WO2024166263A1 - ラテックスインク用フィルム - Google Patents

ラテックスインク用フィルム Download PDF

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Publication number
WO2024166263A1
WO2024166263A1 PCT/JP2023/004216 JP2023004216W WO2024166263A1 WO 2024166263 A1 WO2024166263 A1 WO 2024166263A1 JP 2023004216 W JP2023004216 W JP 2023004216W WO 2024166263 A1 WO2024166263 A1 WO 2024166263A1
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Prior art keywords
latex ink
film
latex
receiving layer
ink
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PCT/JP2023/004216
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English (en)
French (fr)
Japanese (ja)
Inventor
枝保 日野
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Lintec Corp
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Lintec Corp
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Priority to PCT/JP2023/004216 priority Critical patent/WO2024166263A1/ja
Priority to JP2024575960A priority patent/JPWO2024166263A1/ja
Publication of WO2024166263A1 publication Critical patent/WO2024166263A1/ja
Anticipated expiration legal-status Critical
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    • 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
    • B32B27/40—Layered products comprising a layer of synthetic resin comprising polyurethanes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/50—Recording sheets characterised by the coating used to improve ink, dye or pigment receptivity, e.g. for ink-jet or thermal dye transfer recording
    • B41M5/52—Macromolecular coatings

Definitions

  • the present invention relates to a film for latex inks.
  • latex inks are water-based inks in which a pigment is dispersed in water together with latex (polymer). Therefore, there is no emission of volatile organic compounds (VOCs) resulting from organic solvents, which is a problem when using solvent inks, and therefore printed materials using latex inks have the advantage that they can be used safely in a variety of locations, such as restaurants, educational institutions, medical institutions, and commercial facilities.
  • VOCs volatile organic compounds
  • the film for latex ink described in Patent Document 2 comprises a substrate and a printing coating layer to which latex ink is applied.
  • the printing coating layer contains a material having a structure in which a polymeric material having vinyl chloride, vinyl acetate, and a crosslinkable monomer as constituent monomers is crosslinked by a crosslinking agent. This results in a film for latex ink having a printing coating layer with excellent adhesion to both the portion printed with latex ink and the substrate.
  • the “printing coating layer” in Patent Document 2 is referred to as the "latex ink receiving layer” in this specification.
  • the “latex ink receiving layer” refers to the layer to which latex ink is applied and has the function of fixing the printed portion made of the applied latex ink.
  • the latex ink receiving layer of latex ink films is sometimes required to be abrasion resistant.
  • the latex ink receiving layer needs to have a certain degree of softness.
  • the surface of the latex ink receiving layer is easily scratched and has poor abrasion resistance.
  • the "printing coating layer” in Patent Document 2 also has poor abrasion resistance.
  • the latex ink film may be attached to the glass surface of a store, showroom, office, etc., and used for advertising or decorative purposes.
  • an adherend such as a glass surface
  • water or an aqueous solution containing a surfactant is sprayed on the attachment surface (adhesive layer surface) of the latex ink film or the lamination surface of the adherend so that air does not get between the latex ink film and the adherend, and after both are brought into close contact and positioned, the film is attached by scraping out water and the like together with air from the latex ink film side using a squeegee, which is the so-called water lamination.
  • an aqueous solution may also be sprayed on the latex ink receiving layer side, which is the side opposite the adhesive layer.
  • the latex ink receiving layer of a film for latex ink that is applied with water is required to ensure adhesion to the printed area printed with latex ink, even when the latex ink receiving layer is rubbed with a squeegee while in contact with water (in the following explanation, this will also be referred to as "water-resistant adhesion of the ink").
  • the present invention was made in consideration of these problems, and aims to provide a film for latex ink that has excellent ink adhesion and water-resistant ink adhesion while ensuring abrasion resistance.
  • the present inventors have found that a latex ink-receiving layer formed from a resin composition containing an acrylic resin having a crosslinkable functional group, a specific crosslinking agent, a specific ultraviolet-curable acrylate compound, and a photopolymerization initiator can solve the above problems. Based on this finding, the present inventors have further conducted various research and have completed the present invention. That is, the present invention relates to the following [1] to [8].
  • the latex ink receiving layer (X) is formed from a resin composition (x1) containing an acrylic resin (A) having a crosslinkable functional group, a crosslinking agent (B), an ultraviolet-curable acrylate compound (C) which is an ester of an alkylene oxide-modified polyol compound and (meth)acrylic acid, and a photopolymerization initiator (D);
  • the crosslinking agent (B) contains an isocyanurate compound (B1),
  • the isocyanurate compound (B1) includes an isocyanurate compound (B1-1) and a modified product of an isocyanurate compound (B1-2),
  • the isocyanurate compound (B1-1) is a trimer of 1,6-hexamethylene diisocyanate,
  • the modified isocyanurate compound (B1-2) is a trimer of 1,6-hexamethylene diiso
  • [6] A method for using the film for latex ink according to any one of the above [1] to [5] to form a printed portion on a latex ink-receiving layer of the film for latex ink using latex ink.
  • [7] A method for producing a printed matter, comprising a step of forming a printed portion on the latex ink-receiving layer of the film for latex ink according to any one of [1] to [5] above, using latex ink.
  • [8] A printed matter having a latex ink-printed portion on the latex ink-receiving layer of the film for latex ink according to any one of [1] to [5] above.
  • the present invention makes it possible to provide a film for latex ink that has excellent ink adhesion and water-resistant ink adhesion while also ensuring abrasion resistance.
  • FIG. 1 is a schematic cross-sectional view showing one embodiment of a film for latex ink of the present invention.
  • the term “active ingredient” refers to the components contained in the target composition excluding diluting solvents such as water and organic solvents.
  • the term “(meth)acrylic acid” refers to both “acrylic acid” and “methacrylic acid”
  • the term “(meth)acryloyl group” refers to both "acryloyl group” and “methacryloyl group”.
