UV absorbers and their applications

Abstract

This invention relates to ultraviolet absorbers and their applications.

Description

Technical Field

[0001] The present invention belongs to the field of light stabilizers, and specifically relates to ultraviolet absorbers.

Background Art

[0002] Polymer materials are essential basic materials in current social production and life. Their aging problem inevitably affects their use performance, leading to a reduction in lifespan and waste of resources. The main factors causing polymer aging are mainly light and heat. Among them, the influence of ultraviolet rays in natural sunlight on the long-term performance of polymers is particularly significant. Currently, the prevention of outdoor light aging is mainly solved by adding light stabilizers. Such light stabilizers include ultraviolet absorbers and hindered amine light stabilizers. Polymer materials are penetrating and growing from general-purpose and basic materials to special functional types. While special application scenarios also appear in the anti-aging of polymer materials, conventional light stabilizers can no longer fully meet the demand.

[0003] Conventional ultraviolet absorbers cover most of the ultraviolet region (wavelengths 280 - 400 nm) relatively comprehensively, but the absorption efficiency at wavelengths above 380 nm is significantly reduced. In application fields with special requirements on the long-wavelength side (red-shifted region), it is difficult for conventional ultraviolet absorbers to meet the use requirements. Carbon fiber is an emerging material that has attracted attention. Among them, carbon fiber reinforced epoxy resin composite materials are currently the carbon fiber reinforced materials (carbon fiber reinforced materials (CFRM)) with the highest comprehensive indicators such as strength and modulus and the most widely used. However, since epoxy resin itself is easily damaged by ultraviolet-visible light below 420 nm, it decomposes and affects its performance. An ultraviolet absorber with high absorption efficiency at 380 - 420 nm can effectively protect it.

[0004] Polyethylene naphthalate (PEN) is a polymer material with excellent overall performance, including chemical stability, mechanical properties, and heat resistance, and has relatively good application prospects in fields such as optical elements. However, ultraviolet light in the 360-400 nm range easily causes losses in PEN and PEN-containing composite materials, leading to material decomposition. Furthermore, in some fields, there are special blocking requirements for light rays in the 360-430nm wavelength range. For example, special polarizers are required to absorb ultraviolet light as completely as possible or at least 75-85% in the wavelength range below 380nm, while simultaneously transmitting as much as possible above 410nm, for example, at least 95%. Also, glass coatings and films used in automobile windshields, special architectural glass, etc., are required to block as much ultraviolet light below 400nm as possible to meet the higher health needs of people exposed to this environment. To meet these demands, ultraviolet absorbers must be redshifted to higher wavelength ranges and satisfy the requirement of having relatively good absorption efficiency in the 380-410nm range. In addition, optical lenses, display devices, etc., are required to have relatively high absorption of high-energy blue light in the 400nm-445nm wavelength range, thereby protecting the visual health of users of electronic products. In this field, there is a strong demand for UV absorbers that exhibit relatively good absorption effects for most of the ultraviolet region (280-400 nm) while simultaneously maintaining relatively good absorption effects for light rays with wavelengths above 380 nm, particularly light rays in the redshifted region towards longer wavelengths. [Overview of the Initiative]

[0005] This invention introduces a thioether or sulfone group into a conventional benzotriazole absorbent, thereby shifting the cutoff wavelength of the conventional benzotriazole absorbent from 400-410 nm to a maximum of 430 nm in the long-wave direction. Furthermore, by selecting an appropriate alkyl chain segment, the novel structure is ensured to have an appropriate melting point, solubility, and better system compatibility. This makes it applicable to a variety of material systems. One aspect of the present invention is a compound having the structure shown in formula (I) or formula (II), [ka] Here, we provide compounds in which, in formulas (I) and (II), R1 is selected from C1-C20 linear or branched alkyl groups, R2 is selected from C1-C8 linear or branched alkyl groups, and n is an integer selected from 1 to 3. In some embodiments, in formulas (I) and (II), R1 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, and the like. In some embodiments, in formulas (I) and (II), R1 is selected from C5-C20 linear or branched alkyl groups, preferably from C7-C15 linear or branched alkyl groups. In some embodiments, in formulas (I) and (II), R2 is selected from methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, and 1,1-dimethylpropyl groups. In some embodiments, in formula (II), R2 is selected from C2-C6 linear or branched alkyl groups.

[0006] In some embodiments, the above compound has a structure represented by formula (III) or formula (IV), [ka] Here, in formulas (III) and (IV), R1 is selected from C1-C20 linear or branched alkyl groups, and R2 is selected from C1-C8 linear or branched alkyl groups. In some embodiments, in formulas (III) and (IV), R1 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, and the like. In some embodiments, in formulas (III) and (IV), R1 is selected from C5-C20 linear or branched alkyl groups, preferably from C7-C15 linear or branched alkyl groups. In some embodiments, in formulas (III) and (IV), R2 is selected from a C2-C6 linear or branched alkyl group. In some specific embodiments, R2 is selected from a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a 1,1-dimethylpropyl group, and the like.

[0007] In some embodiments, the compound of formula (III) is exemplary, [ka] In some embodiments, the compound of formula (IV) is exemplary, [ka]

[0008] In some preferred embodiments, the compound has the structure shown in RSUV-1 or RSUV-2. [ka] In some embodiments, the absorption wavelength range of the above compound is 280 to 430 nm. The compounds described in the present invention, particularly compound RSUV-1 or RSUV-2, when used as ultraviolet absorbers, can shift the absorption in the ultraviolet region overall towards the longer wavelength compared to conventional ultraviolet absorbers, especially conventional benzotriazole-based ultraviolet absorbers. Here, the absorption cutoff wavelength of RSUV-2 can be further redshifted up to 430 nm, satisfying polymer materials that require absorption in the 280-430 nm range. Furthermore, the compounds of the present invention have a suitable melting point, good solubility, better oligomer resin compatibility, and relatively low chromaticity, resulting in excellent overall performance.

[0009] Another aspect of the present invention further provides a method for producing the above compound, the method comprising reacting a compound having the structure shown in formula (V) with an alkylthiol to produce a compound having the structure shown in formula (I). [ka] Here, In formula (V), X is selected from halogens, for example F, Cl, Br, or I, preferably Cl; R4 is selected from C1-C8 linear or branched alkyl groups, preferably from C2-C6 linear or branched alkyl groups; and n is an integer selected from 1 to 3. In some embodiments, the alkylthiol has the structure shown in HS-R3, where R3 is selected from a C1-C20 linear or branched alkyl group, preferably from a C5-C20 linear or branched alkyl group, and more preferably from a C7-C15 linear or branched alkyl group.

[0010] In some embodiments, the above manufacturing method further includes oxidizing a compound having the structure shown in formula (I) with an oxidizing agent to produce a compound having the structure shown in formula (II). In some embodiments, the oxidizing agent may be a common oxidizing agent in the art, such as hydrogen peroxide. In some embodiments, the manufacturing method includes reacting a compound having the structure shown in formula (VI) with an alkyl thiol to produce a compound having the structure shown in formula (III),

Chemical formula

[0011] A further aspect of the present invention further provides a composition containing the above compound. In some embodiments, the composition further includes one or more additives. In some embodiments, the additives include, but are not limited to, one or more of hindered amine light stabilizers, other ultraviolet absorbers, antioxidants, emulsifiers, nucleating agents, toughening agents, lubricants, antiblocking agents, fillers, dyes, pigments, fluorescent whitening agents, flame retardants, antistatic agents or foaming agents, etc.

