Composition, molded body and coating film

Abstract

To provide an ultraviolet absorbing composition, a molding and a coated film which have heat resistance, light resistance and transparency in addition to such blue light cutting property as to absorb ultraviolet light and light in a blue light region at a wavelength about 400 nm.SOLUTION: A composition has ultraviolet absorbing property, and contains a compound represented by the following general formulae (1) and (2). The composition is used for the application of a resin composition containing a resin, or a photosensitive resin composition containing a photopolymerizable compound and a photopolymerization initiator.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a composition containing an ultraviolet absorber. [Background technology]

[0002] Because ultraviolet light from sunlight is harmful, ultraviolet absorbers are blended into resins to impart ultraviolet absorption properties to molded bodies and coatings. In recent years, it has been pointed out that not only ultraviolet light, but also blue light with wavelengths of around 380nm to 420nm, can cause damage to organic matter and the human body. Therefore, for certain applications, there is a demand for ultraviolet absorbers that can absorb light in the ultraviolet to blue light range.

[0003] For example, in packaging materials for pharmaceuticals, cosmetics, etc., the organic matter contained in the contents deteriorates due to the action of ultraviolet rays contained in sunlight, etc. Also, certain ingredients such as vitamins deteriorate when exposed to light in the short wavelength region of visible light, around 400 to 420 nm, so there is a demand for ultraviolet absorbers that can absorb light in the longer wavelength region.

[0004] In addition, in display devices, it is common to add an ultraviolet absorber to optical films such as polarizing plate protective films to prevent discoloration of these optical films. Furthermore, in order to prevent the near-infrared absorber contained in the anti-reflection film from deteriorating due to ultraviolet light, an ultraviolet absorber is added to the anti-reflection film. Furthermore, various organic materials such as fluorescent materials and phosphorescent materials are used in the light-emitting elements of organic EL displays, and in order to prevent the deterioration of these organic materials due to ultraviolet light, an ultraviolet absorber is added to the surface film, substrate, adhesive, coating film on the polarizing plate surface, etc. of the display.

[0005] In addition, UV absorbers that absorb UV and blue light are required for the purpose of protecting organic matter in various applications such as optical lenses, solar cells, and window films. In recent years, there has been a demand for molded articles and coating films used in the above applications to have even greater UV-shielding properties, heat resistance, and light resistance, and there is a demand for materials that are resistant to discoloration and deterioration due to heating or exposure to UV rays over long periods of time, while maintaining excellent visible transparency and UV-shielding properties.

[0006] For example, Patent Documents 1 and 2 disclose benzotriazole-based ultraviolet absorbers that absorb light in the short wavelength region of visible light of about 400 nm. Yellow dyes are also sometimes used to cut blue light. [Prior art documents] [Patent documents]

[0007] [Patent Document 1] Japanese Patent Application Publication No. 2018-177696 [Patent Document 2] Special Publication No. 2016-514756 Summary of the Invention [Problem to be solved by the invention]

[0008] However, while conventional UV absorbers absorb light in the short wavelength visible light region around 400 nm, they have low heat and light resistance, and have the problem of their UV absorption decreasing when heated or exposed to UV rays over long periods of time. Furthermore, to achieve sufficient absorption in the blue light region around 400 nm, the amount of UV absorber added must be increased, which reduces the transparency of the coating film and molded product. Furthermore, when using yellow dyes to block blue light, their low heat and light resistance means that their blue light blocking performance significantly decreases when heated or exposed to UV rays over long periods of time.

[0009] The present invention aims to provide an ultraviolet absorber-containing composition that has excellent blue light blocking properties, absorbing not only ultraviolet light but also light in the blue light region with a wavelength of around 400 nm, as well as heat resistance, light resistance, and transparency. [Means for solving the problem]

[0010] The composition of the present invention is a composition containing compounds having ultraviolet absorbing properties and represented by the following general formulas (1) and (2). [ka] (In general formulas (1) and (2), R to R 18 R each independently represents a hydrogen atom. 19 , R 20 are each independently a group having 1 to 20 carbon atoms Alkoxy Show the base vinegar. [Effects of the Invention]

[0011] According to the present invention, it is possible to provide a composition, a molded article, and a coating film that have excellent blue light blocking properties, absorbing not only ultraviolet light but also light in the blue light region with a wavelength of around 400 nm, as well as heat resistance, light resistance, and transparency. DETAILED DESCRIPTION OF THE INVENTION

[0012] The composition of the present invention contains compounds having ultraviolet absorbing properties and represented by the following general formulas (1) and (2). [ka] (In general formulas (1) and (2), R to R 18 R each independently represents a hydrogen atom. 19 , R 20 are each independently a group having 1 to 20 carbon atoms Alkoxy Show the base vinegar.

[0013] The composition of the present invention can absorb light in the blue light region around 400 nm in addition to the ultraviolet region due to the action of the ultraviolet-absorbing compound having a naphthalene ring bonded to a triazine ring. It has the unexpected effect of enabling desired wavelength absorption with smaller amounts than conventionally added. Furthermore, since wavelength absorption is possible with small amounts, the amount added can be reduced, so the transparency of molded bodies and coating films is not reduced. It also has the effect of improving transparency more than conventionally. Furthermore, due to its structure, it has excellent heat resistance, and can be kneaded into thermoplastic resins with high melting points and glass transition temperatures, such as engineering plastics. Furthermore, due to its structure, it has excellent light resistance.

[0014] The composition of the present invention can control the wavelength range to be cut depending on the purpose by arbitrarily changing the ratio of the compounds represented by the general formulas (1) and (2). When the amount of the compound represented by the general formula (1) is greater than the amount of the compound represented by the general formula (2) in the ratio, the wavelength range to be cut can be shifted to the longer wavelength side. When the amount of the compound represented by the general formula (1) is less than the amount of the compound represented by the general formula (2), the wavelength range to be cut can be shifted to the shorter wavelength side. Furthermore, due to the action of the alkoxy group having 1 to 20 carbon atoms in the structure, the composition has excellent solubility in organic solvents such as ethers, ketones, esters, alcohols, aromatic hydrocarbons, and non-aromatic hydrocarbons. Note that, 19 , R 20 The greater the number of carbon atoms in the alkoxy group, the better the solubility and the greater the affinity with organic solvents and resins. Therefore, when used in coating or adhesive applications, precipitation due to crystallization is less likely to occur in the coating film and stability over time is improved, so an alkoxy group having 3 to 20 carbon atoms is preferred. Furthermore, the fewer the carbon atoms in the alkoxy group, the smaller the molecular weight, the greater the absorbance, and the better the ultraviolet absorption, so from the perspective of achieving both solubility and ultraviolet absorption, an alkoxy group having 4 to 10 carbon atoms is more preferred. The carbon chain may be linear or branched.

[0015] Examples of the compound represented by general formula (1) include the following compounds. [ka]

[0016] Examples of the compound represented by general formula (2) include the following compounds. [ka]

[0017] The composition of the present invention may contain a compound represented by the following general formula (3). The compound represented by general formula (3) may be intentionally left as a reaction by-product rather than removed in order to impart high solubility to the composition of the present invention. The compound represented by general formula (3) improves solubility but has the property of reducing lightfastness. Therefore, by including the compound in an appropriate range, a good balance between solubility and lightfastness can be maintained. Therefore, the composition of the present invention preferably contains more than 0% and 5% or less of the compound represented by general formula (3) based on 100% by mass of the nonvolatile content of the composition. General formula (3) [ka]

[0018] (In general formula (3), R1~R 18 R each independently represents a hydrogen atom. 19 , R 20 , R 21 each independently represents an alkoxy group having 1 to 20 carbon atoms, and the carbon atoms of the alkoxy group having 1 to 20 carbon atoms may be linked by one or more -O-, -CO-, -COO-, -OCO-, -CONH-, or -NHCO-.

[0019] Examples of the compound represented by general formula (3) include the following compounds. [ka]

[0020] The composition of the present invention may contain a compound represented by the following general formula (4): The compound represented by general formula (4) may be intentionally left as a reaction by-product rather than removed in order to impart high lightfastness to the composition of the present invention. The compound represented by general formula (4) improves lightfastness but has the property of reducing solubility, so by including it in an appropriate range, a good balance between lightfastness and solubility can be maintained. Therefore, the composition of the present invention preferably contains more than 0% and 5% or less of the compound represented by general formula (4) based on 100% by mass of the nonvolatile content of the composition. General formula (4) [ka] (In general formula (4), R1~R 18 each independently represents a hydrogen atom.

[0021] Examples of the compound represented by the general formula (4) include the following compounds. (d-1) [ka]

[0022] In the composition of the present invention, the mass ratio of the compound represented by general formula (1) to the compound represented by general formula (2) is preferably 5:95 to 95:5. For example, when absorbing light in the 400 to 420 nm wavelength range, the mass ratio of the compound represented by general formula (1) to the compound represented by general formula (2) is preferably 50:50 to 95:5. When absorbing light in the 380 to 400 nm wavelength range, the mass ratio is preferably 5:95 to 50:50. Furthermore, from the viewpoint of facilitating reaction control so that the content of the compounds represented by general formulas (3) and (4) is greater than 0% and not more than 5% of the nonvolatile content of the composition (100% by mass), the mass ratio of the compound represented by general formula (1) to the compound represented by general formula (2) is more preferably 15:85 to 85:15.

[0023] The composition of the present invention can contain at least one ultraviolet absorber (C) selected from triazine compounds, benzotriazole compounds, and benzophenone compounds, which are compounds other than those represented by the general formulas (1) to (4). Rather than using the compounds represented by the general formulas (1) and (2) to achieve broad UV blocking across the entire UV range, combining the ultraviolet absorber (C) can more easily and effectively block a broad UV range and the blue light range around 400 nm in wavelength. Furthermore, because the compounds represented by the general formulas (1) and (2) and the ultraviolet absorber (C) mutually protect each other, better light resistance and heat resistance can be achieved.

[0024] <Ultraviolet absorber (C)> Among the ultraviolet absorbers (C), the benzotriazole compounds are generally compounds that absorb light with a wavelength of 360 nm or less, and examples thereof include 2-(5-methyl-2-hydroxyphenyl)benzotriazole, 2-(2-hydroxy-5-t-butylphenyl)-2H-benzotriazole, octyl-3[3-tert-butyl-4-hydroxy-5-(5-chloro-2H-benzotriazol-2-yl)phenyl]propionate and 2-ethylhexyl-3-[3-tert-butyl-4-hydroxy-5-(5-chloro-2H-benzotriazol-2-yl)phenyl]propionate. A mixture of 2-[2-hydroxy-3,5-bis(α,α-dimethylbenzyl)phenyl]propionate, 2-[2-hydroxy-3,5-bis(α,α-dimethylbenzyl)phenyl]-2H-benzotriazole, 2-(3-t-butyl-5-methyl-2-hydroxyphenyl)-5-chlorobenzotriazole, 2-(3,5-di-t-amyl-2-hydroxyphenyl)benzotriazole, 2-(2'-hydroxy-5'-t-octylphenyl)benzotriazole, 5% 2-methoxy-1-methylethyl acetate and 95% benzenepropanoic acid, 3-(2H-benzotriazole) 2-(2H-benzotriazol-2-yl)-4,6-bis(1-methyl-1-phenylethyl)phenol, 2-(2H-benzotriazol-2-yl)-6-(1-methyl-1-phenylethyl)-4-(1,1,3,3-tetramethylbutyl)phenol, 2-(2'-hydroxy-3',5'-di-t-amylphenyl)benzotriazole, 2-(3-t-butyl-5-methyl-2-hydroxyphenyl)- 5-Chlorobenzotriazole, 2-(2-hydroxy-5-t-octylphenyl)benzotriazole, 2-ethylhexyl-3-[3-t-butyl-4-hydroxy-5-(5-chloro-2H-benzotriazol-2-yl)phenyl]propionate, 2-(2H-benzotriazol-2-yl)-6-dodecyl-4-methyl-phenol, 2-(2H-benzotriazol-2-yl)-3-t-butylphenol, 2-(2H-benzotriazol-2-yl)-6-(1-methyl-1-phenylethyl)-4-(1,1-3,2-(2H-benzotriazol-2-yl)-3-methylphenol, 2-(2H-benzotriazol-2-yl)-6-dodecyl-4-methylphenol, 2,2'-methylenebis[6-(2H-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol], etc.

[0025] Commercially available products include "TINUVIN P," "TINUVIN PS," "TINUVIN 109," "TINUVIN 234," "TINUVIN 326," "TINUVIN 328," "TINUVIN 329," "TINUVIN 360," "TINUVIN 384-2," "TINUVIN 900," "TINUVIN 928," "TINUVIN 99-2," and "TINUVIN 1130" manufactured by BASF Japan Ltd.; "ADEKA STAB LA-29" manufactured by ADEKA Corporation; and "RUNA-93" manufactured by Otsuka Chemical Co., Ltd.

[0026] Among the ultraviolet absorbers (C), the triazine compounds other than the compounds represented by the general formulas (1) to (4) are generally compounds that absorb light with a wavelength of 360 nm or less, and examples thereof include 2-[4,6-di(2,4-xylyl)-1,3,5-triazin-2-yl]-5-octyloxyphenol, 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-[3-(dodecyloxy)-2-hydroxypropoxy]phenol, reaction products of 2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine and 2-ethylhexylglycidic acid ester, and 2,4-bis[2-hydroxy-4-butoxyphenyl] -6-(2,4-dibutoxyphenyl)-1,3-5-triazine, 2,4-bis(2-hydroxy-4-butoxyphenyl)-6-(2,4-dibutoxyphenyl)-1,3,5-triazine, 2-[4-[(2-hydroxy-3-(2'-ethyl)hexyl)oxy]-2-hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-[4-[(2-hydroxy-3-(2'-ethyl)hexyl)oxy]-2-hydroxyphenyl-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-hexyloxyphenol (III-5) bisethylhexyloxyphenol methoxyphenyl triazine, and the like.

[0027] Commercially available products include "KEMISORB 102" manufactured by Chemipro Chemicals, "TINUVIN 400," "TINUVIN 405," "TINUVIN 460," "TINUVIN 477-DW," "TINUVIN 479," and "TINUVIN 1577" manufactured by BASF Japan, "ADK STAB LA-46" and "ADK STAB LA-F70" manufactured by ADEKA Corporation, and "CYASORB UV-1164" manufactured by Sun Chemical.

[0028] Among the ultraviolet absorbers (C), benzophenone compounds are generally compounds that absorb light with a wavelength of 360 nm or less, and examples thereof include 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid-3-oxide, 2-hydroxy-4-n-octoxybenzophenone, 2,2-dihydroxy-4-methoxybenzophenone, hexyl 2-(4-diethylamino-2-hydroxybenzoyl)benzoate, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 1,4-bis(4-benzoyl-3-hydroxyphenoxy)butane, 2-hydroxy-4-octoxybenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid, and 2,2',4,4'-tetrahydroxybenzophenone.

[0029] Commercially available products include "KEMISORB 10," "KEMISORB 11," "KEMISORB 11S," "KEMISORB 12," and "KEMISORB 111" manufactured by Chemipro Chemicals, "SEESORB 101" and "SEESORB 107" manufactured by Shipro Chemicals, and "ADEKA STAB 1413" manufactured by ADEKA.

[0030] The content of the ultraviolet absorber (C) is preferably 0.005 to 50 mass %, more preferably 0.01 to 40 mass %, of the nonvolatile content of the composition. The content of the ultraviolet absorber can be designed depending on the target spectral cut rate.

[0031] The content of the compounds represented by general formulas (1) and (2) is preferably 0.005 to 50 mass %, more preferably 0.01 to 40 mass %, of the nonvolatile content of the composition. The content of the ultraviolet absorber can be designed depending on the desired spectral cutoff rate.

[0032] The composition of the present invention can contain a colorant (D) (hereinafter referred to as colorant (D)) that blocks at least 80% of the visible wavelength range of 450 to 650 nm. Preferably, colorant (D) contains two or more chromatic colorants. Because the compounds represented by general formulas (1) and (2) have strong absorption at wavelengths below 420 nm, combining them with a chromatic colorant that absorbs in a specific wavelength range of 450 to 650 nm can cut wavelengths below 700 nm, allowing the use of near-infrared light. For example, they can be used as bandpass materials that adjust the spectrum as needed. Furthermore, the compounds represented by general formulas (1) and (2) protect the colorant (D) from ultraviolet light, improving the lightfastness and heat resistance of the overall composition.

[0033] Examples of the coloring material (D) include blue pigments, yellow pigments, purple pigments, and red pigments. The organic colorant may be an organic pigment, and examples thereof include diketopyrrolopyrrole pigments, azo pigments such as azo, disazo, or polyazo, anthraquinone pigments such as aminoanthraquinone, diaminodianthraquinone, anthrapyrimidine, flavanthrone, anthanthrone, indanthrone, pyranthrone, or violanthrone, quinacridone pigments, perinone pigments, perylene pigments, thioindigo pigments, isoindoline pigments, isoindolinone pigments, quinophthalone pigments, threne pigments, and metal complex pigments. Furthermore, dyes may be used as the organic pigment, and examples thereof include anthraquinone dyes, monoazo dyes, disazo dyes, oxazine dyes, aminoketone dyes, xanthene dyes, quinoline dyes, and triphenylmethane dyes. When using dyes, it is effective to incorporate the polar groups of anionic or cationic dyes into the resin to impart solubility in organic solvents.

