Ultraviolet absorber

Abstract

Provided: a novel ultraviolet absorber that has excellent absorption of UV-A or UV-B, and specifically absorbs only ultraviolet light of a specific wavelength, and can be used in a wide range of applications; and an ultraviolet absorbing resin that, in addition to the aforementioned properties, also has excellent leaching resistance. An ultraviolet absorber, which is a compound of general formula (1) or a resin containing the aforementioned compound as a constituent unit.

Description

[Technical Field]

[0001] This invention relates to an ultraviolet absorber, an ultraviolet-absorbing resin, an ultraviolet-absorbing coating liquid, an ultraviolet-absorbing coating resin sheet, an ultraviolet-absorbing coated glass, an ultraviolet-absorbing molded body, an ultraviolet-absorbing film, a polarizer protective film, a polarizer plate, an image display device, a transport machine, and building material parts, wherein the ultraviolet absorber has excellent ultraviolet absorption properties in the UV-A and UV-B regions. [Previous Technology]

[0002] Ultraviolet radiation is broadly classified according to its wavelength range into: long-wavelength ultraviolet radiation (UV-A; 320–400 nm), medium-wavelength ultraviolet radiation (UV-B; 280–320 nm), and short-wavelength ultraviolet radiation (UV-C; 200–280 nm). Among them, UV-C is almost entirely absorbed by the ozone layer before reaching the Earth's surface, so most of the ultraviolet radiation that reaches the Earth is UV-A and UV-B.

[0003] Depending on their type, the wavelengths of ultraviolet light that are most likely to cause degradation in polymer materials are different. It is known that many polymer materials, such as polyethylene and polyvinyl chloride, will deteriorate significantly due to UV-B, which can lead to discoloration and reduced mechanical strength. Therefore, the addition of ultraviolet absorbers that absorb UV-B is being widely promoted.

[0004] In recent years, due to the search for longer-term stability against ultraviolet light, the demand for a type of ultraviolet absorber is increasing in fields such as displays, solar cells, and automobiles. This absorber should be able to absorb not only UV-B but also up to UV-A. However, conventional organic ultraviolet absorbers have low absorption of long-wavelength ultraviolet light, so the amount added must be increased. But if a large amount is added, it can lead to problems such as exudation and a decrease in the mechanical strength, heat resistance, and transparency of the resin. Furthermore, ultraviolet absorbers that absorb long-wavelength ultraviolet light often tend to color yellow because they absorb up to the visible light region above 400 nm. Previously, it was considered difficult to balance ultraviolet absorption performance in the UV-A region with low coloring.

[0005] Optical films used to improve visibility in display devices such as liquid crystal displays (LCDs) and organic OLED displays have the following problem: in addition to ultraviolet rays contained in sunlight, visibility decreases over time due to degradation such as yellowing caused by prolonged exposure to ultraviolet rays contained in the light source of the display device. Therefore, there is a search for an excellent ultraviolet absorber that can maintain sufficient ultraviolet absorption performance even when the optical film is thinned due to the need for miniaturization of display devices.

[0006] For example, Patent Document 1 discloses a (meth)acrylic film containing a benzotriazole-based ultraviolet absorber. However, generally speaking, the molar absorptivity of benzotriazole-based ultraviolet absorbers in the UV-A region is insufficient, and high concentrations must be added. Therefore, compositions containing benzotriazole-based ultraviolet absorbers have the following problems that need to be solved: they are prone to whitening and embrittlement caused by exudation.

[0007] Furthermore, Patent Document 2 discloses an ultraviolet absorber that has strong absorption over a wide range in the UV-A region and is composed of triazine compounds. However, triazine-based ultraviolet absorbers, which generally absorb ultraviolet light over a wide wavelength band, also absorb visible light above 400 nm, thus presenting the problem of easy staining that needs to be addressed.

[0008] Patent Document 3 discloses a method that combines an ultraviolet absorber with extremely high absorption at wavelengths of 200–300 nm with an ultraviolet absorber with extremely high absorption at wavelengths of 320–400 nm. This achieves both ultraviolet absorption performance at wavelength 380 nm and low coloration. However, to further improve ultraviolet absorption performance and reduce coloration, we hypothesize the need for novel ultraviolet absorbers that absorb only specific wavelengths of ultraviolet light.

[0009] Patent Document 4 discloses a composition of an ultraviolet absorber, characterized by: a maximum absorption wavelength of 350 nm or more and 400 nm or less, a half-width of 55 nm or less, and a molar absorptivity of 20,000 or more at the maximum absorption wavelength. This provides a material that absorbs only specific wavelengths of ultraviolet light and has minimal coloration. However, the compositions disclosed in this invention are complex and costly to synthesize, thus hindering their widespread use.

[0010] In addition, it has been proposed that, in order to prevent the UV absorber from leaching out in the actual use environment or from sublimating due to heat during drying and molding, polymerizable functional groups be given to the UV absorber and the UV absorber itself be hardened into a coating component.

[0011] Patent Document 5 discloses a resin composition obtained by homopolymerization of a benzotriazole derivative compound, and Patent Document 6 discloses a compound obtained by endowing a reactive functional group to the end of a compound having a triazine skeleton. However, since the functional groups that facilitate ultraviolet absorption are all previously known substances such as benzotriazole and triazine, the invention suffers from the problems it seeks to solve, such as insufficient molar absorptivity in the UV-A region and easy staining, as mentioned above. [Prior Art Documents] (Patent Documents)

[0012] Patent Document 1: Japanese Patent Application Publication No. 2019-167411; Patent Document 2: Japanese Patent Application Publication No. 2016-102199; Patent Document 3: Japanese Patent Application Publication No. 2015-165301; Patent Document 4: Japanese Patent Application Publication No. 2010-059235; Patent Document 5: Japanese Patent Application Publication No. 2019-034998; Patent Document 6: Japanese Patent Application Publication No. 2021-178918 [Summary of the Invention]

[0013] [Problem to be Solved by the Invention] The object of the present invention is to provide: a novel ultraviolet absorber that has excellent absorption of UV-A or UV-B, and specifically absorbs only ultraviolet light of a specific wavelength, and can be used in a wide range of applications; and an ultraviolet-absorbing resin, an ultraviolet-absorbing coating liquid, an ultraviolet-absorbing coating resin film, an ultraviolet-absorbing coated glass, an ultraviolet-absorbing molded body, an ultraviolet-absorbing film, a polarizing film, a polarizing plate, an image display device, a transport machine, and building material parts, which, in addition to the aforementioned characteristics, also have excellent resistance to leaching. [Technical Means for Solving the Problem]

[0014] After conducting research to achieve the aforementioned problem, the inventors discovered that the fumonisins possess excellent ultraviolet absorption properties for UV-A or UV-B, and specifically absorb only ultraviolet light of a particular wavelength. Furthermore, by bestowing appropriate substituents upon these fumonisins, they can absorb ultraviolet light of various wavelengths. In addition, the present invention was completed by discovering that by bestowing polymerizable functional groups upon the aforementioned fumonisins, resin compositions with excellent ultraviolet absorption properties can be produced.

[0015] In other words, the present invention is as follows. [1] An ultraviolet absorber, which is a compound represented by general formula (1), or a resin containing the aforementioned compound as a constituent unit: In formula (1), Z1a and Z1b independently represent an arene ring, Y1a and Y1b independently represent a carboxyl group, a carboxyl ester group, a nitro group, an anhydride group, a hydroxyl group, or a group having a polymerizable double bond, R1a and R1b independently represent a halogen atom, a nitro group, a cyano group, a mono- or disubstituted amino group, -RA, -ORA, or -SRA, except that RA represents a hydrocarbon group, k1 and k2 independently represent integers greater than or equal to 0, m1 and m2 independently represent integers from 0 to 4, R2a and R2b independently represent hydrocarbon groups other than halogen atoms, cyano groups, and aryl groups, n1 and n2 independently represent integers from 0 to 4. [2] The ultraviolet absorber as described in [1], wherein in the aforementioned general formula (1), at least one of m1 and m2 is 1 or more. [3] The ultraviolet absorber as described in [1] or [2], wherein in the aforementioned general formula (1), Z1a and Z1b are condensed polycyclic aromatic rings, and both m1 and m2 are integers of 1 or more. [4] The ultraviolet absorber as described in any one of [1] to [3], wherein in the aforementioned general formula (1), Y1a and Y1b are respectively independently represented by the following formula (Y1), the aforementioned compound is a dicarboxylic acid or a derivative thereof, the aforementioned resin is a polyester resin or polyamide resin with the aforementioned compound of dicarboxylic acid as a constituent unit, and in formula (Y1), A1 represents a linear or branched C1-6 alkyl group. [5] The ultraviolet absorber as described in any one of [1] to [3], wherein in the aforementioned general formula (1), Y 1a and Y 1b are each independently represented by the following formula (Y2), the aforementioned compound is a diol, the aforementioned resin is a polyester resin or polycarbonate resin with the aforementioned compound of diol as a constituent unit, and in formula (Y2), A 2 and A 3 independently represent a linear or branched C1-6 alkyl group, and p represents an integer greater than or equal to 0. [6] The ultraviolet absorber as described in any one of [1] to [3], wherein in the aforementioned general formula (1), Y 1a and Y 1b are each independently represented by the following formula (Y3), the aforementioned compound is a diol, the aforementioned resin is a polyester resin or polycarbonate resin with the aforementioned compound of diol as a constituent unit, in formula (Y3), Z 2 represents an aromatic ring, A 4 independently represents a linear or branched C1-4 alkyl group, R 3 independently represents a substituent, q represents an integer of 0 or more, r represents an integer of 1 or more, and s represents an integer of 0 or more. [7] The ultraviolet absorber as described in [6], wherein in the aforementioned general formula (Y3), Z 2 is a condensed polycyclic aromatic ring.[8] The ultraviolet absorber as described in any one of [1] to [3], wherein in the aforementioned general formula (1), Y1a and Y1b are each independently represented by the following formula (Y4), the aforementioned compound is a di(meth)acrylate, the aforementioned resin is a (meth)acrylate resin with the aforementioned compound of di(meth)acrylate as a constituent unit, and in formula (Y4), A5 and A6 independently represent a linear or branched C1-6 alkyl group, R4 represents a hydrogen atom or a methyl group, and t represents an integer greater than or equal to 0. [9] The ultraviolet absorber as described in any one of [1] to [8] has a wavelength band region, i.e., a half-width of 55 nm or less, in which it exhibits absorbance at the maximum absorption wavelength.

[10] The ultraviolet absorber as described in any one of [1] to [9] has a maximum absorption wavelength in the wavelength range of 320 to 400 nm.

[11] The ultraviolet absorber of any one of [1] to

[10] has a molar absorptivity (A 380) at 380 nm to a molar absorptivity (A 400) at 400 nm (A 380 / A 400) ratio of 50 or more.

[12] The ultraviolet absorber of any one of [1] to

[11] contains, relative to all the constituent units of the aforementioned resin, the content of the aforementioned constituent units derived from the fumonisin compound is 1 to 100 mol%.

[13] An ultraviolet absorbing composition comprising: the ultraviolet absorber of [1]; and at least one of a compound containing a triazine ring, a compound containing a benzotriazole ring, or a compound containing a benzophenone ring as a second ultraviolet absorber.

[14] An ultraviolet absorbing resin composition comprising: the ultraviolet absorber of any one of [1] to

[12] ; and any resin; and the content of the aforementioned ultraviolet absorber is 0.1 to 10 by mass relative to the total amount.

[15] An ultraviolet-absorbing coating liquid comprising: any one of [1] to

[12] an ultraviolet absorber,

[13] an ultraviolet-absorbing composition, or

[14] an ultraviolet-absorbing resin composition.

[16] An ultraviolet-absorbing coated resin sheet comprising a resin sheet and an ultraviolet shielding layer, wherein the ultraviolet shielding layer comprises: any one of [1] to

[12] an ultraviolet absorber,

[13] an ultraviolet-absorbing composition, or

[14] an ultraviolet-absorbing resin composition.

[17] An ultraviolet-absorbing coated glass comprising glass and an ultraviolet shielding layer, wherein the ultraviolet shielding layer comprises: any one of [1] to

[12] an ultraviolet absorber,

[13] an ultraviolet-absorbing composition, or

[14] an ultraviolet-absorbing resin composition.

[18] An ultraviolet-absorbing molded article comprising: any one of [1] to

[12] , the ultraviolet-absorbing composition of

[13] , or the ultraviolet-absorbing resin composition of

[14] .

[19] An ultraviolet-absorbing film comprising: any one of [1] to

[12] , the ultraviolet-absorbing composition of

[13] , or the ultraviolet-absorbing resin composition of

[14] .

[20] A polarizer protective film comprising: the ultraviolet-absorbing film of

[19] .

[21] The polarizer protective film of

[20] having a ray transmittance of 5% or less at 350 nm and a b* value of 0.5 or less in the L*a*b* color space (CIELAB).

[22] The polarizer protective film of

[20] or

[21] having a ray transmittance of 8% or less at 380 nm.

[23] A polarizer plate comprising: any one of

[20] to

[22] .

[24] An image display device comprising:

[23] a polarizing plate.

[25] A transport machine comprising a component comprising: any one of [1] to

[12] an ultraviolet absorber,

[13] an ultraviolet absorbing composition, or

[14] an ultraviolet absorbing resin composition.

[26] A building component comprising: any one of [1] to

[12] an ultraviolet absorber,

[13] an ultraviolet absorbing composition, or

[14] an ultraviolet absorbing resin composition. [Efficacy].

[0016] According to the present invention, it is possible to provide: a novel ultraviolet absorber that has excellent ultraviolet absorption properties for UV-A or UV-B, and specifically absorbs only ultraviolet light of a specific wavelength, and can be used in a wide range of applications; and an ultraviolet-absorbing resin, an ultraviolet-absorbing coating liquid, an ultraviolet-absorbing coating resin film, an ultraviolet-absorbing coated glass, an ultraviolet-absorbing molded body, an ultraviolet-absorbing film, a polarizer protective film, a polarizer plate, an image display device, a transport machine, and building material parts, which, in addition to the aforementioned properties, also have excellent resistance to leaching.

Implementation Method

[0018] The embodiments of the present invention (hereinafter referred to as "the present embodiments") are described in detail below, but the present invention is not limited thereto and various modifications can be made without departing from its spirit. Furthermore, in the drawings, the same symbol is used to indicate the same element, and repeated descriptions are omitted. In addition, positional relationships such as up, down, left, and right are assumed to be those shown in the drawings unless otherwise specified. Furthermore, the scale of the drawings is not limited to the scale shown in the illustrations.

[0019] Furthermore, in this embodiment, the designation "C2-8" indicates that the number of carbons in a certain group is 2 or more and 8 or less.

[0020] 1. Ultraviolet absorber The ultraviolet absorber of this embodiment is a compound represented by the following general formula (1), or a resin containing a compound represented by the following general formula (1) as a constituent unit: In formula (1), Z 1a and Z 1b each independently represent an aromatic ring, Y 1a and Y 1b each independently represent a carboxyl group, a hydroxyl group, or a group having a polymerizable double bond, R 1a and R 1b each independently represent a halogen atom, a acetyl group, a nitro group, a cyano group, an amino group, -RA, -ORA, or -SRA, except that RA represents a hydrocarbon group, k1 and k2 each independently represent an integer greater than or equal to 0, m1 and m2 each independently represent an integer from 0 to 4, R 2a and R 2b each independently represent a substituent, n1 and n2 each independently represent an integer from 0 to 4, and m1+n1 and m2+n2 each independently represent an integer less than or equal to 4.

[0021] Having the structure of the above general formula (1), the ultraviolet absorber of this embodiment exhibits excellent ultraviolet absorption for UV-A or UV-B, and specifically absorbs only ultraviolet light of a specific wavelength. Furthermore, by changing each group represented by the above general formula (1) to any structure, the absorption wavelength can be adjusted.

[0022] The ultraviolet absorber of this embodiment may be a compound having a structure represented by general formula (1), or a resin having a structure represented by general formula (1) as a constituent unit.

[0023] Hereinafter, firstly, a compound having a structure represented by general formula (1) will be described, and then a resin will be described.