[0012] In some embodiments, the hindered amine light stabilizer is a hydroxyalkoxyamine stabilizer. In some embodiments, the hindered amine light stabilizer includes, but is not limited to, 1-cyclohexyloxy-2,2,6,6-tetramethyl-4-octadecylaminopiperidine, 1,2,2,6,6-pentamethyl-4-aminopiperidine, bis(1-acyl-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, bis(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, bis(1,2,2,6,6-pentamethyl-4-yl) sebacate, mono(1,2,2,6,6-pentamethyl-4-yl) sebacate, a linear or cyclic condensate of N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)-hexamethylenediamine and 4-tert-octylamino-2,6-dichloro-1,3,5-triazine (UV-944), ethyl 2-[2,2,6,6-tetramethyl-4-(3,5,5-trimethyl-hexanoyloxy)-piperidyl]-3,5,5-trimethylhexanoate, bis(1,2,2,6,6-pentamethyl-4-yl) [[3,5-di-tert-butyl-4-hydroxyphenyl]methyl]butylmalonate, poly[1-(2'-hydroxyethyl)-2,2,6,6-tetramethyl-4-hydroxypiperidyl succinate], 1,5,8,12-tetrakis[2,4-bis(N-butyl-N-1,2,2,6,6-pentamethyl-4-piperidylamino)-1,3,5-triazin-6-yl]-1,5,8,12-tetraazadodecane.

[0013] In some embodiments, the other UV absorbers described above include benzophenone-based UV absorbers, salicylate-based UV absorbers, benzotriazole-based UV absorbers, substituted acrylonitrile-based UV absorbers, triazine-based UV absorbers, oxanilide-based UV absorbers, cyanoacrylate-based UV absorbers, and the like. In some embodiments, the above benzotriazole-based UV absorbers are 2-(2-hydroxy-5-methylphenyl)-2H-benzotriazole, 2-(2-hydroxy-5-tert-octyl)-2H-benzotriazole, 2-(2-hydroxy-3-cumyl-5-tert-octylphenyl)-2H-benzotriazole, 5-chloro-2-(3,5-di-tert-butyl-2-hydroxyphenyl)-2H-benzotriazole, and 5-chloro-2-(3-tert-butyl -2-hydroxy-5-methylphenyl)-2H-benzotriazole, 2-(2-hydroxy-4-octyloxyphenyl)-2H-benzotriazole, 2-(3,5-di-tert-pentyl-2-hydroxyphenyl)-2H-benzotriazole, 2-(3-dodecyl-2-hydroxy-5-methylphenyl)-2H-benzotriazole, 2-(3-tert-butyl-2-hydroxy-5-(2-octyloxycarbonyl)ethylphenyl)-2H-benzotriazole, Dodecylated 2-(2-hydroxy-5-methylphenyl)-2H-benzotriazole, 2-(3-tert-butyl-2-hydroxy-5-(2-octyloxycarbonylethyl)phenyl)-5-chloro-2H-benzotriazole, 2-(3-tert-butyl-5-(2-(2-ethylhexyloxy)-carbonylethyl)-2-hydroxyphenyl)-5-chloro-2H-benzotriazole, 2-(3-tert-butyl-2-hydroxy-5-(2-methoxycarbonylethyl) (Tyl)phenyl)-5-chloro-2H-benzotriazole, 2-(3-tert-butyl-2-hydroxy-5-(2-methoxycarbonylethyl)phenyl)-2H-benzotriazole, 2-(3-tert-butyl-5-(2-(2-ethylhexyloxy)carbonylethyl)-2-hydroxyphenyl)-2H-benzotriazole, 2-(3-tert-butyl-2-hydroxy-5-(2-isooctyloxycarbonylethyl)phenyl-2H-benzotriazole, 2,This includes, but is not limited to, 2'-methylene-bis(4-tert-octyl-(6-2H-benzotriazole-2-yl)phenol), 2-(2-hydroxy-3-α-isopropylphenyl-5-tert-octylphenyl)-2H-benzotriazole, and 2-(2-hydroxy-3-tert-octyl-5-α-isopropylphenylphenyl)-2H-benzotriazole.

[0014] In some embodiments, the antioxidant includes phenolic antioxidants, amine antioxidants, phosphite antioxidants, thioester antioxidants, and benzofuranone antioxidants. In some embodiments, the mass percentage of the compound in the composition is 0.1 to 6%, for example, about 0.1%, about 0.5%, about 1%, about 1.5%, about 2%, about 3%, about 4%, about 4.5%, about 5%, about 5.5%, about 6%, or any value in between. In some embodiments, the above composition is found in one or more of the following: epoxy resin systems and their composite products (e.g., epoxy-reinforced carbon fiber composite materials), polyethylene naphthalate-based products, optical adhesives, optical elements, optical films (e.g., optical films based on triacetylcellulose, polycarbonate, polyacrylate, or polyethylene naphthalate), optical lenses, blue light blocking products (e.g., blue light blocking lenses, blue light blocking display devices, etc.), car windows and their films, car cover films, automotive paints (i.e., automotive coatings, e.g., cathode electrophoresis primers and coatings compounded therewith), and adhesives.

[0015] In some embodiments, the above composition is present in a laminated or multilayer structure. In some embodiments, the composition is a laminated material or multilayer material. In some embodiments, the laminated material or multilayer material may be a reflective sheet and conformal marking sheet, a solar radiation control film, a solar reflector, a reflective printed label, UV-absorbing glass and glass coatings, an electrochromic device, a film / glass window, a windshield and an intermediate layer.

[0016] Further aspects of the present invention provide polymer materials comprising the above-mentioned compounds or compositions, and organic materials that are susceptible to decomposition by oxygen, heat, or light. In some embodiments, the organic material in the polymer material includes, but is not limited to, at least one resin from among polyester, polyurethane, polyacrylic acid, polycarbonate, epoxy and its modified resins, phenolic resin, polyamide, polyimide, polystyrene and its derivatives, polysilane, polysiloxane and its modified forms, poly(vinyl butyral), aminoacrylic acid, hydroxyacrylic acid, acrylic polyurethane, polycyanoacrylate, polyacrylate, ethylene / acrylic acid copolymers and their salts (ionomers), poly(vinyl alcohol), triacetylcellulose, polycarbonate, polyethylene naphthalate, polyethylene terephthalate, polymethyl methacrylate, polycyclopentene, aliphatic diisocyanate, fluorine / silicon-modified polyacrylic acid, and polyisocyanate / polythioether. In some embodiments, the mass percentage of the compound in the polymer material is 0.1 to 6%, for example, about 0.1%, about 0.5%, about 1%, about 1.5%, about 2%, about 3%, about 4%, about 4.5%, about 5%, about 5.5%, about 6%, or any value in between.

[0017] Further aspects of the present invention provide products comprising the above-mentioned compound, composition, or polymer material. In some embodiments, the above products include, but are not limited to, epoxy resin-based and composite products thereof, polyethylene naphthalate-based products, optical adhesives, optical elements, optical films (e.g., optical films based on triacetylcellulose, polycarbonate, polyacrylate, or polyethylene naphthalate), optical lenses, blue light-cutting products (e.g., blue light-cutting lenses, blue light-cutting display devices, etc.), reflective sheets and conformal marking sheets, car windows and films thereof, car cover films, automotive paints (e.g., cathodic electrophoretic primer coatings and coatings composite therewith), solar radiation control films, solar reflectors, reflective printed labels, UV-absorbing glass and glass paints, electrochromic devices, film / glass windows, windshields, and intermediate layers.

[0018] In some embodiments, the product is an epoxy-reinforced carbon fiber composite material comprising epoxy-reinforced carbon fibers and an outer coating thereof, wherein the coating comprises a resin coating and the compound. Preferably, the coating is at least one selected from aminoacrylic resin coatings, hydroxyacrylic resin coatings, polyester resin coatings, acrylic polyurethane coatings, polyurethane resin coatings, epoxy-modified resin coatings, and polysiloxane-modified resin coatings. In some embodiments, the product is an optical film or optical element containing a paint resin substrate and the compound. Preferably, the resin substrate is at least one selected from triacetylcellulose (TAC), polycarbonate, polyacrylate, polyethylene naphthalate, polyethylene terephthalate, polyvinyl alcohol, polymethyl methacrylate, cyclopentene, polyimide, polystyrene and its derivatives, epoxy resin, polyurethane, and polysilane.

