WO2022124202A1 - Composition, composition durcissable et produit durci - Google Patents

Composition, composition durcissable et produit durci Download PDF

Info

Publication number
WO2022124202A1
WO2022124202A1 PCT/JP2021/044350 JP2021044350W WO2022124202A1 WO 2022124202 A1 WO2022124202 A1 WO 2022124202A1 JP 2021044350 W JP2021044350 W JP 2021044350W WO 2022124202 A1 WO2022124202 A1 WO 2022124202A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
meth
formula
particles
composition
Prior art date
Application number
PCT/JP2021/044350
Other languages
English (en)
Japanese (ja)
Inventor
直也 加藤
大樹 野口
隆司 福本
Original Assignee
株式会社クラレ
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 株式会社クラレ filed Critical 株式会社クラレ
Priority to JP2022568237A priority Critical patent/JPWO2022124202A1/ja
Publication of WO2022124202A1 publication Critical patent/WO2022124202A1/fr

Links

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
    • C08F2/44—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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or 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 of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters

Definitions

  • the present invention relates to a composition containing a copolymer having an unsaturated double bond, a curable composition containing the above composition, and a cured product obtained by curing the above curable composition.
  • Various fine particles may be added to the coating agent forming the coating film in order to impart the desired function and design to the base material. Therefore, the coating agent needs to disperse the fine particles well and stabilize the dispersed state.
  • a method for dispersing the fine particles a method of surface-treating the fine particles with a reactive silane coupling agent (see Patent Document 1), a method of using a dispersant (see Patent Document 2), and the like are known.
  • the method of surface-treating the fine particles with a reactive silane coupling agent can improve the dispersibility of the fine particles, and can improve the hardness, scratch resistance, and transparency of the cured product.
  • this method has a problem that the surface treatment step and the steps such as distillation of by-products and solvent replacement after the treatment are complicated.
  • the method using a dispersant has a problem that bleed-out of the dispersant is likely to occur after curing, and bleed-out causes deterioration of physical properties such as hardness, scratch resistance, transparency, solvent resistance, and water resistance. rice field.
  • Patent Document 3 describes a reactive dispersant for metal oxide fine particles obtained by adding a carboxyl group-containing (meth) acrylic compound to a vinyl compound polymer having an epoxy group.
  • Patent Document 4 describes a reactive dispersant for a non-aqueous dispersion medium having a polymerizable unsaturated functional group at one end of an oxyalkylene chain and an acidic polar functional group at the other end.
  • Patent Document 5 describes a phosphoric acid ester having a (meth) acryloyl group as an inorganic fine particle dispersant.
  • the gelation of the composition proceeds by the cross-linking reaction of the polymerizable group.
  • the gelation it is necessary to blow air, add a polymerization inhibitor, etc. in the post-denaturation reaction step, and as a result, there is a problem that the step becomes complicated.
  • the present invention contains a dispersant that suppresses gelation during preparation and has excellent polymerization stability, and is a composition capable of giving a cured product having excellent particle dispersibility and excellent hardness and solvent resistance. It is an object of the present invention to provide a composition as well as a cured product.
  • the present inventors have found that a copolymer containing a specific structure having an unsaturated double bond is excellent in polymerization stability because gelation is suppressed during preparation.
  • a composition showing excellent particle dispersibility can be obtained, and when the curable composition containing the above composition is cured, the cured product has excellent hardness and solvent resistance. , which led to the present invention. That is, the present invention is as follows.
  • R 1 is selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, and an aralkyl group having 7 to 18 carbon atoms.
  • R 2 represents a hydrogen atom or a methyl group.
  • n is an arbitrary integer from 1 to 5.