[0024] 1.1. Fuchsia Compounds Fuchsia compounds have the structure represented by general formula (1) and may have aromatic rings (Z 1a, Z 1b) and substituents (Y 1a, Y 1b, R 1a, R 1b, R 2a, R 2b) bonded to the fuchsia ring as detailed below.

[0025] 1.1.1. The radicals [-Z 1a-(R 1a) k1] and [-Z 1b-(R 1b) k2] Z 1a and Z 1b independently represent aromatic rings bonded to a cycloaliphatic ring. Such aromatic rings are not particularly limited, and examples include: monocyclic aromatic rings such as benzene rings, condensed polycyclic aromatic rings (condensed polycyclic aromatic hydrocarbon rings), and cyclic polycyclic aromatic rings (cyclic polycyclic aromatic hydrocarbon rings), etc. From the viewpoint of the molar absorptivity in the UV-A region, condensed polycyclic aromatic rings are preferred.

[0026] The condensed polycyclic aromatic ring is not particularly limited, and examples include: naphthalene ring, indene ring, azurite ring, anthracene ring, phenanthrene ring, fused tetraphenyl ring, fused pentaphenyl ring, benzo[a]pyrene ring, 1,2-benzo[a]phenanthrene (chrysene) ring, dibenzo(a,h)pyrene ring, pyrene ring, triphenylene ring, corannulene ring, cardinium ring, ovalene ring, etc. Among these, naphthalene ring is preferred.

[0027] The ring of the aromatic hydrocarbon is not particularly limited, and examples include: biphenyl ring, phenylnaphthalene ring, binaphthalene ring and other biaromatic rings; triphenyl ring and other triaromatic rings, etc. Among them, biphenyl ring is preferred.

[0028] There are no particular restrictions on the substitution positions on the cyclohexane rings of Z1a and Z1b, but from the perspective of industrial synthesis methods of cyclohexane compounds, positions 2 and / or 7 are preferred.

[0029] When Z1a and Z1b represent aromatic rings that are naphthalene rings independently, the bonding positions of rings Z1a and Z1b relative to the naphthalene skeleton can be either the 1st or 2nd position of the naphthalene ring. From the viewpoint of the 5% mass reduction temperature, the 1st position of the naphthalene ring is preferred. Furthermore, from the viewpoint of molar absorptivity, the 2nd position of the naphthalene ring is particularly preferred.

[0030] The number of carbons in Z 1a and Z 1b is preferably 6 to 24, more preferably 6 to 18, and even more preferably 6 to 12.

[0031] The aromatic rings Z1a and Z1b may each independently have non-reactive or non-polymerizable substituents R1a and R1b. Substituents R1a and R1b are not particularly limited and can be, for example, halogen atoms, amides, nitros, cyano groups, mono- or disubstituted amino groups, -RA, -ORA, or -SRA, etc. Here, RA represents a hydrocarbon group.

[0032] Halogen atoms can be exemplified by fluorine atoms, chlorine atoms, bromine atoms, iodine atoms, etc.

[0033] Examples of acetyl groups include: acetyl, C1-6 alkyl-carbonyl, etc.

[0034] Examples of mono- or disubstituted amino groups include: dialkylamino, bis(alkylcarbonyl)amino, etc. Examples of dialkylamino groups include: dimethylamino, etc., which are two-C1-4 alkylamino groups. Examples of bis(alkylcarbonyl)amino groups include: diacetylamino, etc., which are two-C1-4 alkyl-carbonyl)amino groups.

[0035] The hydrocarbon groups represented by RA can be exemplified by alkyl, cycloalkyl, aryl, aralkyl, etc.

[0036] Alkyl groups may include, for example, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, secondary butyl, tertiary butyl, and other straight-chain or branched C1-10 alkyl groups. Among these, straight-chain or branched C1-6 alkyl groups are preferred, and straight-chain or branched C1-4 alkyl groups are even more preferred.

[0037] Cycloalkyl can be exemplified by: cyclopentyl, cyclohexyl, etc., which are C5-10 cycloalkyl groups.

[0038] Aryl groups can be exemplified by: phenyl, alkylphenyl, biphenyl, naphthyl, etc., which are C6-12 aryl groups. Alkylphenyl groups can be exemplified by: methylphenyl (or tolyl), dimethylphenyl (or xylylyl), etc., which are mono- to tri-C1-4 alkyl-phenyl groups.

[0039] Aryl groups can be exemplified by: benzyl, phenethyl, etc., which are C6-10 aryl-C1-4 alkyl groups.

[0040] The radical [-OR A] can be exemplified by: alkoxy, cycloalkoxy, aryloxy, arylalkoxy, etc., and more specifically, the radicals corresponding to the hydrocarbon group RA.

[0041] Examples of alkoxy groups include: methoxy, ethoxy, propoxy, n-butoxy, isobutoxy, tert-butoxy, etc., which are straight-chain or branched C1-10 alkoxy groups.

[0042] Examples of cycloalkoxy groups include: cyclohexyloxy and other C5-10 cycloalkoxy groups.

[0043] Aryl groups can be exemplified by, for example, phenoxy groups and other C6-10 aryl groups.

[0044] Arylalkoxy groups can be exemplified by: benzyloxy and other C6-10 aryl-C1-4 alkoxy groups.

[0045] The radical [-SR A] can be exemplified by: alkylthio, cycloalkylthio, arylthio, arylalkylthio, etc., and more specifically, the radicals corresponding to the hydrocarbon radical RA can be exemplified by.

[0046] Examples of alkylthio groups include: methylthio, ethylthio, propylthio, n-butylthio, tributylthio, etc., which are C1-10 alkylthio groups.

[0047] Examples of cycloalkylthio groups include: cyclohexylthio groups and other C5-10 cycloalkylthio groups.

[0048] Examples of aryl thio groups include: thiophenoxy and other C6-10 aryl thio groups.

[0049] Aryl thio groups can be exemplified by: benzyl thio group, etc., which are C6-10 aryl-C1-4 alkyl thio groups.

[0050] Of these substituents R1a and R1b, -RA, -ORA, acetyl, nitro, cyano, and monosubstituted amino groups are preferred; alkyl and alkoxy groups are more preferred; linear or branched C1-6 alkyl groups such as methyl and linear or branched C1-4 alkoxy groups such as methoxy are more preferred; and linear or branched C1-4 alkyl groups such as methyl are particularly preferred. Furthermore, when R1a or R1b is aryl, R1a or R1b can form a cyclic aromatic ring with rings Z1a and Z1b, respectively.

[0051] The substitution numbers k1 and k2 represent the number of bonds formed by substituents R1a and R1b with respect to aromatic rings Z1a and Z1b. The substitution numbers k1 and k2 can be selected according to the type of aromatic rings Z1a and Z1b. The preferred ranges for the substitution numbers k1 and k2 are: integers from 0 to 7, integers from 0 to 6, integers from 0 to 5, integers from 0 to 4, integers from 0 to 3, integers from 0 to 2, 0 or 1, and 0.

[0052] The substitution numbers k1 and k2 can be the same or different. Furthermore, when the substitution number k1 or k2 is 2 or more, the types of two or more bases R1a or R1b substituting in the same ring Z1a and Z1b can be the same or different. Additionally, the types of two or more bases R1a and R1b substituting in different rings Z1a and Z1b can be the same or different. The substitution positions of bases R1a and R1b are not particularly restricted and can be selected according to the types of rings Z1a and Z1b.

[0053] Substitution numbers m1 and m2 represent the number of bonds in the basis [-Z 1a-(R 1a) k1] and the basis [-Z 1b-(R 1b) k2] (hereinafter also referred to as "containing Z 1 basis") for the ring. Substitution numbers m1 and m2 are independently represented by integers from 0 to 4, preferably integers from 1 to 3, preferably 1 or 2, and even more preferably 1.

[0054] Furthermore, from the viewpoint of molar absorption coefficient and absorption wavelength, it is preferable that at least one of m1 and m2 is an integer greater than or equal to 1, more preferably that both are integers greater than or equal to 1, and even more preferably that both are 1.

[0055] Furthermore, when m1 or m2 is 2 or more, the types of substitutions in the two benzene rings forming the fusiform skeleton that are two or more Z1-containing groups on the same benzene ring can be the same or different. In addition, the types of substitutions in the two benzene rings forming the fusiform skeleton that are Z1-containing groups on different benzene rings, that is, the group [-Z1a-(R1a)k1] and the group [-Z1b-(R1b)k2] can be the same or different.

[0056] 1.1.2. R2a and R2b R2a and R2b represent, independently, non-reactive or non-polymerizable substituents bonded to the cyclohexane ring. Such substituents need to be any substituents other than those containing the Z1 group mentioned above.

[0057] Such groups R 2a and R 2b can be exemplified by: alkyl, cycloalkyl and other hydrocarbon groups (except aryl); halogen atoms such as fluorine, chlorine, bromine and iodine atoms; cyano, etc.

[0058] Alkyl groups may include, for example, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, secondary butyl, tertiary butyl, and other straight-chain or branched C1-10 alkyl groups. Among these, straight-chain or branched C1-6 alkyl groups are preferred, and straight-chain or branched C1-4 alkyl groups such as methyl are even more preferred.

[0059] The substitution numbers n1 and n2 represent the number of bonds formed by substituents R2a and R2b to the ring. The substitution numbers n1 and n2 are independently represented as integers from 0 to 4, preferably integers from 0 to 3, more preferably integers from 0 to 2, and even more preferably 0 or 1, especially 0. n1 and n2 can be the same or different from each other.

[0060] Furthermore, when n1 or n2 is 2 or more, the types of substitutions in the two benzene rings forming the fusiform skeleton, specifically the plurality of R2a or R2b substitutions in the same benzene ring, can be the same or different. Additionally, the types of substitutions in the two benzene rings forming the fusiform skeleton, specifically the R2a and R2b substitutions in different benzene rings, can be the same or different. Furthermore, there are no particular restrictions on the substitution positions of R2a and R2b, as long as the substitution occurs at a position other than the substitution position containing the Z1 group.

[0061] m1+n1 and m2+n2 are independent integers from 0 to 4, preferably from 1 to 3, with 1 or 2 being more preferred, and 1 being even better. m1+n1 and m2+n2 can be the same or different from each other.

[0062] 1.1.3. Group Y1a and Group Y1b Y1a and Y1b are each independently a five-membered ring in a cyclopentadienyl ring, more specifically a group bonded to the carbon at the 9-position. Y1a and Y1b may be a carboxyl group, a hydroxyl group, or a reactive or polymerizable substituent having a polymerizable double bond. Such Y1a and Y1b are not particularly limited, and examples include: the following formulas (Y1), (Y2), (Y3), and (Y4).

[0063] 1.1.3.1. Formula (Y1): Dicarboxylic acids and their derivatives are represented by Formula (Y1). When Y1a and Y1b are as shown in Formula (Y1), the compound of this embodiment may be a dicarboxylic acid and its derivative. In Formula (Y1), A1 represents a straight-chain or branched alkyl group.

[0064] Here, the so-called dicarboxylic acid derivatives may include, for example, ester-forming derivatives of formula (Y1) such as alkyl esters (e.g., lower alkyl esters such as methyl ester and ethyl ester), acetic halides (e.g., acetic chloride), and acid anhydrides.

[0065] A1 represents linear or branched alkyl groups, for example: methylene, ethyl alkyl, propyl alkyl, trimethylene, 1,2-butadiene, 1,3-butadiene, tetramethylene, etc., linear or branched C1-6 alkyl groups.

[0066] A1 preferably has 1 to 10 carbons, 1 to 6 is better, and 1 to 4 is even better.

[0067] By using such an A1, there is a tendency to have excellent absorption of ultraviolet light of UV-A or UV-B, and to specifically absorb only ultraviolet light of a specific wavelength, and to further improve the compatibility with other resins to be mixed.

[0068] Y1a and Y1b are representative compounds of the above-mentioned dicarboxylic acids and their derivatives represented by formula (Y1), without particular limitation. Examples include: 9,9-bis(2-carboxyethyl) benzo[a], 9,9-bis(2-carboxypropyl) benzo[a], 9,9-bis(carboxyC4-6 alkyl) benzo[a], 9,9-bis(2-carboxyethyl)2,7-diphenyl benzo[a], 9,9-bis(2-carboxypropyl)2,7-diphenyl benzo[a], 9,9-bis(carboxyC4-6 alkyl)2,7-diphenyl benzo[a], 9,9-bis(2-carboxyethyl)2,7-di(2-naphthyl)fucose, 9,9-bis(2-carboxypropyl)2,7-di(2-naphthyl)fucose, 9,9-bis(carboxylC4-6 alkyl)2,7-di(2-naphthyl)fucose, 9,9-bis(2-carboxyethyl)2,7-di(1-naphthyl)fucose, 9,9-bis(2-carboxypropyl)2,7-di(1-naphthyl)fucose, 9,9-bis(carboxylC4-6 alkyl)2,7-di(1-naphthyl)fucose. Fucose dicarboxylic acid components can be alone or in combination of two or more.

[0069] 1.1.3.2. Formula (Y2): Diol or the following formula (Y2) is used. When Y1a and Y1b are as shown in formula (Y2), the compound of this embodiment may be a diol. In formula (Y2), A2 and A3 independently represent linear or branched alkyl groups, and p represents an integer greater than or equal to 0.

[0070] Examples of straight-chain or branched alkyl groups represented by A2 and A3 include: methylene, ethyl, propyl, trimethylene, 1,2-butadiene, 1,3-butadiene, tetramethylene, etc., which are straight-chain or branched C1-6 alkyl groups. Among them, ethyl and propyl are preferred, with ethyl being particularly preferred.

[0071] The number of carbons in A2 and A3 is preferably 1 to 6, 2 to 6 is better, and 2 to 3 is even better.

[0072] By using such A2 and A3, there is a tendency to have excellent absorption of ultraviolet light of UV-A or UV-B, and to specifically absorb only ultraviolet light of a specific wavelength, and to further improve the compatibility with other resins to be mixed.

[0073] The repetition number p of the alkyl group (A3O)- is an integer greater than or equal to 0, and can be selected from, for example, a range of about 0 to 20, with preferred ranges being: 0 to 15, 0 to 10, 0 to 8, 0 to 5, 0 to 3, 0 to 2, 0 to 1, and especially 0. Furthermore, the repetition number p can be an average value (or an additive average, arithmetic average), that is, an average number of added mol, and this range includes the preferred sample and is the same as the range of integers mentioned above. When p is 2 or greater, the two or more types of A3 in (poly)alkyl group (A3O) p- can be the same or different, but are preferably the same.

[0074] Furthermore, the total number of repetitions p in Y 1a and Y 1b, that is, the total number of alkyl groups in the molecule of diol compound 1 represented by formula (1) (or the average of the total added mol number) [hereinafter referred to only as the total number of p], can be selected from, for example, a range of about 0 to 30, preferably in stages as follows: 0 to 20, 0 to 10, 0 to 6, 0 to 4, 0 to 2, more preferably 0 to 1, and especially 0. Furthermore, the total number of p can be an integer or the average of the total mol number.

[0075] Y1a and Y1b are representative compounds of the above-mentioned diols represented by formula (Y2), and there is no particular limitation. Examples include: diols in which m1 and m2 are 1 and Z1a and Z1b are C6-12 aromatic rings such as benzene ring, naphthalene ring, and biphenyl ring, respectively, and A2 is a straight-chain or branched C1-6 alkyl group and A3 is a straight-chain or branched C2-4 alkyl group, with p being 0 or 1 to 10. More preferably, diols in which m1 and m2 are 1 and Z1a and Z1b are benzene ring or naphthalene ring, respectively, and A2 is a straight-chain or branched C1-4 alkyl group and A3 is a straight-chain or branched C2-3 alkyl group such as ethyl or propyl group, with p being 0 or 1 to 6.

[0076] Furthermore, more preferably, it is a diol compound in which m1 and m2 are 1 and Z1a and Z1b are respectively naphthalene rings and A2 is a straight-chain or branched C2-4 alkyl group and A3 is an ethyl group and p is 0 or 1.

