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  • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
  • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
  • C08J5/18—Manufacture of films or sheets
• • 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
  • B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B32—LAYERED PRODUCTS
  • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
  • B32B27/00—Layered products comprising a layer of synthetic resin
  • B32B27/34—Layered products comprising a layer of synthetic resin comprising polyamides
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  • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
  • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
  • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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  • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
  • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
  • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
  • C08G73/1039—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors comprising halogen-containing substituents
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  • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
  • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
  • C08G73/1042—Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds
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  • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
  • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
  • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
  • C08G73/1046—Polyimides containing oxygen in the form of ether bonds in the main chain
  • C08G73/1053—Polyimides containing oxygen in the form of ether bonds in the main chain with oxygen only in the tetracarboxylic moiety
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  • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
  • C08G73/1057—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain
  • C08G73/1064—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain containing sulfur
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  • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
  • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
  • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
  • C08G73/1075—Partially aromatic polyimides
  • C08G73/1078—Partially aromatic polyimides wholly aromatic in the diamino moiety
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  • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
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  • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
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  • C08J7/043—Improving the adhesiveness of the coatings per se, e.g. forming primers
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  • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
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  • C08J7/046—Forming abrasion-resistant coatings; Forming surface-hardening coatings
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  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
  • C08K5/0041—Optical brightening agents, organic pigments
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  • C08K5/00—Use of organic ingredients
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  • C08K5/00—Use of organic ingredients
  • C08K5/16—Nitrogen-containing compounds
  • C08K5/34—Heterocyclic compounds having nitrogen in the ring
  • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
  • C08K5/3415—Five-membered rings
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  • 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
  • C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
  • C08L33/10—Homopolymers or copolymers of methacrylic acid esters
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  • 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
  • C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
  • C08L33/10—Homopolymers or copolymers of methacrylic acid esters
  • C08L33/12—Homopolymers or copolymers of methyl methacrylate
• • C—CHEMISTRY; METALLURGY
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  • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
  • C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
  • C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
• • C—CHEMISTRY; METALLURGY
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  • C08J2333/00—Characterised by the use 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; Derivatives of such polymers
  • C08J2333/04—Characterised by the use 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; Derivatives of such polymers esters
  • C08J2333/06—Characterised by the use 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; Derivatives of such polymers esters of esters containing only carbon, hydrogen, and oxygen, the oxygen atom being present only as part of the carboxyl radical
  • C08J2333/10—Homopolymers or copolymers of methacrylic acid esters
  • C08J2333/12—Homopolymers or copolymers of methyl methacrylate
• • C—CHEMISTRY; METALLURGY
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  • C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
  • C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
  • C08J2379/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
• • C—CHEMISTRY; METALLURGY
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  • C08J2433/00—Characterised by the use 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; Derivatives of such polymers
  • C08J2433/04—Characterised by the use 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; Derivatives of such polymers esters
  • C08J2433/06—Characterised by the use 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; Derivatives of such polymers esters of esters containing only carbon, hydrogen, and oxygen, the oxygen atom being present only as part of the carboxyl radical
  • C08J2433/10—Homopolymers or copolymers of methacrylic acid esters
  • C08J2433/12—Homopolymers or copolymers of methyl methacrylate
• • C—CHEMISTRY; METALLURGY
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  • C08J2435/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Derivatives of such polymers
  • C08J2435/02—Characterised by the use of homopolymers or copolymers of esters
• • C—CHEMISTRY; METALLURGY
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  • C08J2479/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2461/00 - C08J2477/00
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  • C08J2479/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
• • C—CHEMISTRY; METALLURGY
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  • C08J2483/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen, or carbon only; Derivatives of such polymers
  • C08J2483/04—Polysiloxanes
  • C08J2483/06—Polysiloxanes containing silicon bound to oxygen-containing groups
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• • G—PHYSICS
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  • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
  • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
  • G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
  • G02B1/14—Protective coatings, e.g. hard coatings

Definitions

• the present invention relates to a transparent film, a hard coat film, and a display that contain a polyimide resin.
• Patent Document 1 proposes reducing the refractive index of a transparent polyimide film by blending silica particles with a low refractive index into the transparent polyimide. Patent Document 1 also proposes reducing the coloring of the transparent polyimide film by adding a bluing agent to the polyimide film or a hue adjustment layer provided thereon.