  • the lower limit and upper limit described in stages for the preferred numerical range e.g., the range of the content, etc. can be independently combined.
  • the description "preferably 10 to 90, more preferably 30 to 60” can be combined with the “preferable lower limit (10)” and the “more preferable upper limit (60)” to form “10 to 60.”
  • the numerical values in the examples are numerical values that can be used as upper or lower limits.
  • the film for latex ink of the present invention has a laminated structure in which a latex ink-receiving layer (X) and a substrate (Y) are laminated together.
  • the latex ink receiving layer (X) is formed from a resin composition (x1) containing an acrylic resin (A) having a crosslinkable functional group, a crosslinking agent (B), an ultraviolet-curable acrylate compound (C) which is an ester of an alkylene oxide-modified polyol compound and (meth)acrylic acid, and a photopolymerization initiator (D).
  • the crosslinking agent (B) contains an isocyanurate compound (B1).
  • the isocyanurate compound (B1) includes an isocyanurate compound (B1-1) and a modified product of the isocyanurate compound (B1-2).
  • the isocyanurate compound (B1-1) is a trimer of 1,6-hexamethylene diisocyanate
  • the modified isocyanurate compound (B1-2) is a trimer of 1,6-hexamethylene diisocyanate and has one or more tertiary amino groups.
  • a latex ink receiving layer formed from a resin composition (x1) containing "an acrylic resin (A) having a crosslinkable functional group,” “a crosslinking agent (B) containing an isocyanurate compound (B1),” “an ultraviolet-curable acrylate compound (C) which is an ester of an alkylene oxide-modified polyol compound and (meth)acrylic acid,” and “a photopolymerization initiator (D),” has excellent ink adhesion and water-resistant adhesion while maintaining abrasion resistance, and have completed the present invention after further extensive research.
  • the latex ink film of the present invention will be described in detail below with respect to its configuration, the components constituting the latex ink film (substrate, latex ink receiving layer, adhesive layer, and release liner), the method for producing the latex ink film, and uses of the latex ink film.
  • the "ultraviolet-curable acrylate compound (C), which is an ester of an alkylene oxide-modified polyol compound and (meth)acrylic acid” may be abbreviated as “ultraviolet-curable acrylate compound (C).”
  • the film for latex ink of the present invention has a laminated structure in which a latex ink-receiving layer (X) and a substrate (Y) are laminated together.
  • FIG. 1 A cross-sectional schematic diagram of one embodiment of the film for latex ink of the present invention is shown in Figure 1.
  • the film for latex ink 1 shown in Figure 1 has a laminated structure in which a latex ink-receiving layer (X) is laminated on one surface (Ya) of a substrate (Y).
  • the film for latex ink according to one embodiment of the present invention preferably has a pressure-sensitive adhesive layer (Z) provided on the other surface (Yb) of the substrate (Y), which allows the film for latex ink to be suitably used as a pressure-sensitive adhesive film.
  • the adhesive surface of the pressure-sensitive adhesive layer (Z) may be covered with a release liner. Then, when attaching to an adherend, the release liner may be peeled off to expose the adhesive surface of the pressure-sensitive adhesive layer (Z).
  • a latex ink receiving layer (X) may be provided on both sides (Ya) and (Yb) of the substrate (Y) without providing a pressure-sensitive adhesive layer (Z).
  • another layer may be provided between the latex ink receiving layer (X) and the substrate (Y). Examples of the other layer include an easy-adhesion layer.
  • the film for latex ink of the present invention has a latex ink-receiving layer (X) and a substrate (Y).
  • the film for latex ink according to one embodiment of the present invention may further include a pressure-sensitive adhesive layer (Z) in addition to the latex ink-receiving layer (X) and the substrate (Y).
  • the film for latex ink according to one embodiment of the present invention may further include a pressure-sensitive adhesive layer (Z) and a release liner in addition to the latex ink-receiving layer (X) and the substrate (Y).
  • the latex ink-receiving layer (X), the substrate (Y), the pressure-sensitive adhesive layer (Z), and the release liner will be described in detail below.
  • the film for latex ink of the present invention has a latex ink-receiving layer (X).
  • the latex ink receiving layer (X) is a portion to which latex ink is applied, and has the function of fixing the portion printed with the applied latex ink.
  • the thickness of the latex ink receiving layer (X) is not particularly limited, but is preferably 0.05 ⁇ m to 50 ⁇ m, more preferably 0.1 ⁇ m to 25 ⁇ m, and even more preferably 0.1 ⁇ m to 10 ⁇ m.
  • the latex ink receiving layer (X) is formed from a resin composition (x1) containing an acrylic resin (A) having a crosslinkable functional group, a crosslinking agent (B), an ultraviolet-curable acrylate compound (C), and a photopolymerization initiator (D).
  • the resin composition (x1) By forming the resin composition (x1) from the resin composition (x1) containing the acrylic resin (A) having a crosslinkable functional group, the crosslinking agent (B), the ultraviolet-curable acrylate compound (C), and the photopolymerization initiator (D), a crosslinked structure formed by the reaction between the acrylic resin (A) having a crosslinkable functional group and the crosslinking agent (B) and a polymer structure formed by the ultraviolet-curable acrylate compound (C) and the photopolymerization initiator (D) are mixed on the surface of the latex ink-receiving layer (X), thereby improving ink adhesion and abrasion resistance.
  • the distance between the (meth)acryloyl groups, which are the ultraviolet-curable sites, is extended, so that the hardness of the latex ink-receiving layer (X) is appropriately reduced, and the force applied to the latex ink-receiving layer (X) when rubbed with a squeegee during wet application is alleviated, making it difficult for the ink to peel off during wet application. That is, the water-resistant adhesion of the ink is improved.