[0077] Among them, 9,9-bis(3-hydroxypropyl)-bis(1-naphthyl)futan, 9,9-bis(3-hydroxypropyl)-bis(2-naphthyl)futan and other 9,9-bis(3-hydroxypropyl)-dinaphthylfutan are preferred, and 9,9-bis(3-hydroxypropyl)-2,7-bis(2-naphthyl)futan and other 9,9-bis(3-hydroxypropyl)-2,7-dinaphthylfutan are particularly preferred.

[0078] 1.1.3.3. Formula (Y3): Diol is represented by Y1a and Y1b. When Y1a and Y1b are as shown in Formula (Y3), the compound of this embodiment may be a diol. In Formula (Y3), Z2 represents an aromatic ring, A4 independently represents a straight-chain or branched alkyl group, R3 independently represents a substituent, q represents an integer of 0 or more, r represents an integer of 1 or more, and s represents an integer of 0 or more.

[0079] In formula (Y3), Z2 represents aromatic rings such as: monocyclic aromatic rings like benzene rings, condensed polycyclic aromatic rings (condensed polycyclic aromatic hydrocarbon rings), and cyclic aggregate aromatic rings (cyclic aggregate polycyclic aromatic hydrocarbon rings), etc. From the perspective of the molar absorptivity in the UV-A region, condensed polycyclic aromatic rings are preferred.

[0080] The condensed polycyclic aromatic ring is not particularly limited, and examples include: naphthalene ring, indene ring, azurite ring, anthracene ring, phenanthrene ring, fused tetraphenyl ring, fused pentaphenyl ring, benzo[a]pyrene ring, 1,2-benzo[a]phenanthrene ring, dibenzo[a,h]pyrene ring, pyrene ring, triphenylene ring, sulphene ring, cardinium ring, ovoid ring, etc. Among them, naphthalene ring is preferred.

[0081] The ring of the aromatic hydrocarbon is not particularly limited, and examples include: biphenyl ring, phenylnaphthalene ring, binaphthalene ring and other biaromatic rings; triphenyl ring and other triaromatic rings, etc. Among them, biphenyl ring is preferred.

[0082] The aromatic ring Z2 may have a non-reactive or non-polymerizable substituent R3. Examples of substituent R3 include: alkyl groups and other hydrocarbon groups; halogen atoms such as fluorine, chlorine, and bromine atoms; cyano groups, etc.

[0083] Alkyl groups may include, for example, straight-chain or branched C1-10 alkyl groups such as methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, secondary butyl, and tertiary butyl. Among these, straight-chain or branched C1-6 alkyl groups are preferred, and straight-chain or branched C1-4 alkyl groups such as methyl are even more preferred.

[0084] The substitution number s represents the number of bonds between the substituent R3 and the aromatic ring Z2. The substitution number s is, for example, an integer from 0 to 4, preferably an integer from 0 to 2, and more preferably 0 or 1, especially 0. In addition, there are no particular restrictions on the substitution position of R3, as long as the substitution is at a position other than the substitution position of the group [-(OA 4) q-OH].

[0085] Examples of straight-chain or branched alkyl groups represented by A4 include: methylene, ethyl, propyl, trimethylene, 1,2-butadiene, 1,3-butadiene, tetramethylene, etc., which are straight-chain or branched C1-6 alkyl groups. Preferably, the alkyl group A4 is a straight-chain or branched C2-6 alkyl group, more preferably a straight-chain or branched C2-3 alkyl group, with ethyl and propyl being preferred, and ethyl being particularly preferred.

[0086] The preferred range of the number of repetitions q of oxyalkylene-(OA4)- is: 0–20, 0–15, 0–10, 0–8, 0–5, 0–3, 0–2, 0–1, 0. Furthermore, the number of repetitions q can be an average (or an additive average, arithmetic average), i.e., an average number of added mol, and this range, including the preferred sample, is the same as the aforementioned range of integers. When q is 2 or more, the two or more types of A4 in (poly)oxyalkylene-(OA4)q- can be different, but preferably the same.

[0087] Furthermore, the total number of repetitions q in Y 1a and Y 1b, that is, the total number of alkyl groups in the molecule of diol compound 1 represented by formula (1) (or the average of the total added mol number) [hereinafter referred to only as the total number of q], can be selected from, for example, a range of about 0 to 30, preferably in stages as follows: 0 to 20, 0 to 10, 0 to 6, 0 to 4, 0 to 2, more preferably 0 to 1, and especially 0. Furthermore, the total number of q can be an integer or the average of the total number of mol number.

[0088] The substitution number r represents the number of bonds of the radical [-(OA 4) q-OH] to the Z 2 of the aromatic ring. The substitution number r is, for example, an integer from 1 to 4, preferably an integer from 1 to 2, and more preferably 1. In addition, there is no particular restriction on the substitution position of -(OA 4) q-OH, as long as the substitution is at a position other than the substitution position of R 3.

[0089] Y1a and Y1b are representative compounds of the above-mentioned diols represented by formula (Y3), without particular limitation. Examples include: diols in which m1 and m2 are 0 or 1, Z1a, Z1b, and Z2 are C6-12 aromatic rings such as benzene ring, naphthalene ring, and biphenyl ring, and A4 is a straight-chain or branched C2-4 alkyl group, and q is 0 or 1 to 10. Preferred examples include: diols in which m1 and m2 are 0 or 1, Z1a, Z1b, and Z2 are benzene rings or naphthalene rings, and A4 is a straight-chain or branched C2-3 alkyl group such as ethyl or propyl group, and q is 0 or 1 to 6.

[0090] Preferredly, it is 9,9-bis[4-(2-hydroxyethoxy)phenyl]fu, 9,9-bis[4-(2-(2-hydroxyethoxy)ethoxy)phenyl]fu, 9,9-bis[4-(2-hydroxypropoxy)phenyl]fu, etc., representing 9,9-bis[hydroxy(poly)alkoxyphenyl]fu; or 9,9-bis[6-(2-hydroxyethoxy)-2-naphthyl]fu, 9,9-bis[5-(2-hydroxyethoxy)-1-naphthyl]fu, 9,9-bis[6-(2-(2-hydroxyethoxy)ethoxy)-2-naphthyl]fu, 9,9-bis[6-(2-(2-hydroxyethoxy)ethoxy)-2-naphthyl]fu, etc., representing 9,9-bis[hydroxy(poly)alkoxynaphthyl]fu.

[0091] 1.1.3.4. Formula (Y4): Di(meth)acrylate The following formula (Y4) is used to represent the following compound. When Y1a and Y1b are as shown in formula (Y4), the compound of this embodiment may be a di(meth)acrylate. In formula (Y4), A5 and A6 independently represent linear or branched alkyl groups, R4 represents a hydrogen atom or a methyl group, and t represents an integer greater than or equal to 0.

[0092] Examples of straight-chain or branched alkyl groups represented by A5 and A6 include: methylene, ethyl, propyl, trimethylene, 1,2-butadiene, 1,3-butadiene, tetramethylene, etc., which are straight-chain or branched C1-6 alkyl groups. Preferably, the alkyl groups A5 and A6 are straight-chain or branched C2-6 alkyl groups, more preferably straight-chain or branched C2-3 alkyl groups, with ethyl and propyl being preferred, and ethyl being particularly preferred.

[0093] The number of repetitions t of the alkyl group (A6O) can be selected from, for example, a range of about 0 to 20, with preferred ranges being: 0 to 15, 0 to 10, 0 to 8, 0 to 5, 0 to 3, 0 to 2, 0 to 1, and especially 0. Furthermore, the number of repetitions t can be an average (or an additive average, an arithmetic average), that is, an average number of added mol, and this range includes the preferred sample and is the same as the range of integers mentioned above. When t is 2 or more, the two or more types of A6 in (poly)alkyl group (A6O) t can be the same or different from each other, preferably the same.

[0094] R4 represents a hydrogen atom or a methyl group. When the ultraviolet absorber of this embodiment is used by free radical polymerization, hydrogen atom is preferred because of its excellent reactivity with free radicals.

[0095] Y 1a and Y 1b are representative compounds of the above-mentioned di(meth)acrylates represented by formula (Y4), without particular limitation, and examples include: 9,9-bis((meth)acryl)enyl, 9,9-bis((meth)acryloxyethyl)enyl, 9,9-bis((meth)acryloxymethyl)enyl, 9,9-bis((meth)acryloxypropyl)2,7-diphenylenyl, and 9,9-bis((meth)acryloxypropyl)2,7-di(2-naphthyl)enyl. Two or more di(meth)acrylate components may be used alone or in combination.

[0096] 1.2 Resin Next, a resin comprising a compound represented by general formula (1) as a constituent unit (hereinafter also referred to as "constituent unit F") will be described in detail. The resin of this embodiment, by comprising a compound represented by general formula (1) as a constituent unit, has excellent absorption of UV-A or UV-B, and is able to specifically absorb only ultraviolet light of a specific wavelength.

[0097] The resin used in this embodiment is not particularly limited, and examples include polyester resin, polycarbonate resin, polyamide resin, and acrylic resin. Each resin will be described in detail below, but the resin used in this embodiment is not limited thereto as long as it is included as a constituent unit F.

[0098] 1.2.1. Polyester resin Polyester resin is formed by the stepwise polymerization of diol and dicarboxylic acid to form ester bonds, and has at least one or both of the diol or dicarboxylic acid as the constituent unit F derived from the compound represented by general formula (1). In order to distinguish it from other polyester resins, polyester resin containing such constituent unit F is also called "ultraviolet absorbing polyester resin".

[0099] Relative to all constituent units, the content of constituent unit F in the ultraviolet-absorbing polyester resin, in molar ratio, is preferably 1 to 100 mol%, more preferably 5 to 80 mol%, and even more preferably 10 to 60 mol%. By having the content of constituent unit F within the above range, there is a tendency to further improve ultraviolet absorption and absorption specificity of ultraviolet light at a particular wavelength.

[0100] 1.2.1.1. Diol Component The diol component of the above-mentioned UV-absorbing polyester resin may be entirely composed of unit F, or it may be a combination of unit F and other diol components. There is no particular limitation on the unit F of the diol component; examples include units derived from diols when Y1a and Y1b are as shown in formula (Y2), and units derived from diols when Y1a and Y1b are as shown in formula (Y3). One of these diols may be used alone, or two or more may be used in combination.

[0101] Other diol components are not particularly limited, but may include, for example, at least one diol component selected from the group consisting of aliphatic diols, alicyclic diols and aromatic diols.

[0102] Examples of aliphatic diols include: ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 1,3-pentanediol, 1,4-pentanediol, 1,5-pentanediol, neopentanediol, 1,6-hexanediol, and other C2-8 alkyl diols; polyalkylene glycols (e.g., diethylene glycol, dipropylene glycol, triethylene glycol, and other di or triC2-4 alkyl diols). Ethylene glycol is particularly preferred due to its ability to improve mechanical properties such as elongation at break and flexibility.

[0103] Examples of alicyclic diols include: cyclohexanediols such as cyclohexanediol; di(hydroxyalkyl)cycloalkanes such as cyclohexanediol; hydrides of bisphenol A and other aromatic diols exemplified later.

[0104] Examples of aromatic diols include: hydroquinone, resorcinol and other dihydroxy aromatic hydrocarbons; benzenedimethyl alcohols; bisphenols such as bisphenol A, bisphenol F, bisphenol AD, bisphenol C, bisphenol G, bisphenol S; and biphenols such as p, p'-biphenol.

[0105] Other diol components may be two or more, either alone or in combination.

[0106] 1.2.1.2. Dicarboxylic Acid The dicarboxylic acid component of the above-mentioned UV-absorbing polyester resin may be entirely composed of unit F, or it may be a combination of unit F of the dicarboxylic acid component and other dicarboxylic acid components. There is no particular limitation on the unit F of the dicarboxylic acid component, and for example, it may be derived from the unit of the dicarboxylic acid when Y1a and Y1b are the dicarboxylic acid as shown in formula (Y1). Such dicarboxylic acids may be used alone or in combination of two or more.

[0107] Other dicarboxylic acid components are not particularly limited, but may include, for example, at least one dicarboxylic acid component selected from the group consisting of aliphatic dicarboxylic acids, alicyclic dicarboxylic acids and aromatic dicarboxylic acids.

[0108] There is no particular limitation on aliphatic dicarboxylic acids, and examples include: alkyl dicarboxylic acids (such as succinic acid, adipic acid, sebacic acid, decanedicarboxylic acid, etc., C4-14 alkyl dicarboxylic acids, preferably C6-12 alkyl dicarboxylic acids, etc.), unsaturated aliphatic dicarboxylic acids (such as maleic acid, fumaric acid, iconic acid, etc., C2-10 ene-dicarboxylic acids, etc.). Alkyl dicarboxylic acids are preferred.

[0109] There are no particular limitations on alicyclic dicarboxylic acid components. Examples include: cycloalkyl dicarboxylic acids (such as 1,3-cyclohexanedicarboxylic acid, 1,4-cyclohexanedicarboxylic acid, etc., C5-10 cycloalkyl dicarboxylic acids), di- or tricycloalkyl dicarboxylic acids (such as decahydronaphthalenedicarboxylic acid, norbornyldicarboxylic acid, adamantanedicarboxylic acid, tricyclodecanedicarboxylic acid, etc.), cycloene dicarboxylic acids (such as cyclohexenedicarboxylic acid, etc., C5-10 cycloene-dicarboxylic acids), di- or tricycloene dicarboxylic acids (such as norbornyldicarboxylic acid, etc.), etc.

[0110] The aromatic dicarboxylic acid component is not particularly limited, but may include: monocyclic aromatic dicarboxylic acids [e.g., phthalic acid, terephthalic acid, isophthalic acid, alkyl isophthalic acid (e.g., 4-methyl isophthalic acid, etc., C1-4 alkyl isophthalic acid, etc.), etc., and C6-10 aromatic dicarboxylic acids], condensed polycyclic aromatic dicarboxylic acids [e.g., naphthalenedicarboxylic acid (e.g., 1,5-naphthalenedicarboxylic acid, 1,6-naphthalenedicarboxylic acid, 1,7-naphthalenedicarboxylic acid, 1,8-naphthalenedicarboxylic acid, 2,6-naphthalenedicarboxylic acid, etc.), anthracene dicarboxylic acid, phenanthrene dicarboxylic acid, etc., condensed polycyclic C10-24 aromatic dicarboxylic acids, preferably condensed polycyclic C10-16 aromatic dicarboxylic acids, and even more preferably condensed polycyclic C10-16 aromatic dicarboxylic acids], and C6-10-10-16 aromatic dicarboxylic acids. -14 aromatic dicarboxylic acids, etc.; aryl aromatic dicarboxylic acids [e.g., biphenyl dicarboxylic acid (e.g., 2,2'-biphenyl dicarboxylic acid, 4,4'-biphenyl dicarboxylic acid, etc.) and other C6-10 aryl-C6-10 aromatic dicarboxylic acids, etc.]; diaryl alkyl dicarboxylic acids [e.g., diphenylalkyl dicarboxylic acid (e.g., 4,4'-diphenylmethane dicarboxylic acid, etc.) and other diC6-10 aryl-C1-6 alkyl dicarboxylic acids, etc.]; diaryl ketone dicarboxylic acids [e.g., diphenylketone dicarboxylic acid (e.g., 4,4'-diphenylketone dicarboxylic acid, etc.) and other diC6-10 aryl ketone dicarboxylic acids, etc.], etc.

[0111] Furthermore, the dicarboxylic acid components contained in the UV-absorbing polyester resin are not limited to free carboxylic acids, but also include: ester-forming derivatives of dicarboxylic acids, such as esters [e.g., alkyl esters [e.g., lower alkyl esters such as methyl ester, ethyl ester, etc. (e.g., C1-4 alkyl esters, especially C1-2 alkyl esters)], amide halides (e.g., amide chloride), acid anhydrides, etc. These dicarboxylic acid components can be used alone or in combination of two or more.

[0112] 1.2.1.3. Preparation Method of Polyester Resin Ultraviolet-absorbing polyester resin can be prepared by reacting dicarboxylic acid components with diol components. There are no particular limitations on the manufacturing method of polyester resin; conventional methods can be used, such as transesterification, direct polymerization, melt polymerization, solution polymerization, and interfacial polymerization. In the polymerization reaction, transesterification catalysts, condensation catalysts, heat stabilizers, light stabilizers, and polymerization modifiers can be used.