[0034] (blue pigment) Examples of blue pigments include CI Pigment Blue 1, 1:2, 9, 14, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 17, 19, 25, 27, 28, 29, 33, 35, 36, 56, 56:1, 60, 61, 61:1, 62, 63, 66, 67, 68, 71, 72, 73, 74, 75, 76, 78, and 79. Note that "CI" refers to the Color Index (CI; published by The Society of Dyers and Colourists).

[0035] Blue dyes include, for example, CI Acid Blue 1, 2, 3, 4, 5, 6, 7, 8, 9, 11, 13, 14, 15, 17, 19, 21, 22, 23, 24, 25, 26, 27, 29, 34, 35, 37, 40, 41, 41:1, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52 , 53, 54, 55, 56, 57, 58, 62, 62:1, 63, 64, 65, 68, 69, 70, 73, 75, 78, 79, 80, 81, 83, 8485, 86, 88, 89, 90, 90:1, 91, 92, 93, 95, 96, 99, 100, 103, 104, 108, 109, 11 0, 111, 112, 113, 114, 116, 117, 118, 119, 120, 123, 124, 127, 127:1, 128, 129, 135, 137, 138, 143, 145, 147, 150, 155, 159, 169, 174, 175, 176, 183, 198, 203 , 204, 205, 206, 208, 213, 227, 230, 231, 232, 233, 235, 239, 245, 247, 253, 257, 258, 260, 261, 262, 264, 266, 269, 271, 272, 273, 274, 277, 278, 280, etc.

[0036] Also, CI Direct Blue 1, 2, 3, 4, 6, 7, 8, 8:1, 9, 10, 12, 14, 15, 16, 19, 20, 21, 21:1, 22, 23, 25, 27, 29, 31, 35, 36, 37, 40, 42, 45, 48, 49, 50, 53, 54, 55, 58, 60, 61, 64, 65, 67, 79, 96, 97, 98:1, 101, 106, 107, 108, 109, 111, 116, 122, 123, 124, 128, 129, 130, Examples include 130:1, 132, 136, 138, 140, 145, 146, 149, 152, 153, 154, 156, 158, 158:1, 164, 165, 166, 167, 168, 169, 170, 174, 177, 181, 184, 185, 188, 190, 192, 193, 206, 207, 209, 213, 215, 225, 226, 229, 230, 231, 242, 243, 244, 253, 254, 260, and 263. (yellow pigment) Yellow pigments include, for example, CI Pigment Yellow 1, 1:1, 2, 3, 4, 5, 6, 9, 10, 12, 13, 14, 16, 17, 24, 31, 32, 34, 35, 35:1, 36, 36:1, 37, 37:1, 40, 41, 42, 43, 48, 53, 55, 61, 62, 62:1, 63, 65, 73, 74, 75, 81, 83, 87, 93, 94, 95, 97, 100, 101, 104, 105, 108, 109, 110, 111, 116, 117, 119, 120, 126, 127, 127:1, 128, 129, 133, and 134. , 136, 138, 139, 142, 147, 148, 150, 151, 153, 154, 155, 157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 169, 170, 172, 173, 174, 175, 176, 180, 181, 182, 183, 184, 185, 188, 189, 190, 191, 191:1, 192, 193, 194, 195, 196, 197, 198, 199, 200, 202, 203, 204, 205, 206, 207, 208, etc.

[0037] Yellow dyes include, for example, CI Acid Yellow 2, 3, 4, 5, 6, 7, 8, 9, 9:1, 10, 11, 11:1, 12, 13, 14, 15, 16, 17, 17:1, 18, 20, 21, 22, 23, 25, 26, 27, 29, 30, 31, 33, 34, 36, 38, 39, 40, 40:1, 41, 42, 42:1, 43, 44, 46, 48, 51, 53, 55, 56, 60, 63, 65, 66 , 67, 68, 69, 72, 76, 82, 83, 84, 86, 87, 90, 94, 105, 115, 117, 122, 127, 131, 132, 136, 141, 142, 143, 144, 145, 146, 149, 153, 159, 166, 168, 169, 172, 174, 175, 178, 180, 183, 187, 188, 189, 190, 191, 192, 199, etc.

[0038] Further examples include CI Direct Yellow 1, 2, 4, 5, 12, 13, 15, 20, 24, 25, 26, 32, 33, 34, 35, 41, 42, 44, 44:1, 45, 46, 48, 49, 50, 51, 61, 66, 67, 69, 70, 71, 72, 73, 74, 81, 84, 86, 90, 91, 92, 95, 107, 110, 117, 118, 119, 120, 121, 126, 127, 129, 132, 133, and 134. (purple pigment) Examples of purple pigments include CI Pigment Violet 1, 1:1, 2, 2:2, 3, 3:1, 3:3, 5, 5:1, 14, 15, 16, 19, 23, 25, 27, 29, 31, 32, 37, 39, 42, 44, 47, 49, and 50.

[0039] Examples of purple dyes include CI Acid Violet 1, 2, 3, 4, 5, 5:1, 6, 7, 7:1, 9, 11, 12, 13, 14, 15, 16, 17, 19, 20, 21, 23, 24, 25, 27, 29, 30, 31, 33, 34, 36, 38, 39, 41, 42, 43, 47, 49, 51, 63, 67, 72, 76, 96, 97, 102, 103, and 109.

[0040] Other examples include CI Direct Violet 1, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 16, 17, 18, 21, 22, 25, 26, 27, 28, 29, 30, 31, 32, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 45, 51, 52, 54, 57, 58, 61, 62, 63, 64, 71, 72, 77, 78, 79, 80, 81, 82, 83, 85, 86, 87, 88, 93, and 97. (red pigment) Red pigments include, for example, CI Pigment Red 1, 2, 3, 4, 5, 6, 7, 8, 9, 12, 14, 15, 16, 17, 21, 22, 23, 31, 32, 37, 38, 41, 47, 48, 48:1, 48:2, 48:3, 48:4, 49, 49:1, 49:2, 50:1, 52:1, 52:2, 53, 53:1, 53:2, 53:3, 57, 57:1, 57:2, 58:4, 60, 63, 63:1, 63:2, 64, 64:1, 68, 69, 81, 81:1, 81:2, 81:3, 81:4, 83, 88, 90:1, 1 01, 101:1, 104, 108, 108:1, 109, 112, 113, 114, 122, 123, 144, 146, 147, 149, 151, 166, 168, 169, 170, 172, 173, 174, 175, 176, 177, 178, 179, 181, 184, 185, 187, 188, 190, 193, 194, 200, 202, 206, 207, 208, 209, 210, 214, 216, 220, 221, 224, 230, 231, 232, 233, 235, 236, 237, 238, 239, 242, 243, 245, 247, 249, 250, 251, 253, 254, 255, 256, 257, 258, 259, 260, 262, 263, 264, 265, 266, 267, 268, 269, 270, 271, 272, 273, 274, 275, 276, etc. Orange pigments that function similarly to red pigments include, for example, CI Pigment Orange 36, 38, 43, 51, 55, 59, and 61. Red dyes include, for example, CI Acid Red 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 22, 23, 24, 25, 25:1, 26, 26:1, 26:2, 27, 29, 30, 31, 32, 33, 34, 35, 36, 37, 39, 40, 41, 42, 43, 44, 45, 47, 50, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 20, 22, 23, 24, 3, 54, 55, 56, 57, 59, 60, 62, 64, 65, 66, 67, 68, 70, 71, 73, 74, 76, 76:1, 80, 81, 82, 83, 85, 86, 87, 88, 89, 91, 92, 93, 97, 99, 102, 104, 106, 107, 108, 110, 111, 113, 114, 115, 116, 120, 123, 125, 127, 128, 129, 130, 131, 132, 133, 134, 135, 136, 137, 138, 139, 140, 141, 142, 143, 144, 145, 146, 147, 148, 149, 150, 151, 152, 153, 154, 155, 156, 157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 178, 179, 180, 181, 182, 183, 184, 185, 186, 187, 18 28, 131, 132, 133, 134, 135, 137, 138, 141, 142, 143, 144, 148, 150, 151, 152, 154, 155, 157, 158, 160, 161, 163, 164, 167, 170, 171, 172, 173, 175, 176, 177, 181, 229, 231, 237, 239, 240, 241, 242, 243 9, 252, 253, 255, 257, 260, 263, 264, 266, 267, 274, 276, 280, 286, 289, 299, 306, 309, 311, 323, 333, 324, 325, 326, 334, 335, 336, 337, 340, 343, 344, 347, 348, 350, 351, 353, 354, 356, 388, etc.

[0041] Also, CI Direct Red 1, 2, 2:1, 4, 5, 6, 7, 8, 10, 10:1, 13, 14, 15, 16, 17, 18, 21, 22, 23, 24, 26, 26:1, 28, 29, 31, 33, 33:1, 34, 35, 36, 37, 39, 42, 43, 43:1, 44, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134, 135, 13 9, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 67, 67:1, 68, 72, 72:1, 73, 74, 75, 77, 78, 79, 81, 81:1, 85, 86, 88, 89, 90, 97, 100, 101, 101:1, 107, 108, 110, 114 , 116, 117, 120, 121, 122, 122:1, 124, 125, 127, 127:1, 127:2, 128, 129, 130, 132, 134, 135, 136, 137, 138, 140, 141, 148, 149, 150, 152, 153, 154, 155, 156, 169, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 185, 186, 189, 204, 211, 213, 214, 217, 222, 224, 225, 226, 227, 228, 232, 236, 237, 238, etc.

[0042] Among the coloring materials (D), dyes have good spectral characteristics and excellent color development, but often have problems with light fastness and heat resistance. Therefore, to overcome these problems, it is preferable to use basic dyes as salt-forming compounds that are formed by salt formation using organic acids or perchloric acid. Organic acids are preferably organic sulfonic acids and organic carboxylic acids. Among these, naphthalenesulfonic acids such as Tobias acid and perchloric acid are preferred in terms of resistance. It is also preferred to use it by forming a salt with a resin having an anionic group, and it is also preferred to use it as a salt-forming compound by forming a salt with a resin having a betaine structure and an organic acid. In addition, anionic dyes including acid dyes and direct dyes are preferably used as salt-forming compounds using a compound having a cationic group or a resin having a cationic group as a counter ion in terms of heat resistance, light resistance, and solvent resistance. In addition, for synthesizing the salt-forming compound, it is preferable to use a resin having a cationic group, and it is more preferable to use a resin having a cationic group in a side chain together with an organic acid to form a salt. Furthermore, anionic dyes can also be preferably used in the form of sulfonamidated sulfonic acid amide compounds in terms of durability.

[0043] For coating applications, the preferred colorant (D) is Pigment Blue 15:3 or Pigment Blue 15:6 as the blue pigment, Pigment Yellow 139 as the yellow pigment, or Pigment Violet 23 as the violet pigment. For molding applications, the preferred blue pigment is Pigment Blue 15:3 or Pigment Blue 15:6, Pigment Yellow 147 as the yellow pigment, or Solvent Red 52 as the red pigment.

[0044] The content of the coloring material (D) is preferably 0.005 to 50 mass%, more preferably 0.005 to 20 mass%, and more preferably 0.5 to 50 mass%, of the nonvolatile content of the composition. The content of the ultraviolet absorber can be designed depending on the target spectral cut rate.

[0045] The composition of the present invention may contain one or more near-infrared absorbents (E) having an absorption maximum in a wavelength region of 600 to 1500 nm selected from phthalocyanine compounds, naphthalocyanine compounds, squarylium compounds, cyanine compounds, and diketopyrrolopyrrole compounds. This allows the spectrum to be adjusted appropriately depending on the purpose, and the ultraviolet absorbent of the present invention protects the near-infrared absorbent (E) from deterioration, thereby improving durability.

[0046] The near-infrared absorbent (E) is a compound having a maximum absorption in the wavelength range of 700 to 2,000 nm.

[0047] Cyanine compounds are disclosed in WO 2006 / 006573, WO 2010 / 073857, JP 2013-241598, JP 2016-113501, JP 2016-113504, etc.; phthalocyanine compounds are disclosed in JP 4-23868, JP 06-192584, JP 2000-63691 Naphthalocyanine compounds are disclosed in JP-A-11-152414, JP-A-2000-86919, JP-A-2009-29955, JP-A-2018 / 186490, etc.; indigo compounds are disclosed in JP-A-2013-230412, etc.; immonium compounds are disclosed in JP-A-2005-3361 50, JP 2007-197492, JP 2008-88426, etc.; anthraquinone compounds are disclosed in JP 62-903, JP 1-172458, etc.; pyrrolopyrrole compounds are disclosed in JP 2009-263614, JP 2010-90313, JP 2011-068731, etc.; squarylium compounds are disclosed in Examples of the compounds include those described in JP 2011-132361 A, JP 2016-142891 A, WO 2017 / 135359 A, WO 2018 / 225837 A, JP 2019-001987 A, WO 2020 / 054718 A, etc.; examples of the croconium compounds include those described in WO 2019 / 021767 A, etc.

[0048] (Squarylium compounds) The squarylium compound is preferably a compound represented by the following general formula (5). General formula (5) [ka]

[0049] (In general formula (5), R 1 ~R 4 each independently represents a halogen atom, a cyano group, a nitro group, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aralkyl group, -OR 10 , -COR 11 , -COOR 12 , -OCOR13 , -NR 14 R 15 , -NHCOR 16 , -CONR 17 R 18 , -NHCONR 19 R 20 , -NHCOOR 21 , -SR 22 , -SO2R 23 , -SO2OR 24 , -NHSO2R 25 , -SO2NR 26 R 27 , -B(OR 28 )2, and -NHBR 29 R 30 Represents R 10 ~R 30 each independently represents a hydrogen atom, an alkyl group which may have a substituent, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, or an aralkyl group. 12 R 12 When -SO2OR is hydrogen (i.e., a carboxyl group), the hydrogen atom may dissociate (i.e., a carbonate group) or may be in the form of a salt. 24 R 24 When R is a hydrogen atom (i.e., a sulfo group), the hydrogen atom may be dissociated (i.e., a sulfonate group) or may be in the form of a salt. 1 and R 2 , R 3 and R 4 may be bonded to each other to form a ring.

[0050] Examples of the "substituent" include a halogen atom, a cyano group, a nitro group, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aralkyl group, -OR 100 , -COR 101 , -COOR 102 , -OCOR 103 , -NR 104 R 105 , -NHCOR 106 , -CONR 107 R 108 , -NHCONR 109 R110 , -NHCOOR 111 , -SR 112 , -SO2R 113 , -SO2OR 114 , -NHSO2R 115 or -SO2NR 116 R 117 Examples include: R 100 ~R 117 each independently represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, or an aralkyl group. 102 R 102 When -SO2OR is hydrogen (i.e., a carboxyl group), the hydrogen atom may dissociate (i.e., a carbonate group) or may be in the form of a salt. 114 R 114 When is a hydrogen atom (ie, a sulfo group), the hydrogen atom may be dissociated (ie, a sulfonate group) or may be in the form of a salt.

[0051] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. The number of carbon atoms in the alkyl group is preferably 1 to 20, more preferably 1 to 12, and particularly preferably 1 to 8. The alkyl group may be linear, branched, or cyclic. The number of carbon atoms in the alkenyl group is preferably 2 to 20, more preferably 2 to 12, and particularly preferably 2 to 8. The alkenyl group may be linear, branched, or cyclic. The number of carbon atoms in the alkynyl group is preferably 2 to 20, more preferably 2 to 12, and particularly preferably 2 to 8. The alkynyl group may be linear, branched, or cyclic. The aryl group preferably has 6 to 25 carbon atoms, more preferably 6 to 15 carbon atoms, and particularly preferably 6 to 10 carbon atoms. The alkyl portion of the aralkyl group is the same as the alkyl group described above. The aryl portion of the aralkyl group is the same as the aryl group described above. The aralkyl group preferably has 7 to 40 carbon atoms, more preferably 7 to 30 carbon atoms, and particularly preferably 7 to 25 carbon atoms. The heteroaryl group is preferably a monocyclic ring or a fused ring, more preferably a monocyclic ring or a fused ring having 2 to 8 rings, and particularly preferably a monocyclic ring or a fused ring having 2 to 4 rings. The number of heteroatoms constituting the ring of the heteroaryl group is preferably 1 to 3. The heteroatoms constituting the ring of the heteroaryl group are preferably nitrogen atoms, oxygen atoms, or sulfur atoms. The heteroaryl group is preferably a 5-membered or 6-membered ring. The number of carbon atoms constituting the ring of the heteroaryl group is preferably 3 to 30, more preferably 3 to 18, and particularly preferably 3 to 12. The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, and aralkyl group may have a substituent or may be unsubstituted. Examples of the substituent include the "substituents" described above.