[0019] In some embodiments, the product is a blue light-cutting lens comprising a resin substrate and the compound. Preferably, the resin substrate is at least one selected from aliphatic diisocyanate (ADI), polymethyl methacrylate, polycarbonate, polyamide, fluorine / silicon-modified polyacrylic acid, and polyisocyanate / polythioether. In some embodiments, the product is an automotive paint comprising a cathode electrophoresis primer and a coating compounded therewith, wherein the electrophoresis primer or the coating compounded therewith comprises a resin paint and the compound. Preferably, the cathode electrophoresis primer coating uses an epoxy resin as a substrate, and the cathode electrophoresis primer coating further comprises a polyester resin, a polyurethane resin, an epoxy / polyester hybrid resin, an acrylic resin, a polysiloxane resin, an aminoacrylic resin, a hydroxyacrylic resin, a polysiloxane-modified resin, or an epoxy-modified resin.

[0020] Further aspects of the present invention provide the use of the above-mentioned compounds, compositions, or polymer materials as ultraviolet absorbers. In some embodiments, the compounds of the present invention have a significant redshift effect and are used in application fields sensitive to the 280-430 nm ultraviolet-visible wavelength range, particularly in application fields with special blocking requirements for the 360-430 nm wavelength range. As ultraviolet absorbers, they can be used in fields such as epoxy resins and their composites, polyethylene naphthalate products, optical adhesives, optical elements, optical films (e.g., optical films based on triacetylcellulose, polycarbonate, polyacrylate, or polyethylene naphthalate), optical lenses, blue light blocking products (e.g., blue light blocking lenses, blue light blocking display devices, etc.), reflective sheets and conformal marking sheets, car windows and their films, car cover films, automotive paints (e.g., cathode electrophoresis primers and coatings composited therewith), solar radiation control films, solar reflectors, reflective printed labels, UV-absorbing glass and glass paints, electrochromic devices, film / glass windows, windshields, and intermediate layers.

[0021] The technical solution provided by the present invention has the following advantages: (1) Compared with conventional UV absorbers, the compounds provided by the present invention can shift the absorption in the UV region overall towards the long-wave direction through novel structural modification, causing a clear redshift in the absorption wavelength range and exhibiting a good light absorption effect within the visible light wavelength range of 360 to 430 nm. (2) The compounds provided by the present invention have excellent solubility in general oligomer resins or active monomers, have better compatibility with solvent-free crosslinking systems used in the manufacture of optical devices such as optical adhesive films and optical lenses, and have better convenience and stronger handling properties during processing and use. (3) The compounds provided by the present invention also have a relatively light color and are applicable to light-colored polymer material products. (4) The method for producing the compound provided by the present invention is simple in process and yields a relatively high yield of the target product. (5) The compounds provided by the present invention are very suitable as ultraviolet absorbers in the field of polymer materials, and have excellent protective and blocking effects against visible light in the wavelength range of 280 to 430 nm, have better application performance and a wider range of applications, and contribute to the prevention of photoaging of polymer materials, thus having very important economic and social value. [Modes for carrying out the invention]

[0022] The present invention relates to a compound having the structure shown in formula (I) or formula (II), [ka] Here, we provide compounds in which, in formulas (I) and (II), R1 is selected from C1-C20 linear or branched alkyl groups, R2 is selected from C1-C8 linear or branched alkyl groups, and n is an integer selected from 1 to 3. The present invention further provides compounds having the structure shown in RSUV-1 below (abbreviated as RSUV-1 in the present invention) or compounds having the structure shown in RSUV-2 below (abbreviated as RSUV-2 in the present invention). [ka] The above-mentioned RSUV-1 or RSUV-2 retains the main structure of benzotriazole, introduces a thioether bond or sulfone group to the benzene ring side, and fixes one substituent on the benzene ring having a hydroxyl group to a methyl group, thereby obtaining a modified structure. This shifts the absorption region in which benzotriazole acts as an ultraviolet absorber towards the longer wavelength direction, and the UV absorption cutoff wavelength of the modified structure RSUV-2 having a sulfone group is redshifted from 400-410 nm to 430 nm in the longer wavelength direction, while also improving solubility and compatibility in special systems.

[0023] The compounds of the present invention are used in polymer materials sensitive to the 280-430 nm ultraviolet-visible wavelength range, such as epoxy resin-based products, epoxy-reinforced carbon fiber coatings, polyethylene naphthalate (PEN), PEN copolymers, and modified products. The compounds of the present invention are also used in application fields where there is a special requirement for blocking wavelengths in the 280-430 nm ultraviolet-visible wavelength range, such as car windows and their films, car cover films, optical adhesives, optical elements, optical films, and automotive paints. The present invention further provides an epoxy-reinforced carbon fiber composite material comprising epoxy-reinforced carbon fibers and an outer coating thereof, wherein the coating comprises a resin paint and the compound, and preferably the paint is at least one selected from aminoacrylic resin paint, hydroxyacrylic resin paint, polyester resin paint, acrylic polyurethane paint, polyurethane resin paint, epoxy-modified resin paint, and polysiloxane-modified resin paint.

[0024] Carbon fiber is a rapidly growing and promising material, and among them, carbon fiber reinforced epoxy resin composites (CFRMs) currently boast the highest overall performance in terms of strength, modulus, and other metrics, making them the most widely used carbon fiber reinforced materials. However, epoxy resin itself is susceptible to degradation from ultraviolet-visible light below 420 nm, leading to decomposition and affecting its performance. UV absorbers with high absorption efficiency in the 380-420 nm wavelength range can effectively protect against this degradation. Carbon fiber reinforced polymers (CFRP), also known as carbon fiber reinforced materials (CFRM), are used in aerospace applications, for example, due to their high strength-to-weight ratio. Carbon fiber compositions typically contain carbon fibers embedded in a thermosetting aromatic epoxy substrate. These components are also used in automotive parts, sporting goods, acoustic assemblies, marine components, and aircraft components. The epoxy-reinforced carbon fiber materials can be used in automotive interior and exterior components such as rearview mirrors, tail fins, and spoilers. Carbon fiber reinforced polymer parts can be manufactured, for example, by known molding, vacuum bagging, or compression molding techniques. Prepregs can be used in these methods. The polymer substrate can account for, for example, about 15-50% by weight of the carbon fiber reinforced polymer part (uncoated).

[0025] The present invention further provides a resin coating substrate and an optical film or optical element containing the above compound, preferably the resin substrate is at least one selected from triacetylcellulose (TAC), polycarbonate, polyacrylate, polyethylene naphthalate, polyethylene terephthalate, polyvinyl alcohol, polymethyl methacrylate, cyclopentene, polyimide, polystyrene and its derivatives, epoxy resin, polyurethane, and polysilane. If necessary, the optical film or optical device may further contain additives such as catalysts including crosslinking accelerators, antioxidants, ultraviolet absorbers, hindered amine light stabilizers, antistatic agents, dispersion stabilizers, defoamers, thickeners, dispersants, surfactants, and lubricants.

[0026] Polyethylene naphthalate (PEN) is a polymer material with excellent overall performance, including chemical stability, mechanical properties, and heat resistance, and has relatively good prospects for applications in fields such as optical elements. However, ultraviolet light in the 360-400 nm wavelength range easily causes losses in PEN and PEN-containing composite materials, leading to material decomposition. The benzotriazole absorber of the present invention can effectively and well protect against this problem caused by light. It is even more important that, in addition to protecting the substrate of the optical film itself, photosensitive materials in optical devices also require protection over a very wide wavelength range; for example, dyes in polarizers require good protection in the ultraviolet wavelength range of 280-400 nm. The present invention further provides a blue light cut lens comprising a resin substrate and the above compound, preferably the resin substrate being at least one selected from aliphatic diisocyanate (ADI), polymethyl methacrylate, polycarbonate, polyamide, fluorine / silicon-modified polyacrylic acid, and polyisocyanate / polythioether.