  • X represents any one selected from the group consisting of the formula (x1), the formula (x2), and the formula ( x3 ) shown below, and R3 represents a hydrogen atom or a methyl group.
  • Y is an amino group, a quaternary ammonium salt, a carboxy group, a carboxylate, a hydroxy group, a sulfo group, a sulfonate, a sulfate ester group, a sulfate ester salt, and a phosphoric acid.
  • Z represents O (oxygen atom) or NH (amino group).
  • R4 represents a linking group consisting of an aliphatic hydrocarbon having 1 to 10 carbon atoms, and the linking group may be branched, and any carbon atom is a phosphate ester salt, a quaternary ammonium salt, and a hydroxyl group. It may be substituted with any of the group consisting of bonded carbon atoms.
  • m and p independently represent 0 or 1, respectively.
  • q represents any integer from 5 to 30.
  • ⁇ represents a joint.
  • [2] The composition according to [1], further comprising a solvent.
  • [3] The composition according to [1] or [2], wherein R 1 is a methyl group and n is 1 in the general formula (I).
  • X is the formula (x1) in the general formula (II).
  • R4 is a linking group composed of an aliphatic hydrocarbon having 1 to 5 carbon atoms in the above formula (x1).
  • Z is O (oxygen atom) in the above formula (x1).
  • Y is a carboxylate or a quaternary ammonium salt in the formulas (x1) and (x2).
  • a curable composition comprising the composition according to any one of [1] to [9], a radical polymerization initiator, and a polyfunctional radically polymerizable compound.
  • a composition and curing which contain a dispersant which suppresses gelation at the time of preparation and has excellent polymerization stability can give a cured product having excellent particle dispersibility, hardness and solvent resistance.
  • a sex composition as well as a cured product can be provided.
  • composition of this embodiment contains a copolymer and particles (hereinafter, also simply referred to as “composition”).
  • the copolymer contained in the composition of the present embodiment is excellent in polymerization stability because gelation is suppressed at the time of preparation.
  • a reactive dispersant hereinafter, also simply referred to as “dispersant”
  • the composition of the present embodiment is a fine particle dispersion liquid containing a copolymer and fine particles which are particularly fine particles.
  • the copolymer is a structural unit represented by the following general formula (I) (hereinafter, also referred to as “structural unit (I)”) and a structural unit represented by the following general formula (II) (hereinafter, “structural unit (hereinafter,“ structural unit (I) ”). II) ”is also included. Since the copolymer contains the structural unit (I), gelation is suppressed when the copolymer is prepared, and the polymerization stability is excellent. When the copolymer contains the structural unit (II), a composition having excellent particle dispersibility can be obtained. Further, since the copolymer has a polymerizable group, the cured product described later has excellent hardness and solvent resistance.
  • the structural unit (I) contributes to the formation of a uniform cured product, and the structural unit (II) disperses the particles well. Therefore, when the composition is used as a coating agent, the desired function and design property of the substrate can be obtained. It is expected that a cured film that imparts the above can be formed. Therefore, the copolymer is suitable as a dispersant used in a fine particle dispersion such as a coating agent.
  • R 1 represents any one selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, and an aralkyl group having 7 to 18 carbon atoms. ..
  • the alkyl group having 1 to 18 carbon atoms represented by R 1 is preferably an alkyl group having 1 to 10 carbon atoms, and more preferably an alkyl group having 1 to 6 carbon atoms.
  • the alkenyl group having 2 to 18 carbon atoms represented by R 1 is preferably an alkenyl group having 2 to 10 carbon atoms, and more preferably an alkenyl group having 2 to 6 carbon atoms.
  • Specific examples thereof include a vinyl group, an allyl group, a propenyl group, an isopropenyl group, a butenyl group, an isobutenyl group, a pentenyl group, a hexenyl group (cis-3-hexenyl group and the like), a cyclohexenyl group and the like.
  • the aralkyl group having 7 to 18 carbon atoms represented by R 1 is preferably an aralkyl group having 7 to 14 carbon atoms. Specific examples thereof include a benzyl group, a 2-phenylethyl group, a 2-naphthylethyl group, a diphenylmethyl group and the like.
