hard coat composition may also contain a thermoplastic, thermosetting or photocurable resin material other than the silsesquioxane compound described above.
  • the hard coat composition may contain a radical polymerization initiator in addition to the photocationic polymerization initiator.
  • a top coat layer 5 may be provided on the surface of the hard coat layer 3 .
  • the scratch resistance and antifouling properties are improved.
  • the method of forming the topcoat layer 5 is not particularly limited, and includes roll coating such as bar coating, gravure coating and comma coating, die coating such as slot die coating and fountain die coating, wet methods such as spin coating, spray coating and dip coating; vacuum deposition. , sputtering, CVD, etc. can be used.
  • roll coating such as bar coating, gravure coating and comma coating
  • die coating such as slot die coating and fountain die coating
  • wet methods such as spin coating, spray coating and dip coating
  • vacuum deposition. sputtering, CVD, etc.
  • a wet method is preferred from the viewpoint of promoting hydrolysis.
  • corona treatment is preferable because the treatment can be easily performed at atmospheric pressure.
  • the corona treatment density is preferably 1 W ⁇ min/m 2 or more, more preferably 10 W ⁇ min/m 2 or more, 30 W ⁇ min/m 2 or more, 100 W ⁇ min/m 2 or more, or 500 W ⁇ min/m 2 or more. 3000 W ⁇ min/m 2 or less is preferable, and 600 W ⁇ min/m 2 or less is more preferable. If the treatment density is too low, the effect of surface treatment on improving adhesion may be insufficient, and if the treatment density is too high, the hard coat layer may deteriorate.
  • polyfluoroaromatic hydrocarbons such as bis(trifluoromethyl)benzene; perfluoropropylmethyl ether ( C3F7OCH3 ) , perfluorobutylmethylether ( C4F9OCH3 ) , perfluorobutylethylether (C 4 F 9 OC 2 H 5 ), perfluorohexylmethyl ether (C 2 F 5 CF(OCH 3 )C 3 F 7 ) and other hydrofluoroethers (HFE).
  • the perfluoroalkyl group and alkyl group of the hydrofluoroether may be linear or branched.
  • a hard coat layer formed by curing a silsesquioxane compound having an epoxy group has a hydroxyl group (silanol group) generated by hydrolysis during condensation of a silane compound, and furthermore, an epoxy group during curing. has a hydroxyl group generated with the ring opening of These hydroxyl groups are capable of a condensation reaction with alkoxysilyl groups of perfluoroalkyl compounds.
  • the silsesquioxane compound constituting the hard coat layer is an organic compound containing a Si atom, similar to the alkoxysilyl group of the perfluoro compound, and has a high affinity with each other, and the alkoxysilyl group of the silsesquioxane compound.
  • a silanol group or the like can be condensed with an alkoxysilyl group of the perfluoro compound.
  • the hard coat film including the top coat layer 5 preferably has a water contact angle of 100° or more on the surface (top coat layer 5).
  • the water contact angle is more preferably 105° or more, more preferably 110° or more.
  • a high water contact angle means high water repellency, and is also excellent in resistance to dirt such as finger oil (stain resistance).

Landscapes

  • Chemical & Material Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Plasma & Fusion (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Laminated Bodies (AREA)
  • Paints Or Removers (AREA)
PCT/JP2022/028985 2021-07-28 2022-07-27 ハードコートフィルムおよびその製造方法、ならびにディスプレイ Ceased WO2023008492A1 (ja)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2023538603A JPWO2023008492A1 (https=) 2021-07-28 2022-07-27

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
JP2021-123366 2021-07-28
JP2021123366 2021-07-28
JP2021123365 2021-07-28
JP2021-123365 2021-07-28
JP2021-128495 2021-08-04
JP2021128495 2021-08-04
JP2021128494 2021-08-04
JP2021-128494 2021-08-04

Publications (1)

Publication Number Publication Date
WO2023008492A1 true WO2023008492A1 (ja) 2023-02-02

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WO (1) WO2023008492A1 (https=)

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015087686A1 (ja) * 2013-12-13 2015-06-18 株式会社ダイセル ポリオルガノシルセスキオキサン、ハードコートフィルム、接着シート、及び積層物
WO2016204114A1 (ja) * 2015-06-17 2016-12-22 株式会社ダイセル 硬化性組成物、接着シート、硬化物、積層物、接着シートの製造方法、及び装置
JP2017008148A (ja) * 2015-06-17 2017-01-12 株式会社ダイセル ポリオルガノシルセスキオキサン、硬化性組成物、ハードコートフィルム、及び硬化物
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
JP2019147923A (ja) * 2018-02-28 2019-09-05 日鉄ケミカル＆マテリアル株式会社 シロキサン系硬化性樹脂組成物から成るハードコーティング液を用いた積層体
WO2019207957A1 (ja) * 2018-04-26 2019-10-31 富士フイルム株式会社 ハードコートフィルム、ハードコートフィルムを備えた物品、及び画像表示装置
WO2020255958A1 (ja) * 2019-06-18 2020-12-24 日本精化株式会社 樹脂基材のハードコート形成用組成物およびそれを用いた積層体

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6530027B2 (ja) * 2013-12-13 2019-06-12 株式会社ダイセル ポリオルガノシルセスキオキサン、ハードコートフィルム、接着シート、及び積層物
JP6557041B2 (ja) * 2015-03-31 2019-08-07 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
JP6595813B2 (ja) * 2015-06-17 2019-10-23 株式会社ダイセル ポリオルガノシルセスキオキサン
KR102131994B1 (ko) * 2018-05-03 2020-07-08 주식회사 엘지화학 하드 코팅 필름
WO2020019631A1 (zh) * 2018-07-27 2020-01-30 珠海格力电器股份有限公司 信号传输电路和设备
WO2020235524A1 (ja) * 2019-05-22 2020-11-26 株式会社カネカ 樹脂組成物、その製造方法、及び、多液型硬化性樹脂組成物

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015087686A1 (ja) * 2013-12-13 2015-06-18 株式会社ダイセル ポリオルガノシルセスキオキサン、ハードコートフィルム、接着シート、及び積層物
WO2016204114A1 (ja) * 2015-06-17 2016-12-22 株式会社ダイセル 硬化性組成物、接着シート、硬化物、積層物、接着シートの製造方法、及び装置
JP2017008148A (ja) * 2015-06-17 2017-01-12 株式会社ダイセル ポリオルガノシルセスキオキサン、硬化性組成物、ハードコートフィルム、及び硬化物
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
JP2019147923A (ja) * 2018-02-28 2019-09-05 日鉄ケミカル＆マテリアル株式会社 シロキサン系硬化性樹脂組成物から成るハードコーティング液を用いた積層体
WO2019207957A1 (ja) * 2018-04-26 2019-10-31 富士フイルム株式会社 ハードコートフィルム、ハードコートフィルムを備えた物品、及び画像表示装置
WO2020255958A1 (ja) * 2019-06-18 2020-12-24 日本精化株式会社 樹脂基材のハードコート形成用組成物およびそれを用いた積層体

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