[0052] From the viewpoint of light resistance and heat resistance, the squarylium compound is more preferably a compound represented by the following general formula (3). General formula (6) [ka]

[0053] (In general formula (6), R 5 ~R 8 each independently represents a halogen atom, a cyano group, a nitro group, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aralkyl group, -OR 50 , -COR 51 , -COOR 52 , -OCOR 53 , -NR 54 R 55 , -NHCOR 56 , -CONR 57 R 58 , -NHCONR 59 R 60 , -NHCOOR 61 , -SR 62 , -SO2R 63 , -SO2OR 64 , -NHSO2R 65 or -SO2NR 66 R 67 , -B(OR 68)2, and -NHBR 69 R 70 Represents R 50 ~R 70 each independently represents a hydrogen atom, an alkyl group which may have a substituent, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, or an aralkyl group. 52 R 52 When -SO2OR is hydrogen (i.e., a carboxyl group), the hydrogen atom may dissociate (i.e., a carbonate group) or may be in the form of a salt. 64 R 64 When R is a hydrogen atom (i.e., a sulfo group), the hydrogen atom may be dissociated (i.e., a sulfonate group) or may be in the form of a salt. 5 and R 6 , R 7 and R 8 may be bonded to each other to form a ring.

[0054] The "substituent" has the same meaning as the "substituent" described above.

[0055] Specific examples of squarylium compounds are shown below, but the present invention is not limited to these.

[0056] [ka]

[0057] [ka]

[0058] (Pyrrolopyrrole compounds) The pyrrolopyrrole compound is preferably a compound represented by the following general formula (7).

[0059] General formula (7) [ka]

[0060] (In general formula (7), R 1x and R 1y each independently represents an alkyl group, an aryl group, or a heteroaryl group; R 2 and R 3 each independently represents a hydrogen atom or a substituent, R 2 and R 3 may be bonded to each other to form a ring, R 4 represents a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, -BR 4x R 4y or a metal atom, R 4 is R 1x , R 1y and R 3 may be covalently or coordinately bonded to at least one selected from the group consisting of R 4x R 4y each independently represents a substituent. General formula (7) is described in JP-A-2009-263614, JP-A-2011-68731, and WO 2015 / 166873.

[0061] R 1x and R 1y are each independently preferably an aryl group or a heteroaryl group, more preferably an aryl group. 1x and R 1y The alkyl group, aryl group, and heteroaryl group represented by may have a substituent or may be unsubstituted. Examples of the substituent include an alkoxy group, a hydroxy group, a halogen atom, a cyano group, a nitro group, -OCOR 11 , -SOR 12 , -SO2R 13 etc. R 11 ~R 13 each independently represents a hydrocarbon group or a heteroaryl group. Examples of the substituent include those described in paragraphs 0020 to 0022 of JP-A No. 2009-263614. Among them, examples of the substituent include an alkoxy group, a hydroxy group, a halogen atom, a cyano group, a nitro group, -OCOR 11 , -SOR 12 , -SO2R 13 is preferred. 1x and R 1yThe group represented by the formula: is an alkoxy group having a branched alkyl group, or -OCOR 11 It is preferably an aryl group having as a substituent a group represented by the following formula: The branched alkyl group preferably has 3 to 30 carbon atoms, more preferably 3 to 20 carbon atoms.

[0062] R 2 and R 3 At least one of R is preferably an electron-withdrawing group. 2 represents an electron-withdrawing group, and R 3 represents a heteroaryl group. The heteroaryl group is preferably a 5-membered or 6-membered ring. The heteroaryl group is preferably a monocyclic or fused ring, preferably a monocyclic or fused ring having 2 to 8 rings, more preferably a monocyclic or fused ring having 2 to 4 rings. The number of heteroatoms constituting the heteroaryl group is preferably 1 to 3, more preferably 1 or 2. Examples of heteroatoms include a nitrogen atom, an oxygen atom, and a sulfur atom. The heteroaryl group preferably has one or more nitrogen atoms. The two R in general formula (4) 2 In addition, the two R 3 They may be the same or different.

[0063] R 4 represents a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, or -BR 4x R 4y and is preferably a hydrogen atom, an alkyl group, an aryl group, or a group represented by -BR 4x R 4y More preferably, it is a group represented by -BR 4x R 4y It is particularly preferable that R is a group represented by the following formula: 4x R 4y The substituent represented by is preferably a halogen atom, an alkyl group, an alkoxy group, an aryl group, or a heteroaryl group, more preferably an alkyl group, an aryl group, or a heteroaryl group, and particularly preferably an aryl group. These groups may further have a substituent. 4They may be the same or different.

[0064] Specific examples of pyrrolopyrrole compounds are shown below. In the following structural formulas, Me represents a methyl group, and Ph represents a phenyl group. Examples of pyrrolopyrrole compounds include those described in paragraphs 0016 to 0058 of JP 2009-263614 A, paragraphs 0037 to 0052 of JP 2011-68731 A, paragraphs 0014 to 0027 of JP 2014-130343 A, and paragraphs 0010 to 0033 of WO 2015 / 166873 A. The present invention is not limited to these.

[0065] [ka]

[0066] (Naphthalocyanine compounds) The naphthalocyanine compound is preferably a compound represented by the following general formula (8).

[0067] General formula (8) [ka] (In general formula (8), R 1 ~R 24 each independently represent a halogen atom, a nitro group, a nitrile group, a carboxyl group, a sulfone group, an alkyl group which may have a substituent, an aryl group which may have a substituent, a cycloalkyl group which may have a substituent, an alkoxyl group which may have a substituent, an aryloxy group which may have a substituent, an alkylthio group which may have a substituent, an arylthio group which may have a substituent, an alkylamino group which may have a substituent, an arylamino group which may have a substituent, or a sulfamoyl group which may have a substituent. Z is a polymer moiety containing a monomer unit represented by general formula (9) or a phosphorus compound moiety represented by general formula (10), and * is a bond to Al. General formula (9) [ka] (In the general formula (9), X is —CONH—R 25 -,-COO-R 26 -, -CONH-R 27 -O-, -COO-R 28 -O-, R 25 ~R 28 represents an alkylene group or an arylene group in which carbon atoms may be linked by -O-, -CO-, -COO-, -OCO-, -CONH-, or -NHCO-. 31 represents hydrogen or a methyl group.)

[0068] General formula (10) [ka] (In general formula (10), R 29 and R 30 each independently represents a hydroxyl group, an alkyl group which may have a substituent, an aryl group which may have a substituent, an alkoxyl group which may have a substituent, or an aryloxy group which may have a substituent; R 29 and R 30 may be bonded to each other to form a ring.

[0069] Specific examples of naphthalocyanine compounds are shown below, but the present invention is not limited to these. [ka]

[0070] The content of the near-infrared absorber (E) is preferably 0.005 to 50 mass %, more preferably 0.01 to 40 mass %, of the nonvolatile content of the composition. The content of the ultraviolet absorber can be designed depending on the target spectral cutoff rate.

[0071] The resin composition of the present invention can contain the above-described composition and a resin, such as a thermoplastic resin, a photocurable resin, or a thermosetting resin.

[0072] First, a resin composition containing a thermoplastic resin will be described. The composition is preferably used for, for example, a molded article. Examples of the thermoplastic resin include polyolefin, polycarbonate, polyacrylic, polyester, polyamide, polyetherimide, and cycloolefin resin.

[0073] <Polyolefin> Examples of polyolefin resins include polyethylene, polypropylene, polybutene-1, and poly-4-methylpentene, as well as copolymers thereof. Examples of polyethylene include low-density polyethylene and high-density polyethylene. The polypropylene may be, for example, crystalline or amorphous polypropylene. Examples of copolymers using these include ethylene-propylene random, block or graft copolymers, copolymers of α-olefins and ethylene or propylene, ethylene-vinyl acetate copolymers, ethylene-methyl acrylate copolymers, ethylene-ethyl acrylate copolymers, and ethylene-acrylic acid copolymers. Among these, crystalline or amorphous polypropylene, ethylene-propylene random, block or graft copolymers are preferred, and propylene-ethylene block copolymers are more preferred. Furthermore, polypropylene-based resins are preferred from the viewpoints of being inexpensive and having a small specific gravity, which allows for lightweight molded articles.

[0074] The number average molecular weight of the polyolefin is about 30,000 to 500,000.

[0075] The melt flow rate (MFR) of the polyolefin is preferably 1 to 100 (g / 10 min), where MFR is a value determined in accordance with JISK-7210.

[0076] <Polycarbonate> Polycarbonate is an amorphous resin synthesized by reacting an aromatic dihydroxy compound with a carbonate precursor such as phosgene or a carbonate diester. For synthesis reactions using phosgene, the interfacial method is preferred. For synthesis reactions using a carbonate diester, the transesterification method, in which the reaction is carried out in a molten state, is preferred.

[0077] Examples of the aromatic dihydroxy compound include bis(hydroxyaryl)alkanes such as 2,2-bis(4-hydroxyphenyl)propane (bisphenol A), bis(4-hydroxyphenyl)methane, 1,1-bis(4-hydroxyphenyl)ethane, 2,2-bis(4-hydroxyphenyl)butane, 2,2-bis(4-hydroxyphenyl)octane, bis(4-hydroxyphenyl)phenylmethane, 2,2-bis(4-hydroxy-3-methylphenyl)propane, 1,1-bis(4-hydroxy-3-t-butylphenyl)propane, 2,2-bis(4-hydroxy-3-bromophenyl)propane, 2,2-bis(4-hydroxy-3,5-dibromophenyl)propane, and 2,2-bis(4-hydroxy-3,5-dichlorophenyl)propane; Examples of suitable hydroxyaryl compounds include bis(hydroxyaryl)cycloalkanes such as 1,1-bis(4-hydroxyphenyl)cyclopentane and 1,1-bis(4-hydroxyphenyl)cyclohexane, dihydroxydiaryl ethers such as 4,4'-dihydroxydiphenyl ether and 4,4'-dihydroxy-3,3'-dimethyldiphenyl ether, dihydroxydiaryl sulfides such as 4,4'-dihydroxydiphenyl sulfide and 4,4'-dihydroxy-3,3'-dimethyldiphenyl sulfide, dihydroxydiaryl sulfoxides such as 4,4'-dihydroxydiphenyl sulfoxide and 4,4'-dihydroxy-3,3'-dimethyldiphenyl sulfone, and dihydroxydiaryl sulfone. Also, piperazine, dipiperidyl hydroquinone, resorcinol, and 4,4'-dihydroxydiphenyls may be used in combination.

[0078] Examples of the carbonate precursor include phosgene, diaryl carbonates such as diphenyl carbonate and ditolyl carbonate, and dialkyl carbonates such as dimethyl carbonate and diethyl carbonate.

[0079] The aromatic dihydroxy compound and the carbonate precursor can be used either alone or in combination of two or more kinds.

[0080] The viscosity average molecular weight of the polycarbonate is preferably 15,000 to 30,000, and more preferably 16,000 to 27,000. The viscosity average molecular weight in this specification is a value converted from the solution viscosity measured at 25°C using methylene chloride as a solvent.

[0081] Commercially available polycarbonate products include Iupilon H-4000 (manufactured by Mitsubishi Engineering Plastics Corporation, viscosity average molecular weight 16,000), Iupilon S-3000 (manufactured by Mitsubishi Engineering Plastics Corporation, viscosity average molecular weight 23,000), and Iupilon E-2000 (manufactured by Mitsubishi Engineering Plastics Corporation, viscosity average molecular weight 27,000).

[0082] <Polyacrylic> Polyacrylics are compounds obtained by polymerizing monomers such as methyl methacrylate and / or ethyl methacrylate, and other monomers used as needed, using known methods. Examples of polyacrylics include ethylene-methyl acrylate copolymers, ethylene-ethyl acrylate copolymers, and ethylene-acrylic acid copolymers. In addition to the above-mentioned monomers, monomers such as butadiene, α-methylstyrene, and maleic anhydride can also be added for polymerization, and the heat resistance, fluidity, and impact resistance can be adjusted by adjusting the amount and molecular weight of the monomers.

[0083] <Polyester> Polyesters are resins with ester bonds in the main chain of their molecules, and examples include polycondensates synthesized from dicarboxylic acids (including their derivatives) and diols (dihydric alcohols or dihydric phenols); polycondensates synthesized from dicarboxylic acids (including their derivatives) and cyclic ether compounds; and ring-opening polymerization products of cyclic ether compounds. Polyesters include homopolymers formed from a polymer of dicarboxylic acids and diols, copolymers made from multiple raw materials, and polymer blends formed by mixing these. Dicarboxylic acid derivatives include acid anhydrides and esterified products. There are two types of dicarboxylic acids: aliphatic and aromatic. Aromatic dicarboxylic acids are preferred, as they have improved heat resistance.

[0084] Examples of aromatic dicarboxylic acids include terephthalic acid, isophthalic acid, phthalic acid, chlorophthalic acid, nitrophthalic acid, p-carboxyphenylacetic acid, m-phenylenedigolic acid, p-phenylenediglycolic acid, diphenyldiacetic acid, diphenyl-p,p'-dicarboxylic acid, diphenyl-4,4'-diacetic acid, diphenylmethane-p,p'-dicarboxylic acid, diphenylethane-m,m'-dicarboxylic acid, stilbenzylcarboxylic acid, diphenylbutane-p,p'-dicarboxylic acid, benzophenone-4,4'-dicarboxylic acid, naphthalene-1,4-dicarboxylic acid, naphthalene-1,5-dicarboxylic acid, naphthalene-2,6-dicarboxylic acid, and naphthalene-2,7-dicarboxylic acid. Examples of the carboxylic acid include p-carboxyphenoxyacetic acid, p-carboxyphenoxybutyric acid, 1,2-diphenoxypropane-p,p'-dicarboxylic acid, 1,5-diphenoxypentane-p,p'-dicarboxylic acid, 1,6-diphenoxyhexane-p,p'-dicarboxylic acid, p-(p-carboxyphenoxy)benzoic acid, 1,2-bis(2-methoxyphenoxy)-ethane-p,p'-dicarboxylic acid, 1,3-bis(2-methoxyphenoxy)propane-p,p'-dicarboxylic acid, 1,4-bis(2-methoxyphenoxy)butane-p,p'-dicarboxylic acid, and 1,5-bis(2-methoxyphenoxy)-3-oxypentane-p,p'-dicarboxylic acid. Examples of the aliphatic dicarboxylic acid include oxalic acid, succinic acid, adipic acid, suberic acid, magelaic acid, sebacic acid, dodecanedicarboxylic acid, undecanedicarboxylic acid, maleic acid, and fumaric acid.

[0085] Examples of dihydric alcohols include ethylene glycol, trimethylene glycol, butane-1,3-diol, butane-1,4-diol, 2,2-dimethylpropane-1,4-diol, cis-2-butene-1,4-diol, tetramethylene glycol, pentamethylene glycol, hexamethylene glycol, octamethylene glycol, decamethylene glycol, cyclohexanedimethanol, etc. Among these, ethylene glycol, butane-1,4-diol, and cyclohexanedimethanol are preferred. Examples of dihydric phenols include hydroquinone, resorcinol, and bisphenol A. Examples of the cyclic ether compound include ethylene oxide and propylene oxide.

[0086] The dicarboxylic acids and dihydric alcohols can be used either alone or in combination of two or more.

[0087] <Polyamide> Polyamide is a crystalline resin, and can be synthesized, for example, by a dehydration condensation reaction between a carboxylic acid component and a compound (Am) having two or more amino groups.

[0088] Examples of the carboxylic acid component include adipic acid, sebacic acid, isophthalic acid, terephthalic acid, etc. The carboxylic acid component may be a compound having three or more carboxyl groups. The compound (Am) having two or more amino groups may be, for example, a known compound, and examples thereof include aliphatic polyamines such as ethylenediamine, propylenediamine, trimethylenediamine, tetramethylenediamine, pentamethylenediamine, hexamethylenediamine, and triethylenetetramine; aliphatic polyamines including alicyclic polyamines such as isophoronediamine and dicyclohexylmethane-4,4'-diamine; aromatic polyamines such as phenylenediamine and xylylenediamine; and diaminoalcohols such as 1,3-diamino-2-propanol, 1,4-diamino-2-butanol, 1-amino-3-(aminomethyl)-3,5,5-trimethylcyclohexane-1-ol, 4-(2-aminoethyl)-4,7,10-triazadecan-2-ol, and 3-(2-hydroxypropyl)-o-xylene-α,α'-diamine. Commercially available polyamide products include, for example, nylon 6 (manufactured by Toray Industries, Inc.), nylon 66 (manufactured by Toray Industries, Inc.), nylon 610, and the like.