  • R 1 is selected from the group of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, and an alkenyl group having 2 to 6 carbon atoms. Is preferable, it is more preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, further preferably a hydrogen atom or a methyl group, and even more preferably a methyl group.
  • R 2 represents a hydrogen atom or a methyl group. From the viewpoint of improving the hardness of the obtained cured product, R2 is preferably a methyl group.
  • n is an arbitrary integer from 1 to 5. From the viewpoint of improving the hardness of the obtained cured product, n is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.
  • the structural unit (I) uses, for example, a compound obtained by reacting (meth) acrylic acid with an alcohol having a corresponding unsaturated double bond in a known esterification reaction as a monomer, and polymerizes the compound.
  • a compound obtained by reacting (meth) acrylic acid with an alcohol having a corresponding unsaturated double bond in a known esterification reaction as a monomer, and polymerizes the compound.
  • the ratio of the structural unit (I) in the copolymer is preferably 1 to 40 mol%, more preferably 3 to 25 mol%, and 5 to 15 mol%. % Is more preferable.
  • X represents any one selected from the group consisting of the following formula (x1), formula (x2), and formula (x3). From the viewpoint of improving the dispersibility of the particles, X is preferably the formula (x1) or the formula (x2), and more preferably the formula (x1).
  • Y is an amino group, a quaternary ammonium salt, a carboxy group, a carboxylate, a hydroxy group, a sulfo group, a sulfonate, a sulfate ester group, a sulfate ester salt, and a phosphoric acid.
  • Y is one selected from the group consisting of a quaternary ammonium salt, a carboxylate, a sulfonate, a sulfate ester salt, a phosphate salt, and a phosphate ester salt. Is preferable, and a quaternary ammonium salt or a carboxylate is more preferable.
  • Z represents O (oxygen atom) or NH (amino group), and is preferably O (oxygen atom).
  • R4 represents a linking group composed of an aliphatic hydrocarbon having 1 to 10 carbon atoms.
  • the linking group may be branched, and any carbon atom may be substituted with any one of a group consisting of a phosphate ester salt, a quaternary ammonium salt, and a carbon atom to which a hydroxyl group is bonded.
  • R4 is preferably a linking group composed of an aliphatic hydrocarbon having 1 to 5 carbon atoms.
  • m and p independently represent 0 or 1, respectively. It is preferable that m and p are both 0 and both are 1.
  • q represents an arbitrary integer of 5 to 30, and is preferably 8 to 22.
  • ⁇ represents a joint.
  • the structural unit (II) is, for example, quaternary ammonium salt-containing (meth) acrylates, (meth) acrylic acids, (meth) acrylamides, betaine monomers, hydroxy group-containing (meth) acrylates, styrenes, and polyethylene. It can be obtained by polymerizing glycol (meth) acrylates and the like. From the viewpoint of particle dispersibility, a group consisting of quaternary ammonium salt-containing (meth) acrylates, (meth) acrylic acids, (meth) acrylamides, betaine monomers, hydroxy group-containing (meth) acrylates, and styrenes. It is preferable to use any one selected from the above, and it is more preferable to use quaternary ammonium salt-containing (meth) acrylates or (meth) acrylic acids.
  • Examples of quaternary ammonium salt-containing (meth) acrylates include methacryloylcholine chloride, 2-hydroxy-3 (meth) acryloyloxypropyltrimethylammonium chloride, 2-hydroxy-3 (meth) acryloyloxypropyltriethanolammonium chloride, and 2-. Examples thereof include hydroxy-3 (meth) acryloyloxypropyldimethylbenzylammonium chloride and 2-hydroxy-3 (meth) acryloyloxypropyldimethylphenylammonium chloride.
  • the quaternary ammonium salt-containing (meth) acrylates those having a chloride ion as a counter ion are mentioned above, but the counter ion is a bromide ion, an iodide ion, a fluoride ion, a sulfate ion, a hydrogen sulfate ion, and the like. It may be another ion such as nitrate ion, phosphate ion, hydrogen phosphate ion, dihydrogen phosphate ion, benzenesulfonic acid ion, and hydroxide ion.
  • (meth) acrylic acids examples include ammonium methacrylic acid, ammonium acrylate and the like.
  • the (meth) acrylic acids those having an ammonium ion as a counterion are mentioned above, but they may be other ions such as alkanolammonium ion, sodium ion, and potassium ion.