  • the abrasion resistance is sufficiently ensured by the improved abrasion resistance effect due to the mixture of the polymer structure formed by the ultraviolet-curable acrylate compound (C) and the photopolymerization initiator (D) on the surface of the latex ink-receiving layer (X). It is presumed that the combined use of these factors results in the formation of a latex ink-receiving layer (X) that is excellent in both ink adhesion and water-resistant adhesion of ink while ensuring abrasion resistance.
  • the "acrylic resin having a crosslinkable functional group (A),” the “crosslinking agent (B),” the “ultraviolet-curable acrylate compound (C),” and the “photopolymerization initiator (D)” are also referred to as “component (A),” “component (B),” “component (C),” and “component (D),” respectively.
  • the resin composition (x1) which is the material for forming the latex ink receiving layer (X) may be composed only of components (A), (B), (C), and (D), but may also contain other components in addition to components (A), (B), (C), and (D) in addition to components (A), (B), (C), and (D) as long as the effect of the present invention is not impaired.
  • other components include additives for ink receiving layers that are commonly used in ink receiving layers such as latex ink receiving layers, such as reaction accelerators (catalysts), surface conditioners, plasticizers, fillers, and colorants.
  • the total content of components (A), (B), (C), and (D) is preferably 80% by mass to 100% by mass, more preferably 85% by mass to 100% by mass, and even more preferably 90% by mass to 100% by mass, based on the total amount of the active components of resin composition (x1).
  • the acrylic resin (A) having a crosslinkable functional group, the crosslinking agent (B), the ultraviolet-curable acrylate compound (C), and the photopolymerization initiator (D) contained in the resin composition (x1) are described in detail below.
  • the resin composition (x1) used in the present invention contains an acrylic resin (A) having a crosslinkable functional group.
  • the acrylic resin (A) having a crosslinkable functional group is preferably an acrylic resin (A1) having a structural unit (a1) derived from a crosslinkable functional group-containing monomer (a1') (hereinafter also referred to as monomer (a1')).
  • Examples of the crosslinkable functional group contained in the monomer (a1') include one or more types selected from a hydroxyl group, a carboxyl group, an amino group, an epoxy group, and the like. That is, examples of the monomer (a1') include hydroxyl group-containing monomers, carboxyl group-containing monomers, amino group-containing monomers, and epoxy group-containing monomers, etc. Also included are monomers containing two or more crosslinkable functional groups selected from hydroxyl groups, carboxyl groups, amino groups, and epoxy groups, etc. These monomers (a1') may be used alone or in combination of two or more. Among these, as the monomer (a1'), a hydroxyl group-containing monomer and a carboxy group-containing monomer are preferred.
  • Hydroxyl group-containing monomers include, for example, hydroxyalkyl (meth)acrylates such as 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 3-hydroxybutyl (meth)acrylate, and 4-hydroxybutyl (meth)acrylate; N-methylol acrylamide; ⁇ -caprolactone-modified hydroxy (meth)acrylate; carbonate-modified (meth)acrylate, and the like.
  • hydroxyalkyl (meth)acrylates such as 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 3-hydroxybutyl (meth)acrylate, and 4-hydroxybutyl (meth)acrylate
  • N-methylol acrylamide such as 2-hydroxyethyl (meth)
  • carboxyl group-containing monomers examples include (meth)acrylic acid; and compounds obtained by reacting the terminal hydroxyl group of the hydroxyl group-containing monomer described above with an acid anhydride such as one or more aliphatic dicarboxylic acids selected from succinic anhydride, glutaric anhydride, etc.
  • an acid anhydride such as one or more aliphatic dicarboxylic acids selected from succinic anhydride, glutaric anhydride, etc.
  • the acrylic resin (A) having a crosslinkable functional group may be an acrylic copolymer (A2) having a structural unit (a2) derived from an alkyl (meth)acrylate (a2') (hereinafter also referred to as "monomer (a2')”) together with a crosslinkable functional group-containing monomer (a1').
  • A2' alkyl (meth)acrylate
  • a1' crosslinkable functional group-containing monomer
  • the number of carbon atoms in the alkyl group of the monomer (a2′) is preferably 1 to 24. From the viewpoint of adjusting the glass transition temperature (Tg) of the acrylic resin (A) within an appropriate range and making it easier to exhibit ink adhesion, the number of carbon atoms in the alkyl group is preferably 2 to 20.
  • the alkyl group contained in the monomer (a2') may be a linear alkyl group or a branched alkyl group.
  • Examples of the monomer (a2') include methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, n-pentyl (meth)acrylate, n-hexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, lauryl (meth)acrylate, tridecyl (meth)acrylate, and stearyl (meth)acrylate. These monomers (a2') may be used alone or in combination of two or more.
  • the content of the structural unit (a2) is preferably 1 to 99% by mass, more preferably 5 to 95% by mass, and even more preferably 10 to 90% by mass, based on the total amount of the acrylic copolymer (A2).
  • the acrylic resin (A1) and the acrylic copolymer (A2) may be an acrylic copolymer (A3) further having a structural unit (a3) derived from a monomer (a3') other than the monomers (a1') and (a2').
  • Examples of the monomer (a3') include olefins such as ethylene, propylene, and isobutylene; halogenated olefins such as vinyl chloride and vinylidene chloride; diene monomers such as butadiene, isoprene, and chloroprene; (meth)acrylates having a cyclic structure such as cyclohexyl (meth)acrylate, benzyl (meth)acrylate, isobornyl (meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclopentenyl (meth)acrylate, dicyclopentenyloxyethyl (meth)acrylate, and imide (meth)acrylate; styrene, ⁇ -methylstyrene, vinyl toluene, vinyl formate, vinyl acetate, acrylonitrile, (meth)acrylamide, (meth)acrylonitrile, (meth)acryloylmorpholine,
  • the content of the structural unit (a3) is preferably 1 to 99% by mass, more preferably 5 to 95% by mass, and even more preferably 10 to 90% by mass, based on the total amount of the acrylic copolymer (A3).