[0089] <Polyetherimide> Polyetherimide is an amorphous resin with a glass transition temperature above 180°C, and has good transparency, high strength, high heat resistance, high modulus of elasticity, and broad chemical resistance, which has led to its widespread use in a variety of applications, including automotive, telecommunications, aerospace, electrical / electronics, transportation, and healthcare. One process for producing polyetherimides involves the polymerization of an alkali metal salt of a dihydroxyaromatic compound, such as bisphenol A disodium salt (BPA·Na), with a bis(halophthalimide). The molecular weight of the resulting polyetherimide can be controlled in two ways. The first method is to use a molar excess of the bis(halophthalimide) relative to the alkali metal salt of the dihydroxyaromatic compound. The second method is to prepare the bis(halophthalic anhydride) in the presence of a monofunctional compound, such as phthalic anhydride, which forms an end-capping agent. The phthalic anhydride reacts with a portion of the organic diamine to form a monohalo-bis(phthalimide). The monohalo-bis(phthalimide) serves as an end-capping agent during the polymerization step by reacting with the phenoxide end groups on the growing polymer chain. Commercially available polyetherimide products include ULTEM (manufactured by Saudi Basic Industries Corporation).

[0090] <Cycloolefin> Cycloolefin resins are amorphous resins with alicyclic structures in the main chain and / or side chain. Examples of alicyclic structures include norbornene polymers, monocyclic olefin polymers, cyclic conjugated diene polymers, vinyl alicyclic hydrocarbon polymers, and hydrogenated versions of these. Among these, norbornene polymers are preferred due to their excellent moldability and transparency. Examples of norbornene monomers include bicyclo[2.2.1]hept-2-ene (common name: norbornene), tricyclo[4.3.0.12,5]deca-3,7-diene (common name: dicyclopentadiene), 7,8-benzotricyclo[4.3.0.12,5]dec-3-ene (common name: methanotetrahydrofluorene), and tetracyclo[4.4.0.12,5.17,10]dodec-3-ene (common name: tetracyclododecene). Commercially available cycloolefin resins include, for example, Topas (manufactured by Polyplastics Co., Ltd.) and Apel (manufactured by Mitsui Chemicals, Inc.).

[0091] <Polyvinyl acetal> The polyvinyl acetal is preferably a polyvinyl acetal obtained by acetalizing polyvinyl alcohol with an aldehyde. Polyvinyl acetal is more preferable than polyvinyl butyral resin. Polyvinyl butyral resin can be synthesized, for example, by reacting polyvinyl alcohol with butyral aldehyde under acidic conditions.

[0092] The thermoplastic resins can be used alone or in combination of two or more kinds.

[0093] The content of the compounds represented by general formulas (1) and (2) is preferably 0.01 to 10 parts by mass, more preferably 0.05 to 1 part by mass, relative to 100 parts by mass of the thermoplastic resin.

[0094] The resin composition containing the thermoplastic resin is preferably produced as a masterbatch containing a high concentration of an ultraviolet absorber. When the masterbatch is produced and then melt-kneaded with a diluted resin (thermoplastic resin) to produce a molded product, the ultraviolet absorber can be more easily dispersed uniformly in the molded product, and aggregation of the ultraviolet absorber can be suppressed, compared to a molded product produced without using the masterbatch. As a result, the transparency of the molded product is improved. The masterbatch can be produced, for example, by melt-kneading an ultraviolet absorber and a thermoplastic resin and pelletizing them using a pelletizer. To prevent aggregation of the ultraviolet absorber, it is preferable to first melt-knead the ultraviolet absorber and wax to produce a dispersion, and then melt-knead the dispersion together with the thermoplastic resin to produce the masterbatch. A blend mixer or a three-roll mill is preferably used to produce the dispersion.

[0095] When the composition is prepared as a masterbatch, the amount of the compounds represented by general formulas (1) and (2) is preferably 0.1 to 30 parts by mass, more preferably 0.5 to 3 parts by mass, per 100 parts by mass of the thermoplastic resin. The mass ratio of the masterbatch (X) to the diluent resin (Y) is preferably X / Y = 1 / 5 to 1 / 100. Within this range, the molded product is likely to have good optical properties.

[0096] The composition of the present invention can also be used to prepare a liquid masterbatch, which can then be melt-kneaded with a diluent resin (thermoplastic resin) to produce a molded article. The liquid masterbatch is obtained by dissolving or dispersing an ultraviolet absorber in a liquid resin.

[0097] The liquid resin has a viscosity of 8,000 mPa·s or less at 25°C. The viscosity is preferably 10 to 5,000 mPa·s, and more preferably 100 to 3,000 mPa·s. Within the above range, the UV absorber can be easily dispersed in the liquid masterbatch. The viscosity in this specification is a value measured at 25°C using a B-type viscometer in accordance with JIS K7117-1:1999.

[0098] The content of the liquid resin is preferably 50% by mass or more, more preferably 60 to 95% by mass, and even more preferably 70 to 90% by mass, based on 100% by mass of the liquid masterbatch. By keeping the content within this range, for example, the melt viscosity during melt kneading can be suppressed, making it easier to disperse the UV absorber. Use of this liquid masterbatch allows for the production of molded articles with high transparency.

[0099] The number average molecular weight (Mn) of the liquid resin is preferably 100 to 3000, more preferably 200 to 2000, further preferably 500 to 1500, and particularly preferably 1000 to 1500. An Mn of 200 or more makes it easy to achieve both moldability and transparency for the molded product. An Mn of 2000 or less improves dispersibility and antistatic properties.

[0100] Examples of liquid resins include epoxy resins such as epoxidized soybean oil and epoxidized linseed oil, aliphatic polyesters, polyalkylene glycol resins, polyether ester resins, and acetyl tributyl citrate. However, even when the base resin is polyethylene terephthalate (PET) or polycarbonate and requires high molding temperatures, aliphatic polyesters, polyalkylene glycol resins, polyether ester resins, and acetyl tributyl citrate are preferred because of their high heat resistance and excellent antistatic properties.

[0101] [Aliphatic polyester] It is a resin obtained by reacting an aliphatic polycarboxylic acid with a polyhydric alcohol.

[0102] The aliphatic polycarboxylic acid is an aliphatic carboxylic acid having two or more carboxyl groups, and examples of the aliphatic polycarboxylic acid include succinic acid, maleic acid, fumaric acid, glutaric acid, adipic acid, azelaic acid, sebacic acid, dodecanedicarboxylic acid, tricarballylic acid, 1,3,6-hexanetricarboxylic acid, and 1,3,5-hexanetricarboxylic acid.

[0103] The polyhydric alcohol is an alcohol having two or more hydroxyl groups. Examples of polyhydric alcohols include aliphatic glycols such as ethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol, 1,2-butanediol, 1,3-butanediol, 2-methyl-1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 2,2-dimethyl-1,3-propanediol, 2,2-diethyl-1,3-propanediol, 2-n-butyl-2-ethyl-1,3-propanediol, 3-methyl-1,5-pentanediol, 1,6-hexanediol, 2,2,4-trimethyl-1,3-pentanediol, 2-ethyl-1,3-hexanediol, 2-methyl-1,8-octanediol, 1,9-nonanediol, 1,10-decanediol, and 1,12-octadecanediol; and polyalkylene glycols such as diethylene glycol and dipropylene glycol.

[0104] The aliphatic carboxylic acids and polyhydric alcohols can be used either alone or in combination of two or more.

[0105] The solidification point of the aliphatic polyester is preferably -5°C or lower, more preferably -50°C to -10°C.

[0106] Commercially available aliphatic polyesters include, for example, Adeka Cizer PN-170 (manufactured by Adeka Corporation, viscosity at 25°C 800 mPa·s, freezing point −15°C, adipic acid polyester), Adeka Cizer P-200 (manufactured by Adeka Corporation, viscosity at 25°C 2,600 mPa·s, freezing point −20°C, adipic acid polyester), and Adeka Cizer PN-250 (manufactured by Adeka Corporation, viscosity at 25°C 4,500 mPa·s, freezing point −20°C, adipic acid polyester).

[0107] [Polyether resin] The polyether resin is a resin having repeating units of alkyleneoxy groups. The alkyleneoxy groups preferably have 1 to 6 carbon atoms. The polyether resin preferably has a viscosity of 10,000 mPa·s or less at 25°C. This viscosity makes it suitable for use in liquid masterbatches. The alkyleneoxy groups preferably have 2 to 4 carbon atoms. This improves compatibility while suppressing water absorption.

[0108] Examples of polyether resins include polyethylene glycol, both of which have 2 carbon atoms in their repeating units; polytrimethylene glycol and polypropylene glycol, both of which have 3 carbon atoms in their repeating units; and polytetramethylene glycol and polybutylene glycol, both of which have 4 carbon atoms in their repeating units.

[0109] [Polyetherester resin] The polyether ester resin is an ester compound of an aliphatic polycarboxylic acid resin and an alkylene glycol resin.

[0110] Commercially available polyetherester resins include, for example, Adeka Cizer RS-107 (manufactured by Adeka Corporation, viscosity at 25°C 20 mPa·s, freezing point −47°C, adipic acid ether ester resin) and Adeka Cizer RS-700 (manufactured by Adeka Corporation, viscosity at 25°C 30 mPa·s, freezing point −53°C, a polyetherester resin).

[0111] The solidification point of the liquid resin is preferably -5°C or lower, more preferably -50°C to -10°C.

[0112] The composition of the present specification can be used to prepare a plasticizer dispersion, which is then melt-kneaded with a diluent resin (thermoplastic resin) to produce a molded article.

[0113] The content of the compounds represented by the general formulas (1) and (2) in the plasticizer dispersion is preferably 0.1 to 30% by mass.

[0114] The plasticizer dispersion is prepared by dissolving or dispersing an ultraviolet absorber in a plasticizer.

[0115] Examples of plasticizers include phthalates, adipates, trimellitates, polyesters, phosphates, citrates, epoxidized vegetable oils, and sebacates. Among these, triethylene glycol di-2-ethylhexanoate and triethylene glycol di-n-heptanoate are preferred, and triethylene glycol di-2-ethylhexanoate is more preferred.

[0116] The plasticizers can be used alone or in combination of two or more kinds.

[0117] The content of the plasticizer in the plasticizer dispersion is preferably 60 to 99.9% by mass.

[0118] (Resin-type dispersant) The liquid masterbatch or plasticizer dispersion of the present invention may contain a resin-type dispersant. This allows the UV absorber to be more uniformly dispersed in the liquid masterbatch or plasticizer dispersion, thereby achieving even higher transparency for the molded product. Furthermore, the inclusion of a resin-type dispersant improves the storage stability of the liquid masterbatch or plasticizer dispersion.

[0119] Resin-type dispersants are resins having an adsorption site that has the property of adsorbing to UV absorbers and a relaxation site that is compatible with components other than UV absorbers. Examples of resin-type dispersants include polyurethanes, polyacrylates, and other polycarboxylic acid esters, unsaturated polyamides, polycarboxylic acids, polycarboxylic acid (partial) amine salts, polycarboxylic acid ammonium salts, polycarboxylic acid alkylamine salts, polysiloxanes, long-chain polyaminoamide phosphate salts, hydroxyl group-containing polycarboxylic acid esters, and modified products thereof, oil-based dispersants such as amides formed by the reaction of poly(lower alkylene imines) with polyesters having free carboxyl groups, and salts thereof, water-soluble resins and water-soluble polymer compounds such as (meth)acrylic acid-styrene copolymers, (meth)acrylic acid-(meth)acrylic acid ester copolymers, styrene-maleic acid copolymers, polyvinyl alcohols, and polyvinylpyrrolidone, polyesters, modified polyacrylates, ethylene oxide / propylene oxide adducts, and phosphate esters.

[0120] The resin-type dispersants can be used alone or in combination of two or more kinds.

[0121] Of the above dispersants, polymer dispersants having a basic functional group are preferred because even a small amount added reduces the viscosity of the dispersion. Nitrogen-containing graft copolymers, nitrogen-containing acrylic block copolymers having functional groups in the side chains including tertiary amino groups, quaternary ammonium bases, nitrogen-containing heterocycles, and urethane-based polymer dispersants are preferred.

[0122] The content of the resin-type dispersant is preferably about 5 to 200 mass %, more preferably about 10 to 100 mass %, relative to 100 parts by mass of the ultraviolet absorber.

[0123] Commercially available resin-type dispersants include Disperbyk-101, 103, 107, 108, 110, 111, 116, 130, 140, 154, 161, 162, 163, 164, 165, 166, 170, 171, 174, 180, 181, 182, 183, 184, 185, 190, 2000, 2001, 2020, 2025, 2050, 2070, 2095, 2150, and 2155 manufactured by BYK Japan Co., Ltd. ti-Terra-U, 203, 204, or BYK-P104, P104S, 220S, 6919, or Lactimon, Lactimon-WS, or Bykumen, etc.; SOLSPERSE-3000, 9000, 13000, 13240, 13650, 13940, 16000, 17000, 18000, 20000, 21000, 24000, 26000, 27000, 28000, etc. manufactured by Lubrizol Japan 000, 31845, 32000, 32500, 32550, 33500, 32600, 34750, 35100, 36600, 38500, 41000, 41090, 53095, 55000, 76500, etc.; EFKA-46, 47, 48, 452, 4008, 4009, 4010, 4015, 4020, 4047, 4050, 4055, 4060, 4080, 4400, 4401, 4402 manufactured by BASF Japan Ltd. , 4403, 4406, 4408, 4300, 4310, 4320, 4330, 4340, 450, 451, 453, 4540, 4550, 4560, 4800, 5010, 5065, 5066, 5070, 7500, 7554, 1101, 120, 150, 1501, 1502, 1503, etc., and Ajisper PA111, PB711, PB821, PB822, PB824 manufactured by Ajinomoto Fine-Techno Co., Ltd.

[0124] When the resin-type dispersant is dissolved in an organic solvent, it is preferable to add the liquid resin, heat under reduced pressure, and distill off the solvent before use. In this case, the liquid masterbatch containing this also does not contain an organic solvent, making it easy to use in terms of processing.

[0125] <Method for manufacturing liquid masterbatch> The liquid masterbatch can be prepared by mixing the compounds represented by general formulas (1) and (2) with a liquid resin. A resin-type dispersant is preferably used for the preparation. The mixing can be carried out using a device such as a kneader, a two-roll mill, a three-roll mill, a ball mill, a horizontal sand mill, a vertical sand mill, an annular bead mill, or an attritor.

[0126] <Method of manufacturing plasticizer dispersion> The plasticizer dispersion can be prepared by mixing the compounds represented by the general formulas (1) and (2) with a plasticizer. It is preferable to use a resin-type dispersant for the preparation. The mixing can be carried out using the apparatus described in the "Method for producing a liquid masterbatch" section above.

[0127] The composition of the present specification may contain optional components such as an antioxidant, a light stabilizer, a dispersant, and a wax in addition to the thermoplastic resin and the ultraviolet absorber.

[0128] The resin composition containing the thermoplastic resin is preferably produced as a paint, for example.

[0129] The resin that can be used in the coating material preferably has a glass transition temperature of 30° C. or higher. Examples of the resin include thermoplastic resins such as nitrocellulose and polyester.

[0130] Next, the photosensitive composition of the present invention will be described. The photosensitive composition includes a composition containing compounds represented by general formulas (1) and (2), a photopolymerizable compound, and a photopolymerization initiator. The photosensitive composition can be used for coating layer applications such as hard coat layers, top coat layers, and intermediate layers of various laminates. It is more preferable that the ultraviolet absorber in the photosensitive composition contains a photocurable moiety. The photosensitive composition can also contain a resin. The photosensitive composition can also contain additives known for photocurable compositions and, if necessary, an organic solvent.

[0131] The photopolymerizable compound is a compound containing a vinyl group, a (meth)acryloyl group, or the like, and includes a monomer and an oligomer. Examples of the photopolymerizable compound include methyl (meth)acrylate, ethyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, cyclohexyl (meth)acrylate, β-carboxyethyl (meth)acrylate, polyethylene glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, triethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, phenoxytetraethylene glycol (meth)acrylate, phenoxyhexaethylene glycol (meth)acrylate, trimethylolpropane PO-modified tri(meth)acrylate, trimethylolpropane EO-modified tri(meth)acrylate, isocyanuric acid EO-modified di(meth)acrylate, isocyanuric acid EO-modified tri(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, pentaerythritol, Examples of suitable acrylic acid esters and methacrylic acid esters include butyl acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, 1,6-hexanediol diglycidyl ether di(meth)acrylate, bisphenol A diglycidyl ether di(meth)acrylate, neopentyl glycol diglycidyl ether di(meth)acrylate, dipentaerythritol hexa(meth)acrylate, dipentaerythritol penta(meth)acrylate, tricyclodecanyl (meth)acrylate, ester acrylate, (meth)acrylic acid ester of methylolated melamine, epoxy (meth)acrylate, and urethane acrylate; (meth)acrylic acid, styrene, vinyl acetate, hydroxyethyl vinyl ether, ethylene glycol divinyl ether, pentaerythritol trivinyl ether, (meth)acrylamide, N-hydroxymethyl (meth)acrylamide, N-vinylformamide, and acrylonitrile.