[0027] As electronic products become more commonplace in modern society, the spectrum emitted from display light sources is extremely broad, and within that, high-energy blue light in the 400nm to 445nm wavelength range can cause certain damage to the user's vision. The benzotriazole derivative of the present invention can reduce this damage to vision by absorbing as much of the spectrum in this band as possible. The present invention further provides an automotive paint comprising a cathode electrophoresis primer and a coating compounded therewith, wherein the cathode electrophoresis primer layer or the coating compounded (or tacked) therewith comprises a resin paint and the above compound, and preferably the cathode electrophoresis primer coating uses an epoxy resin as a substrate, and the cathode electrophoresis primer coating further comprises a polyester resin, a polyurethane resin, an epoxy / polyester hybrid resin, an acrylic resin, a polysiloxane resin, an aminoacrylic resin, a hydroxyacrylic resin, a polysiloxane-modified resin, and an epoxy-modified resin.

[0028] Coatings compounded with a cathodic electrophoresis primer include clear coat coating systems, systems compounding a pigment-containing base coating with a clear coat, and single-coat pigment-containing coating systems. Here, the system compounding a pigment-containing base coating with a clear coat may be a process system in which the base coatings are baked separately, or it may be a process system in which the two coatings are ultimately baked together by wet-to-wet spray application. The resins used as cathode electrophoresis primers are typically thermosetting resins used in combination with crosslinking agents and / or curing catalysts. Applicable thermosetting resins include epoxy resins, polyester resins, polyurethane resins, epoxy / polyester hybrid resins, acrylic resins, polysiloxane resins, aminoacrylic resins, hydroxyacrylic resins, polysiloxane-modified resins, and epoxy-modified resins.

[0029] Epoxy resins can be cured using dicyandiamide or acid anhydride. Hydroxy-functional polyester resins can be cured with polyfunctional isocyanates to form polyurethane polyesters. Acid-functional polyester resins can be cured with isocyanurates. Epoxy polyester hybrids can be cured by reaction with each other. Hydroxy-functional acrylic resins can be cured with polyfunctional isocyanates. The amount of crosslinking agent or curing agent depends on the resin and may be, for example, about 3 to 20% by weight based on the weight of the resin. Curing is carried out, for example, thermally. Acrylate resins are produced, for example, from glycidyl acrylate or glycidyl methacrylate. The present invention includes providing a paint composition containing a paint resin, the above compound, a hindered amine light stabilizer, and optionally a UV light absorber, a phenolic antioxidant, and an organic or inorganic pigment compound. Most advantageously, the paint of the present invention is a transparent paint. In addition to transparent coating paints, the paint of the present invention may also be a coloring and tinting paint. A transparent paint is basically defined as one that does not contain pigments.

[0030] The paint composition may also contain other conventional additives such as fluidizers and lubricants. Based on the total amount of paint compounds, the amount of paint resin present in the paint formulation is approximately 20-98% by weight, preferably approximately 30-96% by weight, and more preferably approximately 50-96% by weight. The manufacture and application of the paint are publicly known. The paint formulation can be applied by spray application (including electrostatic spray application), dip application, and roll application. The paint can be applied to one coating to reach a coating thickness of approximately 5 to 200 microns, for example, 20 microns, 40 microns, 50 microns, 60 microns, 80 microns, 100 microns, 120 microns, 150 microns, 180 microns and any value in between, preferably the coating thickness is 10 to 100 microns, more preferably about 20 to 40 microns. The paint of the present invention exhibits improved durability and excellent external weather resistance. To further clarify the object, technical proposal, and advantages of the present invention, the invention will be described in more detail below with reference to examples. The specific examples described herein are for interpretation purposes only and are not intended to limit the invention. Furthermore, in the following description, descriptions of known structures and techniques will be omitted to avoid unnecessary confusion of the concepts of this disclosure. Such structures and techniques are also described in many publications.

[0031] term: Unless otherwise defined, all technical and scientific terms used in this invention have the same meanings as they commonly have in the art to which this invention pertains. For the purposes of interpreting this specification, the following definitions apply, and where appropriate, terms used in the singular form also have a plural form, and vice versa. As used herein, the term "C1-Cn" includes C1-C2, C1-C3, ..., C1-Cn. For example, the "C1-C8" group refers to a group having 1 to 8 carbon atoms in that portion, i.e., the group contains 1, 2, 3, 4, 5, 6, 7, or 8 carbon atoms. Accordingly, for example, "C1-C4 alkyl group" refers to an alkyl group containing 1 to 4 carbon atoms, i.e., the alkyl group is selected from methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, and tert-butyl. In this specification, a numerical range, such as "1 to 3," refers to each integer within a given range, i.e., 1, 2, or 3.

[0032] As used herein, the term “alkyl group” refers to a optionally substituted linear or optionally substituted branched saturated aliphatic hydrocarbon system. The “alkyl group” as used herein may preferably have 1 to 8 carbon atoms, or 1 to 6 carbon atoms, or 1 to 5 carbon atoms, or 1 to 4 carbon atoms, or 1 to 3 carbon atoms. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, 2-methyl-1-propyl, 2-methyl-2-propyl, 2-methyl-1-butyl, 3-methyl-1-butyl, 2-methyl-3-butyl, 2,2-dimethyl-1-propyl, 2-methyl-1-pentyl, 3-methyl-1-pentyl, 4-methyl-1-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 2,2-dimethyl-1-butyl, 3,3-dimethyl-1-butyl, 2-ethyl-1-butyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, and hexyl groups, as well as longer alkyl groups such as heptyl and octyl groups. Where a numerical range appears in a group as defined herein, for example, “alkyl group”, for example, “C1-C6 alkyl group”, means an alkyl group that may consist of one carbon atom, two carbon atoms, three carbon atoms, four carbon atoms, five carbon atoms, or six carbon atoms, and alkyl groups herein also include cases where no numerical range is specified.

[0033] Sunlight (especially UV irradiation in the 280nm-400nm range) can cause degradation of plastics, leading to color changes and a decrease in optical and mechanical performance. Suppressing degradation by photo-oxidation is crucial for outdoor applications where long-term durability is essential. For example, the absorption of ultraviolet light by polyethylene terephthalate begins at around 360nm, increases significantly below 320nm, and is very pronounced below 300nm. Polyethylene naphthalate strongly absorbs ultraviolet light in the 310-370nm range, with the absorption end extending to approximately 410nm, and maximum absorption values ​​appearing at 352nm and 337nm. Chain severance occurs in the presence of oxygen, and the main photo-oxidation products are carbon monoxide, carbon dioxide, and carboxylic acid. In addition to the direct photodegradation of ester groups, oxidation reactions that similarly form carbon dioxide via peroxide radicals must also be considered. A UV-absorbing layer can protect a multilayer optical film by reflecting, absorbing, scattering, or a combination thereof of ultraviolet light. Typically, the UV-absorbing layer may contain any polymer composition that reflects, scatters, or absorbs ultraviolet irradiation while simultaneously withstanding ultraviolet irradiation for extended periods. Examples of such polymers include PMMA, CoPMMA, organosilicon thermoplastics, fluorine-containing polymers, and their copolymers and blends. An exemplary UV-absorbing layer contains a PMMA / PVDF blend.

[0034] The optical layer may optionally incorporate several types of additives to absorb ultraviolet light. Examples of such additives include at least one of the following: ultraviolet absorbers, hindered amine light stabilizers, or antioxidants thereof. A particularly desirable ultraviolet absorber is a redshift ultraviolet absorber (RUVA) that absorbs at least 70% (at least 80%, and especially preferably more than 90%, of ultraviolet light in the wavelength range of 180 nm to 400 nm) of ultraviolet light. UV absorbers must meet the following conditions: good thermal stability, not changing due to heat during processing, low thermal volatility; strong absorption of ultraviolet light (especially wavelengths of 290-400 nm); good chemical stability, not causing harmful reactions with material components in the product; good miscibility, able to disperse uniformly in the material, not blooming or seeping; good photochemical stability of the absorber itself, not decomposing or discoloring; colorless, non-toxic, and odorless; resistance to immersion cleaning; and being inexpensive and readily available. UV absorbers are classified according to their chemical structure into salicylate-based, benzophenone-based, benzotriazole-based, substituted acrylonitrile-based, triazine-based, and other systems.