[0113] The transesterification catalyst is not particularly limited, and examples include compounds of alkaline earth metals (magnesium, calcium, barium, etc.) and transition metals (manganese, zinc, cobalt, titanium, etc.) (alkoxides, organic acid salts, inorganic acid salts, metal oxides, etc.). Among them, manganese acetate and calcium acetate can be used appropriately.

[0114] There is no particular limitation on the type of condensation catalyst. Examples include compounds of alkaline earth metals, transition metals, Group 13 metals (such as aluminum), Group 14 elements (such as germanium), and Group 15 metals (such as antimony). More specifically, examples include germanium compounds such as germanium dioxide, germanium hydroxide, germanium oxalate, germanium tetraethoxide, and germanium n-butoxide; antimony compounds such as antimony trioxide, antimony acetate, and antimony glycol; and titanium compounds such as tetra-n-propyl titanate, tetra-isopropyl titanate, tetra-n-butyl titanate, and titanium oxalate. These catalysts can be used alone or in combination of two or more.

[0115] The heat stabilizer is not particularly limited, but may include, for example, trimethyl phosphate, triethyl phosphate, triphenyl phosphate, phosphorous acid, trimethyl phosphite, triethyl phosphite and other phosphorus compounds.

[0116] In the reaction, the ratio of dicarboxylic acid component to diol component can be selected from the same range as described above, and an excess of a predetermined component can be used as needed. For example, diol components such as ethylene glycol that can be distilled from the reaction system can be used in excess of the proportion of units introduced into the polyester resin. Furthermore, the reaction can be carried out in the presence or absence of a solvent.

[0117] The reaction can be carried out in an inert gas environment (nitrogen, helium, etc.). Furthermore, the reaction can also be carried out under reduced pressure (e.g., around 1×10² to 1×10⁴ Pa). The reaction temperature can be adjusted according to the polymerization method; for example, in melt polymerization, the reaction temperature can be 150–300°C, preferably 180–290°C, and more preferably around 200–280°C.

[0118] 1.2.1.3. Physical Properties of Polyester Resin The glass transition temperature of ultraviolet-absorbing polyester resin is preferably 90–190°C, more preferably 100–180°C, and even more preferably 110–170°C. With a glass transition temperature above 90°C, the heat resistance of the ultraviolet-absorbing polyester resin tends to be further improved. Furthermore, with a glass transition temperature below 190°C, the elongation of the ultraviolet-absorbing polyester resin tends to be further improved. The glass transition temperature can be measured by the method described in the examples below.

[0119] The weight-average molecular weight of the UV-absorbing polyester resin is preferably 30,000 to 200,000, more preferably 35,000 to 150,000, and even more preferably 40,000 to 110,000. With a weight-average molecular weight within the above range, the UV-absorbing polyester resin tends to have longer molecular chains, resulting in improved mechanical properties such as elongation at break and flexibility, and thus improved elongation. Furthermore, in this embodiment, the weight-average molecular weight can be determined by gel permeation chromatography (GPC) converted to polystyrene. More specifically, it can be determined by the methods described in the examples below.

[0120] 1.2.2. Polycarbonate resin Polycarbonate resin is formed by the stepwise polymerization of diol and phosgene to form carbonate groups, and has at least a portion of the diol as the constituent unit F derived from the compound represented by general formula (1). In order to distinguish it from other polycarbonates, polycarbonate resin containing such constituent unit F is also called "ultraviolet-absorbing polycarbonate resin".

[0121] The content of constituent unit F in the UV-absorbing polycarbonate resin, relative to all glycol units, is preferably 1 to 100 mol%, more preferably 5 to 80 mol%, and even more preferably 10 to 60 mol%. By having the proportion of UV absorber within the above range, there is a tendency to further improve UV absorption and the absorption specificity of UV light at specific wavelengths.

[0122] 1.2.1.1. The diol component of the diol UV-absorbing polycarbonate resin may consist entirely of unit F, or may be a combination of unit F and other diol components. The unit F of the diol component is not particularly limited, and examples include: units derived from diols when Y1a and Y1b are as shown in formula (Y2), and units derived from diols when Y1a and Y1b are as shown in formula (Y3). One of these diols may be used alone, or two or more may be used in combination.

[0123] Other diol components are not particularly limited, but may include, for example, at least one diol component selected from the group consisting of aliphatic diols, alicyclic diols and aromatic diols.

[0124] Examples of aliphatic diols include: ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 1,3-pentanediol, 1,4-pentanediol, 1,5-pentanediol, neopentanediol, 1,6-hexanediol, and other C2-8 alkyl diols; polyalkyl diols (e.g., diethylene glycol, dipropylene glycol, triethylene glycol, and other di or tri C2-4 alkyl diols), etc., which can improve mechanical properties such as elongation at break and softness, and therefore ethylene glycol is particularly good.

[0125] Examples of alicyclic diols include: cyclohexanediols such as cyclohexanediol; di(hydroxyalkyl)cycloalkanes such as cyclohexanediol; hydrides of bisphenol A and other aromatic diols exemplified later.

[0126] Examples of aromatic diols include: hydroquinone, resorcinol and other dihydroxy aromatic hydrocarbons; benzenedimethyl alcohols; bisphenols such as bisphenol A, bisphenol F, bisphenol AD, bisphenol C, bisphenol G, bisphenol S; and biphenols such as p, p'-biphenol.

[0127] Other diol components may be two or more, either alone or in combination.

[0128] 1.2.2.2. Method for Preparing Polycarbonate Resin Ultraviolet-absorbing polycarbonate resin can be manufactured by reacting a diol component with phosgene or a diester (diphenyl carbonate, etc.) using conventional methods, such as the phosgene method (solvent method) and the transesterification method (melt method). The diol component only needs to contain at least the ultraviolet absorber represented by the general formula (1), and may contain other diol components as needed. From the viewpoint of eliminating the need for solvents, the transesterification method is preferred among these methods.

[0129] In the transesterification method, the ratio of diester to diol component per mol can be, for example, 0.8 to 1.5 mol, preferably about 0.9 to 1.2 mol.

[0130] Transesterification can be carried out in the presence of a catalyst, such as various catalysts used in transesterification, such as nitrogen-containing compounds, metal compounds, etc.

[0131] Examples of nitrogen-containing compounds include: quaternary ammonium hydroxide (e.g., tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrabutylammonium hydroxide, etc., tetraalkylammonium hydroxide; trimethylbenzylammonium hydroxide, etc., trialkylarylammonium hydroxide, etc.); tertiary amines (trimethylamine, triethylamine, etc., trialkylamines; dimethylbenzylammonium hydroxide, etc., dimethyl-arylamines; triphenylamine, etc., triarylamines, etc.), etc.

[0132] Metal compounds can include, for example, metal compounds containing the following metals: alkali metals (sodium, etc.), alkaline earth metals (magnesium, calcium, barium, etc.), transition metals (manganese, zinc, cadmium, lead, cobalt, titanium, etc.), Group 13 elements (aluminum, etc.), Group 14 elements (germanium, etc.), and Group 15 metals (antimony, etc.). More specifically, examples include: alkoxides, organic acid salts (acetates, propionates, etc.), inorganic acid salts (borates, carbonates, etc.), oxides, hydroxides, etc. of the aforementioned metals.

[0133] Such catalysts can be used alone or in combination of two or more. Among these catalysts, nitrogen-containing compounds such as tetraammonium hydroxide are preferred, and tetraalkylammonium hydroxide such as tetramethylammonium hydroxide is preferred. The amount of catalyst used can be, for example, 0.01×10⁻⁴ to 100×10⁻⁴ mol relative to 1 mol of diol, preferably about 0.1×10⁻⁴ to 40×10⁻⁴ mol.

[0134] In addition, the reaction can be carried out in the presence of additives such as stabilizers (antioxidants, heat stabilizers, etc.) as needed.

[0135] The reaction can usually be carried out in an inert gas environment (nitrogen; helium, argon, etc.). Furthermore, the reaction can also be carried out under reduced pressure (e.g., around 1×10² to 1×10⁴ Pa). The reaction temperature can be selected according to the polymerization method; for example, the reaction temperature in the transesterification process can be 150–320°C, preferably 200–310°C, and more preferably around 250–300°C. In particular, when diphenyl carbonate is used as the diester, it is more effective to simultaneously distill off the phenols under high temperature and reduced pressure while carrying out the polycondensation.

[0136] 1.2.2.3. Physical Properties of Polycarbonate Resin The glass transition temperature of ultraviolet-absorbing polycarbonate resin is preferably 90–190°C, more preferably 100–180°C, and even more preferably 110–170°C. With a glass transition temperature above 90°C, the heat resistance of the ultraviolet-absorbing polycarbonate resin tends to be further improved. Furthermore, with a glass transition temperature below 190°C, the elongation of the ultraviolet-absorbing polycarbonate resin tends to be further improved. The glass transition temperature can be measured by the method described in the examples below.

[0137] The weight-average molecular weight of the UV-absorbing polycarbonate resin is preferably 30,000 to 200,000, more preferably 35,000 to 150,000, and even more preferably 40,000 to 110,000. With a weight-average molecular weight within the above range, the UV-absorbing polycarbonate resin tends to have longer molecular chains, resulting in improved mechanical properties such as elongation at break and flexibility, and thus improved elongation. Furthermore, in this embodiment, the weight-average molecular weight can be determined by gel permeation chromatography (GPC) converted to polystyrene. More specifically, it can be determined by the methods described in the examples below.

[0138] 1.2.3. Polyamide resin Polyamide resin is formed by the stepwise polymerization of diamine and dicarboxylic acid to form amide bonds, and has at least a portion of the dicarboxylic acid as the constituent unit F of the compound represented by general formula (1). In order to distinguish it from other polyamides, polyamide resin containing such constituent unit F is also called "ultraviolet-absorbing polyamide resin".

[0139] The percentage of constituent unit F contained in the ultraviolet-absorbing polyamide resin, relative to all dicarboxylic acid units, is preferably 1 to 100 mol%, more preferably 5 to 80 mol%, and even more preferably 10 to 60 mol%. By having the proportion of constituent unit F within the above range, there is a tendency to further improve ultraviolet absorption and absorption specificity of ultraviolet light at a particular wavelength.

[0140] 1.2.3.1. The dicarboxylic acid component of the dicarboxylic acid ultraviolet-absorbing polyamide resin may be entirely composed of unit F, or it may be a combination of unit F of the dicarboxylic acid component and other dicarboxylic acid components. There is no particular limitation on the unit F of the dicarboxylic acid component; for example, it may be derived from the unit of the dicarboxylic acid when Y1a and Y1b are as shown in formula (Y1). One of these dicarboxylic acids may be used alone, or two or more may be used in combination.

[0141] Other dicarboxylic acid components are not particularly limited, but may include, for example, at least one dicarboxylic acid component selected from the group consisting of aliphatic dicarboxylic acids, alicyclic dicarboxylic acids and aromatic dicarboxylic acids.

[0142] There is no particular limitation on aliphatic dicarboxylic acids, and examples include: alkyl dicarboxylic acids (such as succinic acid, adipic acid, sebacic acid, decanedicarboxylic acid, etc., C4-14 alkyl dicarboxylic acids, preferably C6-12 alkyl dicarboxylic acids, etc.), unsaturated aliphatic dicarboxylic acids (such as maleic acid, fumaric acid, iconic acid, etc., C2-10 ene-dicarboxylic acids, etc.). Alkyl dicarboxylic acids are preferred.

[0143] There are no particular limitations on alicyclic dicarboxylic acid components. Examples include: cycloalkyl dicarboxylic acids (such as 1,3-cyclohexanedicarboxylic acid, 1,4-cyclohexanedicarboxylic acid, etc., C5-10 cycloalkyl dicarboxylic acids), di- or tricycloalkyl dicarboxylic acids (such as decahydronaphthalenedicarboxylic acid, norbornyldicarboxylic acid, adamantanedicarboxylic acid, tricyclodecanedicarboxylic acid, etc.), cycloene dicarboxylic acids (such as cyclohexenedicarboxylic acid, etc., C5-10 cycloene-dicarboxylic acids), di- or tricycloene dicarboxylic acids (such as norbornyldicarboxylic acid, etc.), etc.

[0144] The aromatic dicarboxylic acid component is not particularly limited, but may include: monocyclic aromatic dicarboxylic acids [e.g., phthalic acid, terephthalic acid, isophthalic acid, alkyl isophthalic acid (e.g., 4-methyl isophthalic acid, etc., C1-4 alkyl isophthalic acid, etc.), etc., and C6-10 aromatic dicarboxylic acids], condensed polycyclic aromatic dicarboxylic acids [e.g., naphthalenedicarboxylic acid (e.g., 1,5-naphthalenedicarboxylic acid, 1,6-naphthalenedicarboxylic acid, 1,7-naphthalenedicarboxylic acid, 1,8-naphthalenedicarboxylic acid, 2,6-naphthalenedicarboxylic acid, etc.), anthracene dicarboxylic acid, phenanthrene dicarboxylic acid, etc., condensed polycyclic C10-24 aromatic dicarboxylic acids, preferably condensed polycyclic C10-16 aromatic dicarboxylic acids, and even more preferably condensed polycyclic C10-16 aromatic dicarboxylic acids], and C10-10-16 aromatic dicarboxylic acids. -14 aromatic dicarboxylic acids, etc.; aryl aromatic dicarboxylic acids [e.g., biphenyl dicarboxylic acid (e.g., 2,2'-biphenyl dicarboxylic acid, 4,4'-biphenyl dicarboxylic acid, etc.) and other C6-10 aryl-C6-10 aromatic dicarboxylic acids, etc.]; diaryl alkyl dicarboxylic acids [e.g., diphenylalkyl dicarboxylic acid (e.g., 4,4'-diphenylmethane dicarboxylic acid, etc.) and other diC6-10 aryl-C1-6 alkyl dicarboxylic acids, etc.]; diaryl ketone dicarboxylic acids [e.g., diphenylketone dicarboxylic acid (e.g., 4,4'-diphenylketone dicarboxylic acid, etc.) and other diC6-10 aryl ketone dicarboxylic acids, etc.], etc.

[0145] Furthermore, the dicarboxylic acid components in the UV-absorbing polyamide resin, other than the UV absorber, are not limited to free carboxylic acids, but also include: ester-forming derivatives of dicarboxylic acids, such as esters [e.g., alkyl esters [e.g., lower alkyl esters such as methyl ester, ethyl ester, etc. (e.g., C1-4 alkyl esters, especially C1-2 alkyl esters)], amide halides (e.g., amide chloride), acid anhydrides, etc. These dicarboxylic acid components can be used alone or in combination of two or more.

[0146] 1.2.3.2. Diamine There are no particular limitations on diamines, and examples include: aliphatic diamines, alicyclic diamines, aromatic diamines, etc. Diamines can be one or two or more in combination.

[0147] Aliphatic diamines can be exemplified as: alkyl diamines (e.g., ethylenediamine, propylenediamine, 1,3-trimethylenediamine, 1,4-tetramethylenediamine, 1,5-pentamethylenediamine, 1,6-hexamethylenediamine, 1,7-heptamethylenediamine, 1,8-octamethylenediamine, 1,9-nonamethylenediamine, 1,10-decamethylenediamine, 1,11-undecamethylenediamine, 1,12-dodecamethylenediamine, 2-methyl-1,5-pentamethylenediamine, 2,2,4-trimethyl-1,6-hexamethylenediamine, 2,4,4-trimethyl-1,6-hexamethylenediamine, 2-methyl-1,8-octamethylenediamine, 5-methyl-1,9-nonamethylenediamine, etc., C2-20 alkyl diamines, preferably C2-12 alkyl diamines, and even more preferably C2-20 alkyl diamines). Aliphatic diamines, such as 8-alkyldiamine, can be present alone or in combination of two or more.

[0148] Examples of alicyclic diamines include: monocyclic cycloalkyl diamines, bridged cycloalkyl diamines, isophorone diamines, etc. Alicyclic diamines can be used alone or in combination of two or more.