  • the molecular weight of the acrylic resin (A) having a crosslinkable functional group is not particularly limited, but it is preferable that the number average molecular weight is 3,000 to 100,000.
  • the number average molecular weight is a polystyrene-equivalent value measured by gel permeation chromatography (GPC) using a differential refractometer.
  • the hydroxyl value of the acrylic resin (A) having a crosslinkable functional group is preferably 5.0 mgKOH/g to 25.0 mgKOH/g, more preferably 6.0 mgKOH/g to 24.0 mgKOH/g, and even more preferably 7.0 mgKOH/g to 23.0 mgKOH/g.
  • the hydroxyl value of the acrylic resin (A) having a crosslinkable functional group is equal to or more than the lower limit, the ink adhesion is easily improved, and the stability of the latex ink receiving layer is easily improved.
  • the hydroxyl value of the acrylic resin (A) having a crosslinkable functional group is the above upper limit or less, the stability of the coating liquid (a solution containing the resin composition (x1)) used for forming the latex ink receiving layer (X) is easily improved.
  • the hydroxyl value of the acrylic resin (A) having a crosslinkable functional group means a value measured in accordance with JIS K0070:1992.
  • the acid value of the acrylic resin (A) having a crosslinkable functional group is preferably 10.0 mgKOH/g or less, more preferably 1.0 mgKOH/g to 9.0 mgKOH/g, and even more preferably 2.0 mgKOH/g to 8.0 mgKOH/g.
  • the acid value of the acrylic resin (A) having a crosslinkable functional group means a value measured in accordance with JIS K0070:1992.
  • the glass transition temperature (Tg) of the acrylic resin (A) having a crosslinkable functional group is preferably 100° C. or lower, more preferably 95° C. or lower, and even more preferably 90° C. or lower.
  • the glass transition temperature (Tg) of the acrylic resin (A) having a crosslinkable functional group is lower than the curing temperature of the latex ink, the ink adhesion is more likely to be improved.
  • the glass transition temperature (Tg) of the acrylic resin (A) having a crosslinkable functional group is usually 30° C. or higher, preferably 40° C. or higher, and more preferably 50° C. or higher, from the viewpoint of making it easier to improve the sticking resistance.
  • anti-sticking property means “the property of suppressing sticking between the latex ink-receiving layer (X) and the back surface of the substrate (Y) that occurs when the laminate is wound up in the process of forming the latex ink-receiving layer (X) on the surface of the substrate (Y) and producing a laminate of the substrate (Y) and the latex ink-receiving layer (X).
  • the glass transition temperature (Tg) of the acrylic resin (A) having a crosslinkable functional group means a value measured in accordance with JIS K 7121:1987 using a differential scanning calorimeter (manufactured by TA Instruments Japan, product name "DSC Q2000”) at a heating rate of 20°C/min.
  • the resin composition (x1) used in the present invention contains a crosslinking agent (B).
  • the crosslinking agent (B) contains an isocyanurate compound (B1). If the crosslinking agent (B) does not contain an isocyanurate compound (B1), the ink adhesion of the latex ink receiving layer (X) cannot be made good.
  • the crosslinking structure formed by the reaction with the acrylic resin (A) having a crosslinkable functional group by using the crosslinking agent (B) containing the isocyanurate compound (B1) contributes to the ink adhesion, making the ink adhesion excellent.
  • the crosslinking agent (B) does not contain the isocyanurate compound (B1), the adhesion between the latex ink receiving layer (X) and the substrate (Y) cannot be ensured. It is presumed that the use of the crosslinking agent (B) containing the isocyanurate compound (B1) forms a latex ink receiving layer (X) having a crosslinking structure that is excellent in adhesion between the latex ink receiving layer (X) and the substrate (Y), particularly adhesion to the substrate (Y) containing a polyester resin such as polyethylene terephthalate, due to the influence of the polar group of the isocyanurate compound (B1).
  • the content of the isocyanurate compound (B1) is preferably 50% by mass to 100% by mass, more preferably 70% by mass to 100% by mass, even more preferably 80% by mass to 100% by mass, and still more preferably 90% by mass to 100% by mass, based on the total amount of the crosslinking agent (B), from the viewpoint of making it easier to improve ink adhesion.
  • the isocyanurate compound (B1) will be described in detail below.
  • the isocyanurate compound (B1) includes an isocyanurate compound (B1-1) and a modified product of an isocyanurate compound (B1-2).
  • the total content of the isocyanurate compound (B1-1) and the modified isocyanurate compound (B1-2) in the isocyanurate compound (B1) is preferably 80% by mass to 100% by mass, more preferably 90% by mass to 100% by mass, and even more preferably 95% by mass to 100% by mass, based on the total amount of the isocyanurate compound (B1).
  • the isocyanurate compound (B1) includes an isocyanurate compound (B1-1).
  • the isocyanurate compound (B1-1) is a trimer of 1,6-hexamethylene diisocyanate, and specifically, is a compound represented by the following formula (1).
  • the isocyanurate compound (B1) includes a modified product (B1-2) of an isocyanurate compound.
  • the modified isocyanurate compound (B1-2) is a trimer of 1,6-hexamethylene diisocyanate and has one or more tertiary amino groups.
  • An example of a method for introducing one or more tertiary amino groups into the compound of formula (1) to form a modified product is a method of reacting the compound of formula (1) with a modifying agent having a hydroxyl group and a tertiary amino group.
  • a modifying agent having a hydroxyl group and a tertiary amino group examples include N,N-dimethylaminohexanol (e.g., Kao Corporation, Kaorizer No. 25), N,N-dimethylaminoethoxyethoxyethanol (e.g., Kao Corporation, Kaorizer No. 23NP), N,N-dimethylaminoethoxyethanol (e.g., Kao Corporation, Kaorizer No.