• the transparent film of the present invention contains one or more polyimide-based resins selected from the group consisting of polyimides and polyamideimides, and a bluing agent. From the viewpoints of lowering the refractive index and improving transparency, the transparent film may contain, as a resin component, in addition to the polyimide-based resin, a resin other than the polyimide-based resin (hereinafter, sometimes referred to as "other resin").
• the content of fluoroalkyl-substituted benzidine relative to the total amount of diamine components (100 mol%) is preferably 50 mol% or more, more preferably 60 mol% or more, even more preferably 70 mol% or more, and may be 80 mol% or more, 85 mol% or more, or 90 mol% or more.
• a high content of fluoroalkyl-substituted benzidine tends to suppress coloration of the film and increase mechanical strength such as pencil hardness and elastic modulus.
• the refractive index of the transparent film is preferably 1.60 or less.
• the refractive index of the transparent film is more preferably 1.58 or less, even more preferably 1.56 or less, particularly preferably 1.54 or less, and may be 1.52 or less.
• the refractive index of a film containing only polyimide-based resin as a resin component is generally higher than 1.60, and light is reflected a lot (high reflectance) due to the difference in refractive index between the air interface and the interface with other components, so the light transmittance is low.
• a mixed resin system of polyimide-based resin and other resins has a lower refractive index than the case of polyimide-based resin alone, so light reflection at the interface is reduced and the total light transmittance is high.
• the tensile modulus of the transparent film is preferably 3.0 GPa or more, more preferably 3.5 GPa or more, even more preferably 4.5 GPa or more, and may be 5.0 GPa or more, 5.5 GPa or more, or 6.0 GPa or more.
• the transparent film may have anisotropy in the tensile modulus in the plane. When the transparent film is a stretched film, the tensile modulus in the stretching direction tends to be greater than the tensile modulus in the direction perpendicular to the stretching direction.
• the siloxane-based hard coat material contains a curable compound having a siloxane bond as a curable resin component.
• the siloxane-based curable compound is preferably one having an epoxy group as a polymerizable functional group, and among them, a polyorganosiloxane compound containing an alicyclic epoxy group is preferable.
• Such siloxane-based hard coat materials are disclosed in WO2014/204010, WO2018/096729, WO2020/040209, etc., and the descriptions therein can be referred to and incorporated by reference.
• the transparent film of the present invention and the laminate comprising a functional layer such as a hard coat layer on the transparent film have high total light transmittance and little coloration, and therefore can be used as a display material, and can be used as a cover window provided on the surface of an image display panel, a transparent substrate for a display, a transparent substrate for a touch panel, etc.
• a hard coat film comprising a hard coat layer on a transparent film has excellent scratch resistance and can therefore be suitably used as a cover window material.
• DMF Dimethylformamide
• tetracarboxylic dianhydride were added thereto in the ratios (mol%) shown in Table 1, and the mixture was reacted by stirring under a nitrogen atmosphere for 5 to 10 hours to obtain a polyamic acid solution with a solid content of 18% by weight.
• pyridine 5.5 g was added as an imidization catalyst to 100 g of polyamic acid solution, and after complete dispersion, 8 g of acetic anhydride was added and stirred at 90°C for 3 hours. After cooling to room temperature, 100 g of 2-propyl alcohol (IPA) was added at a rate of 2-3 drops/second while stirring the solution, causing polyimide to precipitate. Further, 150 g of IPA was added, and after stirring for about 30 minutes, suction filtration was performed using a Kiriyama funnel. The obtained solid was washed with IPA and then dried for 12 hours in a vacuum oven set at 120°C to obtain polyimide resins 1 and 2 (PI1, PI2).
• IPA 2-propyl alcohol
• Example 1 Polyimide resin 1 (PI1) and a commercially available acrylic resin ("Parapet G” manufactured by Kuraray; a copolymer of methyl methacrylate/methyl acrylate (monomer ratio 87/13), glass transition temperature 109°C, acid value 0.0 mmol/g; hereinafter referred to as "acrylic resin") were dissolved in methylene chloride in a weight ratio of 55:45 to prepare a solution with a solids concentration of 11% by weight.