[0035] UV-326 is one such example. UV-326 is a benzotriazole-based light stabilizer with the chemical name 2'-(2'-hydroxy-3'-tert-butyl-5'-methylphenyl)-5-chlorobenzotriazole. UV-326 can absorb ultraviolet light in the 280-370 nm range, exhibits good stability, low toxicity, and is non-irritating to the human body. It is widely applied in paints, synthetic rubber, synthetic fibers, and photosensitive materials, effectively improving the lightfastness of these materials and reducing phenomena such as yellowing and aging caused by UV excitation in sunlight. UV-326 has the following structure. [ka] Basf's commercially available redshift ultraviolet absorber Carboprotect also belongs to the benzotriazole (BTZ) class of ultraviolet absorbers, exhibits solid form, has a melting point of 132-136°C, and a molecular weight (g / mol) of 560. It is a redshift ultraviolet light absorber that protects aromatic hydrocarbon epoxy resin systems and is recommended for use in carbon or glass fiber reinforced composite materials. It can redshift light up to a wavelength of 420 nm. Carboprotect has the following properties: [ka] [Brief explanation of the drawing]

[0036] [Figure 1] The synthesis routes for the target products RSUV-1 and RSUV-2 are shown. [Figure 2] This is the LC-MS spectrum of the target product, RSUV-1. [Figure 3] This is the nuclear magnetic resonance hydrogen spectrum of the target product, RSUV-1. [Figure 4] This is the LC-MS spectrum of the target product, RSUV-2. [Figure 5] This is the nuclear magnetic resonance hydrogen spectrum of the target product, RSUV-2.

[0037] List of items 1. A compound having the structure shown in formula (I) or formula (II), [ka] Here, in formulas (I) and (II), R1 is selected from C1-C20 linear or branched alkyl groups, R2 is selected from C1-C8 linear or branched alkyl groups, and n is an integer selected from 1 to 3, which constitutes a compound.

[0038] 2. The above compound has the structure shown in formula (III) or formula (IV), [ka] Herein, in formulas (III) and (IV), R1 is selected from a C1-C20 linear or branched alkyl group, and R2 is selected from a C1-C8 linear or branched alkyl group, as described in item 1. 3. In formulas (I), (II), (III), and / or (IV), R1 is selected from C5-C20 linear or branched alkyl groups, preferably from C7-C15 linear or branched alkyl groups, and R2 is selected from C2-C6 linear or branched alkyl groups. Preferably, the compound is the compound described in item 1 or 2, having the structure shown in RSUV-1 or RSUV-2. [ka] 4. The compound described in item 1, wherein the absorption wavelength range of the above compound is 280-430 nm. 5. A composition comprising any one of the compounds listed in items 1 to 4. 6. The composition described in item 5, further comprising one or more additives, preferably, the additives comprising one or more of the following: hindered amine light stabilizers, other ultraviolet absorbers, antioxidants, emulsifiers, nucleating agents, toughening agents, lubricants, antiblocking agents, fillers, dyes, pigments, fluorescent whitening agents, flame retardants, antistatic agents, or foaming agents. 7. A polymer material comprising a compound described in any one of items 1 to 4 or a composition described in item 5 or 6, and an organic material that is susceptible to decomposition by oxygen, heat or light, preferably the organic material being at least one resin from among polyester, polyurethane, polyacrylic acid, polycarbonate, epoxy and modified resins thereof, phenolic resin, polyamide, polyimide, polystyrene and its derivatives, polysilane, polysiloxane and its modified form, poly(vinyl butyral), aminoacrylic acid, hydroxyacrylic acid, acrylic polyurethane, polycyanoacrylate, polyacrylate, ethylene / acrylic acid copolymer system and its salts (ionomers), poly(vinyl alcohol), triacetylcellulose, polycarbonate, polyethylene naphthalate, polyethylene terephthalate, polymethyl methacrylate, polycyclopentene, aliphatic diisocyanate, fluorine / silicon-modified polyacrylic acid, and polyisocyanate / polythioether. 8. A product comprising a compound described in any one of items 1 to 4, a composition described in item 5 or 6, or a polymer material described in claim 7.

[0039] 9. The above products are selected from epoxy resin-based and composite products thereof, polyethylene naphthalate-based products, optical adhesives, optical elements, optical films, optical lenses, blue light cut products, reflective sheets and conformal marking sheets, car windows and their films, car cover films, automotive paints, solar radiation control films, solar reflectors, reflective printed labels, UV absorbing glass and glass paints, electrochromic devices, films / glass windows, windshields or intermediate layers. Preferably, the product is an epoxy-reinforced carbon fiber composite material comprising epoxy-reinforced carbon fibers and an outer coating thereof, wherein the coating comprises a resin paint and a compound described in any one of items 1 to 4, and the paint is preferably at least one selected from aminoacrylic resin paint, hydroxyacrylic resin paint, polyester resin paint, acrylic polyurethane paint, polyurethane resin paint, epoxy-modified resin paint, and polysiloxane-modified resin paint. Preferably, the above product is an optical film or optical element comprising a paint resin substrate and a compound described in any one of items 1 to 4, wherein the resin substrate is preferably at least one selected from triacetylcellulose, polycarbonate, polyacrylate, polyethylene naphthalate, polyethylene terephthalate, polyvinyl alcohol, polymethyl methacrylate, polycyclopentene, polyimide, polystyrene and its derivatives, epoxy resin, polyurethane, and polysilane. Preferably, the above product is a blue light cut lens comprising a resin substrate and a compound described in any one of items 1 to 4, wherein the resin substrate is preferably at least one selected from aliphatic diisocyanate, polymethyl methacrylate, polycarbonate, polyamide, fluorine / silicon-modified polyacrylic acid, and polyisocyanate / polythioether. Preferably, the product is an automotive paint comprising a cathode electrophoresis primer and a coating compounded therewith, wherein the electrophoresis primer or the coating compounded therewith comprises a resin paint and a compound described in any one of items 1 to 4, the cathode electrophoresis primer coating uses an epoxy resin as a substrate, and the cathode electrophoresis primer coating further comprises a polyester resin, a polyurethane resin, an epoxy / polyester hybrid resin, an acrylic resin, a polysiloxane resin, an aminoacrylic resin, a hydroxyacrylic resin, a polysiloxane-modified resin, or an epoxy-modified resin, as described in item 8. 10. Use of any one of the compounds described in items 1 to 4, the composition described in claim 5 or 6, or the polymer material described in claim 7 as an ultraviolet absorber. [Examples]

[0040] The following examples use three sets of conventional products, including the following, as comparative products: (1) Comparative product 1: Conventional UV absorber (hereinafter abbreviated as UV-326), (2) Comparative product 2: Basf Co. commercially available redshift UV absorber Carboprotect, (3) Comparative product 3: The structure is shown below (hereinafter abbreviated as EX16) [ka] The reagents used in the examples, whose manufacturers are not specified, are all standard products that are readily available on the market.

[0041] Example 1: Synthesis Method Following the synthesis route shown in Figure 1, two target products, RSUV-1 and RSUV-2, were obtained. Specifically, the results were as follows: Step 1 response: UV326 (200.0 g, 0.63 mol), dodecyl mercaptan (NDM, 154.5 g, 0.76 mol), potassium carbonate (121.5 g, 0.89 mol), and N,N-dimethylformamide (DMF, 1000 ml) were added sequentially to a 2000 ml four-necked round-bottom flask. The mixture was heated to reflux and reacted for 5-7 hours until the raw materials had completely reacted. The reaction was then terminated, the mixture was cooled to 110-120°C, and the inorganic salts in the reaction solution were removed by suction filtration. The mother liquor was distilled under reduced pressure to remove the DMF. Then, 1000 ml of xylene was added to dissolve the materials. A small amount of acetic acid was added at 80-90°C to adjust the pH of the solution to neutral. Washing water was added and the mixture was washed 3-4 times with 200 ml each time. After completion, the mixture was heated and dehydrated under reflux until no more water was evaporated. When producing the sulfonated product RSUV-2, the reaction product from this step can be used directly in the next step without purification. When it is necessary to obtain the thioether product RSUV-1, xylene is removed by vacuum distillation, the temperature is lowered to 50°C, 1000 ml of methanol / xylene mixed solution is added for crystallization, the temperature is lowered to room temperature, and then the crystallization is maintained for 3 hours. The mixture is then filtered by suction, dried, and 303.5 g of yellow solid powder is obtained, with a yield of 97%. The LC-MS detection results were [M+1]=482.2, [M-1]=480.2, and the spectrum is shown in Figure 2. The nuclear magnetic resonance hydrogen spectrum is shown in Figure 3.