[0132] Examples of the photopolymerization initiator include acetophenone-based compounds, benzoin-based compounds, benzophenone-based compounds, thioxanthone-based compounds, triazine-based compounds, oxime ester-based compounds, phosphine-based compounds, quinone-based compounds, borate-based compounds, carbazole-based compounds, imidazole-based compounds, titanocene-based compounds, etc. Among these, oxime ester-based compounds are preferred in terms of high sensitivity.

[0133] Next, a composition (paint, adhesive) containing the compounds represented by general formulas (1) and (2) and a thermosetting resin will be described. The composition preferably further contains a curing agent. In other words, the adhesive of this specification preferably contains an ultraviolet absorber, an adhesive resin, and a curing agent.

[0134] The adhesive resin has a glass transition temperature of -50 to -20°C. Examples of types of adhesive resin include acrylic resin, polyester, and urethane resin. The adhesive resin preferably has a functional group that can react with a curing agent. Examples of the functional group include a carboxyl group and a hydroxyl group.

[0135] Examples of the curing agent include an isocyanate curing agent, an epoxy curing agent, an aziridine curing agent, and a metal chelate curing agent.

[0136] The molded article of the present invention can be produced by melting and kneading a resin composition containing the compounds represented by general formulas (1) and (2) and a resin, followed by molding. When the composition is a masterbatch, it is preferable to produce the molded article by melting and kneading the masterbatch and diluted resin. In the present invention, the molded article is obtained by pouring the resin into a mold. The molded article also includes articles obtained without using a mold, such as plastic films, and molded articles. It is preferable to use the thermoplastic resin already described as the diluted resin.

[0137] The melt kneading is preferably carried out using, for example, a single screw kneading extruder, a twin screw kneading extruder, a tandem twin screw kneading extruder, etc. The melt kneading temperature varies depending on the type of thermoplastic resin, but is usually about 150 to 320°C.

[0138] Examples of the molding method include extrusion molding, injection molding, blow molding, etc. Examples of the extrusion molding method include compression molding, pipe extrusion molding, laminate molding, T-die molding, inflation molding, melt spinning, etc.

[0139] The molding temperature is usually 160 to 320°C, depending on the softening point of the diluted resin.

[0140] The molded article of the present invention can be used for, for example, pharmaceutical packaging materials, food packaging materials, displays, glass interlayers, optical lenses, solar cells, window films, and eyeglass lenses.

[0141] For packaging materials for medicines and foods, it is preferable to use thermoplastic resins such as polyesters, cycloolefin resins, etc. These molded articles have improved flexibility and visibility, and can suppress deterioration of the contents.

[0142] Molded articles usable for displays, glass interlayers, optical lenses, and solar cells may be any molded articles made of a thermoplastic resin, but are preferably films made of a resin that is transparent to the desired wavelength. Examples of resins that make up such molded articles include polyetherimide, polyethersulfone-based resin, polyethylene terephthalate-based resin, polyimide-based resin, polysulfone-based resin, polyarylate-based resin, polyamide, polycarbonate-based resin, olefin polymer-based resin having an alicyclic structure (alicyclic olefin polymer-based resin), and cellulose ester-based resin.

[0143] The coating film of the present invention can be prepared by applying a coating material containing a composition containing the compounds represented by general formulas (1) and (2) and a resin, and an organic solvent, to a substrate or the like, and then drying the coating material. Examples of the coating film include hard coat layers, top coat layers, coating layers such as intermediate layers of various laminates, and pressure-sensitive adhesive layers.

[0144] The coating film layers such as the hard coat layer, top coat layer, and intermediate layers of various laminates can be applied to substrates or the like to form a film that blocks ultraviolet light and suppress deterioration of organic materials or the like in applications such as display materials, sensor materials, optical control materials, various industrial coating materials, automobile parts, home appliances, building materials for houses and the like, and toiletries.

[0145] The pressure-sensitive adhesive layer can be prepared, for example, by coating the pressure-sensitive adhesive layer on a release sheet and drying it, and then laminating a substrate onto the pressure-sensitive adhesive layer to produce a pressure-sensitive adhesive sheet.

[0146] The pressure-sensitive adhesive sheet of the present specification is preferably used by being attached to various substrates for applications such as displays (e.g., televisions, personal computers, smartphones, etc.), automobile parts, sensor components, home appliances, building materials for housing, etc., and glass interlayer applications. By containing the ultraviolet absorber of the present invention, the pressure-sensitive adhesive sheet can absorb ultraviolet light and light in the short wavelength region of visible light contained in backlights and sunlight, thereby suppressing adverse effects on the eyes and human body and suppressing deterioration of display elements. Note that sheet, film, and tape are synonyms.

[0147] <Uses and effects> By using the composition, molded article, and coating film of the present invention in the following applications, it is possible to reduce damage to organic matter and the human body caused by ultraviolet light with a wavelength of less than 400 nm and light in the blue light region around 400 nm.

[0148] In display applications, the present invention can be used, for example, in optical films that can be used in televisions, personal computers, smartphones, etc. A laminate using the molded article or coating film of the present invention can suppress adverse effects on the eyes by absorbing ultraviolet light and light in the short wavelength region of visible light contained in the backlight of a display, and can also suppress deterioration of the display elements of a display by absorbing ultraviolet light and light in the short wavelength region of visible light contained in sunlight.

[0149] In glass interlayer applications, it can be used, for example, in laminated glass in automobiles, buildings, etc. Laminated glass using a molded article containing the above composition can absorb ultraviolet light contained in sunlight and light in the short wavelength region of visible light, thereby suppressing adverse effects on the eyes and human body.

[0150] In lens applications, the composition can be used, for example, in lenses that can be used in eyeglasses, optical sensors, etc. When used in eyeglasses, lenses using a molded article containing the composition can, for example, absorb ultraviolet light contained in sunlight and light in the short wavelength region of visible light, thereby suppressing adverse effects on the eyes and the human body, and when used in optical sensors, can increase the sensitivity of the sensor by cutting out light of unnecessary wavelengths that could become noise.

[0151] In packaging materials for pharmaceuticals, drugs, cosmetics, etc., certain ingredients such as vitamins contained in the contents are degraded even by light in the short wavelength region of visible light, around 400 to 420 nm, so this product can reduce degradation more effectively than conventional UV absorbers.

[0152] In addition, because ultraviolet light and light in the blue light region around 400 nm degrade resins, this technology can reduce degradation in all applications that use resins, extending the lifespan of materials and ultimately contributing to waste reduction. [Example]

[0153] The present invention will be described in more detail below. Note that the present invention is not limited to the Examples. Furthermore, "parts by mass" is expressed as "parts" and "% by mass" is expressed as "%".

[0154] <Method for producing ultraviolet absorbing dye (A)> A 300 mL Erlenmeyer flask was charged with 160 parts of nitrobenzene, 8 parts of cyanuric chloride, and 17.4 parts of aluminum chloride, and the mixture was stirred to form a suspension. Next, while cooling with ice water, 21.9 parts of 2-naphthol was added in small portions. The mixture was then gradually returned to room temperature and stirred overnight to obtain a reaction solution. Meanwhile, a 500 mL beaker was charged with 38.1 parts of water, 10.0 parts of 35% hydrochloric acid, and 45.0 parts of methanol, and the reaction solution was added dropwise. After stirring for 30 minutes, the mixture was filtered to obtain a wet cake. 45 g of methanol was sprinkled onto the wet cake, washed, and filtered to obtain a wet cake. The obtained wet cake was dried overnight at 80°C to obtain UV-absorbing dye (A).

[0155] UV-absorbing dye (A) [ka]

[0156] (Method for Identifying Compounds) NMR was used to identify the compounds used in the present invention. <Measurement conditions> Equipment:BRUKER AVANCE400 Resonance frequency: 400MHz (1H-NMR) Solvent: dimethyl sulfoxide-d8 Tetramethylsilane was used as the internal standard for 1H-NMR, and chemical shift values ​​were expressed in δ values ​​(ppm), and coupling constants in Hertz. s stands for singlet, d for doublet, and m for multiplet. The contents of the obtained NMR spectrum are as follows: δ=12.05(s,3H),8.70(d,J=8.4Hz,3H),8.07(d,J=8.8Hz,3H),7.93(d,J=8.0Hz,3H),7.46-7.50(m,3H),7.38-7.42(m,3H),7.34(d,J=9.2Hz,3H)

[0157] As described above, NMR measurement of the ultraviolet absorbing dye (A) was performed, and the results supported the above structure. The structures of other compounds were also identified by NMR in the same manner as above, but the data are omitted here.

[0158] <Method of manufacturing ultraviolet absorbing composition 1> [UV-absorbing composition 1] A 300 mL Erlenmeyer flask was charged with 8 parts of UV-absorbing dye (A) and 80 parts of N-methyl-2-pyrrolidone, and the mixture was stirred to dissolve. Next, 5.4 parts of tripotassium phosphate was charged and stirred to form a suspension. Next, 5.8 parts of 1-iodobutane was charged, heated to 110°C with stirring, and stirred for 3 hours to obtain a reaction solution. Meanwhile, a 1 L beaker was charged with 400 parts of water, and the reaction solution was added dropwise in small amounts. After stirring overnight, the mixture was filtered to obtain a wet cake. The wet cake was reslurried in 400 g of water, stirred for 3 hours, and then filtered to obtain a wet cake. The obtained wet cake was dried overnight at 80°C, and the resulting dried product was pulverized with an 80 mesh sieve to obtain UV-absorbing composition 1. The composition of UV-absorbing composition 1 is shown in Table 1-2.

[0159] (Method for identifying the composition) The obtained ultraviolet absorbing composition was identified by UPLC (ultra performance liquid chromatography). <Measurement conditions> Equipment: Waters ACQUITY UPLC H-Class / MS TAP XEVO TQD Column: SunShell C30 2.6μm 50mm x 2.1mm ID Eluent: 50 mM ammonium acetate aqueous solution (pH 4.2) / DMF = 75 / 25 Identification was carried out by comparing the molecular ion peak of the mass spectrum obtained from the measurement results with the mass number (theoretical value) obtained by calculation. Table 1-1 shows the theoretical molecular weight and the measured values ​​obtained by mass spectrometry for the ultraviolet-absorbing composition of the present invention. The measured values ​​of the compounds represented by general formulas (1) to (3) are determined by the nature of the measurement to have an H (proton) added to the compound, so if the mass number is the theoretical molecular weight + (plus) 1, the compound will match. The measured values ​​of the compound represented by general formula (4) are determined by the nature of the measurement to have an H (proton) removed from the compound, so if the mass number is the theoretical molecular weight - (minus) 1, the compound will match.

[0160] [Table 1-1]

[0161] [Ultraviolet absorbing composition 2] A 300 mL Erlenmeyer flask was charged with 8 parts of UV-absorbing dye (A) and 80 parts of N-methyl-2-pyrrolidone, and the mixture was stirred to dissolve. Next, 7.0 parts of tripotassium phosphate was charged and stirred to form a suspension. Next, 6.1 parts of 1-iodobutane was charged, heated to 80°C with stirring, and stirred for 3 hours to obtain a reaction solution. Meanwhile, a 1 L beaker was charged with 400 parts of water, and the reaction solution was added dropwise in small amounts. After stirring overnight, the mixture was filtered to obtain a wet cake. The wet cake was reslurried in 400 parts of water, stirred for 3 hours, and filtered to obtain a wet cake. The obtained wet cake was dried overnight at 80°C, and the resulting dried product was pulverized with an 80 mesh filter to obtain UV-absorbing composition 2. The composition of UV-absorbing composition 2 is shown in Table 1-2.

[0162] [Ultraviolet absorbing composition 3] A 300 mL Erlenmeyer flask was charged with 8 parts of UV-absorbing dye (A) and 80 parts of N-methyl-2-pyrrolidone, and the mixture was stirred to dissolve. Next, 7.0 parts of tripotassium phosphate was charged and stirred to form a suspension. Next, 6.1 parts of 1-iodobutane was charged, heated to 110°C with stirring, and stirred for 3 hours to obtain a reaction solution. Meanwhile, a 1 L beaker was charged with 400 parts of water, and the reaction solution was added dropwise in small amounts. After stirring overnight, the mixture was filtered to obtain a wet cake. The wet cake was reslurried in 400 parts of water, stirred for 3 hours, and filtered to obtain a wet cake. The obtained wet cake was dried overnight at 80°C, and the resulting dried product was pulverized with an 80 mesh sieve to obtain UV-absorbing composition 3. The composition of UV-absorbing composition 3 is shown in Table 1-2.

[0163] [Ultraviolet absorbing composition 4] A 300 mL Erlenmeyer flask was charged with 8 parts of UV-absorbing dye (A) and 80 parts of N-methyl-2-pyrrolidone, and the mixture was stirred to dissolve. Next, 7.4 parts of tripotassium phosphate was charged and stirred to form a suspension. Next, 6.4 parts of 1-iodobutane was charged, heated to 110°C with stirring, and stirred for 3 hours to obtain a reaction solution. Meanwhile, a 1 L beaker was charged with 400 parts of water, and the reaction solution was added dropwise in small amounts. After stirring overnight, the mixture was filtered to obtain a wet cake. The wet cake was reslurried in 400 parts of water, stirred for 3 hours, and filtered to obtain a wet cake. The obtained wet cake was dried overnight at 80°C, and the resulting dried product was pulverized with an 80 mesh sieve to obtain UV-absorbing composition 4. The composition of UV-absorbing composition 4 is shown in Table 1-2.

[0164] [UV-absorbing composition 5] A 300 mL Erlenmeyer flask was charged with 8 parts of UV-absorbing dye (A) and 80 parts of N-methyl-2-pyrrolidone, and the mixture was stirred to dissolve. Next, 7.7 parts of tripotassium phosphate was charged and stirred to form a suspension. Next, 6.7 parts of 1-iodobutane was charged, heated to 110°C with stirring, and stirred for 3 hours to obtain a reaction solution. Meanwhile, a 1 L beaker was charged with 400 parts of water, and the reaction solution was added dropwise in small amounts. After stirring overnight, the mixture was filtered to obtain a wet cake. The wet cake was reslurried in 400 parts of water, stirred for 3 hours, and filtered to obtain a wet cake. The obtained wet cake was dried overnight at 80°C, and the resulting dried product was pulverized with an 80 mesh sieve to obtain UV-absorbing composition 5. The composition of UV-absorbing composition 5 is shown in Table 1-2.

[0165] [Ultraviolet absorbing composition 6] A 300 mL Erlenmeyer flask was charged with 8 parts of UV-absorbing dye (A) and 80 parts of N-methyl-2-pyrrolidone, and the mixture was stirred to dissolve. Next, 8.4 parts of tripotassium phosphate was charged and stirred to form a suspension. Next, 7.3 parts of 1-iodobutane was charged, heated to 110°C with stirring, and stirred for 3 hours to obtain a reaction solution. Meanwhile, a 1 L beaker was charged with 400 parts of water, and the reaction solution was added dropwise in small amounts. After stirring overnight, the mixture was filtered to obtain a wet cake. The wet cake was reslurried in 400 parts of water, stirred for 3 hours, and filtered to obtain a wet cake. The obtained wet cake was dried overnight at 80°C, and the resulting dried product was pulverized with an 80 mesh sieve to obtain UV-absorbing composition 6. The composition of UV-absorbing composition 6 is shown in Table 1-2.

[0166] [UV absorbing composition 7] A 300 mL Erlenmeyer flask was charged with 8 parts of UV-absorbing dye (A) and 80 parts of N-methyl-2-pyrrolidone, and the mixture was stirred to dissolve. Next, 5.4 parts of tripotassium phosphate was added and stirred to form a suspension. Next, 5.8 parts of 1-iodobutane was added, heated to 70°C with stirring, and stirred for 3 hours to obtain a reaction solution. Meanwhile, a 1 L beaker was charged with 400 parts of water, and the reaction solution was added dropwise in small amounts. After stirring overnight, the mixture was filtered to obtain a wet cake. The wet cake was reslurried in 400 parts of water, stirred for 3 hours, and filtered to obtain a wet cake. The obtained wet cake was dried overnight at 80°C, and the resulting dried product was pulverized with an 80 mesh sieve to obtain UV-absorbing composition 7. The composition of UV-absorbing composition 7 is shown in Table 1-2.

[0167] [UV absorbing composition 8] A 300 mL Erlenmeyer flask was charged with 8 parts of UV-absorbing dye (A) and 80 parts of N-methyl-2-pyrrolidone, and the mixture was stirred to dissolve. Next, 5.0 parts of tripotassium phosphate was charged and stirred to form a suspension. Next, 5.2 parts of 1-iodobutane was charged, heated to 70°C with stirring, and stirred for 3 hours to obtain a reaction solution. Meanwhile, a 1 L beaker was charged with 400 parts of water, and the reaction solution was added dropwise in small amounts. After stirring overnight, the mixture was filtered to obtain a wet cake. The wet cake was reslurried in 400 parts of water, stirred for 3 hours, and filtered to obtain a wet cake. The obtained wet cake was dried overnight at 80°C, and the resulting dried product was pulverized with an 80 mesh filter to obtain UV-absorbing composition 8. The composition of UV-absorbing composition 8 is shown in Table 1-2.