  • Examples of (meth) acrylamides include acrylamide, methacrylamide, 3- (acrylamide propyl) trimethylammonium chloride, 3-[(3-acrylamide propyl) (dimethyl) ammonio] propan-1-sulfonate, N, N-dimethylacrylamide, Examples thereof include N, N-dimethylaminopropylacrylamide, acryloylmorpholine, N-isopropylacrylamide, N, N-diethylacrylamide, N-hydroxyethylacrylamide, N-hydroxyethylmethacrylate and the like.
  • betaine monomers include N, N-dimethyl-N- (2-methacryloxyethyl) -N- (3-sulfopropyl) ammonium betaine, 2-methacryloyloxyethyl phosphorylcholine, 2-[2- (methacryloxy).
  • hydroxy group-containing (meth) acrylates examples include 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, 3-hydroxypropyl methacrylate, 3-hydroxypropyl methacrylate, 4-hydroxybutyl methacrylate, 4-hydroxybutyl acrylate and the like.
  • styrenes examples include sodium p-styrene sulfonate, p-vinylbenzoic acid, p-vinylaniline and the like.
  • the ratio of the structural unit (II) in the copolymer is preferably 1 to 80 mol%, more preferably 3 to 60 mol%, and 5 to 30. It is more preferably mol%, and even more preferably 10 to 20 mol%.
  • the copolymer may contain structural units derived from other radically polymerizable monomers other than the structural unit (I) and the structural unit (II).
  • the structural unit derived from the monomer constituting the copolymer is a copolymer composed of the structural unit (I), the structural unit (II), and the structural unit derived from the radically polymerizable monomer. It is one of the embodiments.
  • Examples of the vinyl monomer include styrene, 2-methylstyrene, vinyl acetate, vinyl chloride and the like.
  • Examples of the alkyl (meth) acrylate include methyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, pentyl (meth) acrylate, hexyl (meth) acrylate, and 2-ethylhexyl (meth) acrylate.
  • Examples of the (meth) acrylic acid ester having a cyclic structure include cyclohexyl (meth) acrylate, dicyclopentanyl (meth) acrylate, dicyclopentenyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, and adamantyl (meth). Examples thereof include acrylate, 3-hydroxyadamantyl (meth) acrylate, 2-methyl-2-adamantyl (meth) acrylate and the like.
  • Examples of the (meth) acrylate at the end of the silane or silyl group include 2-trimethylsilyloxyethyl (meth) acrylate.
  • Examples of the unsaturated dicarboxylic acid include maleic anhydride and its derivatives.
  • a hydroxyl group-containing polyvalent (meth) acrylic acid ester may be used as the radically polymerizable monomer.
  • the hydroxyl group-containing polyvalent (meth) acrylic acid ester include glycerol di (meth) acrylate, trimethylolpropane di (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol di (meth) acrylate, and dipentaerythritol. Examples thereof include monohydroxypenta (meth) acrylate.
  • the copolymer further contains a structural unit derived from an alkyl (meth) acrylate.
  • the radically polymerizable monomer is preferably methyl (meth) acrylate and butyl (meth) acrylate, and more preferably methyl methacrylate.
  • One type of these radically polymerizable monomers may be used alone, or two or more types may be used in combination.
  • the ratio of the above other structural units in the copolymer can be appropriately determined according to the ratio of the structural units (I) and the structural units (II).
  • the ratio of the other structural units may be the value obtained by subtracting the total ratio (mol%) of the structural units (I) and the structural units (II) from the total structural units (mol%) in the copolymer. can.
  • the ratio of other structural units in the copolymer is preferably 20 to 95 mol%, more preferably 40 to 90 mol%. It is preferably 65 to 85 mol%, more preferably 65 to 85 mol%.
  • the method for producing the copolymer is not particularly limited, and the monomer forming the structural unit (I) and the structural unit (II) by a known polymerization method, and optionally other structural units. Can be produced by copolymerizing. Further, in the production of the copolymer, a polymerization initiator, a chain transfer agent, a polymerization terminator and the like may be used, if necessary.
  • the content ratio of the copolymer in the composition is not particularly limited, but is usually 0.1 to 15% by mass with respect to 100% by mass of the total of the copolymer, the particles, and the solvent described later. Further, from the viewpoint of further improving the dispersibility, the hardness of the cured product and the solvent resistance, the content ratio of the copolymer is 0.5 to 100% by mass of the total of the copolymer, the particles and the solvent described later. It is preferably 10% by mass, more preferably 0.5 to 5% by mass.