  • the modifier may have a ring structure, but is preferably a compound not having a ring structure as described above. Also, the modifier is preferably an organic nonmetallic compound not having a metal element as described above. That is, the modifier is preferably an acyclic organic nonmetallic compound having a hydroxyl group and a tertiary amino group.
  • the reaction between the compound of formula (1) and the modifier is preferably carried out, for example, by putting the compound of formula (1) and the modifier into a nitrogen-substituted reaction vessel and stirring at a reaction temperature of 60°C to 100°C for 1 hour to 5 hours.
  • the isocyanurate compound (B1) can be prepared, for example, by appropriately adjusting the ratio of the amounts of the compound of the above formula (1) and the modifier added to a reaction vessel when the compound of the above formula (1) and the modifier are reacted with each other.
  • the proportion of the modifier added to the compound of formula (1) is preferably 0.01 to 10 parts by mass, and more preferably 0.05 to 5 parts by mass, relative to 100 parts by mass of the compound of formula (1).
  • an isocyanurate compound (B1) containing an isocyanurate compound (B1-1) and a modified product of the isocyanurate compound (B1-2) can be prepared.
  • the content of the modified isocyanurate compound (B1-2) is preferably 0.5 mol % to 10 mol %, more preferably 1 mol % to 5 mol %, based on the total amount of the isocyanurate compound (B1).
  • the content of the crosslinking agent (B) is preferably 3.0 parts by mass or more, more preferably 5.0 parts by mass or more, and even more preferably 7.0 parts by mass or more, relative to 100 parts by mass of the acrylic resin (A) having a crosslinkable functional group, and is preferably 40 parts by mass or less, more preferably 30 parts by mass or less, and even more preferably 20 parts by mass or less.
  • the resin composition (x1) used in the present invention contains an ultraviolet-curable acrylate compound (C) which is a component capable of being cured (polymerized) by irradiation with ultraviolet light.
  • the ultraviolet-curable acrylate compound (C) is an ester of an alkylene oxide-modified polyol compound and (meth)acrylic acid.
  • an ester of a polyol compound that is not modified with alkylene oxide and (meth)acrylic acid is used, the water-resistant adhesion of the ink to the latex ink-receiving layer (X) cannot be made good.
  • the ultraviolet-curable acrylate compound (C) may be used alone or in combination of two or more kinds.
  • the alkylene oxide-modified polyol compound constituting the ultraviolet-curable acrylate compound (C) is, from the viewpoint of improving abrasion resistance, preferably an alkylene oxide-modified product of a divalent to decavalent polyol, more preferably an alkylene oxide-modified product of a trivalent to hexavalent polyol, even more preferably an alkylene oxide-modified product of a tetravalent to hexavalent polyol, and even more preferably an alkylene oxide-modified product of a hexavalent polyol.
  • the alkylene group constituting the alkylene oxide modified product preferably has 2 to 4 carbon atoms, more preferably 2 to 3 carbon atoms, and further preferably 2 carbon atoms.
  • polyols constituting the alkylene oxide-modified polyol compound include trimethylolethane, trimethylolpropane, trimethylolbutane, ditrimethylolpropane, tritrimethylolpropane, pentaerythritol, dipentaerythritol, tripentaerythritol, glycerin, polyglycerin, 1,3,5-pentanetriol, sorbitol, adonitol, arabitol, xylitol, and mannitol.
  • pentaerythritol and dipentaerythritol are preferred, and dipentaerythritol is more preferred.
  • the number of alkylene oxides in one molecule of the ultraviolet-curable acrylate compound (C) is preferably 2 to 34, more preferably 3 to 20, and even more preferably 4 to 16, from the viewpoint of improving abrasion resistance.
  • the number of (meth)acryloyl groups in the ultraviolet-curable acrylate compound (C) is preferably 2 or more, and more preferably 2 to 6, from the viewpoint of improving the effects of the present invention.
  • the ultraviolet-curable acrylate compound (C) may be a complete ester or a partial ester, but is preferably a complete ester.
  • the ultraviolet-curable acrylate compound (C) contains one or more compounds selected from the group consisting of compounds represented by the following general formula (2) and compounds represented by the following general formula (3).
  • X represents a -R 1 O- group.
  • R 1 in the -R 1 O- group is preferably an alkylene group having 2 to 4 carbon atoms, more preferably an alkylene group having 2 to 3 carbon atoms, and even more preferably an alkylene group having 2 carbon atoms (ethylene group).
  • a, b, c, d, e and f each represent the number of -R 1 O-.
  • the value of a+b+c+d+e+f is preferably 2 to 34, more preferably 3 to 20, even more preferably 4 to 16, still more preferably 6 to 16, even more preferably 8 to 16, and even more preferably 10 to 16.
  • the multiple -R 1 O- groups may be the same or different, but are preferably the same from the viewpoint of ease of availability of the compound.
  • Y represents a -R 2 O- group.
  • R 2 in the -R 2 O- group is preferably an alkylene group having 2 to 4 carbon atoms, more preferably an alkylene group having 2 to 3 carbon atoms, and even more preferably an alkylene group having 2 carbon atoms (ethylene group).
  • g, h, i, and j each represent the number of --R 2 O--.
  • the value of g+h+i+j is preferably from 2 to 34, more preferably from 3 to 20, even more preferably from 4 to 16, still more preferably from 4 to 12, even more preferably from 4 to 10, and even more preferably from 4 to 8.
  • the multiple --R 2 O-- groups may be the same or different, but are preferably the same from the viewpoint of ease of availability of the compound.
  • the ultraviolet-curable acrylate compound (C) contains a compound represented by the above general formula (1).
  • any photopolymerization initiator generally used when curing the ultraviolet-curable acrylate compound (C) with ultraviolet light can be appropriately used.
