WO2022186019A1 - Composition durcissable aux rayons actiniques, objet durci et film - Google Patents

Composition durcissable aux rayons actiniques, objet durci et film Download PDF

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Publication number
WO2022186019A1
WO2022186019A1 PCT/JP2022/007447 JP2022007447W WO2022186019A1 WO 2022186019 A1 WO2022186019 A1 WO 2022186019A1 JP 2022007447 W JP2022007447 W JP 2022007447W WO 2022186019 A1 WO2022186019 A1 WO 2022186019A1
Authority
WO
WIPO (PCT)
Prior art keywords
meth
acrylate
active energy
organic solvent
mass
Prior art date
Application number
PCT/JP2022/007447
Other languages
English (en)
Japanese (ja)
Inventor
尭 長野
広樹 松下
解 麸山
Original Assignee
Dic株式会社
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 Dic株式会社 filed Critical Dic株式会社
Priority to CN202280015606.5A priority Critical patent/CN116888162A/zh
Priority to JP2023503745A priority patent/JPWO2022186019A1/ja
Publication of WO2022186019A1 publication Critical patent/WO2022186019A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/04—Polymerisation in solution
    • C08F2/06—Organic solvent
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate

Definitions

  • a film having a hard coat layer is produced by curing the hard coat agent by irradiation with an active energy ray to form a hard coat layer, and then rewinding the hard coat layer.
  • energy ray-curable compositions compositions containing pentaerythritol triacrylate and dipentaerythritol hexaacrylate, which are highly crosslinked active energy ray-curable resins, as curable compounds are widely used.
  • a technique of adding an antistatic agent to the hard coating agent is generally employed.
  • a method has been proposed in which a compound having a polyoxyethylene chain and a quaternary ammonium salt is added as an antistatic agent to a hard coating agent (see, for example, Patent Document 1).
  • a method has been proposed in which two types of copolymers made from polymerizable monomers having a quaternary ammonium salt are added as antistatic agents to a hard coating agent (see, for example, Patent Document 2).
  • an active energy ray-curable compound having a specific Hansen solubility parameter hydrogen bond term, a leveling agent, and two or more specific organic solvents are used.
  • excellent antistatic performance and antifouling property can be achieved while preventing poor appearance due to quaternary ammonium salt compounds even when produced under high humidity conditions, and the present invention was completed.
  • the amount of the organic solvent (E1) is 5 to 50 parts by mass, and the amount of the organic solvent (E2) is 50 to 95 parts by mass in 100 parts by mass of the organic solvent (E).
  • Active energy ray-curable composition (2) The active energy ray-curable composition of (1), wherein the resin (B) has an alicyclic structure.
  • the Hansen solubility parameter refers to the solubility parameter introduced by Hildebrand divided into three components, the dispersion term ( ⁇ D), the polarization term ( ⁇ P), and the hydrogen bonding term ( ⁇ H). is shown in The dispersion term ( ⁇ D) indicates the effect of dispersion force, the polarization term ( ⁇ P) indicates the effect of dipole force, and the hydrogen bond term ( ⁇ H) indicates the effect of hydrogen bond force.
  • the definition and calculation of the Hansen Solubility Parameter can be found in Charles M. et al. Hansen, Hansen Solubility Parameters; A Users Handbook (CRC Press, 2007).
  • Hansen solubility parameters can be estimated from the chemical structure of organic solvents for which parameter values are not described in literature.
  • HSPiP Hansen Solubility Parameters in Practice
  • a compound (A) having a ⁇ H of 10.0 to 12.5 has moderate compatibility with a resin (B) having a quaternary ammonium salt, which will be described later.
  • a resin (B) having a quaternary ammonium salt By having moderate compatibility of these components, it is possible to prevent excessive aggregation of the resin (B) having a quaternary ammonium salt in the coating film, especially during production in a high-humidity environment. Whitening of the cured product and cured coating film due to is suppressed.
  • the antistatic properties of the resin (B) having a quaternary ammonium salt are not hindered by aggregation, and as a result, both excellent appearance and antistatic properties can be achieved.
  • the reaction between the polyisocyanate and the (meth)acrylate can be carried out by a conventional urethanization reaction. Moreover, in order to accelerate the progress of the urethanization reaction, it is preferable to carry out the urethanization reaction in the presence of a urethanization catalyst.
  • the urethanization catalyst include amine compounds such as pyridine, pyrrole, triethylamine, diethylamine, and dibutylamine; phosphorus compounds such as triphenylphosphine and triethylphosphine; dibutyltin dilaurate, octyltin trilaurate, octyltin diacetate, and dibutyltin. Diacetate, organic tin compounds such as tin octylate, organic zinc compounds such as zinc octylate, and the like.
  • Leveling agent (C) The leveling agent (C) (hereinafter sometimes referred to as “(C) component”) is used to adjust the surface tension of the coating film and smoothen the coating film surface.
  • a leveling agent By using a leveling agent, an appropriate contact angle can be obtained even when coating is performed under high humidity conditions. More specifically, the presence of the leveling agent lowers the surface tension (surface energy) of the coating film and increases the water contact angle. .
  • the presence of the leveling agent (C) on the outermost surface of the coating film suppresses excessive surface segregation and aggregation of the resin (B), and prevents deterioration of the appearance such as whitening.
  • a commercial item can also be used as a leveling agent.
  • the boiling point of the component (E2) is not particularly limited, it is preferably 110°C or lower, more preferably 100°C or lower.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polymerisation Methods In General (AREA)
  • Paints Or Removers (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