[0042] Response in the second step (Step 2) The solution after reflux dehydration was cooled to room temperature, formic acid (66.4 g, 1.27 mol) and sodium tungstate (catalyst amount) were added, and hydrogen peroxide solution (194 g, 2.86 mol) was added dropwise. After the addition was complete, the temperature was raised to 50-70°C and maintained for 3-5 hours to complete the reaction. The solution was allowed to stand to separate the aqueous phase at the bottom, and a small amount of sodium sulfite aqueous solution was added to remove the remaining hydrogen peroxide solution. The solution was then washed three times each with saturated brine and pure water, the temperature was raised to 110-140°C, and xylene was removed by vacuum distillation. The solution was then cooled to 50°C, 1000 ml of methanol was added to crystallize it, and after cooling to room temperature, it was maintained for 3 hours to crystallize. The solution was filtered by suction, dried, and 264 g of yellow solid powder was obtained, with a yield of 76%. The LC-MS detection results were [M+1]=514.2, [M-1]=512.2, and the spectrum is shown in Figure 4. The nuclear magnetic resonance hydrogen spectrum is shown in Figure 5.

[0043] Example 2 Absorption Spectrum Comparative product 1 (UV-326) and RSUV-1 and RSUV-2 manufactured according to the present invention were each dissolved in chloroform and prepared as a unified 10 mg / L chloroform solution. The absorption spectra were tested using a UV-Vis spectrophotometer (instrument model (UV-2600, Shimadzu Corporation, Japan)). A comparison of the absorption spectra is shown in Table 1 below. [Table 1] As can be seen from Table 1, the ultraviolet absorbers of products RSUV-1 and RSUV-2 manufactured in this invention are generally redshifted towards the long wave direction. Among them, RSUV-1 shows significantly stronger absorption in the 360-450 nm wavelength range than the conventional product (comparative product 1). RSUV-2 has a cutoff wavelength of 430 nm and can provide more anti-photoaging protection for substrates sensitive to the 360-430 nm wavelength range.

[0044] Example 3 Solubility / Suitability Test Many optical devices, such as optical adhesive films and optical lenses, utilize solvent-free crosslinking systems during fabrication and molding. Such systems avoid problems like reduced accuracy due to shrinkage and device contamination by solvents. However, auxiliary agents such as UV absorbers are dissolved only by oligomeric resins or active monomers. Therefore, relatively high solubility or compatibility of UV absorbers in these materials is required. The solubility of comparative product 3 (EX16) and RSUV-1 and RSUV-2 produced in the present invention was tested in typical oligomer resins (cyclohexanedimethylene diisocyanate (H6XDI, purity ≥99.7%, Manka Chemical), hexamethylene diisocyanate (HDI) trimer (Desmodur N3300, Covestro), and tripropylene glycol diacrylate (≥80% (GC), Aladdin Reagent). Test method: The mass of UV absorber soluble in 100 grams of oligomer at an ambient temperature of 20°C. The test results are shown in Table 2 below. [Table 2] As can be seen from Table 2, in terms of solubility, RSUV-1 and RSUV-2 produced in the present invention exhibit better solubility as ultraviolet absorbers in several typical oligomeric resins compared to the comparative compound EX16. Therefore, they have better compatibility with solvent-free crosslinking systems, are more convenient to use as additives, and are easier to handle.

[0045] Example 4: Color Test Two grams each of comparative product 2 (Carboprotect) and RSUV-1 and RSUV-2 manufactured according to the present invention were dissolved in 18 grams of dimethylformamide (DMF) solvent. The completely dissolved solutions were transferred to cuvettes, and the Gardner chromaticity values ​​permeated through the solvent were tested. The instrument used was a Ci7600 benchtop spectrophotometer (X-rite, USA). The test results are shown in Table 3 below. [Table 3] As can be seen from Table 3, commercially available redshift ultraviolet absorbers such as Carboprotect have a very dark color, which has a significant impact on the final product in which they are used, especially light-colored products. On the other hand, RSUV-1 and RSUV-2 manufactured in the present invention, and especially RSUV-1, have a significantly lighter color as ultraviolet absorbers, giving them a relatively large advantage in applications. Examples 2 to 4 show that, compared to the conventional UV absorber UV-326, the commercially available redshift UV absorber Carboprotect, and EX16 with a similar structure, the UV absorber provided by the present invention has clearly superior overall performance, particularly in terms of light absorption performance, solubility, and chromaticity, and therefore has the potential for a wider range of applications.

[0046] Example 5: Application of UV absorbers in epoxy-reinforced carbon fiber coatings This embodiment relates to a coating for epoxy-reinforced carbon fiber surfaces. The coating is a two-component acrylic clear coat system based on isocyanate curing. Different ultraviolet absorbers were added to component A (see Table 4) of the two-component acrylic clear coat, and Desmodur N3300 (Covestro) was used for component B in both cases. When used, the two components were uniformly mixed according to a weight percentage ratio of component A:component B = 100:21 and then spray-applied. In this formulation, the molar ratio of isocyanate group:hydroxyl group was calculated to be 1.09:1. [Table 4] Note: DBTDL (dibutyltin dilaurate) was used as a catalyst, and it was prepared as a 5% methylpentyl ketone solution. Test method: (1) The paint materials in Table 4 were mixed in the specified ratios and sprayed onto an epoxy-reinforced carbon fiber plate (purchased from Weisheng New Materials Technology Co., Ltd.) to a film thickness of 30-35 microns. The plate was then baked in an 80°C drying chamber for 45 minutes until it cured into a film. The test plate was left at room temperature in the dark for one week before being subjected to the test. (2) The test plates were placed in a xenon lamp aging test chamber (model: Atlas Ci4400), and the test standard referred to SAE J2527. The test plates were removed every 2000 hours, and the gloss of the coating at 20 degrees was measured. The colorimeter used was a BYK triangular gloss meter (model: micro-TRI-gloss). After 6000 hours of testing, the adhesion was tested, and the reference standard was ISO 2409-2013. The test results are shown in Table 5 below. [Table 5] As can be seen from Table 5, compared to the conventional UV absorber UV-326, RSUV-1 and RSUV-2 manufactured in this invention can effectively improve the gloss and adhesion of epoxy-reinforced carbon fiber coatings as UV absorbers. Compared to UV-326, RSUV-1 shows a certain degree of improved protective effect, while RSUV-2 shows a significant improvement in protective effect. At the same time, RSUV-2 has a lighter color, less impact on coatings or other polymer products, and a wider range of applications.

[0047] Example 6: Comparison of UV 326, RSUV2, and Carboprotect epoxy-reinforced carbon fiber coatings [Table 6] Note: DBTDL (dibutyltin dilaurate) was used as a catalyst, and it was prepared as a 5% methyl amyl ketone solution. The coating materials listed in Table 6 were mixed in the specified ratios and sprayed onto an epoxy-reinforced carbon fiber plate (purchased from Weisheng New Materials Technology Co., Ltd.) to a film thickness of 45 microns. The plate was then baked in an 80°C drying chamber for 45 minutes until it cured into a film. The test plate was left at room temperature in the dark for one week before being subjected to the test. (2) The test plates were placed in a xenon lamp aging test chamber (model: Atlas Ci4400) and exposed using the ISO 11341 (2004) protocol. The test plates were periodically removed and the adhesion strength was measured, with ASTM D 3359-09 as the reference standard. The test results are shown in Table 7 below. [Table 7] Adhesion test: OB: No delamination 1B: <5% delamination 2B: 5% to 15% delamination 3B: 15% to 35% delamination 4B: 35-65% delamination 5B: >65% delamination The results above demonstrate that the UV absorber of the present invention exhibits superior performance compared to UV 326 and current state-of-the-art Carboprotect UV absorbers. Both UV 326 and Carboprotect fail after 2400 hours with extensive delamination of grade 5B, while RSUV-2 shows grade 2B delamination after 3200 hours. The UV absorber RSUV-2 of the present invention protects coatings on photounstable CFRM substrates and can prevent delamination better than commercially available controls.