  • the particles contained in the composition of the present embodiment are at least one selected from the group consisting of inorganic particles and organic pigment particles.
  • the particles may be appropriately selected according to the function desired for the use of the curable composition, but are preferably inorganic particles from the viewpoints of dispersibility, hardness of the cured product, chemical resistance and the like, and are inorganic. More preferably, it is at least one selected from the group consisting of compound particles, metal particles, and carbon particles.
  • the inorganic particles include calcium carbonate, magnesium carbonate, barium sulfate, titanium oxide, magnesium oxide, zinc oxide, zirconium oxide, aluminum oxide, antimony oxide, tin oxide, cerium oxide, indium oxide, aluminum hydroxide and silica (silicon dioxide).
  • the inorganic particles may be surface-treated with a silane coupling agent, a titanate-based coupling agent, or the like.
  • the organic pigment particles include phthalocyanine pigments and azo facial amounts. The particles may be contained alone or in combination of two or more.
  • the average primary particle size of the particles is not particularly limited, but if it is too small, the thickening tends to be large, and if it is too large, the dispersibility in the composition may be lowered.
  • the average primary particle diameter of the particles is preferably 100 ⁇ m or less, more preferably 50 ⁇ m or less, further preferably 10 ⁇ m or less, and 1 ⁇ m or less. It is even more preferable to have. Further, the lower limit is not limited as long as the effect of the present invention is not impaired, and the average primary particle diameter of the particles may be, for example, 0.1 nm or more.
  • the average primary particle size of the particles can be determined, for example, by a laser diffraction / scattering method and electron microscope observation.
  • the content ratio of the particles in the composition is not particularly limited, but is usually 0.1 to 20% by mass with respect to 100% by mass of the total of the copolymer, the particles, and the solvent described later. Further, from the viewpoint of further improving dispersibility and handleability, the content ratio of the particles is preferably 0.1 to 15% by mass with respect to 100% by mass of the total of the copolymer, the particles, and the solvent described later. , 0.5 to 15% by mass, more preferably 1 to 15% by mass.
  • the composition of the present embodiment preferably contains a solvent from the viewpoint of dispersibility and handleability.
  • the "solvent” means a substance that can be used in producing a composition containing a copolymer and particles, and can be included in the composition. Further, the “solvent” is literally distinguished from the “solvent” that can be used in producing the curable composition described later. On the other hand, the “solvent” and the “solvent” can use the same substance, or different substances can be used. In addition, a “solvent” can be included in the curable composition.
  • esters examples include methyl acetate, ethyl acetate, butyl acetate, ⁇ -butyrolactone, propylene glycol monomethyl ether acetate and the like.
  • aromatic hydrocarbons examples include toluene, xylene and the like.
  • amides include N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone and the like.
  • the above-mentioned radically polymerizable monomer can also be used as the solvent as long as the effect of the present invention is not impaired. That is, it may be a composition containing a copolymer containing the structural unit (I) and the structural unit (II), particles, and a radically polymerizable monomer.
  • the solvent may be contained alone or in combination of two or more.
  • the content ratio of the solvent in the composition is not particularly limited, but is usually 50 to 99% by mass with respect to 100% by mass of the total of the copolymer, the particles, and the solvent described later. Further, from the viewpoint of further improving the dispersibility and handleability, the content ratio of the solvent is preferably 75 to 95% by mass, preferably 80% by mass, based on 100% by mass of the total of the copolymer, the particles, and the solvent described later. More preferably, it is ⁇ 90% by mass.
  • the method for producing the composition of the embodiment is not particularly limited, and can be obtained, for example, by mixing a copolymer, particles, and if necessary, a solvent by a known method.
  • the curable composition of this embodiment contains the above-mentioned composition, a radical polymerization initiator, and a polyfunctional radically polymerizable compound.