• acrylic resin a commercially available acrylic resin
• This solution was applied to a non-alkali glass plate and dried by heating in an atmospheric environment for 15 minutes at 60°C, 15 minutes at 90°C, 15 minutes at 120°C, 15 minutes at 150°C, and 15 minutes at 180°C.
• the film was then peeled off from the non-alkali glass plate to obtain Film 1 with a thickness of 50 ⁇ m.
• the surface that was in contact with the non-alkali glass plate during the application and drying of the film may be referred to as the "support surface".
• Example 2 Except for changing the coating thickness, a film having a thickness of 110 ⁇ m was obtained in the same manner as in Example 1.
• the obtained film was uniaxially stretched with fixed ends at a temperature of 215° C. and a stretching ratio of 120% (the MD length was 2.20 times that of the film before stretching) in the MD direction as the stretching direction using a stretching machine equipped with a heating oven to obtain a stretched film having a thickness of 50 ⁇ m.
• ⁇ Refractive index> The film was cut into 3 cm squares, and the orientation angle was measured using a retardation measuring device (OPTIPRO 21-255MA, manufactured by Shintech) to determine the direction in which the refractive index was maximum.
• the refractive index of all stretched films was maximum in the stretching direction (MD).
• the refractive indexes in the direction in which the refractive index was maximum (MD) and in the direction perpendicular thereto (TD) were measured using a prism coupler (2010/M, manufactured by Metricon).
• the refractive index at a wavelength of 589 nm obtained by Cauchy dispersion fitting of the measured values at wavelengths of 404 nm, 594 nm, and 827 nm was taken as the refractive index of the film.
• Table 2 shows the compositions and evaluation results of the films of Examples 1 to 6 and Comparative Examples 1 to 5.
• the composition values in Table 2 are weight ratios (parts by weight) with the total of the resin components being 100.
• the films of Examples 1 to 6 which contain a bluing agent and an ultraviolet absorbing agent, exhibited high transparency with a total light transmittance of 90% or more, little coloring with a YI of 1.0 or less, and excellent light resistance with a ⁇ YI of 1.8 or less.
• the films of Examples 1 to 6 were placed on white paper and visually checked for coloring, and in all cases there was only a slight change from the white color.
• Comparative Examples 2 and 3 which contained an ultraviolet absorber but no bluing agent, showed a high total light transmittance equivalent to that of Comparative Example 1, but had a large YI, and when placed on white paper and visually checked for coloration, they were visually colored yellow.
• Comparative Example 4 which contained 80 ppm of bluing agent, had a reduced YI compared to Comparative Examples 2 and 3, but a total light transmittance below 90%. When the film of Comparative Example 4 was placed on white paper and visually checked for coloration, they were visually colored blue.
• the film of Comparative Example 5 which was made of polyimide alone, had a refractive index exceeding 1.60, a low total light transmittance, and poor transparency.
• the amount of UV absorber was reduced compared to Example 4 to suppress coloration, so the film had poor light resistance and showed a large ⁇ YI.
• ⁇ Siloxane-based hard coat composition In a reaction vessel equipped with a thermometer, a stirrer, and a reflux condenser, 66.5 g (270 mmol) of 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane ("SILQUEST A-186" manufactured by Momentive Performance Materials) and 16.5 g of 1-methoxy-2-propanol (PGME) were charged and stirred uniformly. A solution of 0.039 g (0.405 mmol) of magnesium chloride as a catalyst dissolved in a mixture of 9.7 g (539 mmol) of water and 5.8 g of methanol was dropped into this mixture over 5 minutes and stirred until it became uniform.
• SILQUEST A-186 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane
• PGME 1-methoxy-2-propanol
• the weight average molecular weight in terms of polystyrene measured using a Tosoh GPC apparatus "HLC-8220GPC" (columns: TSKgel GMH XL ⁇ 2, TSKgel G3000H XL , TSKgel G2000H XL ) was 3000.
• the residual rate of epoxy groups calculated from the 1 H-NMR spectrum measured using a Bruker 400 MHz-NMR with deuterated acetone as a solvent was 95% or more.