[0168] [UV absorbing composition 9] A 300 mL Erlenmeyer flask was charged with 8 parts of ultraviolet absorbing dye (A) and 80 parts of N-methyl-2-pyrrolidone, and the mixture was stirred to dissolve. Next, 4.3 parts of tripotassium phosphate was charged and stirred to form a suspension. Next, 4.4 parts of 1-iodobutane was charged, heated to 70°C with stirring, and stirred for 3 hours to obtain a reaction solution. Meanwhile, 400 parts of water was charged into a 1 L beaker, and the reaction solution was added dropwise in small amounts. After stirring overnight, the mixture was filtered to obtain a wet cake. The wet cake was reslurried in 400 parts of water, stirred for 3 hours, and filtered to obtain a wet cake. The obtained wet cake was dried overnight at 80°C, and the resulting dried product was pulverized with an 80 mesh sieve to obtain ultraviolet absorbing composition 9. The composition of ultraviolet absorbing composition 9 is shown in Table 1-2.

[0169] [UV-absorbing composition 10] A 300 mL Erlenmeyer flask was charged with 8 parts of UV-absorbing dye (A) and 80 parts of N-methyl-2-pyrrolidone, and the mixture was stirred to dissolve. Next, 3.7 parts of tripotassium phosphate was added and stirred to form a suspension. Next, 3.8 parts of 1-iodobutane was added, heated to 70°C with stirring, and stirred for 3 hours to obtain a reaction solution. Meanwhile, a 1 L beaker was charged with 400 parts of water, and the reaction solution was added dropwise in small amounts. After stirring overnight, the mixture was filtered to obtain a wet cake. The wet cake was reslurried in 400 parts of water, stirred for 3 hours, and filtered to obtain a wet cake. The obtained wet cake was dried overnight at 80°C, and the resulting dried product was pulverized with an 80 mesh sieve to obtain UV-absorbing composition 10. The composition of UV-absorbing composition 10 is shown in Table 1-2.

[0170] [UV absorbing composition 11] A 300 mL Erlenmeyer flask was charged with 8 parts of UV-absorbing dye (A) and 80 parts of N-methyl-2-pyrrolidone, and the mixture was stirred to dissolve. Next, 8.4 parts of tripotassium phosphate was added and stirred to form a suspension. Next, 8.4 parts of 1-iodohexane was added, heated to 75°C with stirring, and stirred for 3 hours to obtain a reaction solution. Meanwhile, a 1 L beaker was charged with 400 parts of water, and the reaction solution was added dropwise in small amounts. After stirring overnight, the mixture was filtered to obtain a wet cake. The wet cake was reslurried in 400 parts of water, stirred for 3 hours, and filtered to obtain a wet cake. The obtained wet cake was dried overnight at 80°C, and the resulting dried product was pulverized with an 80 mesh sieve to obtain UV-absorbing composition 11. The composition of UV-absorbing composition 11 is shown in Table 1-2.

[0171] [UV absorbing composition 12] A 300 mL Erlenmeyer flask was charged with 8 parts of UV-absorbing dye (A) and 80 parts of N-methyl-2-pyrrolidone, and the mixture was stirred to dissolve. Next, 8.4 parts of tripotassium phosphate was added and stirred to form a suspension. Next, 8.5 parts of 1-bromo-2-ethylhexane was added, heated to 75°C with stirring, and stirred for 3 hours to obtain a reaction solution. Meanwhile, a 1 L beaker was charged with 400 parts of water, and the reaction solution was added dropwise in small amounts. After stirring overnight, the mixture was filtered to obtain a wet cake. The wet cake was reslurried in 400 parts of water, stirred for 3 hours, and filtered to obtain a wet cake. The obtained wet cake was dried overnight at 80°C, and the resulting dried product was pulverized with an 80 mesh sieve to obtain UV-absorbing composition 12. The composition of UV-absorbing composition 12 is shown in Table 1-2.

[0172] [UV absorbing composition 13] A 300 mL Erlenmeyer flask was charged with 8 parts of UV-absorbing dye (A) and 80 parts of N-methyl-2-pyrrolidone, and the mixture was stirred to dissolve. Next, 8.4 parts of tripotassium phosphate was added and stirred to form a suspension. Next, 6.1 parts of 2-bromoethyl methyl ether was added, heated to 75°C with stirring, and stirred for 3 hours to obtain a reaction solution. Meanwhile, a 1 L beaker was charged with 400 parts of water, and the reaction solution was added dropwise in small amounts. After stirring overnight, the mixture was filtered to obtain a wet cake. The wet cake was reslurried in 400 parts of water, stirred for 3 hours, and filtered to obtain a wet cake. The obtained wet cake was dried overnight at 80°C, and the resulting dried product was pulverized with an 80-mesh sieve to obtain UV-absorbing composition 13. The composition of UV-absorbing composition 13 is shown in Table 1-2.

[0173] [UV absorbing composition 14] A 300 mL Erlenmeyer flask was charged with 8 parts of UV-absorbing dye (A) and 80 parts of N-methyl-2-pyrrolidone, and the mixture was stirred to dissolve. Next, 7.4 parts of tripotassium phosphate was charged and stirred to form a suspension. Next, 6.3 parts of 1-bromo-2-(2-methoxyethoxy)ethane was charged, heated to 40°C with stirring, and stirred for 3 hours to obtain a reaction solution. Meanwhile, 400 parts of water was charged into a 1 L beaker, and the reaction solution was added dropwise in small amounts. After stirring overnight, the mixture was filtered to obtain a wet cake. The wet cake was reslurried in 400 parts of water, stirred for 3 hours, and filtered to obtain a wet cake. The resulting wet cake was dried overnight at 80°C, and the resulting dried product was pulverized with an 80-mesh filter to obtain UV-absorbing composition 14. The composition of UV-absorbing composition 14 is shown in Table 1-2.

[0174] [Table 1-2]

[0175] The comparative materials used in the comparative examples were the following ultraviolet absorbers or yellow dyes.

[0176] (Comparative Material 1) Tinuvin 970 (BASF Japan, benzotriazole-based UV absorber) (Comparative material 2) Tinuvin 460 (BASF Japan, triazine-based UV absorber) (Comparative Material 3) LA-F70 (ADEKA Corporation, triazine-based UV absorber) (Comparison material 4) ACID YELLOW 3

[0177] (Comparative material 1) is a benzotriazole-based UV absorber with a structure different from that of the present invention. (Comparative material 2) and (Comparative material 3) are triazine-based UV absorbers, neither of which has a naphthalene ring. (Comparative material 4) is a yellow dye.

[0178] <Solution spectroscopy> (Examples 1-1 to 1-14, Comparative Examples 1-1 to 1-4)

[0179] The ultraviolet-visible absorption spectra were measured for the ultraviolet absorbing compositions 1 to 14 and the comparative materials 1 to 4. The results are shown in Table 2. The method for preparing the solution for measuring absorbance and the measurement conditions are as follows.

[0180] <Solution preparation method> (Example 1-1) One part of UV absorber 1 and 1,000 parts of tetrahydrofuran were mixed and completely dissolved, followed by uniformly mixing 2 parts of the solution and 98 parts of tetrahydrofuran to prepare a solution with a concentration of 20 ppm.

[0181] The ultraviolet absorbing compositions 2 to 14 and the comparative materials 1 to 4 were also adjusted to the concentrations shown in Table 2. In this specification, Examples 1-11 to 1-14 containing ultraviolet absorbent compositions 11 to 14 are reference examples, and other examples containing ultraviolet absorbent compositions 11 to 14 are also reference examples.

[0182] <Measurement conditions> Device: U-3500 (Hitachi) Measurement wavelength: 260~ 700nm Solvent: tetrahydrofuran Concentration: See Table 2

[0183] [Maximum absorption wavelength] The maximum absorption wavelength of the obtained absorption spectrum is shown in Table 2.

[0184] [UV absorption] The evaluation criteria for the ultraviolet to visible absorption spectrum are as follows: ◎: The absorbance of the maximum absorption wavelength of 360 to 400 nm is 0.8 or more 〇: The absorbance at the maximum absorption wavelength of 360 to 400 nm is 0.4 or more and less than 0.8 △: The absorbance at the maximum absorption wavelength of 360 to 400 nm is 0.2 or more and less than 0.4 ×: The absorbance at the maximum absorption wavelength of 360 to 400 nm is less than 0.2

[0185] [Maximum wavelength with transmittance of 5% or less] The obtained absorbance was used to calculate Abs(1) by normalizing the absorbance at the maximum absorption wavelength of 360 to 400 nm to 1. Next, the transmittance was calculated using the following formula to create a transmission spectrum. T[%]=0.1 n n = Abs(1) × 2 Table 2 shows the maximum wavelengths at which the transmittance is 5% or less in the above calculation formula.

[0186] [Table 2]

[0187] As shown in Table 2, it was confirmed that the ultraviolet absorbing composition of the present invention has high ultraviolet absorption properties and also absorbs blue light in the 392 to 410 nm region with a transmittance of 5% or less. It was also confirmed that the blue light blocking region can be controlled in the range of 392 to 410 nm by adjusting the ratio of the compounds represented by general formula (1) and general formula (2) in the composition.

[0188] <Molded body>

[0189] The coloring materials (D) used in the examples are shown below. (D-1) CI Pigment Blue PB15:6 (D-2) CI Solvent Red SR52 (D-3) CI Pigment Yellow PY147

[0190] The near-infrared absorbents (E) used in the examples are shown below. [ka] (E-5) [ka]

[0191] The thermoplastic resins used in the examples are listed below. (F-1) Polyethylene (Suntec LD M2270, MFR = 7 g / 10 min, manufactured by Asahi Kasei Chemicals Corporation) (F-2-2) Polyethylene (Novatec UJ790, MFR = 50 g / 10 min, manufactured by Japan Polyethylene Co., Ltd.) (F-3) Polypropylene (Novatec PP FA3EB, MFR = 10.5 g / 10 min, manufactured by Japan Polypropylene Corporation) (F-4) Polypropylene (Prime Polypro J226T, MFR = 20 g / 10 min, manufactured by Prime Polymer Co., Ltd.) (G-1) Polyester MA-2101M (Polyester, Unitika Ltd., crystalline resin, melting point 264°C, MFR 45g / 10min (280°C / 2.16kg)) (G-2) Iupilon S-3000 (polycarbonate resin, manufactured by Mitsubishi Engineering Plastics Corporation, amorphous resin, glass transition temperature 145°C, MFR 15g / 10min (300°C / 1.2kg)) (G-3) Topas 6013M-07 (cycloolefin resin, manufactured by Polyplastics Co., Ltd., amorphous resin, glass transition temperature 142°C, MFR 13g / 10min (260°C / 2.16kg)) (G-4) APEL (cycloolefin resin, manufactured by Mitsui Chemicals, amorphous resin, glass transition temperature 135°C, MFR 11g / 10min or more (260°C / 2.16kg)) (G-5) Amilan CM3001-N (Polyamide, manufactured by Toray Industries, crystalline resin, melting point 265°C, MFR 7g / 10min or more (235°C / 2.16kg)) (G-6) ULTEM (Polyetherimide, manufactured by Saudi Basic Industries Corporation, amorphous resin, glass transition temperature 217°C, MFR 8g / 10min or more (337°C / 6.6kg))

[0192] The liquid resins used in the examples are listed below. (H-1): Uniol D-1200 (NOF Corporation, polyalkylene glycol resin, polypropylene glycol resin, number average molecular weight 1200, viscosity 200 mPa s) (H-2): PEG-400 (Sanyo Chemical Industries, Ltd., polyalkylene glycol resin, polypropylene glycol resin, number average molecular weight 400, viscosity 90 mPa s) (H-3): Uniol D-400 (NOF Corporation, polyalkylene glycol resin, polypropylene glycol resin, number average molecular weight 400, viscosity 100 mPa s) (H-4): Adeka Cizer RS-107 (ADEKA Corporation, ether ester resin, adipic acid ether ester resin, number average molecular weight 430, viscosity 20 mPa s) (H-5): Adeka Cizer RS-700 (ADEKA Corporation, ether ester resin, number average molecular weight 550, viscosity 30 mPa s) (H-6): Adeka Cizer PN-250 (manufactured by ADEKA Corporation, fatty acid polyester, adipic acid polyester, number average molecular weight 2100, viscosity 4,500 mPa·s) (H-7): Adeka Cizer PN-350 (manufactured by ADEKA Corporation, fatty acid polyester, adipic acid polyester, number average molecular weight 4500, viscosity 10,000 mPa·s)

[0193] The plasticizers used in the examples are listed below. (I-1) Triethylene glycol di-2-ethylhexanoate (I-2) Triethylene glycol di-n-heptanoate

[0194] <Resin-type dispersant (J)> (Production of Resin-Type Dispersant Solution (J-1)) BYK-LPN6919 (manufactured by BYK Japan) with a non-volatile content of 60% was added with the same amount of liquid resin (H-4) as BYK-LPN6919, and the mixture was heated to 100°C and reduced pressure to distill off the solvent, yielding a resin-type dispersant solution (J-1) with a non-volatile content of BYK-LPN6919 / liquid resin (H-4) ratio of 1 / 1.

[0195] [Synthesis of ethylenically unsaturated monomer (e-5)] A reaction vessel equipped with a stirrer and thermometer was charged with 60 parts of 2-isocyanatoethyl methacrylate, 29 parts of 3-(dimethylamino)propylamine, and 120 parts of tetrahydrofuran (THF), and stirred at room temperature for 5 hours. After confirming the completion of the reaction by FT-IR, the solvent was distilled off using a rotary evaporator, yielding 73 parts of the following ethylenically unsaturated monomer (e-5) as a pale yellow, transparent liquid (yield 82%). The resulting compound was identified by 1H-NMR.

[0196] [Synthesis of ethylenically unsaturated monomer (e-9)] A reaction vessel equipped with a stirrer and a thermometer was charged with 6.6 parts of the ethylenically unsaturated monomer (e-5) obtained by the synthesis of the ethylenically unsaturated monomer (e-5) and 5 parts of ion-exchanged water, and after stirring at room temperature, 8 parts of a 35% aqueous solution of hydrochloric acid was added dropwise. The completion of the reaction was confirmed by amine value measurement, and 20 parts of an aqueous solution of the ethylenically unsaturated monomer (e-9) was obtained as a pale yellow, transparent liquid. The resulting compound was identified by 1H-NMR.

[0197] [ka]

[0198] (Production of Resin-Type Dispersant Solution (J-2)) A reaction vessel equipped with a gas inlet tube, condenser, stirring blade, and thermometer was charged with 17.7 parts of methyl methacrylate, 53.2 parts of n-butyl methacrylate, and 13.2 parts of tetramethylethylenediamine. The mixture was stirred at 50 ° C for 1 hour while flowing nitrogen, and the system was purged with nitrogen. Next, 2.6 parts of ethyl bromoisobutyrate, 5.6 parts of cuprous chloride, and 100 parts of PGMAc were charged, and the temperature was raised to 110 ° C under a nitrogen stream to initiate polymerization of the first block. After 4 hours of polymerization, the polymerization solution was sampled and the nonvolatile content was measured. The polymerization conversion rate was confirmed to be 98% or more based on the nonvolatile content. Next, 20 parts of PGMAc, 21.2 parts of ethylenically unsaturated monomer (e-5) as the second block monomer, and 27 parts of an aqueous solution of ethylenically unsaturated monomer (e-9) (non-volatile content 38%) were added to the reaction vessel, and the mixture was stirred at 110°C under a nitrogen atmosphere to continue the reaction. After 2 hours, the polymerization solution was sampled and the non-volatile content was measured. It was confirmed that the polymerization conversion rate of the second block was 98% or higher based on the non-volatile content, and the reaction solution was cooled to room temperature to terminate the polymerization. PGMAc was added to the block copolymer solution synthesized above so that the nonvolatile content was 40% by mass. In this way, a resin-type dispersant solution was obtained with an amine value per nonvolatile content of 50 mg KOH / g, a quaternary ammonium salt value of 20 mg KOH / g, a weight-average molecular weight (Mw) of 9,800, and a nonvolatile content of 40% by mass. Furthermore, a liquid resin (H-4) in an amount equal to the nonvolatile content of this resin-type dispersant solution was added, and the mixture was heated to 100°C and reduced pressure to distill off PGMAc and water, thereby obtaining a resin-type dispersant solution (J-2) in which the nonvolatile content of this resin-type dispersant solution / liquid resin (H-4) was 1 / 1.

[0199] Example 2-1 <Masterbatch manufacturing> Two parts of the ultraviolet absorbing dye 1 and 98 parts of the polyolefin resin (F-1) were fed into a twin-screw extruder (manufactured by The Japan Steel Works, Ltd.) with a screw diameter of 30 mm through the same feed port, melted and kneaded at 240°C, and then cut into pellets using a pelletizer to produce a masterbatch (K-1).

[0200] <Film molding> 90 parts of the diluted polyolefin resin (F-1) was mixed with 10 parts of the obtained masterbatch (D-1), and the mixture was melt-mixed at a temperature of 180°C using a T-die molding machine (manufactured by Toyo Seiki Seisaku-sho, Ltd.) to form a film (X-1) having a thickness of 250 μm.