[0048] Example 7: Application of UV absorbers in optical films Optical films have a relatively wide range of applications, and as the main support substrate for optical films, polymer films need to possess excellent optical properties. Such polymers include triacetylcellulose (TAC), polycarbonate, polyacrylate, and polyethylene naphthalate (PEN). To achieve certain optical properties, such as complete blocking of ultraviolet light (280-400 nm) or protection of certain special devices from ultraviolet light in a specific wavelength range (the 360-400 nm sensitive wavelength range for the aforementioned PEN film), ultraviolet absorbers are usually added. In this example, the ultraviolet blocking performance of the ultraviolet absorber was investigated. (1) The ingredients were prepared according to the following proportions: Triacetylcellulose (acetyl content 60-61%): 100 units Dichloromethane: 400 copies Methanol: 40 copies Biphenyldiphenyl phosphate: 6 parts UV absorbers UV-326 / RSUV-1 / RSUV-2: 0.5 parts (2) All materials were added in the above proportions, and the mixture was sealed and stirred for 3 hours until a uniform, transparent adhesive solution was formed. The adhesive solution was applied to form a film, which was then dried in a drying chamber at 125°C for 30 minutes. A 200-micron TAC film was produced. (3) The UV absorption value of the optical adhesive film was tested. The optical adhesive film manufactured as described above was cut into 25mm x 60mm test sample pieces, and its absorption spectrum was tested using a UV-Vis spectrophotometer (model number UV-2600, Shimadzu Corporation, Japan). The absorption characteristics of the optical film are shown in Table 6 below. [Table 8] As can be seen from Table 6, RSUV-1 and RSUV-2 manufactured in this invention, as ultraviolet absorbers, can better cover the wavelength range required for optical films, and at the same time, they do not exhibit negative absorption in higher wavelength ranges and do not affect normal optical requirements.

[0049] Example 8: Application of UV absorbers in blue light-blocking lenses Within the visible light wavelength range, the wavelength region of blue light is 380nm to 500nm. Studies have shown that short-wavelength blue light between 400nm and 455nm, due to its short wavelength and high energy, can be damaging to retinal pigment epithelial cells and potentially cause visual damage such as macular degeneration. However, medium-to-long-wavelength blue light between 445nm and 500nm is beneficial because it is involved in the mechanism of a biological rhythm called the "circadian rhythm period." If high-energy blue light between 400nm and 445nm can be blocked in displays or eye lenses, it will provide direct health benefits to users of electronic products. Taking blue light cut lenses as an example, blue light can generally be effectively filtered by film plating and the addition of blue-violet light absorbers. While the film layer reflection method can effectively filter most blue light, its filtering effect is relatively limited for low-wavelength (380nm to 420nm) blue-violet light. In this case, a redshift ultraviolet absorber that has a relatively good absorption effect in the 380-420nm range can provide a better blue light blocking effect. There are many types of lens resins, including polycarbonate, polymethacrylate, and polyurethane-based resins. Among these, polyurethane-based optical resins have excellent overall performance and represent an important direction of development in new optical resins in recent years. This example verifies the effect of the redshift ultraviolet absorber of the present invention on polyurethane resin.

[0050] (1) Raw material composition Cyclohexanedimethylene diisocyanate (H6XDI, purity ≥99.7%, Wanhua Chemical): 500g 2,3-Dithio(2-mercapto)-1-propanthol (purity ≥98%, Sigma-Aldrich): 223.5g Tetra(3-mercaptopropionic acid) pentaerythritol ester (purity ≥ 98%, Sigma-Aldrich): 314.5g Dibutyltin dichloride (99% purity, Nishiya Reagent) catalyst: 1.5g Ultraviolet absorber UV-329 (Tianjin Li'anlong New Materials Co., Ltd.): 1.5g Test sample: UV-326 / RSUV-2: 1.5g (2) Lens manufacturing process Dibutyltin dichloride, UV-329 ultraviolet absorber, test sample, and cyclohexanedimethylene diisocyanate (H6XDI) were added while stirring in the above proportions, and mixed until dissolved. After dissolution was complete, 2,3-dithio(2-mercapto)-1-propanthol and tetra(3-mercaptopropionic acid) pentaerythritol ester were added, and all materials were stirred and mixed. The mixture was then filtered through a filter film and poured into a lens mold, where it was degassed under reduced pressure for 1 hour. The molar ratio of NCO to SH groups in the resin was 1:1. The degassed liquid resin was placed in a drying box, gradually heated to 120°C to polymerize and cure, maintained at 120°C for 2 hours to fully cure the resin, and after primary curing, the resin was allowed to cool naturally to room temperature, followed by secondary curing at room temperature. After 48 hours, the resin was demolded to obtain a resin lens. (3) Test for blocking rate of blue light The transmittance of the lenses manufactured as described above was tested in each wavelength range in reference to GB / T38120-2019 "Technical Requirements for the Application of Blue Light Cut Films for Photohealth and Photosafety," and the results are shown in Table 7 below. [Table 9] As can be seen from Table 7, after adding RSUV-2 manufactured according to the present invention as an ultraviolet absorber, the lens exhibits significantly enhanced absorption in the blue light region, enabling it to effectively block high-energy harmful blue light.

[0051] Example 9 Application of UV absorbers in cathodic electrophoretic coatings and their composite coatings Cathophoretic coatings (electro-coats) are widely used in fields such as industrial equipment and automobiles, providing excellent corrosion and chemical resistance to metal substrates in these fields. The main resin of cathophoretic coatings is generally selected from resins including epoxy resins, polyester resins, polyurethane resins, and epoxy / polyester hybrid resins. Among these, epoxy ester-based or epoxy-modified resins are core components. Epoxy resins are very sensitive to ultraviolet light, and damage to epoxy resins occurs not only in the conventional ultraviolet wavelength range but also in the near-ultraviolet wavelength range. The wavelength range of RSUV-2 provided by the present invention exceeds the coverage wavelength of conventional ultraviolet absorbers, and in particular, it can provide a relatively good ultraviolet blocking effect even at 380-430 nm, thus providing a superior protective effect to cathophoretic coatings. (1) Raw material composition A typical single-component solvent-type clear coat was selected (see Table 8 below for the composition). [Table 10] Note: Setalux 1766, Setalux 1795, Setalux 91795, Setal 168: Hydroxyacrylic resin, anti-sagging resin, purchased from Zhanxin Resin (China) Co., Ltd.; Cymel 303, Cymel 1168: Amino resin, purchased from Changxin Resin (Guangdong) Co., Ltd.; BYK 378, BYK 306: Organic silicone leveling agent, purchased from Bi-Ke Auxiliary Agents (Shanghai) Co., Ltd.; Nacure 5225: Acid catalyst, purchased from King Industries Inc., USA.

[0052] (2) Test method Based on the above acrylic acid amino clear coat formulation, three sets of test paint samples were obtained by adding different types of light stabilizers. Paint test plates were prepared by spray coating according to the following method. The substrate was uniformly a steel plate with electrophoretic coating (purchased from ACT Test Panels LLC., USA, specification ECOAT:U32AD800). Each of the three sets of clear coats was sprayed to a film thickness of 40 microns, leveled at room temperature for 10 minutes, and baked in a drying chamber at 140°C for 30 minutes. The xenon lamp test conditions were as follows: The test plate was placed in a xenon lamp aging test box (model: Atlas Ci4400 xenon lamp aging test box), and the test standard referred to ISO 11341 (2004). The test plate was removed every 7 days and the adhesion of the coating was tested, with the reference standard being ISO 2409-2013. The test results are shown in Table 9 below. [Table 11] As can be seen from the results in Table 9, RSUV-2 manufactured according to the present invention can maintain adhesion between the clear coat and the cathodic electrophoretic coating for a relatively long period of time. As can be seen from Examples 5 to 8, RSUV-1 and RSUV-2 provided by the present invention are well usable as ultraviolet absorbers in various fields, have a wide range of applications, and possess strong industrial practicality.