• Example 11 An acrylic hard coat composition was applied to the support surface of the film (content of bluing agent: 20 ppm) produced in Example 2 using a coater so that the dry film thickness was 10 ⁇ m, and the solvent was removed at 120° C. Thereafter, under a nitrogen atmosphere, ultraviolet rays were irradiated using a high-pressure mercury lamp so that the accumulated light amount was 1950 mJ/cm 2 to cure the hard coat resin composition, thereby obtaining a hard coat film having an acrylic hard coat layer with a thickness of 10 ⁇ m.
• Example 12 A siloxane-based hard coat composition was applied to the support surface of the film prepared in Example 2 by a coater so that the dry film thickness was 10 ⁇ m, and the solvent was removed at 120° C. Thereafter, ultraviolet rays were irradiated under an atmospheric condition using a high-pressure mercury lamp so that the accumulated light amount was 1950 mJ/cm 2 , thereby curing the hard coat resin composition, and a hard coat film having a siloxane-based hard coat layer with a thickness of 10 ⁇ m was obtained.
• Example 13 A hard coat film having a thickness of 10 ⁇ m and an acrylic hard coat layer was obtained in the same manner as in Example 11, except that the film prepared in Example 6 (content of bluing agent: 60 ppm) was used instead of the film prepared in Example 2.
• Example 14 A hard coat film having an acrylic hard coat layer was obtained in the same manner as in Example 13, except that the thickness of the hard coat layer was changed to 5 ⁇ m.
• Example 15 A hard coat film having a siloxane-based hard coat layer having a thickness of 10 ⁇ m was obtained in the same manner as in Example 12, except that the film prepared in Example 6 was used instead of the film prepared in Example 2.
• Example 16> A hard coat film having a siloxane-based hard coat layer was obtained in the same manner as in Example 15, except that the thickness of the hard coat layer was changed to 20 ⁇ m.
• the hard coat films of Examples 11 to 16 were evaluated for total light transmittance, yellowness index (YI), and light resistance by a carbon arc test in the same manner as described above.
• the pencil hardness of the hard coat layer surface was evaluated under a load of 750 g according to JIS K5600.
• the hard coat films of Examples 11 and 12 had slightly higher YI than the transparent film of Example 2, but showed higher total light transmittance than Example 2 and had light resistance equivalent to that of Example 2. A similar tendency was observed when Example 6 was compared with Examples 13 to 16.
• FS Blue 1556 is a blue dye (Disperse Blue 354: 2-[4-(dihexylamino)-2-methylbenzylidene]-3-(dicyanomethylene)-2,3-dihydrobenzo[b]thiophene 1,1-dioxide) manufactured by Arimoto Chemical Industry Co., Ltd.
• E 4B403 (manufactured by Dainichiseika Color & Chemicals Mfg. Co., Ltd.)
• BL-G207 manufactured by Sanyo Pigment Co., Ltd.
• Ultramarine Blue 51 (manufactured by Holliday Pigments) is ultramarine blue (inorganic pigment).
• the transmission spectrum was measured in the wavelength range of 350 to 850 nm using an ultraviolet-visible-near infrared spectrophotometer ("V-770" manufactured by JASCO Corporation), and the wavelength (maximum absorption wavelength) ⁇ max at which the transmittance became minimum in the wavelength range of 500 to 700 nm (absorption band of the bluing agent) and the transmittance T 0 at the maximum absorption wavelength were determined.
• V-770 ultraviolet-visible-near infrared spectrophotometer
• Examples 21 to 23 which used a pigment-based bluing agent, showed a smaller change in yellowness ⁇ YI 2 after the xenon light fastness test, which is more severe than the carbon arc test, than the ⁇ YI 2 of Examples 24 to 29, which used a dye-based bluing agent, and thus exhibited excellent light fastness. It is believed that Examples 21 to 23 showed a smaller change in transmittance ⁇ T 2 at the absorption maximum wavelength of the bluing agent compared to Examples 24 to 29, and thus exhibited excellent light fastness because deterioration of the bluing agent in the xenon light fastness test was suppressed.
• Examples 24 to 29 have lower haze than Examples 21 to 23, and it is understood that the dye-based bluing agent is superior in terms of transparency.
• Examples 24 to 28, which used an anthraquinone-based dye as the bluing agent, have smaller ⁇ YI2 and ⁇ T2 than Example 29, and therefore it is understood that the anthraquinone-based dye has high lightfastness among dyes.

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