  • the content ratio of the composition in the curable composition is not particularly limited, but is 10 to 99% by mass with respect to 100% by mass of the total of the composition, the radical polymerization initiator, the polyfunctional radical polymerization compound and the solvent described later. Is more preferable, 20 to 60% by mass is more preferable, and 30 to 50% by mass is further preferable. When the content of the composition is within the above range, a cured product having excellent hardness and solvent resistance can be efficiently obtained.
  • radical polymerization initiator As the radical polymerization initiator, a thermal radical polymerization initiator that generates radicals by heat and a photoradical polymerization initiator that generates radicals by light are preferable from the viewpoint of further improving the curability of the cured product.
  • thermal radical polymerization initiator include azo compound systems such as 2,2'-azobisisobutyronitrile (AIBN) and 2,2'-azobis (2,4-dimethylvalero) nitrile (ADVN); benzoyl.
  • Diacyl peroxides such as peroxides; Peroxyesters such as t-butylperoxybenzoate; Hydroperoxides such as cumenehydroperoxides; Dialkyl peroxides such as dicumyl peroxides; Ketone peroxides such as methylethyl ketone peroxides and acetylacetone peroxides; Peroxyketals; Alkyl peroxide type; Examples thereof include organic peroxides such as percarbonate type.
  • the photoradical polymerization initiator a commercially available product can be used.
  • Irgacure registered trademark, the same shall apply hereinafter
  • Irgacure184 Irgacure2959
  • Irgacure127 Irgacure907
  • Irgacure369 Irgacure379
  • Irgacure819 Irgacure784, Irgacure784, Irgacure784, Irgacure784, Irgacure784, Irgacure.
  • the radical polymerization initiator may be used alone or in combination of two or more.
  • the content of the radical polymerization initiator in the curable composition is preferably 0.001 part by mass or more, preferably 0.01 part by mass with respect to 100 parts by mass of the composition.
  • the amount is more preferably 0.1 parts by mass or more, and further preferably 0.1 part by mass or more.
  • the content of the radical polymerization initiator in the curable composition is preferably 5 parts by mass or less, and more preferably 3 parts by mass or less with respect to 100 parts by mass of the composition.
  • the curable composition can be a cured product having excellent hardness by containing a polyfunctional radically polymerizable compound.
  • examples of the polyfunctional radically polymerizable compound include trimethyl propanetri (meth) acrylate, tripropylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, dipropylene glycol di (meth) acrylate, and pentaerythritol tri (meth).
  • A-DPH polyfunctional acrylate, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.
  • AH-600 UA-306H, UA-306T, UA-306I, UA-510H, etc.
  • urethane acrylate manufactured by Kyoeisha Chemical Co., Ltd.
  • One type of the polyfunctional radically polymerizable compound may be used alone, or two or more types may be used in combination.
  • compositions fine particle dispersion
  • ⁇ 1-methoxy-2-propanol manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.
  • the copolymers (A-1) and (A-2) obtained in Production Examples 1 and 2 are derived from the structural unit (I) derived from compound 1 and the structural unit (II) derived from methacryloylcholine chloride or MAA. It has a structural unit (II).
  • the copolymers (B-1) to (B-5) obtained in Production Examples 3 to 7 do not have either the structural unit (I) or the structural unit (II).
  • Example 2 and 3 Comparative Examples 1 to 3
  • Preparation of Compositions (C-2, C-3, D-1 to D-3) The same method as in Example 1 except that the formulations shown in Table 2 were used.
  • the composition (C-2, C-3, D-1 to D-3) which is a fine particle dispersion was obtained.
  • the coating film is partially or wholly peeled off along the edge of the cut, and / or some eyes are partially or wholly peeled off.
  • the cross-cut area is clearly affected by more than 35% but not more than 65%.
  • ⁇ Solvent resistance> The cured film on the PET film was wiped off using 0.5 g of cotton impregnated with 1 mL of acetone, and the state after wiping was evaluated according to the following criteria. Evaluation Criteria A: The cured film was not wiped off after 10 times. B: The cured film was not wiped off once, but was wiped off within 10 times. C: The cured film was wiped off once.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