[0149] Examples of monocyclic cycloalkyl diamines include: diaminocyclohexane (1,4-diaminocyclohexane, etc.), methylcyclohexanediamine (3-methyl-1,4-diaminocyclohexane, etc.), etc.; bis(aminomethyl)cyclohexane (1,4-aminomethylcyclohexane, etc.), bis(aminomethyl)methylcyclohexane, etc. Monocyclic cycloalkyl diamines are often: C4-10 cycloalkyl diamines, bis(aminomethyl)C4-10 cycloanes.

[0150] Bridged cycloalkyl diamines can be exemplified as: bicyclooctane diamine, bicyclononane diamine, tricyclododecane diamine, norbornane diamine, etc.; bis(aminomethyl)bicyclooctane, bis(aminomethyl)bicyclononane, bis(aminomethyl)tricyclododecane, bis(aminomethyl)norbornane, etc., etc. Bridged cycloalkyl diamines are often: C6-14 bis or tricycloalkyl diamines, bis(aminomethyl)C6-14 bis or tricycloalkyl.

[0151] Examples of aromatic diamines include: aromatic diamines (e.g., m-phenylenediamine, p-phenylenediamine, etc., C6-10 aromatic diamines), aminoalkyl-amino aromatics [e.g., α-(3-aminophenyl)ethylamine, etc., aminoC1-4alkyl-aminoC6-10 aromatics, etc.], aromatic aliphatic diamines [e.g., di(aminoalkyl)aromatics (e.g., m-xylenediamine, p-xylenediamine, etc., di(aminoC1-4alkyl)C6-10 aromatics, etc.], etc. Aromatic diamines can be alone or in combination of two or more.

[0152] Furthermore, the polymer component of the ultraviolet-absorbing polyamide resin may consist only of the above-mentioned dicarboxylic acid component and diamine component, or may include aminocarboxylic acid component [aminocarboxylic acid (e.g. 6-aminoadipic acid, 12-aminododecanoic acid, etc.), lactamine (ε-caprolactam, etc.) etc.] as polymer component as needed.

[0153] The proportion of such aminocarboxylic acid components may be, for example, 0.5 mol or less, preferably 0.3 mol or less, even more preferably 0.2 mol or less, and particularly 0.1 mol or less, relative to 1 mol of dicarboxylic acid components.

[0154] 1.2.3.3. Preparation Method of Polyamide Resin Ultraviolet-absorbing polyamide resin can be manufactured by conventional methods. For example, polyamide resin can be manufactured by reacting a dicarboxylic acid component with a diamine component (polymerization or condensation). The polymerization method (manufacturing method) can be appropriately selected according to the type of dicarboxylic acid component used, etc. Examples of conventional methods include: melt polymerization (or melt condensation, a method of polymerizing a dicarboxylic acid component and a diamine component in a melt mixture), solution polymerization (or solution condensation), interfacial polymerization (or interfacial condensation), etc.

[0155] Specifically, melt polycondensation involves heating raw materials such as a salt prepared from dicarboxylic acid and diamine components, and the dicarboxylic acid and diamine components, to a temperature above their melting point to melt them, while removing detached components such as water and alcohols from the reaction system under reduced pressure. Furthermore, solution polycondensation involves removing detached components in a solvent using condensing agents such as azeotropic agents, acid acceptors such as tertiary amines, and condensing agents such as triphenyl phosphite / pyridine mixtures. Additionally, interfacial polycondensation involves dissolving dicarboxylic acid amide halides in a nonpolar solvent and reacting them with diamine components at the interface with an aqueous solution of an alkaline compound such as sodium hydroxide.

[0156] In the melt polycondensation method, the salts of the dicarboxylic acid component and the diamine component can be dissolved separately in a solvent and mixed to obtain a precipitate. In this case, the solvent is not particularly limited as long as it can dissolve both the dicarboxylic acid component and the diamine component, and examples include: ethers (e.g., cyclic ethers such as tetrahydrofuran and 1,4-dioxane), ketones (e.g., chain ketones such as methyl ethyl ketone; cyclic ketones such as cyclohexanone), halogenated solvents (e.g., halogenated hydrocarbons such as dichloromethane and chloroform), amides (e.g., N,N'-dimethylacetamide, N,N'-dimethylmethamide), sulfides (e.g., dimethylsulfides), and nitrogen-containing solvents (e.g., N-methylpyrrolidone). Two or more solvents can be used alone or in combination.

[0157] Furthermore, in melt polycondensation, when any component (e.g., the diamine component) is easily volatile, an excess of the easily volatile component (e.g., a proportion exceeding the theoretical amount by 0.01 to 3 mol%) can be used. Additionally, to prevent the diamine component from volatile, the reaction can be carried out under pressure in the initial stage of the reaction. The polymerization reaction can be carried out under normal pressure or reduced pressure, but in the later stage of polymerization, it is preferable to reduce the pressure up to approximately 150 Pa to promote the removal of components such as water and alcohols from the reaction system.

[0158] 1.2.3.3. Physical Properties of Polyamide Resin Ultraviolet Absorption The glass transition temperature of the polyamide resin can be selected from a range of 120°C or higher (e.g., 140°C or higher), for example, 150°C or higher (e.g., 160–400°C), preferably 165°C or higher (e.g., 165–370°C), more preferably 170°C or higher (e.g., 175–350°C), particularly 180°C or higher (e.g., 190–320°C), and can also be set to 200°C or higher (e.g., 200–350°C, preferably 210–300°C, more preferably 215–280°C). The glass transition temperature can be measured by the method described in the examples described later.

[0159] The weight-average molecular weight of the UV-absorbing polyamide resin is preferably 30,000 to 200,000, more preferably 35,000 to 150,000, and even more preferably 40,000 to 110,000. With a weight-average molecular weight within the above range, the UV-absorbing polyamide resin tends to have longer molecular chains, resulting in improved mechanical properties such as elongation at break and flexibility, and thus improved elongation. Furthermore, in this embodiment, the weight-average molecular weight can be determined by gel permeation chromatography (GPC) converted to polystyrene. More specifically, it can be determined by the methods described in the examples below.

[0160] 1.2.4. (Meth)acrylate resins (meth)acrylate resins are polymerized from (meth)acrylates, and as (meth)acrylates, they have a constituent unit F derived from the compound represented by general formula (1). In order to distinguish them from other (meth)acrylate resins, (meth)acrylate resins containing such a constituent unit F are also called "ultraviolet-absorbing (meth)acrylate resins". When the ultraviolet absorber represented by the general formula (1) of the present invention is a reactive di(meth)acrylate, it can be subjected to free radical polymerization, that is, it can be set as an ultraviolet-absorbing (meth)acrylate resin with the ultraviolet absorber component as a constituent unit.

[0161] Compared to all free radical polymerizable compounds, the content of the constituent unit F in the ultraviolet-absorbing (meth)acrylic resin is preferably 1 to 100 mol%, more preferably 5 to 80 mol%, and even more preferably 10 to 60 mol%, on a molar basis. By having the proportion of the ultraviolet absorber within the above range, there is a tendency to further improve ultraviolet absorption and absorption specificity of ultraviolet light at a particular wavelength.

[0162] 1.2.4.1. (Meth)acrylate monomers The (meth)acrylate monomers of (meth)acrylate resins can be entirely composed of unit F, or can be a combination of (meth)acrylate unit F and other free radical polymerizable components. The (meth)acrylate unit F is not particularly limited, and for example, can be derived from (meth)acrylate units when Y1a and Y1b are as shown in formula (Y4). These (meth)acrylates can be used alone or in combination of two or more.

[0163] Other free radical polymerizable components are not particularly limited, and examples include: vinyl compounds, monofunctional (meth)acrylates, polyfunctional (meth)acrylates, etc.

[0164] Examples of vinyl compounds include: aromatic vinyl compounds such as styrene, α-methylstyrene, and vinylstyrene; aliphatic vinyl esters such as vinyl acetate, vinyl propionate, and trimethylvinyl acetate; and N-vinylpyrrolidone, N-vinylacetamide, and other N-vinyl compounds.

[0165] Monofunctional (meth)acrylates can be exemplified as: (meth)acrylate alkyl esters [e.g., (meth)acrylate methyl acrylate, (meth)acrylate ethyl acrylate, (meth)acrylate butyl acrylate, etc. (meth)acrylate C 1 -20 alkyl esters, etc., hydroxyalkyl esters of (meth)acrylate, alkoxyalkyl esters of (meth)acrylate, cyclohexyl esters of (meth)acrylate, aryl esters of (meth)acrylate (e.g., phenyl methacrylate), aryloxyalkyl esters of (meth)acrylate (e.g., phenoxyethyl methacrylate), arylalkyl esters of (meth)acrylate (e.g., benzyl methacrylate), aryloxy((poly)alkoxy)alkyl esters of (meth)acrylate (e.g., phenoxyethoxyethyl methacrylate), alkylaryloxy((poly)alkoxy)alkyl esters of (meth)acrylate (e.g., nonylphenoxy(poly)ethoxyethyl methacrylate), arylaryl(oxy((poly)alkoxy)alkyl esters) of (meth)acrylate (e.g., 2-(o-phenylphenoxy)ethyl methacrylate, phenylphenoxy(poly)ethoxyethyl methacrylate), etc.); with (Meth)acrylates containing sulfur atoms [e.g., alkyl thioacrylates (e.g., methyl thioacrylate, etc.), aryl thioacrylates (e.g., benzene thioacrylate, etc.), aryl alkyl thioacrylates (e.g., benzene thioacrylate, etc.), aryl thioalkyl acrylates (e.g., ethyl phenyl thioacrylate, etc.)]; N,N-dialkyl (meth)acrylamides (e.g., N,N-dimethyl (meth)acrylamide), N,N-dialkylaminoalkyl ((N,N-dimethylaminoethyl) acrylate, etc.), mono(meth)acrylates of bisphenols or their alkyl oxide adducts (e.g., mono(meth)acrylates of ethylene oxide adducts of bisphenol A, etc.), (meth)acrylates with a benzoyl skeleton (e.g., 9-(meth)acryloxymethyl benzoyl, etc.).

[0166] Examples of multifunctional (meth)acrylates include: difunctional (meth)acrylates [e.g., C2-10 alkyldiol dimethacrylates such as ethylene glycol dimethacrylate and butanediol dimethacrylate; polyalkylene glycol dimethacrylates such as diethylene glycol dimethacrylate, and dimethacrylates of bisphenol A (or its epoxy alkyl adducts)], trifunctional or higher (meth)acrylates [e.g., trimethylolpropane trimethacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate, etc., triol or tetraol (meth)acrylates], oligomeric (meth)acrylates [urethane (meth)acrylates, epoxy (meth)acrylates, polyester (meth)acrylates, etc.], etc. These monofunctional and multifunctional (meth)acrylates can also be used alone or in combination of two or more.

[0167] 1.2.4.2. Preparation method of (meth)acrylic resin UV-absorbing (meth)acrylic resin can be prepared by reaction of (meth)acrylate. There is no particular limitation on the manufacturing method of (meth)acrylic resin, and conventional methods can be used for preparation, such as free radical polymerization, in which polymerization initiators, photosensitizers, etc. can be used.

[0168] 1.2.4.1. The polymerization initiator hardening component may contain a polymerization initiator. This polymerization initiator may be a thermal polymerization initiator (thermal free radical generator) or a photopolymerization initiator (photofree radical generator).

[0169] Examples of thermal polymerization initiators include: organic peroxides [dialkyl peroxides (e.g., di(tributyl)peroxide, etc.), diacylperoxides (e.g., lauryl peroxide, benzoyl peroxide, etc.), peracids (or peresters) (e.g., tributyl hydroperoxide, cumene hydroperoxide, tributyl peracetate, etc.), ketone peroxides, peroxycarbonates, peroxyketals], azo compounds [e.g., azonitrile compounds such as 2,2'-azobis(isobutyronitrile), azoamide compounds, azomid compounds, etc.], etc. These thermal polymerization initiators can be used alone or in combination of two or more.

[0170] Examples of photopolymerization initiators include: benzoin derivatives (benzoin, benzoin ethyl ether, benzoin alkyl ethers, etc.), acetophenone derivatives (acetophenone, 2-hydroxy-2-methyl-1-phenylprop-1-one, etc.), aminoacetophenone {2-methyl-1-[4-(methylthio)phenyl]-2-(N-morpholino)aminoacetone-1, etc.}, anthraquinone derivatives (anthraquinone, 2-methylanthraquinone, etc.), thioxanthone derivatives (2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, 2-chlorothioxanthone, etc.), ketals (acetophenone dimethyl ketal, benzil dimethyl ketal, etc.), benzophenone (benzophenone, etc.), xanthone derivatives, etc. These photopolymerization initiators can be used alone or in combination of two or more.

[0171] The amount of polymerization initiator (thermal or photopolymerization initiator) used relative to the total amount of free radical polymerizable components of 100 parts by mass can be 0.1 to 15 parts by mass, preferably 0.5 to 10 parts by mass (e.g., 1 to 8 parts by mass), and more preferably about 2 to 5 parts by mass.

[0172] The photopolymerization initiator can be combined with a photosensitizer. Examples of photosensitizers include: tertiary amines {such as trialkylamines, trialkylolamines (triethanolamine, etc.), dialkylaminobenzoates such as N,N-dimethylaminobenzoate [e.g., ethyl p-(dimethylamino)benzoate], bis(dialkylamino)benzophenone, 4,4-bis(diethylamino)benzophenone, etc.} and other commonly used photosensitizers. Two or more of these photosensitizers can be used alone or in combination.

[0173] The amount of photosensitizer used relative to 100 parts by weight of polymerization initiator can be 1 to 200 parts by weight, preferably 5 to 150 parts by weight, and more preferably about 10 to 100 parts by weight.

[0174] UV absorbers with a di(meth)acrylate structure provide active energy (active energy line) and are easily cured, thus producing UV-absorbing (meth)acrylate resins. More useful activation energies include: thermal energy and / or light energy (UV rays, X-rays, electron beams, etc.).

[0175] When using thermal energy, the heating temperature may be, for example, 50 to 200°C, preferably 60 to 150°C, and even more preferably around 70 to 120°C.

[0176] In addition, when irradiating (e.g., irradiating with ultraviolet light), the irradiation energy can be appropriately selected according to the application, for example: 50 to 10000 mJ / cm2, preferably 70 to 8000 mJ / cm2, and more preferably around 100 to 5000 mJ / cm2 (e.g., 500 to 3000 mJ / cm2).

[0177] Hardening can be carried out in air or in an inert gas environment (e.g., nitrogen, inert gas, etc.).

[0178] 1.2.4.1. Physical properties of acrylic resins: Ultraviolet absorption. The glass transition temperature of (meth)acrylic resins can be selected from the range of -60°C to 300°C, preferably -40°C to 250°C, and even more preferably -20°C to about 200°C. The glass transition temperature can be measured by the method described in the examples below.

[0179] The weight-average molecular weight of the UV-absorbing (meth)acrylic resin can be selected from the range of 400 to 15,000 (e.g., 600 to 12,000), and can be approximately 800 to 10,000 (e.g., 1,000 to 7,500), or more preferably 1,200 to 6,000 (e.g., 1,500 to 5,000). Furthermore, in this embodiment, the weight-average molecular weight can be determined by gel permeation chromatography (GPC) converted to polystyrene. More specifically, it can be determined by the methods described in the examples below.

[0180] 1.3. Physical Properties The chloroform compound and the resin having the constituent unit F (hereinafter also collectively referred to as "ultraviolet absorber") of this embodiment may be in a crystalline form or an amorphous form, depending on their chemical structure and manufacturing method. Furthermore, when the ultraviolet absorber is in a crystalline form, multiple crystalline polymorphs may exist, and when used for the purposes of this invention, it may be in any form or a mixture thereof.

[0181] The half-width at half-maximum (WWHM) of the ultraviolet absorber in this embodiment is preferably 55 nm or less, more preferably 50 nm or less, even more preferably 40 nm or less, and even more preferably 30 nm or less. The lower the WWHM, the better, for example, it is 3 nm or more. By having a WWHM of 55 nm or less, it is possible to selectively absorb only a specific range of ultraviolet light, thus achieving both excellent UV absorption and low colorimetric properties. Here, the WWHM refers to the wavelength band that exhibits a wavelength width of more than 1 / 2 of the absorbance when the absorbance is at its maximum, based on the absorption wavelength.