  • Specific examples include 1-hydroxycyclohexyl phenyl ketone, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzyl diphenyl sulfide, tetramethylthiuram monosulfide, azobisisobutyronitrile, benzyl, dibenzyl, diacetyl, ⁇ -chloroanthraquinone, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, 2,4,6-trimethylzoyldiphenylphosphine oxide, bis(2,6-dimethoxybenzoyl)-2,4,4-trimethyl-pentylphosphine oxide,
  • the content of the photopolymerization initiator (D) is preferably 0.1 to 10 parts by mass per 100 parts by mass of the ultraviolet-curable acrylate compound (C).
  • the total content of the acrylic resin (A) having a crosslinkable functional group and the ultraviolet-curable acrylate compound (C) is preferably 80% by mass or more, more preferably 85% by mass or more, and even more preferably 90% by mass or more, based on the total content (100% by mass) of the acrylic resin (A) having a crosslinkable functional group, the crosslinking agent (B), the ultraviolet-curable acrylate compound (C), and the photopolymerization initiator (D), from the viewpoint of making it easier to exert the effects of the present invention.
  • it is preferably 97% by mass or less, and more preferably 95% by mass or less.
  • the content ratio [(A)/(C)] of the acrylic resin (A) having a crosslinkable functional group and the ultraviolet-curable acrylate compound (C) is, in terms of mass ratio, preferably 2/98 to 70/30, more preferably 3/97 to 50/50, even more preferably 4/96 to 30/70, still more preferably 5/95 to 20/80, and even more preferably 5/95 to 16/84, from the viewpoint of forming a latex ink-receiving layer (X) having superior abrasion resistance.
  • the amount of crosslinked structure formed by the acrylic resin (A) having a crosslinkable functional group and the crosslinking agent (B) in the latex ink-receiving layer (X) is very small compared to the polymer structure formed by the ultraviolet-curable acrylate compound (C) and the photopolymerization initiator (D), it is possible to achieve excellent ink adhesion and water-resistant adhesion of ink while ensuring abrasion resistance.
  • the film for latex ink of the present invention has a substrate (Y).
  • the substrate (Y) supports the latex ink receiving layer (X) and also functions as a support for supporting the printed portion formed on the latex ink receiving layer (X).
  • the substrate (Y) is not particularly limited, but is preferably a resin film.
  • a substrate (Y) as a resin film, the rigidity, flexibility, etc. of the film for latex ink can be improved, and the film for latex ink can be made easy to handle. This is also advantageous from the viewpoint of reducing the production cost and weight of the film for latex ink.
  • the substrate (Y) is preferably a resin film having transparency.
  • a printed matter having a printed portion formed on the latex ink receiving layer of the film for latex ink can be suitably used for applications such as glass decoration in stores, showrooms, offices, etc.
  • polyester-based resins such as polyethylene terephthalate, polybutylene terephthalate, and polyethylene naphthalate
  • polyolefin resins such as polyethylene and polypropylene
  • polyester-based resins and polyolefin-based resins are preferred, polyester-based resins are more preferred, and polyethylene terephthalate is even more preferred.
  • the resin film may be composed of only one type of resin, or may be composed of two or more types of resin.
  • the resin film is a multi-layered body.
  • the uppermost layer of the multi-layered body is preferably a polyester-based resin, and more preferably polyethylene terephthalate.
  • the resin film may be unstretched or may be stretched uniaxially, e.g., vertically or horizontally, or biaxially.
  • the resin film may contain, together with these resins, additives for the substrate, such as a surface conditioner, a plasticizer, an ultraviolet absorber, a light stabilizer, and a colorant.
  • additives for the substrate such as a surface conditioner, a plasticizer, an ultraviolet absorber, a light stabilizer, and a colorant.
  • the content of the additive for the substrate is preferably 10% by mass or less, more preferably 5% by mass or less, and even more preferably 3% by mass or less, based on the total amount of the substrate (Y).
  • the thickness of the substrate (Y) is not particularly limited, but is preferably 15 ⁇ m to 300 ⁇ m, and more preferably 30 ⁇ m to 200 ⁇ m.
  • the film for latex ink of one embodiment of the present invention may have a pressure-sensitive adhesive layer (Z).
  • the film for latex ink according to one embodiment of the present invention has the pressure-sensitive adhesive layer (Z)
  • the film for latex ink can be suitably used as a pressure-sensitive adhesive film.
  • the adhesive constituting the adhesive layer is not particularly limited, and examples include acrylic adhesives, urethane adhesives, and silicone adhesives.
  • the thickness of the adhesive layer (Z) is not particularly limited, but from the viewpoint of improving the handleability when using the latex ink film as an adhesive film, it is preferably 5 ⁇ m to 100 ⁇ m, more preferably 10 ⁇ m to 70 ⁇ m, and even more preferably 15 ⁇ m to 50 ⁇ m.
  • the film for latex ink of one embodiment of the present invention may have a release liner in addition to the pressure-sensitive adhesive layer (Z).
  • a release liner By covering the adhesive surface of the adhesive layer (Z) of one embodiment of the latex ink film of the present invention with a release liner, the adhesive surface of the adhesive layer (Z) can be suitably protected during transportation and storage of the latex ink film.
  • the release liner is not particularly limited, and any release liner commonly used in the field of pressure-sensitive adhesive films can be used as appropriate.
  • the release liner include a laminate in which a release layer is provided on the surface of a film substrate or a paper substrate.
  • the film substrate include polyester resins such as polyethylene terephthalate, and polyolefin resins such as polyethylene resin and polypropylene resin.
  • the paper base material include fine paper, kraft paper, and glassine paper.
  • materials constituting the release layer include silicone, long-chain alkyl resins, and fluorine-based resins.