L'invention concerne : une composition comprenant un copolymère qui comprend une unité structurale représentée par la formule générale (I) ci-dessous et une unité structurale représentée par la formule générale (II) ci-dessous et au moins un type de particules choisies dans le groupe constitué par des particules inorganiques et des particules de pigments organiques ; une composition durcissable comprenant la composition ; et un produit durci comprenant la composition durcissable.
PCT/JP2021/044350 2020-12-08 2021-12-02 Composition, composition durcissable et produit durci WO2022124202A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2022568237A JPWO2022124202A1 (fr) 2020-12-08 2021-12-02

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2020-203700 2020-12-08
JP2020203700 2020-12-08

Publications (1)

Publication Number Publication Date
WO2022124202A1 true WO2022124202A1 (fr) 2022-06-16

Family

ID=81974452

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2021/044350 WO2022124202A1 (fr) 2020-12-08 2021-12-02 Composition, composition durcissable et produit durci

Country Status (3)

Country Link
JP (1) JPWO2022124202A1 (fr)
TW (1) TW202231801A (fr)
WO (1) WO2022124202A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPWO2019208353A1 (ja) * 2018-04-23 2021-04-22 株式会社クラレ 硬化性に優れる組成物

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6218410A (ja) * 1985-07-17 1987-01-27 Ricoh Co Ltd 非水系樹脂分散液
JPH0258513A (ja) * 1988-08-25 1990-02-27 Ricoh Co Ltd 含弗素グラフト共重合体
JP2009063985A (ja) * 2006-12-27 2009-03-26 Fujifilm Corp 顔料分散組成物、硬化性組成物、並びにカラーフィルタ及びその製造方法
CN102452936A (zh) * 2010-10-18 2012-05-16 中国石油化工股份有限公司 一种丙烯酸酯化合物和聚合物及其制备方法和应用
JP2015010168A (ja) * 2013-06-28 2015-01-19 東洋インキＳｃホールディングス株式会社 光学的立体造形用樹脂組成物、及び立体造形物
WO2016052141A1 (fr) * 2014-09-29 2016-04-07 富士フイルム株式会社 Composition durcissable par un rayonnement d'énergie active et film antistatique
JP2020007503A (ja) * 2018-07-11 2020-01-16 株式会社クラレ 活性エネルギー線硬化性組成物