[0182] The ultraviolet absorber of this embodiment preferably has a maximum absorption wavelength in the wavelength range of 320 to 400 nm. Since the maximum absorption wavelength is within the above range, it can appropriately absorb ultraviolet light in the long wavelength region that is generally considered difficult to absorb.

[0183] The molar absorptivity (A 380) at 380 nm is preferably 200 to 2000 L / (mol)·cm, preferably 400 to 1500 L / (mol)·cm, and even better 600 to 1000 L / (mol)·cm.

[0184] The molar absorptivity (A 400) at 400 nm is preferably 0.5 to 50 L / (mol)·cm, preferably 1.0 to 25 L / (mol)·cm, and even more preferably 2.0 to 10 L / (mol)·cm.

[0185] The molar absorptivity (Amax) at the maximum absorption wavelength is preferably 20,000 to 100,000 L / (mol)·cm, preferably 30,000 to 90,000 L / (mol)·cm, and even better 40,000 to 80,000 L / (mol)·cm.

[0186] By having the molar absorptivity (A 380) or molar absorptivity (A 400) within the above range, there is a tendency to further improve the excellent UV absorption in the long wavelength region and further reduce the colorimetric properties.

[0187] The ratio of molar absorptivity (A 380) to molar absorptivity (A 400) (A 380 / A 400) is preferably 50 or higher, preferably 100 or higher, and even better than 200 or higher. Furthermore, the higher the upper limit of the ratio (A 380 / A 400), the better, for example, below 1000. By achieving a ratio (A 380 / A 400) of 50 or higher, excellent UV absorption in the long wavelength region and low tinting strength can be balanced.

[0188] The melting point of the ultraviolet absorber in this embodiment may be, for example, about 100 to 250°C, and preferably in stages below the range of 150 to 240°C, 175 to 230°C, and 180 to 225°C.

[0189] The 5% mass reduction temperature of the ultraviolet absorber in this embodiment can be, for example, around 250 to 500°C, and preferably in stages below the range of 350 to 480°C, 370 to 450°C, and 400 to 430°C.

[0190] 2. Ultraviolet Absorbing Composition The ultraviolet absorbing composition of this embodiment includes: the ultraviolet absorber of this embodiment; and at least one of the following compounds as a second ultraviolet absorber: a triazine ring-containing compound, a benzotriazole ring-containing compound, or a benzophenone ring-containing compound. The ultraviolet absorber of this embodiment may be the aforementioned compound, or a resin such as an ultraviolet-absorbing polyester resin, an ultraviolet-absorbing polycarbonate resin, an ultraviolet-absorbing polyamide resin, or an ultraviolet-absorbing (meth)acrylic resin. As described above, by mixing the ultraviolet absorber of this embodiment with the second ultraviolet absorber in any proportion, it is possible to absorb ultraviolet light of a wider range of wavelengths.

[0191] The second ultraviolet absorber can be freely selected according to the target absorption wavelength and compatibility with the resin described later. As an example, when the purpose is to absorb ultraviolet light of a wide wavelength in the UV-A region, a compound containing a triazine ring is preferred; when the purpose is to make it compatible with a general-purpose resin, a compound containing a benzotriazole ring is preferred; and when the purpose is to make it compatible with a low-polarity resin, a compound containing a benzophenone ring is preferred. The proportion of the second ultraviolet absorber contained in the ultraviolet absorbing composition of this embodiment can be freely selected according to the purpose, and is preferably 0.01 to 50% by mass.

[0192] 3. Ultraviolet-absorbing resin composition The ultraviolet-absorbing resin composition of this embodiment includes: the ultraviolet absorber of this embodiment; and any resin. The ultraviolet absorber of this embodiment may be: the above-mentioned compound; or ultraviolet-absorbing polyester resin, ultraviolet-absorbing polycarbonate resin, ultraviolet-absorbing polyamide resin, or ultraviolet-absorbing (meth)acrylic resin, etc.

[0193] Relative to the total amount of the ultraviolet-absorbing resin composition, the content of the ultraviolet absorber in this embodiment is preferably 0.1 to 10% by mass, more preferably 0.5 to 8.0% by mass, and even more preferably 1.0 to 5.0% by mass. If the amount of ultraviolet absorber used is 0.1% by mass or more, there is a tendency to further improve the ultraviolet absorption performance. On the other hand, by using the amount of ultraviolet absorber at 10% by mass or less, there is a tendency to further improve physical properties such as rigidity and toughness.

[0194] In addition, any resin can be, for example, thermoplastic resin or thermosetting resin.

[0195] The ultraviolet-absorbing resin composition can be processed into any form, such as flake, sheet, or film, as needed. Due to its excellent formability and processability, thermoplastic resins are preferred as the resin composition used in the ultraviolet-absorbing resin composition.

[0196] 3.1. Thermoplastic resin Thermoplastic resin is not particularly limited as long as it is compatible with the ultraviolet absorber of this embodiment. Examples include: polyolefin resins such as chain olefin resins and cyclic olefin resins (or cyclic olefin resins); (meth)acrylic resins; styrene resins such as polystyrene, AS (acrylonitrile-styrene) resin, and ABS (acrylonitrile-butadiene-styrene) resin; polyester resins such as polyalkyl acrylate resins, polyacrylate resins, polyethylene terephthalate, and polycarbonate resins; polyamide resins; cellulose resins such as triacetyl cellulose; ethylene resins such as polyvinyl chloride, polyvinyl acetate, and polyvinyl alcohol; thermoplastic polyurethane resins, etc.

[0197] 3.2. Thermosetting resin Thermosetting resin is only required to be compatible with the ultraviolet absorber of this embodiment, and there is no particular limitation. Examples include: phenolic resin; epoxy resin; melamine resin; urea resin; unsaturated polyester resin; alkyd resin; thermosetting polyurethane resin; thermosetting polyimide resin, etc.

[0198] 3.3. Method for Preparing the Composition Conventional methods can be used for the melt-blending of ultraviolet-absorbing resin compositions, such as: single-spindle extruders, bi-spindle extruders, Henschel mixers, Banbury mixers, Tandem mixers, Ko-Kneader mixers, etc. Generally, it is preferable to manufacture by melt-blending using a bi-spindle extruder because it can achieve uniform and complete mixing.

[0199] 3.4. Other Components In addition, the UV-absorbing resin composition may contain various additives as needed [e.g., fillers or reinforcing agents, colorants (pigments), conductive agents, flame retardants, plasticizers, lubricants, stabilizers (antioxidants, UV absorbers, heat stabilizers, etc.), release agents, antistatic agents, dispersants, flow modifiers, leveling agents, defoamers, surface modifiers, stress-reducing agents (silicone oils, silicone rubbers, various plastic powders, various engineering plastic powders, etc.), heat resistance modifiers (sulfur compounds and polysilanes, etc.), carbon materials, etc.]. These additives may be used alone or in combination of two or more.

[0200] 4. Ultraviolet-absorbing coating liquid The ultraviolet-absorbing coating liquid of this embodiment comprises: the ultraviolet absorber of this embodiment, the ultraviolet-absorbing composition of this embodiment, or the ultraviolet-absorbing resin composition of this embodiment; and a solvent. Thus, the ultraviolet absorber, ultraviolet-absorbing composition, or ultraviolet-absorbing resin composition of this embodiment, when dissolved in any solvent, can be configured as an ultraviolet-absorbing coating liquid.

[0201] Examples of solvents that can be used in UV-absorbing coating solutions include: aromatic solvents such as benzene, toluene, and xylene; ketone solvents such as diacetone alcohol, acetone, cyclohexanone, cyclopentanone, methyl ethyl ketone, and methyl isopropyl ketone; cycloalkane solvents such as cyclohexane, ethylcyclohexane, and 1,2-dimethylcyclohexane; halogen-containing solvents such as dichloromethane and chloroform; and ether solvents such as tetrahydrofuran and dioxane. From the viewpoint of obtaining a suitable viscosity for coating, the concentration of resin in the coating solution can be 1% to 50% by mass. A single solvent can be used, or two or more solvents can be used in any proportion.

[0202] The ultraviolet-absorbing coating liquid may be formulated with the following additives as needed: defoamer, leveling agent, antioxidant, light stabilizer, lubricant, flame retardant, antistatic agent, etc. These additives may be used alone or in combination of two or more.

[0203] 5. Ultraviolet-absorbing coated resin film and ultraviolet-absorbing coated glass. The ultraviolet-absorbing coated resin film of this embodiment comprises a resin film and an ultraviolet-shielding layer, wherein the ultraviolet-shielding layer includes: the ultraviolet absorber, ultraviolet-absorbing composition, or ultraviolet-absorbing resin composition of this embodiment. Furthermore, the ultraviolet-absorbing coated glass of this embodiment comprises glass and an ultraviolet-shielding layer, wherein the ultraviolet-shielding layer includes: the ultraviolet absorber, ultraviolet-absorbing composition, or ultraviolet-absorbing resin composition of this embodiment.

[0204] The resin sheet is not particularly limited as long as it can be coated with the ultraviolet absorber, ultraviolet absorbing composition, or ultraviolet absorbing resin composition of this embodiment. Examples of such sheets are made of the following resins: polycarbonate resins, polyamide resins, polyvinyl alcohol resins, cellulose ester resins such as triacetyl cellulose and cellulose acetate propionate films, polyester resins such as polyethylene terephthalate and polyethylene naphthalate, polyacrylate resins, polyimide resins, cycloolefin resins, polyurethane resins, polyether resins, polyolefin resins such as polyethylene and polypropylene, etc.

[0205] Glass can be coated with ultraviolet-absorbing coating liquid without any special restrictions. Examples include float glass, tempered glass, semi-tempered glass, chemically tempered glass, green glass, or quartz glass.

[0206] There are no restrictions on the method of applying the ultraviolet shielding layer. The application of ultraviolet absorbers, ultraviolet absorbing compositions, or ultraviolet absorbing resin compositions can be carried out by applying an ultraviolet absorbing coating liquid to resin films and glass.

[0207] Coating methods can include, for example: curtain coating, extrusion coating, roller coating, rotary coating, dip coating, bar coating, spray coating, slide coating, printing coating, gravure coating, mold coating, gap coating, and immersion coating, etc.

[0208] There are no restrictions on the drying method of the ultraviolet-absorbing coating liquid, and drying methods such as heating drying and vacuum drying can be used.

[0209] 6. Ultraviolet-absorbing film and ultraviolet-absorbing molded body. The ultraviolet-absorbing film of this embodiment includes: the ultraviolet absorber, ultraviolet-absorbing composition, or ultraviolet-absorbing resin composition of this embodiment. The ultraviolet-absorbing molded body of this embodiment includes: the ultraviolet absorber, ultraviolet-absorbing composition, or ultraviolet-absorbing resin composition of this embodiment.

[0210] The ultraviolet-absorbing molded body can be formed in any way to be an ultraviolet-absorbing molded body. The shape of the molded body is not particularly limited, and examples include: two-dimensional structures such as thin films, sheets, and plates; and three-dimensional structures such as rods, tubes, tubes, and vacuum tubes. Furthermore, due to its excellent optical properties, mechanical properties, and high heat resistance, the ultraviolet-absorbing molded body of the present invention is particularly suitable for use in optical components such as optical films, optical lenses, and optical sheets.

[0211] In addition, UV-absorbing thermoformed articles may contain various additives as needed [e.g., fillers or reinforcing agents, colorants (pigments), conductive agents, flame retardants, plasticizers, lubricants, stabilizers (antioxidants, UV absorbers, heat stabilizers, etc.), release agents, antistatic agents, dispersants, flow modifiers, leveling agents, defoamers, surface modifiers, stress-reducing agents (silicone oils, silicone rubbers, various plastic powders, various engineering plastic powders, etc.), heat resistance modifiers (sulfur compounds and polysilanes, etc.), carbon materials, etc.]. These additives may be used alone or in combination of two or more.

[0212] Ultraviolet-absorbing molded articles can be manufactured using methods such as injection molding, injection compression molding, extrusion molding, transfer molding, blow molding, pressure molding, casting, etc.

[0213] The ultraviolet absorber of this embodiment, i.e., the resin or ultraviolet-absorbing resin composition, can be formed into a thin film and thus constitute an ultraviolet-absorbing film. In this case, it can be configured as a single-layer film consisting only of the ultraviolet absorber of this embodiment, i.e., the resin or ultraviolet-absorbing resin composition.

[0214] There are no particular limitations on the method for forming a single-layer thin film, and examples include: solution casting, expansion method, T-die method and other melt extrusion, curtain method, etc. Among these, from the viewpoint that it not only has excellent productivity but also can prevent the reduction of optical properties caused by residual solvent, melt extrusion method such as T-die method is preferred, while from the viewpoint that it can not only control the film thickness with high precision but also form a single-layer thin film, solution casting method is preferred.

[0215] Solution casting can obtain a single-layer film by dissolving a UV-absorbing polyester resin, UV-absorbing polycarbonate resin, UV-absorbing polyamide resin, UV-absorbing (meth)acrylic resin, or a UV-absorbing resin composition in a solvent to obtain a coating liquid, applying the coating liquid to a substrate, drying and removing the solvent, and then peeling off the substrate. The substrate can be a resin film or resin sheet, or glass. From a production point of view, a resin film is preferred, and a resin film that has been demolded in a manner that allows for easy peeling is even more preferred.

[0216] There are no restrictions on the coating method of the coating liquid. Examples of coating methods include: curtain coating, extrusion coating, roller coating, spin coating, dip coating, bar coating, spray coating, slant coating, printing coating, gravure coating, mold coating, gap coating, and immersion coating, etc.

[0217] There are no restrictions on the drying method of the coating liquid, and drying methods such as heating drying and vacuum drying can be used.

[0218] Melt extrusion methods such as the T-die method can adjust the glass transition temperature and melting point of UV-absorbing polyester resin, UV-absorbing polycarbonate resin, UV-absorbing polyamide resin, UV-absorbing (meth)acrylic resin, or UV-absorbing resin composition, and form it using conventional methods. Specific forming conditions are: the melt temperature of the extruded resin is preferably Tg+80°C or higher, more preferably Tg+100°C or higher, and preferably Tg+180°C or lower, more preferably Tg+150°C or lower. The aforementioned melt temperature, for example in the T-die method, refers to the melt temperature of the resin in an extruder equipped with a T-die. When the melt temperature of the extruded resin is above the lower limit of the aforementioned range, the resin's fluidity can be sufficiently improved to achieve good formability, and when it is below the upper limit, resin deterioration can be suppressed.

[0219] The ultraviolet-absorbing film of the present invention is not only a single-layer film, but can also be a laminated film formed by laminating with other films.

[0220] There are no particular limitations on the forming method of the laminated film, and examples include: co-extrusion molding, solution casting, extrusion lamination, etc. From the viewpoint that it not only has excellent productivity but also prevents the degradation of optical and mechanical properties caused by residual solvents, co-extrusion molding is preferred.

[0221] One type of co-extrusion molding method, namely co-extrusion T-die method, includes, for example, the feed block method and the multi-manifold method. From the viewpoint of reducing the thickness variation of each layer, the multi-manifold method is particularly good.

[0222] The ultraviolet-absorbing film of the present invention can be an unstretched film, or, from the viewpoint of mechanical properties, a stretched film. Furthermore, stretching is a more effective method for thinning. If the unstretched film has a thickness of approximately 50 μm or more, the film thickness can be controlled by clamping it into the rolls after die casting from the T-die, thereby improving film thickness accuracy. By selecting stretching conditions that can obtain uniform stretching pressure for the stretching process, a film with good thickness accuracy can be produced.

[0223] The stretching process involves heating the ultraviolet-absorbing thin film prepared by any of the aforementioned methods to a suitable temperature between its melting point and glass transition point. The stretching can be either biaxial or uniaxial, and can be selected to suit subsequent embodiments. For example, for use as a polarizer protection film as described later, biaxial stretching with less hysteresis caused by stretching is more suitable. Biaxial stretching can be performed by stretching the film in both longitudinal and transverse directions, and the in-plane hysteresis Ro can be set to be canceled out in both directions, making it close to zero. On the other hand, for use as a 1 / 4λ phase difference film or other films where appropriate phase difference is required, uniaxial stretching is more suitable.