Claims

1. A compound having the structure shown in formula (I) or formula (II), 【Chemistry 1】 Here, in equations (I) and (II), R １ R is selected from C1-C20 linear or branched alkyl groups. ２ n is selected from linear or branched alkyl groups of C1-C8, and n is an integer selected from 1 to 3. compound.

2. The compound has a structure represented by formula (III) or formula (IV), 【Chemistry 2】 Here, in equations (III) and (IV), R １ R is selected from C1-C20 linear or branched alkyl groups. ２ It is selected from C1-C8 linear or branched alkyl groups. The compound according to claim 1, characterized in that it is a compound according to claim 1.

3. In formulas (I), (II), (III), and / or (IV), R １ R is selected from C5-C20 linear or branched alkyl groups, preferably selected from C7-C15 linear or branched alkyl groups. ２ It is selected from C2-C6 linear or branched alkyl groups. Preferably, the compound has the structure shown in RSUV-1 or RSUV-2. The compound according to claim 1, characterized in that it is a compound according to claim 1. 【Transformation 3】

4. The compound according to claim 1, characterized in that the absorption wavelength range of the compound is 280 to 430 nm.

5. A composition comprising the compound described in any one of claims 1 to 4.

6. The composition according to claim 5, wherein the composition further comprises one or more additives, preferably the additives comprising one or more of the following: hindered amine light stabilizers, other ultraviolet absorbers, antioxidants, emulsifiers, nucleating agents, toughening agents, lubricants, antiblocking agents, fillers, dyes, pigments, fluorescent whitening agents, flame retardants, antistatic agents, or foaming agents.

7. A polymer material comprising a compound according to any one of claims 1 to 4 or a composition according to claim 5 or 6, and an organic material that is susceptible to decomposition by oxygen, heat or light, preferably the organic material being at least one resin from among polyester, polyurethane, polyacrylic acid, polycarbonate, epoxy and modified resins thereof, phenolic resin, polyamide, polyimide, polystyrene and derivatives thereof, polysilane, polysiloxane and modified thereof, poly(vinyl butyral), aminoacrylic acid, hydroxyacrylic acid, acrylic polyurethane, polycyanoacrylate, polyacrylate, ethylene / acrylic acid copolymer system and salts thereof (ionomers), poly(vinyl alcohol), triacetylcellulose, polycarbonate, polyethylene naphthalate, polyethylene terephthalate, polymethyl methacrylate, polycyclopentene, aliphatic diisocyanate, fluorine / silicon-modified polyacrylic acid, and polyisocyanate / polythioether.

8. A product comprising a compound according to any one of claims 1 to 4, a composition according to claim 5 or 6, or a polymer material according to claim 7.

9. The aforementioned products are selected from epoxy resin-based and composite products thereof, polyethylene naphthalate-based products, optical adhesives, optical elements, optical films, optical lenses, blue light-cutting products, reflective sheets and conformal marking sheets, car windows and their films, car cover films, automotive paints, solar radiation control films, solar reflectors, reflective printed labels, UV-absorbing glass and glass paints, electrochromic devices, films / glass windows, windshields or intermediate layers. Preferably, the product is an epoxy-reinforced carbon fiber composite material comprising epoxy-reinforced carbon fibers and an outer coating thereof, wherein the coating comprises a resin paint and a compound according to any one of claims 1 to 4, and the paint is preferably at least one selected from aminoacrylic resin paint, hydroxyacrylic resin paint, polyester resin paint, acrylic polyurethane paint, polyurethane resin paint, epoxy-modified resin paint, and polysiloxane-modified resin paint. Preferably, the product is an optical film or optical element comprising a paint resin substrate and a compound according to any one of claims 1 to 4, wherein the resin substrate is preferably at least one selected from triacetylcellulose, polycarbonate, polyacrylate, polyethylene naphthalate, polyethylene terephthalate, polyvinyl alcohol, polymethyl methacrylate, polycyclopentene, polyimide, polystyrene and its derivatives, epoxy resin, polyurethane, and polysilane. Preferably, the product is a blue light cut lens comprising a resin substrate and a compound according to any one of claims 1 to 4, wherein the resin substrate is preferably at least one selected from aliphatic diisocyanate, polymethyl methacrylate, polycarbonate, polyamide, fluorine / silicon-modified polyacrylic acid, and polyisocyanate / polythioether. Preferably, the product is an automotive paint comprising a cathode electrophoresis primer and a coating compounded therewith, wherein the electrophoresis primer or the coating compounded therewith comprises a resin paint and a compound according to any one of claims 1 to 4, the cathode electrophoresis primer coating uses an epoxy resin as a substrate, and the cathode electrophoresis primer coating further comprises a polyester resin, a polyurethane resin, an epoxy / polyester hybrid resin, an acrylic resin, a polysiloxane resin, an aminoacrylic resin, a hydroxyacrylic resin, a polysiloxane-modified resin, and an epoxy-modified resin. The product according to claim 8, characterized in that it is the product described in claim 8.

10. Use of the compound described in any one of claims 1 to 4 as an ultraviolet absorber.

11. Use of the composition according to claim 5 as an ultraviolet absorber.

12. Use of the polymer material according to claim 7 as an ultraviolet absorber.

13. A product comprising the composition described in claim 5.

14. A product comprising the polymer material described in claim 7.

15. The aforementioned products are selected from epoxy resin-based and composite products thereof, polyethylene naphthalate-based products, optical adhesives, optical elements, optical films, optical lenses, blue light-cutting products, reflective sheets and conformal marking sheets, car windows and their films, car cover films, automotive paints, solar radiation control films, solar reflectors, reflective printed labels, UV-absorbing glass and glass paints, electrochromic devices, films / glass windows, windshields or intermediate layers. Preferably, the product is an epoxy-reinforced carbon fiber composite material comprising epoxy-reinforced carbon fibers and an outer coating thereof, wherein the coating comprises a resin paint and a compound according to any one of claims 1 to 4, and the paint is preferably at least one selected from aminoacrylic resin paint, hydroxyacrylic resin paint, polyester resin paint, acrylic polyurethane paint, polyurethane resin paint, epoxy-modified resin paint, and polysiloxane-modified resin paint. Preferably, the product is an optical film or optical element comprising a paint resin substrate and a compound according to any one of claims 1 to 4, wherein the resin substrate is preferably at least one selected from triacetylcellulose, polycarbonate, polyacrylate, polyethylene naphthalate, polyethylene terephthalate, polyvinyl alcohol, polymethyl methacrylate, polycyclopentene, polyimide, polystyrene and its derivatives, epoxy resin, polyurethane, and polysilane. Preferably, the product is a blue light cut lens comprising a resin substrate and a compound according to any one of claims 1 to 4, wherein the resin substrate is preferably at least one selected from aliphatic diisocyanate, polymethyl methacrylate, polycarbonate, polyamide, polymethyl methacrylate, fluorine / silicon-modified polyacrylic acid, and polyisocyanate / polythioether. Preferably, the product is an automotive paint comprising a cathode electrophoresis primer and a coating compounded therewith, wherein the electrophoresis primer or the coating compounded therewith comprises a resin paint and a compound according to any one of claims 1 to 5, the cathode electrophoresis primer coating uses an epoxy resin as a substrate, and the cathode electrophoresis primer coating further comprises a polyester resin, a polyurethane resin, an epoxy / polyester hybrid resin, an acrylic resin, a polysiloxane resin, an aminoacrylic resin, a hydroxyacrylic resin, a polysiloxane-modified resin, and an epoxy-modified resin. The product according to claim 13 or 14, characterized in that it is the product according to claim 13 or 14.

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