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6218410A (ja) * 1985-07-17 1987-01-27 Ricoh Co Ltd 非水系樹脂分散液
JPH0258513A (ja) * 1988-08-25 1990-02-27 Ricoh Co Ltd 含弗素グラフト共重合体
JP2009063985A (ja) * 2006-12-27 2009-03-26 Fujifilm Corp 顔料分散組成物、硬化性組成物、並びにカラーフィルタ及びその製造方法
CN102452936A (zh) * 2010-10-18 2012-05-16 中国石油化工股份有限公司 一种丙烯酸酯化合物和聚合物及其制备方法和应用
JP2015010168A (ja) * 2013-06-28 2015-01-19 東洋インキＳｃホールディングス株式会社 光学的立体造形用樹脂組成物、及び立体造形物
WO2016052141A1 (fr) * 2014-09-29 2016-04-07 富士フイルム株式会社 Composition durcissable par un rayonnement d'énergie active et film antistatique
JP2020007503A (ja) * 2018-07-11 2020-01-16 株式会社クラレ 活性エネルギー線硬化性組成物

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPWO2019208353A1 (ja) * 2018-04-23 2021-04-22 株式会社クラレ 硬化性に優れる組成物
JP7194176B2 (ja) 2018-04-23 2022-12-21 株式会社クラレ 硬化性に優れる組成物

Also Published As

Publication number Publication date
TW202231801A (zh) 2022-08-16
JPWO2022124202A1 (fr) 2022-06-16

Similar Documents

Publication Publication Date Title
JP4614813B2 (ja) 低屈折率膜形成用組成物およびその硬化膜付基材
JP5483810B2 (ja) 樹脂組成物
WO2015058344A1 (fr) Composition de revêtement aqueuse et son procédé de fabrication
TWI815807B (zh) 活性能量線硬化型硬塗劑、硬化塗膜、積層薄膜
WO2002102907A1 (fr) Composition de revetement et article revetu de ladite composition
WO2015152171A1 (fr) Liquide de revêtement permettant la formation de revêtement transparent et procédé permettant la production dudit liquide de revêtement, sol de dispersion de résine organique et substrat portant un revêtement transparent et procédé permettant la production dudit substrat
KR20160063334A (ko) 무기 입자 분산액, 무기 입자 함유 조성물, 도막, 도막 부착 플라스틱 기재, 표시 장치
US20110172331A1 (en) Reactive monomer-dispersed silica sol and production method thereof, and curable composition and cured article thereof
JP2009035595A (ja) ハードコート膜付基材およびハードコート膜形成用塗布液
JP6295652B2 (ja) 光硬化性重合体、光硬化性樹脂組成物、その硬化物、及び硬化塗膜
JP6637950B2 (ja) コーティング組成物、及びこれを用いた化粧シート
WO2022124202A1 (fr) Composition, composition durcissable et produit durci
JP2008031234A (ja) 活性エネルギー線硬化被膜形成組成物用の顔料分散剤
JP2009256577A (ja) コート剤およびクリアコートフィルム
JP5245190B2 (ja) 液状硬化性組成物及び硬化膜
JP2005297414A (ja) プライマー用組成物及びこれを用いたガスバリア性積層フィルム
JP6703828B2 (ja) 光硬化性防眩樹脂組成物
JP2013159782A (ja) 透明性良好なシリカ微粒子とアクリルポリマーのハイブリッド樹脂及びそれを用いた活性エネルギー線硬化性組成物
JP2023058077A (ja) 樹脂改質用モノマー組成物
JP6470498B2 (ja) 透明被膜形成用の塗布液および透明被膜付基材の製造方法
JP5885500B2 (ja) 透明被膜形成用塗料および透明被膜付基材
JP2008248098A (ja) 液状硬化性組成物、硬化膜及び帯電防止用積層体
TWI726054B (zh) 透明被膜形成用塗布液及附有透明被膜之基材
JP6639846B2 (ja) 透明被膜形成用塗布液及び透明被膜付基材
JP2006001984A (ja) ハードコート用組成物とその製造方法

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 21903306

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2022568237

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 21903306

Country of ref document: EP

Kind code of ref document: A1