La présente invention concerne une composition durcissable aux rayons actiniques caractérisée en ce qu'elle comprend un composé durcissable aux rayons actiniques (A) présentant un paramètre de solubilité de Hansen dans lequel le terme de liaison hydrogène δH est compris entre 10,0 et 12,5, une résine (B) comprenant un sel d'ammonium quaternaire, un agent d'étalement (C), un initiateur de polymérisation (D), et des solvants organiques (E), les solvants organiques (E) comprenant un solvant organique (E1) comportant un groupe hydroxyle et un solvant organique (E2) présentant un paramètre de solubilité de Hansen dans lequel le terme de liaison hydrogène δH est inférieur ou égal à 9,0 et présentant un point d'ébullition inférieur à celui du solvant organique (E1), la quantité du solvant organique (E1) étant de 5 à 50 parties en masse et la quantité du solvant organique (E2) étant de 50 à 95 % en masse, pour 100 parties en masse du solvant organique (E).
PCT/JP2022/007447 2021-03-02 2022-02-24 Composition durcissable aux rayons actiniques, objet durci et film WO2022186019A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CN202280015606.5A CN116888162A (zh) 2021-03-02 2022-02-24 活性能量线硬化性组合物、硬化物及膜
JP2023503745A JPWO2022186019A1 (fr) 2021-03-02 2022-02-24

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2021-032419 2021-03-02
JP2021032419 2021-03-02

Publications (1)

Publication Number Publication Date
WO2022186019A1 true WO2022186019A1 (fr) 2022-09-09

Family

ID=83155085

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2022/007447 WO2022186019A1 (fr) 2021-03-02 2022-02-24 Composition durcissable aux rayons actiniques, objet durci et film

Country Status (4)

Country Link
JP (1) JPWO2022186019A1 (fr)
CN (1) CN116888162A (fr)
TW (1) TW202239789A (fr)
WO (1) WO2022186019A1 (fr)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007332181A (ja) * 2006-06-12 2007-12-27 Nippon Kasei Chem Co Ltd 帯電防止組成物、帯電防止層および帯電防止フィルム
JP2010174201A (ja) * 2009-02-02 2010-08-12 Sony Corp 帯電防止ハードコートフィルム、及び紫外線硬化性樹脂材料組成物
JP2011225796A (ja) * 2010-04-01 2011-11-10 Toyo Ink Sc Holdings Co Ltd 帯電防止コーティング用組成物
JP2013177509A (ja) * 2012-02-28 2013-09-09 Toyo Ink Sc Holdings Co Ltd 帯電防止コーティング用組成物
WO2018003294A1 (fr) * 2016-06-27 2018-01-04 Dic株式会社 Composition durcissable par rayonnement d'énergie active, et film mettant en œuvre celle-ci
JP2019073616A (ja) * 2017-10-16 2019-05-16 Dic株式会社 活性エネルギー線硬化性組成物及びそれを用いたフィルム

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111732887A (zh) * 2020-06-24 2020-10-02 邦弗特(东莞)新材料有限公司 一种溶剂型喷涂光固化抗菌涂料及其制备方法和应用

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007332181A (ja) * 2006-06-12 2007-12-27 Nippon Kasei Chem Co Ltd 帯電防止組成物、帯電防止層および帯電防止フィルム
JP2010174201A (ja) * 2009-02-02 2010-08-12 Sony Corp 帯電防止ハードコートフィルム、及び紫外線硬化性樹脂材料組成物
JP2011225796A (ja) * 2010-04-01 2011-11-10 Toyo Ink Sc Holdings Co Ltd 帯電防止コーティング用組成物
JP2013177509A (ja) * 2012-02-28 2013-09-09 Toyo Ink Sc Holdings Co Ltd 帯電防止コーティング用組成物
WO2018003294A1 (fr) * 2016-06-27 2018-01-04 Dic株式会社 Composition durcissable par rayonnement d'énergie active, et film mettant en œuvre celle-ci
JP2019073616A (ja) * 2017-10-16 2019-05-16 Dic株式会社 活性エネルギー線硬化性組成物及びそれを用いたフィルム

Also Published As

Publication number Publication date
JPWO2022186019A1 (fr) 2022-09-09
CN116888162A (zh) 2023-10-13
TW202239789A (zh) 2022-10-16

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