[0224] 7. Polarizing film The ultraviolet-absorbing film of this embodiment can be used as a polarizing film.

[0225] The total thickness of the polarizer protective film is preferably 5 to 90 μm, more preferably 10 to 80 μm, and even more preferably 20 to 50 μm. By having a total thickness within the above range, it can be more suitable as a polarizer protective film.

[0226] The transmittance of the polarizer protective film at 350 nm in this embodiment is preferably 5% or less, more preferably 3% or less, and even more preferably 1% or less. By having the transmittance of the polarizer at a wavelength of 350 nm within the above range, it is possible to prevent the polarizer from being degraded by ultraviolet rays contained in external light, etc., and thus it can be used more appropriately as a polarizer protective film.

[0227] In this embodiment, the b* value in the L*a*b* color space (CIELAB) of the polarizer protective film is preferably 0.8 or less, more preferably 0.6 or less, and even more preferably 0.5 or less. Furthermore, a b* value of -0.8 or more is preferred, more preferably -0.6 or more, and even more preferably -0.5 or more. By having a b* value within the above range, a polarizer protective film with excellent legibility can be obtained. Moreover, the aforementioned b* value is assumed to be a value calculated according to JIS Z8781-4:2013.

[0228] A value of a* is preferably below 0.3, less preferably below 0.2, and even better below 0.1. In addition, an a* value of -0.4 or higher is preferred, more preferably above -0.3, and even better above -0.2.

[0229] Furthermore, the L* value is preferably below 100, below 99, or below 98. In addition, the L* value is preferably above 90, above 92, or above 94.

[0230] The transmittance of the polarizer protective film at 380 nm in this embodiment is preferably 8% or less, more preferably 5% or less, and even more preferably 1% or less. By having the transmittance of the polarizer at a wavelength of 380 nm within the above range, it is possible to prevent the polarizer from being degraded by ultraviolet rays contained in external light, etc., and thus it can be used more appropriately as a polarizer protective film.

[0231] 8. Polarizing Plate The polarizing plate of this embodiment has the aforementioned polarizer protective film, and may be further provided with other layers as needed. Next, the polarizing plate of this embodiment will be described with reference to Figures 1A and 1B. This polarizing plate includes the polarizer protective film of this embodiment. Figures 1A and 1B are schematic cross-sectional views illustrating one aspect of the polarizing plate.

[0232] The polarizing plate 20 shown in Figure 1A has the following layers stacked in sequence: a phase retardation film 21, a polarizer 23, and a polarizer protective film 10. As shown in the figure, an adhesive layer 22 can be provided between the phase retardation film 21 and the polarizer 23, and an adhesive layer 24 can also be provided between the polarizer 23 and the polarizer protective film 10.

[0233] The polarizing plate 30 shown in Figure 1B has the following layers stacked in sequence: a phase retardation film 31, a polarizing film protective film 10, a polarizing film 34, and a polarizing film protective film 10. An adhesive layer or an adhesive layer 32 may be provided between the phase retardation film 31 and the polarizing film protective film 10, and adhesive layers 33 and 35 may also be provided between the polarizing film 34 and the polarizing film protective film 10.

[0234] The polarizer protective film 10 may be supplied with the following treatments to improve the adhesion between it and the polarizers 23, 34: corona treatment and plasma treatment, and surface modification treatment by a strongly alkaline aqueous solution such as sodium hydroxide and potassium hydroxide. These surface modification treatments may be performed after the film-forming step or after the stretching step.

[0235] Polarizing films 23 and 34 are not particularly limited as long as they are known materials. Examples include: products made by dyeing and stretching a hydrophilic polymer film using dichroic substances such as iodine and dichroic dyes, such as polyvinyl alcohol films, partially formaldehyde-modified polyvinyl alcohol films, partially saponified films based on ethylene-vinyl acetate copolymers, etc.; polyolefin-based oriented films such as dehydrated polyvinyl alcohol products and dehydrochlorinated polyvinyl chloride products. In addition, examples include: polarizing films obtained by dyeing a polyvinyl alcohol film with iodine and then uniaxially stretching it.

[0236] The polarizer protective film 10 can use the above-mentioned polarizer protective film. The polarizer protective film 10 and the polarizers 23, 34 formed of polyvinyl alcohol resin or the like can be bonded together with an ultraviolet-curing adhesive (adhesive layer 24, 33, 35).

[0237] 9. Image Display Device The image display device of this embodiment includes the aforementioned polarizing plate. Next, the image display device of this embodiment will be described with reference to Figures 2A and 2B. The image display device of this embodiment is not particularly limited as long as it includes the aforementioned polarizing plate; examples include organic electroluminescent (EL) display devices and liquid crystal display devices. Furthermore, the image display device is not limited to devices that are marketed as finished products in standalone form, but can also be part of information processing devices, such as smartphones, as described later. Figure 2A is a schematic cross-sectional view illustrating one aspect of an organic EL display device of this embodiment, and Figure 2B is a schematic cross-sectional view illustrating one aspect of a liquid crystal display device of this embodiment.

[0238] As shown in Figure 2A, the organic EL display device 40 sequentially includes: an organic EL display panel 41, a polarizing plate 20 having the polarizing protective film 10 of this embodiment, and a front panel 43. In the organic EL display device 40, by using the polarizing plate 20 having the polarizing protective film 10, it is possible to suppress the deterioration of the polarizing plate 20 due to ultraviolet rays and moisture permeation, and it also has excellent mechanical strength against bending, etc., and can be made thinner.

[0239] Furthermore, the OLED display device 40 may be equipped with other components such as a touch detector 42 as needed. By equipping the touch detector 42, the OLED display device 40 can not only perform the functions of a display device, but also the functions of an information input interface. The layers constituting the OLED display device 40 can be bonded together separately using adhesives or bonding agents.

[0240] As shown in Figure 2B, the liquid crystal display device 50 sequentially includes: a light source 51, a polarizing plate 30, a liquid crystal panel 52, and a front panel 53. The light source 51 can be a direct-lit type with the light sources evenly distributed directly below the liquid crystal panel, or it can be a side-lit type with a reflector and a light guide plate. Furthermore, although the front panel 53 is shown in Figure 2B, the liquid crystal display device 50 may not have a front panel 53. The liquid crystal display device 50 may further include a touch detector (not shown).

[0241] Furthermore, the screen of the image display device is not limited to a quadrilateral, but can have a circular, elliptical, or polygonal shape such as a triangle or pentagon. Also, the image display device can be flexible, changing its shape by warping, bending, rolling, or folding. For example, as shown in Figure 3, the image display device includes a roll-up display that allows the image display device 61, which is housed in a roller shape within the image display device housing 62, to be pulled out for use.

[0242] 10. The ultraviolet absorber, ultraviolet absorbing composition, or ultraviolet absorbing resin composition, ultraviolet absorbing coating liquid, ultraviolet absorbing coating resin film, ultraviolet absorbing coated glass, ultraviolet absorbing molded body, ultraviolet absorbing film, polarizer protective film, polarizer plate or image display device of this embodiment can be suitably used as components of transportation machinery such as automobiles, ships, and aircraft.

[0243] 11. The ultraviolet absorber, ultraviolet-absorbing composition, or ultraviolet-absorbing resin composition, ultraviolet-absorbing coating liquid, ultraviolet-absorbing coating resin film, ultraviolet-absorbing coated glass, ultraviolet-absorbing molded body, ultraviolet-absorbing film, polarizer protective film, polarizer plate, or image display device of this embodiment can be used as building components such as structural materials like columns and beams, roofing materials, wall materials, flooring materials, and building equipment such as doors and windows. In particular, it can be suitably used as a window component for the purpose of absorbing ultraviolet rays that intrude during lighting. [Example 1]

[0244] The present invention will be described in more detail below with reference to embodiments, but the present invention is not limited to these embodiments. The evaluation method and raw materials are as follows.

[0245] 1. Evaluation Method 1.1. Glass Transfer Temperature (Tg) Using a differential scanning calorimeter (Seiko Instruments Co., Ltd. "DSC 6220"), the sample was added to an aluminum pan, and Tg was measured in the range of 30°C to 200°C according to JIS K 7121.

[0246] 1.2 Weight average molecular weight was determined using a gel permeation chromatography system (manufactured by TOSOH Corporation, "HLC-8120GPC"). The sample was dissolved in chloroform, and the weight average molecular weight Mw of each resin was converted to polystyrene.

[0247] 1.3. 5% mass reduction temperature: Using a thermogravimetric analyzer (PerkinElmer Co., Ltd. "TGA 4000"), the temperature at which the sample mass has decreased by 5% was measured at a heating rate of 10°C / min. 1.4. Film thickness: Using a thickness gauge (Mitutoyo Co., Ltd. "Micrometer"), three points were measured at equal intervals along the long side of the film, and the average value was calculated.

[0248] 1.5. Mole Absorption Coefficient, Maximum Absorption Wavelength, and Half-width: For each sample, a tetrahydrofuran solution of a suitable concentration for the determination described below was prepared, and the ultraviolet-visible spectrum was measured using a UV-Vis spectrophotometer (V-650, manufactured by Nippon Spectrophotometer Co., Ltd.) in a 1 cm quartz optical tube. The suitable concentration for determination referred to here is the absorbance range of 0.1 to 2.0. The mole absorption coefficient was calculated from the slope obtained by taking at least three absorbance points within this range. Furthermore, the maximum absorption wavelength and half-width were calculated from the obtained spectrum.

[0249] 1.4. Transmittance According to JIS K7361:1997, the transmittance of each film at 350 nm and 380 nm was measured using a UV-Vis spectrophotometer (V-650 manufactured by Japan Spectrophotometer Co., Ltd.).

[0250] 1.5. L*a*b* color space: According to JIS Z8729, a UV-Vis spectrophotometer (V-650, manufactured by Japan Spectrophotometer Co., Ltd.) was used to measure each thin film. L* value represents lightness, and a* and b* values ​​represent hue.

[0251] 2. Fumarate Compounds 2.1. Example 1: Preparation of DNFDP-m 200 mL of 1,4-dioxane and 54.7 g (0.17 mol) of 2,7-dibromo-9H-fumarate were added to a reactor and stirred until the fumarate was dissolved. Then, 3.0 mL of a 40% by mass methanol solution of trimethylbenzyl ammonium hydroxide (TRITON B40 manufactured by Tokyo Chemical Co., Ltd.) was added dropwise while the mixture was cooled to 10°C, and the mixture was stirred for 30 minutes. Next, 37.9 g (0.44 mol) of methyl acrylate was added, and the mixture was stirred for approximately 3 hours. After the reaction was complete, 200 mL of toluene and 50 mL of 0.5 N hydrochloric acid were added for washing. After removing the aqueous layer, the organic layer was washed three times with 30 mL of distilled water. The solvent was distilled off to obtain 9,9-bis(2-methoxycarbonylethyl)-2,7-dibromofumarate (DBrFDP-m).

[0252] Then, 192.3 g (0.39 mol) of DBrFDP-m, 200 g (1.2 mol) of 2-naphthylboronic acid, 4.3 L of dimethoxyethane, and 1 L of 2M sodium carbonate aqueous solution were fed into the reactor. 22.4 g (19.4 mmol) of tetra(triphenylphosphine)palladium(O) [or Pd(PPh3)4] was added under a nitrogen gas flow, and the mixture was heated under reflux at an internal temperature of 71–78 °C for 5 hours to allow the reaction to proceed. After cooling to room temperature, 2.0 L of toluene and 500 mL of deionized water were added, and the mixture was separated and extracted five times to wash the surface. The organic layer changed from deep orange to brown. The insoluble matter was filtered and concentrated to obtain brown crude crystals. The crude crystals were dissolved by heating with a mixture of 1.5 kg of ethyl acetate and 300 g of isopropanol (IPA), cooled in ice water to below 10 °C, and stirred for 1 hour to allow crystals to precipitate. The precipitated crystals were filtered and dried under reduced pressure to obtain 130 g of grayish-brown crystals. The grayish-brown crystals were purified by column chromatography (silicone gel support, developing solvent chloroform:ethyl acetate (v / v) = 4:1), recrystallized with methanol, and dried under reduced pressure to obtain 9,9-bis(2-methoxycarbonylethyl)-2,7-di(2-naphthyl)furan (DNFDP-m). The results of 1H-NMR (nuclear magnetic resonance) and FD-MS (field desorption-mass spectrometry) are shown below.

[0253]

[0254]

[0255] 2.2. Example 2: Preparation of DNFPO In a nitrogen atmosphere, in a 20 L split flask, DNFDP-m (1.2 kg, 2.03 mol) obtained as described above and tetrahydrofuran (THF, 9.78 kg) were added, and the mixture was cooled to below 10°C in an ice-water bath. Sodium borohydride (230 g, 6.08 mol) was added in small amounts over 13 minutes, followed by the dropwise addition of boron trifluoride ether complex (856 g, 6.09 mol) over 45 minutes. The mixture was then heated to room temperature and stirred for 4 hours. After cooling in an ice-water bath, acetone (1.0 kg, 17.2 mol) was added dropwise over 1 hour, and the solvent was removed by concentration under reduced pressure. Then, 12 kg of chloroform, 1.0 kg of deionized water, and 3.0 kg of ice were added, and the aqueous layer was removed. Furthermore, the process of adding 4.0 kg of ion-exchanged water and removing the aqueous layer was performed twice (washing twice with ion-exchanged water), and only the organic layer was removed. The resulting organic layer was concentrated under reduced pressure to obtain 9,9-bis(3-hydroxypropyl)-2,7-bis(2-naphthyl)furan (DNFPO). The results of 1H-NMR and FD-MS are shown below.

[0256]

[0257] 2.3. Example 3: Preparation of DNFPA In a 500 mL three-necked flask equipped with a Dean-Stark reactor, 30.0 g (0.06 mol) of DNFPO, 10.5 g (0.15 mol) of acrylic acid, 55 g of toluene, and 0.12 g (1.0 mmol) of 2-methoxyphenol, prepared as described above, were fed in. After purging the system with nitrogen, the temperature was raised to 95°C, and the aforementioned components were homogenized. Then, 1.33 g (7.0 mmol) of p-toluenesulfonic acid monohydrate was added, and the system was purged with nitrogen again and refluxed for dehydration for 4 hours. The reaction temperature was 110–115°C.

[0258] The obtained solution was washed with 195 g of toluene and 20 g of 20% saline solution (internal temperature 60-70°C), then neutralized with 20 g of 10% caustic soda solution (10% sodium hydroxide aqueous solution) and 20 g of 20% saline solution (internal temperature 60-70°C), and the pH of the aqueous layer was confirmed to be above 10. 500 ppm of 2-methoxyphenol was added to the organic layer, and after homogenization, the solution was washed twice with 20 g of 20% saline solution and twice with 20 g of deionized water (internal temperature 60-70°C), and the pH of the aqueous layer was confirmed to be 7. Then, 6 g of activated carbon (FP-6 manufactured by Mizusawa Chemical Co., Ltd.) was added to the organic layer and stirred at room temperature for 1 hour. After filtration through cerium silicate, the mixture was concentrated and dried under reduced pressure at 100°C overnight to obtain 9,9-bis(3-propenyloxypropyl)-2,7-bis(2-naphthyl)furan.

[0259] 2.4. Example 4: Modification of DPFDP-m 192.3 g (0.39 mol) of DBrFDP-m obtained as described above, 150 g (1.2 mol) of phenylboronic acid, 4.3 L of dimethoxyethane, and 1 L of 2M sodium carbonate aqueous solution were fed into a reactor. 22.4 g (19.4 mmol) of tetra(triphenylphosphine)palladium(O) [or Pd(PPh3)4] was added under a nitrogen gas flow, and the mixture was heated under reflux at an internal temperature of 71–78 °C for 5 hours to allow the reaction to proceed. After cooling to room temperature, 2.0 L of toluene and 500 mL of deionized water were added, and the mixture was separated and extracted five times to wash the surface. The organic layer changed from deep orange to brown. The insoluble matter was filtered and concentrated to obtain brown crude crystals. The crude crystals were dissolved by heating in a mixture of 1.5 kg ethyl acetate and 300 g isopropanol (IPA), then cooled in ice water to below 10°C and stirred for 1 hour to allow crystallization. The precipitated crystals were filtered and dried under reduced pressure to obtain 110 g of grayish-brown crystals. The grayish-brown crystals were purified by column chromatography (silicone gel support, developing solvent chloroform:ethyl acetate (v / v) = 4:1), recrystallized with methanol, and dried under reduced pressure to obtain 9,9-bis(2-methoxycarbonylethyl)-2,7-diphenyl benzoylene (DPFDP-m).