[0201] (Examples 2-2 to 2-14, Comparative Examples 2-1 to 2-5) As in Example 2-1, the materials shown in Table 3 were used to form films (X-2) to (X-14) and (XX-1) to (XX-5) each having a thickness of 250 μm.

[0202] [Blue light blocking] The transmittance of the obtained film was measured using an ultraviolet-visible-near infrared spectrophotometer (manufactured by Shimadzu Corporation) and evaluated as to whether it satisfied the following conditions. ◎: Light transmittance at 400 nm wavelength is less than 1%: Very good Good: Light transmittance at 400 nm wavelength is 1% or more but less than 5%: Good △: Light transmittance at 400 nm wavelength is 5% or more but less than 10%: Not practical ×: Light transmittance at wavelength 400 nm is 10% or more over the entire range: Not practical

[0203] [Transparency] The transparency of the obtained film was evaluated visually according to the following criteria. ○: No turbidity observed. : Good △: Slight turbidity observed. : Practical range ×: Clear turbidity is observed. : Not suitable for practical use.

[0204] [Lightfastness] The obtained film was exposed to a xenon weather meter at an illuminance of 60 W / m2 at 300 to 400 nm for 100 hours. ○: The decrease in absorbance at the maximum absorption wavelength is less than 5%: Good △: The decrease in absorbance at the maximum absorption wavelength is 5% or more, but less than 10%: Practical range ×: The decrease in absorbance at the maximum absorption wavelength is 10% or more: not practical.

[0205] [Table 3]

[0206] (Example 2-15) <Masterbatch manufacturing> Two parts of the ultraviolet absorbing dye 1 and 98 parts of the polyester (G-1) were fed into a twin-screw extruder (manufactured by The Japan Steel Works, Ltd.) having a screw diameter of 30 mm through the same feed port, melt-kneaded at 240°C, and then cut into pellets using a pelletizer to produce a masterbatch (K-15).

[0207] <Film molding> 95 parts of the diluted resin polyester (G-1) was mixed with 10 parts of the obtained masterbatch (K-21), and the mixture was melt-mixed at a temperature of 180°C using a T-die molding machine (manufactured by Toyo Seiki Seisakusho) to form a film (X-15) with a thickness of 250 μm.

[0208] (Examples 2-16 to 2-28, Comparative Examples 2-6 to 2-10) In the same manner as in Example 2-15, films (X-16) to (X-28) and (XX-6) to (XX-10) each having a thickness of 250 μm were molded using the materials shown in Table 4-1.

[0209] (Example 2-29) <Production of liquid masterbatch> A liquid masterbatch (K-29) was prepared by kneading 10 parts of the ultraviolet absorber 1 and 90 parts of the liquid resin (H-1) with a roll.

[0210] <Film molding> 99.5 parts of the thermoplastic resin (G-1) diluted with 0.5 parts of the liquid masterbatch (K-29) was mixed, and the mixture was melt-mixed at 300°C using a T-die molding machine (manufactured by Toyo Seiki Seisakusho) to form a film (X-29) with a thickness of 250 μm.

[0211] (Examples 2-30 to 2-42) As in Example 2-29, films (X-30) to (X-42) each having a thickness of 250 μm were formed using the materials listed in Table 4-2.

[0212] (Example 2-43) <Production of liquid masterbatch> A liquid masterbatch (K-43) was prepared by dispersing 10 parts of ultraviolet absorbing dye 1, 20 parts of resin-type dispersant (J-1), and 70 parts of liquid resin (H-1) in a bead mill.

[0213] <Film molding> 99.5 parts of the thermoplastic resin (G-1) used as the diluted resin was mixed with 0.5 parts of the liquid masterbatch (K-43), and the mixture was melt-mixed at 300°C using a T-die molding machine (manufactured by Toyo Seiki Seisakusho) to form a film (X-43) with a thickness of 250 μm.

[0214] (Examples 2-44 to 2-56) In the same manner as in Example 2-61, films (X-44) to (X-56) each having a thickness of 250 μm were formed using the materials shown in Table 4-2.

[0215] (Example 2-57) <Production of plasticizer dispersion> A plasticizer dispersion (K-57) was prepared by dispersing 10 parts of the ultraviolet absorber 1 and 90 parts of the plasticizer (I-1) using beads.

[0216] <Film molding> 98 parts of the thermoplastic resin (G-1) diluted with 2 parts of the obtained plasticizer dispersion (K-57) was mixed, and the mixture was melt-mixed at a temperature of 280°C using a T-die molding machine (manufactured by Toyo Seiki Seisaku-sho, Ltd.) to form a T-die film (X-57) having a thickness of 250 μm.

[0217] (Examples 2-58 to 2-70) As in Example 2-57, films (X-58) to (X-70) each having a thickness of 250 μm were formed using the materials shown in Table 4-3.

[0218] (Example 2-71) <Production of plasticizer dispersion> A plasticizer dispersion (K-71) was prepared by dispersing 10 parts of ultraviolet absorbing dye 1, 20 parts of resin-type dispersant (J-1), and 70 parts of plasticizer (I-1) in a bead mill.

[0219] <Film molding> 99.5 parts of the thermoplastic resin (G-1) diluted with 0.5 parts of the obtained plasticizer dispersion (K-101) was mixed, and the mixture was melt-mixed at a temperature of 280°C using a T-die molding machine (manufactured by Toyo Seiki Seisakusho) to form a film (X-71) with a thickness of 250 μm.

[0220] (Examples 2-72 to 2-84) As in Example 2-71, films (X-72) to (X-84) each having a thickness of 250 μm were formed using the materials shown in Table 4-3.

[0221] [Table 4-1]

[0222] [Table 4-2]

[0223] [Table 4-3]

[0224] [Blue light blocking] The transmittance of the obtained film was measured using an ultraviolet-visible-near infrared spectrophotometer (manufactured by Shimadzu Corporation) and evaluated as to whether it satisfied the following conditions. ◎: Light transmittance at 400 nm wavelength is less than 1%: Very good Good: Light transmittance at 400 nm wavelength is 1% or more but less than 5%: Good △: Light transmittance at 400 nm wavelength is 5% or more but less than 10%: Not practical ×: Light transmittance at wavelength 400 nm is 10% or more over the entire range: Not practical

[0225] [Transparency] The transparency of the obtained film was evaluated visually according to the following criteria. ○: No turbidity observed. : Good △: Slight turbidity observed. : Practical range ×: Clear turbidity is observed. : Not suitable for practical use.

[0226] [Haze value] The haze value of the obtained film was measured using a haze meter and evaluated according to the following criteria. ◎+: Less than 0.2 Very good ◎: 0.2 or more and less than 0.5, very good 〇: 0.5 or more and less than 2 Good △: 2 or more but less than 5 Good × :5 or more Not practical

[0227] [Lightfastness] The obtained film was exposed to a xenon weather meter at an illuminance of 60 W / m2 at 300 to 400 nm for 100 hours. ○: The decrease in absorbance at the maximum absorption wavelength is less than 5%: Good △: The decrease in absorbance at the maximum absorption wavelength is 5% or more, but less than 10%: Practical range ×: The decrease in absorbance at the maximum absorption wavelength is 10% or more: not practical.

[0228] [Table 4-4]

[0229] As shown in Table 4-4, the molded article of the present invention has high UV absorption per unit weight and high light resistance in the UV to blue light range. It was found that it can sufficiently block blue light around 400 nm. Furthermore, it was found that the film has high transparency and low haze because it can be used in a practical range even with a small amount of addition.

[0230] Example 3-1 <Masterbatch manufacturing> Two parts of the ultraviolet absorbing dye 1 and 98 parts of the thermoplastic resin (G-1) were fed into a twin-screw extruder (manufactured by The Japan Steel Works, Ltd.) with a screw diameter of 30 mm through the same feed port, melted and kneaded at 300°C, and then cut into pellets using a pelletizer to produce a masterbatch (K-15).

[0231] <Film molding> 90 parts of the thermoplastic resin (G-1) diluted with 10 parts of the masterbatch (K-15) were mixed, and the mixture was melt-mixed at 300°C using a T-die molding machine (manufactured by Toyo Seiki Seisaku-sho, Ltd.). The mixture was then allowed to dwell at 300°C for 20 minutes. A film (Y-1) having a thickness of 250 μm was then molded.

[0232] (Examples 3-2 to 3-70, Comparative Examples 3-1 to 3-5) As in Example 3-1, films (Y-2) to (Y-70) and (YY-1) to (YY-5) each having a thickness of 250 μm were formed using the materials shown in Tables 4-1 to 4-3.

[0233] [Blue light blocking effect after retention] The transmittance of the obtained film was measured using an ultraviolet-visible-near infrared spectrophotometer (manufactured by Shimadzu Corporation) and evaluated as to whether it satisfied the following conditions. ◎: Light transmittance at 400 nm wavelength is less than 1%: Very good Good: Light transmittance at 400 nm wavelength is 1% or more but less than 5%: Good △: Light transmittance at 400 nm wavelength is 5% or more but less than 10%: Not practical ×: Light transmittance at wavelength 400 nm is 10% or more over the entire range: Not practical

[0234] [Heat resistance] The obtained films (Y-1) to (Y-80) were evaluated by comparing the difference in ultraviolet absorbance with the films (X-17) to (X-96) and (XX-11) to (XX-20) obtained in Examples (2-17) to (2-96) and Comparative Examples (2-11) to (2-20). The evaluation criteria were as follows: ◎: Difference in light transmittance at 400 nm wavelength is less than 1%: Good 〇: Difference in light transmittance at wavelength 400 nm is 1% or more but less than 5%: Practical range △: Difference in light transmittance at wavelength 400 nm is 5% or more but less than 10%: Not practical ×: Difference in light transmittance at wavelength 400 nm is 10% or more: Not practical

[0235] The raw materials and compounding ratios of Examples 3-1 to 3-100 and Comparative Examples 3-1 to 3-10 are the same as those of Examples 2-21 to 2-120 and Comparative Examples 2-11 to 2-20, respectively, and therefore Table 5 lists only the results.

[0236] [Table 5]

[0237] As shown in Table 5, the molded article using the ultraviolet absorber of the present invention has a small change in blue light blocking property due to the residence time during melt mixing during film molding, confirming that it has good heat resistance.

[0238] Example 4-1 <Production of UV-absorbing masterbatch> One part of UV absorber 3, one part of UV absorber C-1, and 98 parts of UV absorber polyester (G-1) were fed into a twin-screw extruder (manufactured by The Japan Steel Works, Ltd.) with a screw diameter of 30 mm through the same feed port, melt-kneaded at 240°C, and then cut into pellets using a pelletizer to produce a masterbatch (K-85).

[0239] <Film molding> 90 parts of the diluted resin polyester (G-1) was mixed with 10 parts of the obtained masterbatch (K-85), and the mixture was melt-mixed at a temperature of 180°C using a T-die molding machine (manufactured by Toyo Seiki Seisaku-sho, Ltd.) to form a film (Z-1) with a thickness of 250 μm.

[0240] (Examples 4-2 to 4-3) In the same manner as in Example 4-1, films (Z-2) to (Z-3) each having a thickness of 250 μm were formed using the materials shown in Table 6-1.

[0241] [Spectral characteristics] The transmittance of the obtained film was measured using an ultraviolet-visible-near infrared spectrophotometer (manufactured by Shimadzu Corporation) and evaluated as to whether it satisfied the following conditions. ◎: Light transmittance of 360 to 400 nm wavelength is less than 1% across the entire range: Very good Good: Light transmittance of 360 to 400 nm wavelength is 1% or more but less than 5%: Good △: Light transmittance of 360-400 nm wavelength is 5% or more but less than 10%: Not practical ×: Light transmittance of 360 to 400 nm wavelength is 10% or more over the entire range: Not practical

[0242] [Lightfastness] The obtained film was exposed to a xenon weather meter at an illuminance of 60 W / m2 at 300 to 400 nm for 100 hours. ○: The decrease in absorbance at the maximum absorption wavelength is less than 5%: Good △: The decrease in absorbance at the maximum absorption wavelength is 5% or more, but less than 10%: Practical range ×: The decrease in absorbance at the maximum absorption wavelength is 10% or more: not practical.

[0243] [Heat resistance] The heat resistance was evaluated in the same manner as in Example 3. The evaluation criteria were as follows. ◎: Difference in light transmittance at 400 nm wavelength is less than 1%: Good 〇: Difference in light transmittance at wavelength 400 nm is 1% or more but less than 5%: Practical range △: Difference in light transmittance at wavelength 400 nm is 5% or more but less than 10%: Not practical ×: Difference in light transmittance at wavelength 400 nm is 10% or more: Not practical

[0244] [Transparency] The transparency of the obtained film was evaluated visually according to the following criteria. ○: No turbidity observed. : Good △: Slight turbidity observed. : Practical range ×: Clear turbidity is observed. : Not suitable for practical use.

[0245] (Example 4-4) <Production of UV / visible light absorbing masterbatch> One part of UV absorber 3, one part of colorant D-1, one part of colorant D-2, one part of colorant D-3, and 96 parts of UV absorber polyester (G-1) were fed into a twin-screw extruder (manufactured by The Japan Steel Works, Ltd.) with a screw diameter of 30 mm through the same feed port, melt-kneaded at 240°C, and then cut into pellets using a pelletizer to produce a masterbatch (K-88).

[0246] <Film molding> 90 parts of the diluted resin polyester (G-1) was mixed with 10 parts of the obtained masterbatch (K-124), and the mixture was melt-mixed at a temperature of 180°C using a T-die molding machine (manufactured by Toyo Seiki Seisaku-sho, Ltd.) to form a film (Z-4) with a thickness of 250 μm.

[0247] (Examples 4-5 to 4-6) In the same manner as in Example 4-4, films (Z-5) to (Z-6) having a thickness of 250 μm were formed using the materials shown in Table 6-1.

[0248] [Spectral characteristics] The transmittance of the obtained film was measured using an ultraviolet-visible-near infrared spectrophotometer (manufactured by Shimadzu Corporation) and evaluated as to whether it satisfied the following conditions. ◎: The light transmittance at wavelengths of 400 to 650 nm is less than 1% over the entire range. 〇: Light transmittance of 400 to 650 nm wavelength is 1% or more but less than 5%: Practical range △: Light transmittance of wavelength 400 to 650 nm is 5% or more but less than 10%: Not practical ×: Light transmittance of wavelengths 400 to 650 nm is 10% or more across the entire range: not practical

[0249] The light resistance and heat resistance were evaluated in the same manner as in Example 4-1.

[0250] (Examples 4-7) <Production of ultraviolet and near-infrared masterbatches> One part of UV absorber 3, one part of near-infrared collecting dye E-1, and 98 parts of UV absorber polyester (G-1) were fed into a twin-screw extruder (manufactured by The Japan Steel Works, Ltd.) with a screw diameter of 30 mm through the same feed port, melt-kneaded at 240°C, and then cut into pellets using a pelletizer to produce a masterbatch (K-91).

[0251] <Film molding> 90 parts of the diluted resin polyester (G-1) was mixed with 10 parts of the obtained masterbatch (K-91), and the mixture was melt-mixed at a temperature of 180°C using a T-die molding machine (manufactured by Toyo Seiki Seisaku-sho, Ltd.) to form a film (Z-7) with a thickness of 250 μm.

[0252] (Examples 4-8 to 4-11) In the same manner as in Example 4-7, films (Z-8) to (Z-11) each having a thickness of 250 μm were formed using the materials shown in Table 6-1.

[0253] [Spectral characteristics] The transmittance of the obtained film was measured using an ultraviolet-visible-near infrared spectrophotometer (manufactured by Shimadzu Corporation) and evaluated as to whether it satisfied the following conditions. ◎: Light transmittance at wavelengths of 400 nm and 700 to 800 nm is less than 1%: Good 〇: Light transmittance at wavelengths of 400 nm and 700 to 800 nm is 1% or more but less than 5%: Practical range △: Light transmittance of 400 nm wavelength and 700 to 800 nm wavelength is 5% or more but less than 10%: Not practical ×: Light transmittance at wavelengths of 400 nm and 700 to 800 nm is 10% or more: Not practical

[0254] The light resistance and heat resistance were evaluated in the same manner as in Example 4-1.

[0255] (Examples 4-12) <Production of UV / NIR absorbent masterbatch> One part of UV absorber 3, one part of UV absorber C-1, one part of near-infrared collecting dye E-1, and 97 parts of UV absorber polyester (G-1) were fed into a twin-screw extruder (manufactured by The Japan Steel Works, Ltd.) with a screw diameter of 30 mm through the same feed port, melt-kneaded at 240°C, and then cut into pellets using a pelletizer to produce a masterbatch (K-96).

[0256] <Film molding> 90 parts of the diluted resin polyester (G-1) was mixed with 10 parts of the obtained masterbatch (K-96), and the mixture was melt-mixed at a temperature of 180°C using a T-die molding machine (manufactured by Toyo Seiki Seisaku-sho, Ltd.) to form a film (Z-12) with a thickness of 250 μm.