  • the thickness of the release liner is not particularly limited, but is preferably 10 ⁇ m to 150 ⁇ m, more preferably 20 ⁇ m to 130 ⁇ m, and even more preferably 30 ⁇ m to 100 ⁇ m.
  • the method for producing the film for latex ink of the present invention is not particularly limited, and may be appropriately selected depending on the configuration of the film for latex ink.
  • ⁇ Method of forming latex ink receiving layer (X)> As a method for forming the latex ink receiving layer (X), it is preferable to apply the resin composition (x1) to one surface (Ya) of the substrate (Y) to form a coating film, dry the coating film, and then cure and crosslink the coating film with ultraviolet light to form the latex ink receiving layer (X). In order to improve the workability in applying the resin composition (x1) to the substrate (Y), it is preferable to further dilute the resin composition (x1) with a dilution solvent to give it the form of a solution.
  • the dilution solvent examples include organic solvents such as methyl ethyl ketone, acetone, ethyl acetate, tetrahydrofuran, dioxane, cyclohexane, n-hexane, toluene, xylene, n-propanol, and isopropanol.
  • concentration of the active ingredient in the solution of the resin composition (x1) is preferably 10 to 50% by mass.
  • Examples of methods for applying the solution of the resin composition (x1) include the Mayer bar coating method, the gravure coating method, the roll coating method, the knife coating method, and the die coating method.
  • the coating film is dried to remove the dilution solvent from the coating film (drying step).
  • the heating conditions for drying the coating film are, for example, a drying temperature of 60° C. to 120° C. and a drying time of 30 seconds to 3 minutes.
  • the ultraviolet irradiation conditions are preferably an integrated dose (integrated light amount) of 5 to 1200 mJ/cm 2 , and more preferably 50 to 500 mJ/cm 2 .
  • the ultraviolet light can be irradiated by using, for example, a high-pressure mercury lamp, an electrodeless UV lamp, a xenon lamp, an LED, or the like as an ultraviolet light source.
  • the acrylic resin (A) having a crosslinkable functional group is reacted with the crosslinking agent (B) to form a crosslinked structure (crosslinking step).
  • the crosslinking conditions are not particularly limited, and for example, the crosslinking may be carried out by leaving the composition in a normal environment (e.g., 23°C, relative humidity 50°C) for 1 to 14 days, or by leaving the composition in an environment of 40°C to 60°C for 1 to 3 days.
  • the ultraviolet irradiation process may be carried out before the crosslinking process, during the crosslinking process, or after the crosslinking process.
  • the crosslinking process and the ultraviolet irradiation process may be carried out simultaneously, or the crosslinking process and the ultraviolet irradiation process may each be carried out multiple times. Furthermore, at least one of the ultraviolet irradiation process and the crosslinking process may be carried out simultaneously with the drying process.
  • the pressure-sensitive adhesive layer (Z) is formed on the other surface (Yb) of the substrate (Y) on which the latex ink-receiving layer (X) is not formed.
  • the pressure-sensitive adhesive layer (Z) is formed, for example, by applying a composition for forming the pressure-sensitive adhesive layer (Z) (composition for forming a pressure-sensitive adhesive layer) to the other surface (Yb) of the substrate (Y).
  • the pressure-sensitive adhesive layer (Z) may be formed by applying the composition for forming a pressure-sensitive adhesive layer to the release surface of a release liner, and then the pressure-sensitive adhesive layer (Z) may be attached (transferred) to the other surface (Yb) of the substrate (Y).
  • the method for applying the composition for forming a pressure-sensitive adhesive layer is the same as that described above for the resin composition (x1).
  • the latex ink film of the present invention is preferably used for printing using latex ink. Therefore, according to the present invention, there is provided a method of using the film for latex ink to form a printed portion on a latex ink-receiving layer of the film for latex ink with latex ink.
  • the present invention also provides a method for producing a printed matter, which includes a step of forming a printed portion on the latex ink-receiving layer of the film for latex ink using latex ink.
  • a printed matter having a printed portion with latex ink on the latex ink-receiving layer of the film for latex ink.
  • Latex ink contains a liquid dispersion medium and a dispersoid composed of at least a material containing a resin, which is dispersed (emulsified and/or suspended) in the dispersion medium.
  • Latex inks have a low environmental impact.
  • latex inks have the advantage of being able to express deep colors with a thin layer.
  • the latex particles that make up latex inks contain a binder (resin), which is generally advantageous in terms of improving the adhesion of pigment colorants to recording media.
  • latex inks have the advantage of being able to be printed on demand because they can be produced using the inkjet method.
  • the latex ink is preferably a water-based ink, since water-based inks suppress the generation of volatile organic substances resulting from organic solvents, and therefore are safer and have a smaller impact on the environment.
  • the resin contained in the latex ink is not particularly limited, but examples thereof include vinyl resins, acrylic resins, styrene resins, alkyd resins, polyester resins, polyurethane resins, silicone resins, fluorine resins, epoxy resins, phenoxy resins, polyolefin resins, and modified resins thereof (e.g., modified resins modified to be water-soluble), and one or more selected from these may be used in combination.
  • acrylic resins, styrene resins, water-soluble polyurethane resins, water-soluble polyester resins, and water-soluble acrylic resins are preferred, and acrylic resins are more preferred.
  • the latex ink used in the film for latex ink of one embodiment of the present invention is preferably a latex ink containing an acrylic resin, from the viewpoint of further improving the adhesion between the latex ink-receiving layer (X) and the printed portion.
  • the content of the resin in the latex ink is preferably 1% by mass to 20% by mass, and more preferably 2% by mass to 10% by mass, based on the total amount of the latex ink.
  • Latex ink contains water as a dispersion medium.
  • the content of the dispersion medium (water) in the latex ink is preferably 50% by mass to 98% by mass, more preferably 60% by mass to 97% by mass, and even more preferably 70% by mass to 96% by mass, based on the total amount of the latex ink.