[0260] 2.5. Example 5: Preparation of BNEF In a 1 L split-type flask, 45 g of 9-dysperidone (0.25 mol, manufactured by OSAKA GAS CHEMICALS Co., Ltd.), 188 g (1 mol) of ethylene glycol mono(2-naphthyl) ether, and 1 g of 3-mercaptopropionic acid were added, and the mixture was heated to 60°C until completely dissolved. Then, 54 g of sulfuric acid was slowly added, and the mixture was stirred for 5 hours while maintaining the temperature at 60°C. The conversion rate of 9-dysperidone was confirmed by HPLC (high performance liquid chromatography) to be over 99%. After neutralization with 48% caustic soda solution, 400 g of xylene was added, and the mixture was washed several times with distilled water. After cooling, crystals were precipitated. The crystals were then filtered and dried to obtain 9,9-bis[6-(2-hydroxyethoxy)-2-naphthyl]dysperidone (BNEF).

[0261] 2.6. Example 6: BPEF Example 6 uses BPEF: 9,9-bis[4-(2-hydroxyethoxy)phenyl] benzo[a ...

[0262] 2.7. Example 7: Preparation of FDP-m 200 mL of 1,4-dioxane and 33.2 g (0.2 mol) of benzo[a]pyrene were added to a reactor. After dissolving the benzo[a]pyrene by stirring, 3.0 mL of a 40% by mass methanol solution of trimethylbenzylmethylammonium hydroxide (TRITON B40 manufactured by Tokyo Chemical Co., Ltd.) was added dropwise while cooling to 10°C, and the mixture was stirred for 30 minutes. Then, 37.9 g (0.44 mol) of methyl acrylate was added, and the mixture was stirred for about 3 hours. After the reaction was completed, 200 mL of toluene and 50 mL of 0.5 N hydrochloric acid were added for washing. After removing the aqueous layer, the organic layer was washed three times with 30 mL of distilled water. The solvent was distilled off to obtain 9,9-bis(methyl propionate)benzo[a]pyrene. Furthermore, after dissolving it in 300 mL of isopropanol at 70°C, it was cooled to 10°C to recrystallize it, thereby obtaining 9,9-bis(methyl propionate) fumonisin (FDP-m).

[0263] The evaluation results of the light absorption properties of the various fumaroles obtained in the above manner are shown in Table 1.

[0264] [Table 1] Tinuvin 928: Manufactured by BASF, UV absorber; LA-F70: Manufactured by ADKEA, UV absorber.

[0265] Each of the fumonisins in Examples 1-7 is an ultraviolet absorber with a narrow half-width and the ability to selectively absorb only a specific range of ultraviolet light, thus achieving both excellent UV absorption and low colorfastness. In particular, the fumonisins in Examples 1-3 have a larger molar absorptivity at 380 nm relative to their molar absorptivity at 400 nm, thus achieving both excellent UV absorption and low colorfastness in the long wavelength region. Furthermore, compared to conventional benzotriazole-based ultraviolet absorbers such as those shown in Comparative Example 1, each of the above-mentioned fumonisins exhibits a 5% reduction in mass, a higher temperature, and superior heat resistance.

[0266] 3. Resin 3.1. Example 8 0.90 mol of BPEF, 2.10 mol of ethylene glycol (EG), 0.90 mol of FDP-m, 0.10 mol of DNFDP-m, 2 × 10⁻⁴ mol of manganese acetate tetrahydrate as a transesterification catalyst, and 8 × 10⁻⁴ mol of calcium acetate monohydrate were added, and the mixture was slowly heated to melt while stirring. After the temperature reached 230°C, 14 × 10⁻⁴ mol of trimethyl phosphate and 20 × 10⁻⁴ mol of germanium oxide were added, and the temperature was slowly increased and the pressure reduced until it reached below 270°C and 0.13 kPa, while removing EG. After reaching the predetermined stirring torque, the contents were removed from the reactor to prepare ultraviolet-absorbing polyester resin granules.

[0267] After analyzing the obtained particles by 1H-NMR, the results showed that 90 mol% of the diol component introduced into the ultraviolet-absorbing polyester resin was derived from BPEFm and 10 mol% was derived from EG, and 90 mol% of the dicarboxylic acid component introduced into the resin was derived from FDP-m and 10 mol% was derived from DNFDP-m.

[0268] 3.2. Examples 9-13 Except for the changes in the monomer composition of the diol and dicarboxylic acid components used as shown in Table 2 below, the same procedures as in Example 8 were followed to obtain UV-absorbing polyester resins.

[0269] The proportions of each component in the ultraviolet-absorbing polyester resin described in Examples 8 to 13 are shown in Table 2.

[0270] [Table 2]

[0271] Any of the ultraviolet-absorbing polyester resins in Examples 8 to 13 are ultraviolet absorbers with a high ratio (A 380 / A 400) of molar absorptivity (A 380) to molar absorptivity (A 400), while taking into account both excellent UV absorption in the long wavelength region and low colorability.

[0272] In addition, all of the ultraviolet-absorbing polyester resins show that: the Tg is controlled in the range of 130 to 160°C, the weight average molecular weight is controlled in the range of 50,000 to 110,000, and the processability such as elongation and mechanical properties such as elongation at break or softness are excellent. Moreover, compared with the previously known benzotriazole and triazine ultraviolet absorbers, the 5% mass reduction temperature is higher and the heat resistance is also better.

[0273] The ultraviolet-absorbing polyester resins obtained in Examples 8-13 were dissolved in tetrahydrofuran to prepare 50 mg / L solutions, and the absorbance was measured. The evaluation results are shown in Figure 4. As shown in Figure 4, the ultraviolet-absorbing polyester resins of Examples 8-13 exhibited high absorbance for ultraviolet light across a wide wavelength range and low absorbance for visible light.

[0274] 4. Resin Composition and Film 4.1. Examples 14-19, Comparative Examples 3-6 (Preparation of UV Absorbing Resin Composition) 95 parts by weight of dried granules of the base polymer (PC: polycarbonate, Iupilon S-3000, manufactured by Mitsubishi Engineering-Plastics Co., Ltd., PMMA: polymethyl methacrylate, PARAPET HR-S, manufactured by KURARAY Co., Ltd.) as shown in Table 3 below were dry-kneaded with 5 parts by weight of UV absorber to obtain raw material. The raw material was then fed into a biaxial extrusion apparatus (manufactured by TECHNOVEL Co., Ltd., model "KZW 15 / 45", screw diameter D = 15 mm, L / D = 32) and kneaded at a screw temperature of 280°C and a rotation speed of 200 rpm to prepare a UV absorbing resin composition.

[0275] (Preparation of UV-absorbing film) The UV-absorbing resin composition obtained as described above is fed into a biaxial extrusion apparatus equipped with a T-die. A film of the thickness shown in Table 3 below is extruded and wound into a roll to produce a UV-absorbing film. The evaluation results of each UV-absorbing film are shown in Table 3 below. As shown in Table 3, the UV-absorbing films of Examples 14-19 exhibit high UV absorption performance and low colorfastness. These UV-absorbing films are particularly suitable for use as polarizer protective films.

[0276] [Table 3]

[0277] 4.2. Examples 20-25 (Preparation of UV-absorbing film) The UV-absorbing polyester resin obtained in Examples 8-13 above was supplied to a biaxial extrusion device equipped with a T-die. The film with a thickness of 50 μm was extruded and wound into a roll. Then, a tenter frame was used to perform simultaneous biaxial stretching at a stretching temperature of Tg + 10°C to produce a UV-absorbing film with the thickness shown in Table 4 below.

[0278] The evaluation results for each ultraviolet-absorbing film are shown in Table 4 below. [Table 4]

[0279] The ultraviolet-absorbing films of Examples 17-22 are films with a thickness of less than 14 μm and exhibit high ultraviolet absorption performance. [Industrial Applicability]

[0280] The ultraviolet absorber of the present invention is industrially available as a raw material for ultraviolet-absorbing coating liquids and compositions or for films obtained using such materials. [Simplified Explanation of the Diagram]

[0017] Figure 1A is a schematic cross-sectional view illustrating a polarizing plate according to one embodiment of the present invention. Figure 1B is a schematic cross-sectional view illustrating a polarizing plate according to another embodiment of the present invention. Figure 2A is a schematic cross-sectional view illustrating an image display device (OLED) according to one embodiment of the present invention. Figure 2B is a schematic cross-sectional view illustrating an image display device (LCD) according to one embodiment of the present invention. Figure 3 is a schematic cross-sectional view illustrating a rollable display according to one embodiment of the present invention. Figure 4 is a graph showing the absorbance of the ultraviolet-absorbing polyester resin obtained in Examples 8 to 13. [Biomaterial Storage]

[0282] Domestic storage information (please note in order of storage institution, date, and number) None Foreign storage information (please note in order of storage country, institution, date, and number) None

Claims

1. An ultraviolet absorber, which is a compound represented by general formula (1) or a resin containing the aforementioned compound as a constituent unit: In formula (1), Z 1a and Z 1b each independently represent an aromatic ring, Y 1a and Y 1b each independently represent a carboxyl group, a carboxyl ester group, a nitro group, an anhydride group, a hydroxyl group, or a group having a polymerizable double bond, R 1a and R 1b each independently represent a halogen atom, a nitro group, a cyano group, a mono- or disubstituted amino group, -RA, -OR A, or -SR A, except that RA represents a hydrocarbon group, k1 and k2 each independently represent an integer greater than or equal to 0, m1 and m2 each independently represent an integer from 0 to 4, R 2a and R 2b each independently represent a hydrocarbon group other than a halogen atom, a cyano group, or an aryl group, n1 and n2 each independently represent an integer from 0 to 4, and m1+n1 and m2+n2 each independently represent an integer less than or equal to 4.

2. The ultraviolet absorber as claimed in claim 1, wherein, In the aforementioned general formula (1), at least one of m1 and m2 is 1 or more.

3. The ultraviolet absorber as claimed in claim 1, wherein, In the aforementioned general formula (1), Z1a and Z1b are condensed polycyclic aromatic rings, and m1 and m2 are both integers greater than or equal to 1.

4. The ultraviolet absorber as claimed in claim 1, wherein, In the aforementioned general formula (1), Y1a and Y1b are each independently represented by the following formula (Y1), the aforementioned compound is a dicarboxylic acid or a derivative thereof, the aforementioned resin is a polyester resin or polyamide resin with the aforementioned compound of dicarboxylic acid as a constituent unit, and in formula (Y1), A1 represents a linear or branched C1-6 alkyl group.

5. The ultraviolet absorber as claimed in claim 1, wherein, In the aforementioned general formula (1), Y1a and Y1b are each independently represented by the following formula (Y2), the aforementioned compound is a diol, the aforementioned resin is a polyester resin or polycarbonate resin with the aforementioned compound of diol as a constituent unit, in formula (Y2), A2 and A3 independently represent linear or branched C1-6 alkyl groups, and p represents an integer greater than or equal to 0.

6. The ultraviolet absorber as claimed in claim 1, wherein, In the aforementioned general formula (1), Y1a and Y1b are each independently represented by the following formula (Y3), the aforementioned compound is a diol, the aforementioned resin is a polyester resin or polycarbonate resin with the aforementioned compound of diol as a constituent unit, in formula (Y3), Z2 represents an aromatic ring, A4 independently represents a straight-chain or branched C1-4 alkyl group, R3 independently represents a substituent, q represents an integer of 0 or more, r represents an integer of 1 or more, and s represents an integer of 0 or more.

7. The ultraviolet absorber as claimed in claim 6, wherein, In the aforementioned general formula (Y3), Z2 is a condensed polycyclic aromatic ring.

8. The ultraviolet absorber as claimed in claim 1, wherein, In the aforementioned general formula (1), Y1a and Y1b are each independently represented by the following formula (Y4), the aforementioned compound is a di(meth)acrylate, the aforementioned resin is a (meth)acrylate resin with the aforementioned compound of di(meth)acrylate as a constituent unit, in formula (Y4), A5 and A6 independently represent a straight-chain or branched C1-6 alkyl group, R4 represents a hydrogen atom or a methyl group, and t represents an integer greater than or equal to 0.

9. The ultraviolet absorber as claimed in claim 1, wherein the wavelength band in which it exhibits absorbance at more than half of the wavelength of maximum absorption, i.e., the half-width is less than 55 nm.

10. The ultraviolet absorber as claimed in claim 1, having a maximum absorption wavelength in the wavelength range of 320 to 400 nm.

11. The ultraviolet absorber as claimed in claim 1, wherein the ratio (A 380 / A 400) of its molar absorptivity at 380 nm (A 380) to its molar absorptivity at 400 nm (A 400) is 50 or more.

12. The ultraviolet absorber as claimed in claim 1, wherein, The content of the aforementioned constituent units derived from the fumaryl compound is 1 to 100 mol, relative to all the constituent units of the aforementioned resin.

13. An ultraviolet-absorbing composition comprising: the ultraviolet absorber described in claim 1; and at least one of a triazine ring-containing compound, a benzotriazole ring-containing compound, or a benzophenone ring-containing compound as a second ultraviolet absorber.

14. A UV-absorbing resin composition comprising: the UV absorber described in claim 1; and any resin; and wherein the content of the aforementioned UV absorber is 0.1 to 10% by mass relative to the total amount.

15. An ultraviolet-absorbing coating liquid comprising: an ultraviolet absorber as described in any one of claims 1 to 12, an ultraviolet-absorbing composition as described in claim 13, or an ultraviolet-absorbing resin composition as described in claim 14.

16. An ultraviolet-absorbing coated resin sheet comprising a resin sheet and an ultraviolet-shielding layer, wherein the ultraviolet-shielding layer comprises: an ultraviolet absorber as described in any one of claims 1 to 12, an ultraviolet-absorbing composition as described in claim 13, or an ultraviolet-absorbing resin composition as described in claim 14.

17. An ultraviolet-absorbing coated glass comprising glass and an ultraviolet-shielding layer, wherein the ultraviolet-shielding layer comprises: an ultraviolet absorber as described in any one of claims 1 to 12, an ultraviolet-absorbing composition as described in claim 13, or an ultraviolet-absorbing resin composition as described in claim 14.

18. An ultraviolet-absorbing molded article comprising: an ultraviolet absorber as described in any one of claims 1 to 12, an ultraviolet-absorbing composition as described in claim 13, or an ultraviolet-absorbing resin composition as described in claim 14.

19. An ultraviolet-absorbing film comprising: an ultraviolet absorber as described in any one of claims 1 to 12, an ultraviolet-absorbing composition as described in claim 13, or an ultraviolet-absorbing resin composition as described in claim 14.

20. A polarizer protective film comprising: the ultraviolet-absorbing film of claim 19.

21. The polarizer protective film as claimed in claim 20, wherein the ray transmittance at 350 nm is less than 5%, and the b* value in the L*a*b* color space (CIELAB) is less than 0.

5.

22. The polarizer protective film as claimed in claim 20, wherein the transmittance of the split beam at 380 nm is less than 8%.

23. A polarizing plate comprising: the polarizing protective film as described in claim 20.

24. An image display device comprising: the polarizing plate described in claim 23.

25. A transport machine comprising a component including: an ultraviolet absorber as described in any one of claims 1 to 12, an ultraviolet-absorbing composition as described in claim 13, or an ultraviolet-absorbing resin composition as described in claim 14.

26. A building component comprising a component including: any one of claims 1 to 12, the ultraviolet absorber of claim 13, or the ultraviolet absorbent resin composition of claim 14.

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