[0257] (Examples 4-13 to 4-16) In the same manner as in Example 4-12, films (Z-13) to (Z-16) each having a thickness of 250 μm were formed using the materials shown in Table 6-1.

[0258] [Spectral characteristics] The transmittance of the obtained film was measured using an ultraviolet-visible-near infrared spectrophotometer (manufactured by Shimadzu Corporation) and evaluated as to whether it satisfied the following conditions. ◎: Light transmittance of wavelengths 300 to 420 nm and wavelengths 700 to 800 nm is less than 1%: Good 〇: Light transmittance for wavelengths of 300 to 420 nm and wavelengths of 700 to 800 nm is 1% or more but less than 5%: Practical range △: Light transmittance for wavelengths of 300 to 420 nm and wavelengths of 700 to 800 nm is 5% or more but less than 10%: Not practical ×: Light transmittance of 10% or more for wavelengths of 300 to 420 nm and wavelengths of 700 to 800 nm: Not practical

[0259] The light resistance and heat resistance were evaluated in the same manner as in Example 4-1, and the results are shown in Table 6-2.

[0260] [Table 6-1]

[0261] [Table 6-2]

[0262] <Paint> (Example 5-1) The following composition was mixed with stirring to prepare a paint. UV absorber 1 0.5 parts Polyester (Vylon GK250, manufactured by Toyobo Co., Ltd.) 9.5 parts Methyl ethyl ketone 90.0 parts

[0263] (Examples 5-2 to 5-14, Comparative Examples 5-1 to 5-5) As shown in Table 7, the paints of Examples 5-2 to 5-14 and Comparative Examples 5-1 to 5-5 were prepared in the same manner as in Example 5-1, respectively.

[0264] (Creation of coating film) The resulting coating material was applied to a glass substrate having a thickness of 1000 μm using a bar coater so that the dry film thickness was 10 μm, and then dried at 100° C. for 2 minutes to form a coating film. (Evaluation of coating film) The resulting coating films were evaluated by the following methods.

[0265] [Blue light blocking] The transmittance of the obtained coated product was measured using an ultraviolet-visible-near infrared spectrophotometer (manufactured by Shimadzu Corporation) and evaluated as to whether or not it satisfied the following conditions. ◎: Light transmittance at 400 nm wavelength is less than 1%: Very good Good: Light transmittance at 400 nm wavelength is 1% or more but less than 5%: Good △: Light transmittance at 400 nm wavelength is 5% or more but less than 10%: Not practical ×: Light transmittance at wavelength 400 nm is 10% or more over the entire range: Not practical

[0266] [Transparency] The transparency of the resulting coated product was evaluated visually, and the evaluation criteria were as follows: ○: No turbidity observed. Good △: Slight turbidity is observed. ×: Clear turbidity is observed. Not suitable for practical use.

[0267] [Lightfastness] The resulting coated product was exposed to light of 300 to 400 nm at an illuminance of 60 W / m2 for 100 hours using a xenon weather meter. ○: The decrease in absorbance at the maximum absorption wavelength is less than 5%: Good △: The decrease in absorbance at the maximum absorption wavelength is 5% or more, but less than 10%: Practical range ×: The decrease in absorbance at the maximum absorption wavelength is 10% or more: not practical.

[0268] [Table 7]

[0269] As shown in Table 7, coating films using the UV absorbers of the present invention have high UV absorption in the blue light region and high light resistance. It was found that they can adequately block blue light around 400 nm. Furthermore, it was found that even a small amount of addition is sufficient to achieve a practical range, so the transparency of the coating material is not impaired.

[0270] <Photocurable composition> (Example 6-1) The raw materials were mixed with stirring to prepare a photocurable composition according to the following composition. UV absorber 1 1.0 parts Photopolymerizable compound (multifunctional acrylate "KAYARAD DPHA" manufactured by Nippon Kayaku Co., Ltd.) 18.0 copies Photopolymerization initiator (IGM Resin BV "Omnirad184") 1.0 part Propylene glycol monomethyl ether 80.0 parts

[0271] (Examples 6-2 to 6-14, Comparative Examples 6-1 to 6-5) As shown in Table 8, photocurable compositions of Examples 6-2 to 6-14 and Comparative Examples 6-1 to 6-5 were prepared in the same manner as in Example 6-1, respectively.

[0272] (Creation of coating film) The photocurable composition was applied to a 1 mm thick glass substrate using a bar coater to a dry film thickness of 6 μm. The resulting coating was dried at 100°C for 1 minute and then cured by irradiating it with 400 mJ / cm2 of ultraviolet light from a high-pressure mercury lamp to produce a coated product. (Evaluation of coating film) The resulting coating films were evaluated by the following methods.

[0273] [Blue light blocking] The transmittance of the obtained coated product was measured using an ultraviolet-visible-near infrared spectrophotometer (manufactured by Shimadzu Corporation) and evaluated as to whether or not it satisfied the following conditions. ◎: Light transmittance at 400 nm wavelength is less than 1%: Very good Good: Light transmittance at 400 nm wavelength is 1% or more but less than 5%: Good △: Light transmittance at 400 nm wavelength is 5% or more but less than 10%: Not practical ×: Light transmittance at wavelength 400 nm is 10% or more over the entire range: Not practical

[0274] [Lightfastness] The resulting coated product was exposed to light of 300 to 400 nm at an illuminance of 60 W / m2 for 100 hours using a xenon weather meter. ○: The decrease in absorbance at the maximum absorption wavelength is less than 5%: Good △: The decrease in absorbance at the maximum absorption wavelength is 5% or more, but less than 10%: Practical range ×: The decrease in absorbance at the maximum absorption wavelength is 10% or more: not practical.

[0275] [Transparency] The transparency of the resulting coated product was evaluated visually, and the evaluation criteria were as follows: ○: No turbidity observed. Good △: Slight turbidity is observed. ×: Clear turbidity is observed. Not suitable for practical use.

[0276] [Scratch resistance] The coated sample was placed in a Gakushin tester and shaken 10 times with steel wool at a load of 250 g. The coated sample was then removed and the degree of scratching was judged visually on a 5-point scale as shown below. The higher the score, the better the scratch resistance of the cured film. 5: No scratches at all. 4: There are some minor scratches. 3: There is a scratch, but the base material is not visible. 2: There are scratches and some of the hardened film has peeled off. 1: The cured film has peeled off, leaving the base material exposed.

[0277] [Table 8]

[0278] As shown in Table 8, coating films using the UV absorbers of the present invention have high UV absorption in the blue light region and high light resistance. It can also be seen that they can adequately block blue light around 400 nm. It was also found that even a small amount of addition achieves a practical range without impairing the transparency of the coating. Furthermore, it was found that they have good scratch resistance.

[0279] <Adhesive> (Adhesive resin manufacturing example L-1) Using a reactor equipped with a stirrer, reflux condenser, nitrogen inlet tube, thermometer, and dropping tube, 96.0 parts of n-butyl acrylate, 4.0 parts of 2-hydroxyethyl acrylate (50% of the total amount), 0.2 parts of 2,2'-azobisisobutylnitrile as a polymerization initiator, and 150 parts of ethyl acetate as a solvent were charged into a reaction vessel under a nitrogen atmosphere. The remaining 50% of the total amount and an appropriate amount of ethyl acetate were then charged into a dropping vessel. Next, heating was initiated and the start of the reaction in the reaction vessel was confirmed. Then, under reflux, the contents of the dropping tube and 0.01 parts of an ethyl acetate diluted solution of 2,2'-azobisisobutylnitrile were added dropwise. After the addition, the reaction was continued for 5 hours while maintaining the reflux state. After the reaction was completed, the mixture was cooled and an appropriate amount of ethyl acetate was added to obtain the acrylic adhesive resin, Example F-1. The pressure-sensitive adhesive resin obtained in Production Example F-1 had a weight-average molecular weight of 500,000, a non-volatile content of 40%, and a viscosity of 3,200 mPa·s.

[0280] (Adhesive resin manufacturing example L-2) Using a reactor equipped with a stirrer, reflux condenser, nitrogen inlet tube, thermometer, and dropping tube, 96.0 parts of n-butyl acrylate, 50% of the total amount of 4.0 parts of acrylic acid, 0.2 parts of 2,2'-azobisisobutylnitrile as a polymerization initiator, and 150 parts of ethyl acetate as a solvent were charged into a reaction vessel under a nitrogen atmosphere. The remaining 50% of the total amount and an appropriate amount of ethyl acetate were then charged into the dropping vessel. Next, heating was initiated and the start of the reaction in the reaction vessel was confirmed. Then, under reflux, the contents of the dropping tube and 0.01 parts of a diluted solution of 2,2'-azobisisobutylnitrile in ethyl acetate were added dropwise. After the addition was completed, the reaction was continued for 5 hours while maintaining reflux. After the reaction was completed, the mixture was cooled and an appropriate amount of ethyl acetate was added to obtain the acrylic adhesive resin, Production Example F-2. The resulting adhesive resin of Production Example F-2 had a weight-average molecular weight of 600,000, a nonvolatile content of 40%, and a viscosity of 4,000 mPa·s.

[0281] (Example 7-1) As an adhesive resin, 100 parts of the nonvolatile content of the adhesive resin of Production Example L-1 was mixed with 1 part of UV absorber 1, 0.1 parts of KBM-403 (manufactured by Shin-Etsu Chemical Co., Ltd.) as a silane coupling agent, and 0.4 parts of a trimethylolpropane adduct of tolylene diisocyanate (abbreviated as TDI-TMP, NCO value = 13.2, nonvolatile content = 75%) as a curing agent, and the mixture was stirred thoroughly to obtain an adhesive. Then, this adhesive was applied to a release film of a 38 μm thick polyethylene terephthalate substrate so that the thickness after drying was 50 μm, and dried in a hot air oven at 100 ° C. for 2 minutes. Then, a 25 μm thick polyethylene terephthalate film was attached to the adhesive layer side, and the mixture was aged at room temperature for 7 days to obtain an adhesive sheet.

[0282] (Examples 7-2 to 7-14, Comparative Examples 7-1 to 7-5) As shown in Table 9, pressure-sensitive adhesive sheets of Examples 7-2 to 7-14 and Comparative Examples 7-1 to 7-5 were obtained in the same manner as in Example 7-1.

[0283] (Evaluation of adhesive sheets) [Adhesive strength] The resulting adhesive sheet was prepared in a size of 25 mm wide x 150 mm long. In an atmosphere of 23°C and 50% relative humidity, the release film was peeled off from the adhesive sheet, and the exposed adhesive layer was attached to a glass plate and pressed back and forth once with a 2 kg roll. After leaving it for 24 hours, the adhesive strength was measured using a tensile tester in a 180° peel test, in which the sheet was peeled in a 180° direction at a rate of 300 mm / min, and evaluated based on the following evaluation criteria (in accordance with JIS Z0237:2000). ○: "Adhesive strength 10N / 25mm or more" ×: "Adhesive strength less than 10N / 25mm"

[0284] [Holding force] The resulting adhesive sheet was prepared to a size of 25 mm wide x 150 mm long. In accordance with JIS Z0237:2000, the release sheet was peeled off from the adhesive sheet, and the adhesive layer was attached to a 25 mm wide x 25 mm wide section of the bottom edge of a polished stainless steel plate measuring 30 mm wide x 150 mm long. The adhesive was then pressed back and forth once with a 2 kg roll, and the sheet was then left to stand for 70,000 seconds in a 40°C atmosphere under a 1 kg load to measure the holding power. The length of downward displacement of the top edge of the adhesive sheet surface was measured for evaluation. Evaluation criteria ○: "The adhesive sheet misalignment length is less than 0.5 mm. Good." ×: "The adhesive sheet has shifted by 0.5 mm or more. Not suitable for practical use."

[0285] [Blue light blocking] The transmittance of the obtained pressure-sensitive adhesive sheet was measured using an ultraviolet-visible-near infrared spectrophotometer (manufactured by Shimadzu Corporation), and it was evaluated whether or not the following conditions were satisfied. ◎: Light transmittance at 400 nm wavelength is less than 1%: Very good Good: Light transmittance at 400 nm wavelength is 1% or more but less than 5%: Good △: Light transmittance at 400 nm wavelength is 5% or more but less than 10%: Not practical ×: Light transmittance at wavelength 400 nm is 10% or more over the entire range: Not practical

[0286] [Lightfastness] The obtained pressure-sensitive adhesive sheet was exposed to an illuminance of 60 W / m2 at 300 to 400 nm for 100 hours using a xenon weather meter. ○: The decrease in absorbance at the maximum absorption wavelength is less than 5%: Good △: The decrease in absorbance at the maximum absorption wavelength is 5% or more, but less than 10%: Practical range ×: The decrease in absorbance at the maximum absorption wavelength is 10% or more: not practical.

[0287] [Transparency] The transparency of the resulting pressure-sensitive adhesive sheet was evaluated visually, and the evaluation criteria were as follows: ○: No turbidity observed. Good △: Slight turbidity is observed. ×: Clear turbidity is observed. Not suitable for practical use.

[0288] [Stability over time] The release liner was peeled off from the pressure-sensitive adhesive sheet, and the sheet was laminated to a PET film (Lumirror T60, 50 μm thick, manufactured by Toray Industries, Inc.). This sheet was then cut to 3 cm × 10 cm, and a 1 mm thick glass plate was attached to the opposite side of the pressure-sensitive adhesive sheet. A 2 kg load was applied using a tape pressure roller to press the glass plate together, producing a three-layer laminate of PET / pressure-sensitive adhesive layer / glass plate. This laminate was left to stand in an environment at 100°C for up to 120 hours, and then observed using an optical microscope at 50x magnification to determine whether there were any crystallized dye particles of 0.5 mm or more in the adhesive layer. A similar laminate was also left to stand in an environment at -40°C, and similar precipitates were observed. The evaluation criteria were as follows, with a score of △ or better being considered acceptable for practical use. ◎+: No precipitate was observed after 120 hours under any environment. ◎: Under any environment, there was one or less precipitate after 120 hours ○: Under any environment, there was one or less precipitate after 80 hours △: Under any environment, there was one or less precipitate after 50 hours. ×: One or more precipitates were observed after 50 hours under any environment.

[0289] [Table 9]

[0290] As shown in Table 9, the adhesive using the UV absorber of the present invention has high UV absorption in the blue light region and high light resistance. It was found that it can sufficiently block blue light around 400 nm. Furthermore, it was found that the transparency of the adhesive sheet is not impaired because even a small amount of addition reaches a practical range. Furthermore, it was found to have good adhesive strength, holding power, and stability over time.

Claims

1. A composition comprising compounds having ultraviolet absorbing properties and represented by the following general formulas (1) and (2): 【Chemical 1】 (In general formulas (1) and (2), R １ ~R １８ R each independently represents a hydrogen atom. １９ , R ２０ each independently represents an alkoxy group having 1 to 5 carbon atoms.

2. The compound includes a compound represented by the following general formula (3): The composition according to claim 1, wherein the compound represented by general formula (3) is contained in an amount of more than 0% and not more than 5% based on 100% by mass of the nonvolatile content of the composition. 【Chemistry 2】 (In general formula (3), R １ ~R １８ R each independently represents a hydrogen atom. １９ , R ２０ , R ２１ each independently represents an alkoxy group having 1 to 5 carbon atoms.

3. It contains a compound represented by the following general formula (4): The composition according to claim 1, wherein the compound represented by general formula (4) is contained in an amount of more than 0% and not more than 5% based on 100% by mass of the nonvolatile content of the composition. 【Chemistry 3】 (In general formula (4), R １ ~R １８ each independently represents a hydrogen atom.)

4. A composition comprising the ultraviolet absorber according to any one of claims 1 to 3, and at least one ultraviolet absorber (C) selected from the group consisting of triazine-based compounds, benzotriazole-based compounds, and benzophenone-based compounds, which are compounds other than the compounds represented by general formulas (1) to (4).

5. A coloring composition comprising the composition according to any one of claims 1 to 3 and a coloring material (D) that blocks light in the visible wavelength range of 450 to 650 nm.

6. The colored composition according to claim 5 , wherein the colorant (D) contains two or more chromatic colorants.

7. A composition according to any one of claims 1 to 3, and a near-infrared absorber (E) having an absorption maximum in a wavelength region of 600 to 1500 nm, A near-infrared absorbing composition, wherein the near-infrared absorbent (E) having an absorption maximum in a wavelength region of 600 to 1500 nm is at least one selected from a phthalocyanine compound, a naphthalocyanine compound, a squarylium compound, a cyanine compound, and a diketopyrrolopyrrole.

8. A resin composition comprising the composition according to any one of claims 1 to 3 and a resin.

9. The resin composition according to claim 8, wherein the resin is a thermoplastic resin.

10. A photosensitive composition comprising the composition according to any one of claims 1 to 4, a photopolymerizable compound, and a photopolymerization initiator.

11. A molded article obtained by molding the resin composition according to claim 8 or 9.

12. A coating film formed from the resin composition according to claim 8 or 9, or the photosensitive resin composition according to claim 10.

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