  • Latex inks typically contain a colorant.
  • a colorant various dyes, various pigments, etc. can be used.
  • the content of the colorant in the latex ink is preferably 0.1% by mass to 20% by mass, and more preferably 0.2% by mass to 10% by mass, based on the total amount of the latex ink.
  • the latex ink may contain components other than those described above (other components).
  • examples of such components include dispersants, antifungals, antirust agents, pH adjusters, surfactants, plasticizers, ultraviolet absorbers, and light stabilizers.
  • the printed portion using the latex ink is formed by applying a latex ink onto the latex ink receiving layer (X) of the film for latex ink.
  • the latex ink is preferably a latex ink containing an acrylic resin, from the viewpoint of further improving the adhesion between the latex ink receiving layer (X) and the printed portion.
  • the method for applying the latex ink is not particularly limited, and various printing methods can be used, but the inkjet method is preferred. Examples of the inkjet method include the piezo method and the thermal jet method.
  • the film for latex ink may be heated. The heating temperature is not particularly limited, but is preferably 40° C. to 90° C.
  • the latex ink is preferably a latex ink containing an acrylic resin from the viewpoint of further improving the adhesion between the latex ink receiving layer (X) and the printed part.
  • each layer was measured using a constant pressure thickness gauge manufactured by Tecrock Corporation (model number: "PG-02J", standard specifications: JIS K6783: 1994, JIS Z1702: 1994, JIS Z1709: 1995).
  • the resin composition was prepared using the following acrylic resin (A) having a crosslinkable functional group, a crosslinking agent (B), an ultraviolet-curable acrylate compound (C), and a photopolymerization initiator (D).
  • An acrylic resin having a crosslinkable functional group and a hydroxyl value of 11.0 mgKOH/g, an acid value of 3.9 mgKOH/g, and a glass transition temperature (Tg) of 90° C. was used.
  • UV-curable acrylate compound (C) "Hexafunctional (alkylene oxide modified)": Ethylene oxide modified dipentaerythritol hexaacrylate (ethoxylated dipentaerythritol hexaacrylate) was used.
  • the ethylene oxide-modified dipentaerythritol hexaacrylate is an ester of a polyol compound (the number of moles of ethylene oxide is 12) which is an ethylene oxide-modified dipentaerythritol, and acrylic acid, and is a complete ester having six acryloyl groups.
  • Trifunctional (alkylene oxide modified) Ethylene oxide modified pentaerythritol tetraacrylate (ethoxylated pentaerythritol tetraacrylate) was used.
  • the ethylene oxide-modified pentaerythritol tetraacrylate is an ester of a polyol compound (the mole number of ethylene oxide is 4) which is an ethylene oxide-modified product of pentaerythritol, and acrylic acid, and is a complete ester having four acryloyl groups.
  • Pentaerythritol tetraacrylate was used.
  • the pentaerythritol tetraacrylate is an ester of pentaerythritol and acrylic acid, and is a complete ester having four acryloyl groups.
  • Tin-based catalyst (Other additives) Tin-based catalyst
  • the substrate (Y) As the substrate (Y), a polyethylene terephthalate sheet with an easy-adhesion layer (thickness: 50 ⁇ m) was prepared. Then, the coating liquid (active ingredient concentration: 10 mass%, dilution solvent: ethyl acetate) of the resin composition adjusted to the formulation (effective ingredient conversion amount) shown in Table 1, in which the acrylic resin (A) having a crosslinkable functional group, the crosslinking agent (B), the ultraviolet-curable acrylate compound (C) (or the ultraviolet-curable acrylate compound (C')), and the photopolymerization initiator (D) and the tin catalyst are mixed, was applied to the easy-adhesion layer side of the substrate (Y) using a Mayer bar so that the film thickness after drying is 1 ⁇ m.
  • the coating liquid active ingredient concentration: 10 mass%, dilution solvent: ethyl acetate
  • the coating film formed by coating the substrate (Y) was heated at 90°C for 1 minute using a hot air dryer to remove the dilution solvent contained in the coating film (drying step), and then irradiated with ultraviolet light having a peak wavelength of 365 nm at an integrated light intensity of 150 mJ/ cm2 (ultraviolet light curing step), and further left to stand for 7 days in an environment of 23°C and a relative humidity of 50% to crosslink (crosslinking step).
  • a latex ink-receiving layer (X) having a thickness of 1 ⁇ m was formed, and films for latex ink of Examples 1 to 4 and Comparative Example 1 were obtained.
  • an acrylic pressure-sensitive adhesive composition was applied to the release agent side of the release liner so as to give a film thickness after drying of 20 ⁇ m, and the applied film was heated at 90° C. for 1 minute using a hot air dryer to remove the solvent contained in the acrylic pressure-sensitive adhesive composition, thereby forming an acrylic pressure-sensitive adhesive layer. Thereafter, the acrylic pressure-sensitive adhesive layer formed on the release liner was bonded to the surface of the substrate (Y) opposite the latex ink receiving layer (X) to obtain inkjet printing sheets having latex ink films of Examples 1 to 4 and Comparative Example 1.
  • a rating of 4 or higher was considered to be acceptable.
  • the latex ink films of Examples 1 to 4 have excellent ink adhesion and water-resistant ink adhesion while ensuring abrasion resistance.
  • a film for latex ink formed from a resin composition (x1) in which a polyol compound that is not modified with alkylene oxide and a UV-curable acrylate compound (C'), which is an ester of acrylic acid, are blended instead of the UV-curable acrylate compound (C), has insufficient water-resistant adhesion of the ink.

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JP2005171079A (ja) * 2003-12-11 2005-06-30 Konica Minolta Holdings Inc 着色組成物、インクジェット記録用インク、インクジェット記録方法、カラートナー、光記録媒体、感熱転写記録材料、及びカラーフィルター
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