EP-4739662-A1 - ULTRAVIOLET ABSORBER AND USE THEREOF

Abstract

An ultraviolet absorber having a structure represented by formula (I) or formula (II) as disclosed herein and compositions, polymer materials, articles of manufacture, methods and uses thereof.

Inventors

• YANG, WEI
• SUN, Donghui
• LI, YANQING
• ZHAO, PENGBO
• LUO, Hai
• LI, CAI

Assignees

• Rianlon (Zhongwei) New Material Co., Ltd.

Dates

Publication Date

20260513

Application Date

20240703

Claims (15)

1. What is claimed is: 1. A compound having a structure represented by formula (I) or formula (II), from C1-C20 linear or branched alkyl, R 2 is selected from C1-C8 linear or branched alkyl, and n is selected from an integer of 1-3.
2. 2. The compound according to claim 1, wherein the compound has a structure represented by formula (III) or formula (IV), from C1-C20 linear or branched alkyl, and R 2 is selected from C1-C8 linear or branched alkyl.
3. 3. The compound according to claim 1, wherein in formula (I), formula (II), formula (III), and/or formula (IV), R1 is selected from C5-C20 linear or branched alkyl, preferably C7-C15 linear or branched alkyl, and R2 is selected from C2-C6 linear or branched alkyl; preferably, the compound has a structure represented by RSUV-1 or RSUV-2: 43 2.
4. 4. The mpound has an absorption wavelength ranging from 280 nm to 430 nm.
5. 5. A composition comprising the compound according to any one of claims 1-4.
6. 6. The composition according to claim 5, wherein the composition further comprises one or more additives; preferably, the additive comprises one or more of a hindered amine light stabilizer, an additional ultraviolet absorber, an antioxidant, an emulsifier, a nucleating agent, a toughening agent, a lubricant, an anti-blocking agent, a filler, a dye, a pigment, a fluorescent brightener, a flame retardant, an antistatic agent, or a foaming agent.
7. 7. A polymer material, wherein the polymer material comprises the compound according to any one of claims 1-4, and an organic material susceptible to degradation induced by oxygen, heat, or light; preferably, the organic material is at least one resin of polyester, polyurethane, polyacrylic acid, polycarbonate, epoxy and modified resins thereof, phenolic resin, polyamide, polyimide, polystyrene and derivatives thereof, polysilane, polysiloxane and modifications thereof, poly(vinyl butyral), amino acrylic acid, hydroxyl acrylic acid, polyurethane acrylate, polycyanoacrylate, polyacrylate, ethylene/acrylic acid copolymers and salts thereof (ionomers), poly(vinyl alcohol), cellulose triacetate, polycarbonate, polyethylene naphthalate, polyethylene terephthalate, polyvinyl alcohol, polymethyl methacrylate, polycyclopentene, aliphatic isocyanate, polymethyl methacrylate, fluorine/silicon-modified polyacrylic acid, and polyisocyanate/polythioether. 44
8. 8. An article of manufacture comprising the compound according to any one of claims 1-4.
9. 9. The article of manufacture according to claim 8, wherein the article of manufacture is selected from an epoxy resin-based article of manufacture and composite articles of manufacture thereof, a polyethylene naphthalate-based article of manufacture, an optical adhesive, an optical element, an optical film, an optical lens, an anti-blue light article of manufacture, a reflective sheet and a conformable marking sheet, a vehicle window and a film thereof, a vehicle paint protection film, an automotive paint, a solar control film, a solar reflector, a reflective printed label, a UV absorbing glass and a glass coating material, an electrochromic device, a film/a glazing, a windshield, or a middle layer; preferably, the article of manufacture is an epoxy-reinforced carbon fiber composite material comprising an epoxy-reinforced carbon fiber and an outer layer coating thereof; the coating comprises a resin coating material and the compound according to any one of claims 1-4; the coating material is preferably selected from at least one of an amino acrylic resin coating material, a hydroxyl acrylic resin coating material, a polyester resin coating material, a polyurethane acrylate coating material, a polyurethane resin coating material, an epoxy-modified resin coating material, and a polysiloxane-modified resin coating material; preferably, the article of manufacture is an optical film or an optical element comprising a coating material resin substrate and the compound according to any one of claims 1-4; the resin substrate is preferably selected from at least one of cellulose triacetate, polycarbonate, polyacrylate, polyethylene naphthalate, polyethylene terephthalate, polyvinyl alcohol, polymethyl methacrylate, polycyclopentene, polyimide, polystyrene and derivatives thereof, an epoxy resin, polyurethane, and polysilane; preferably, the article of manufacture is an anti-blue light lens comprising a resin substrate and the compound according to any one of claims 1-4; the resin substrate is preferably selected from at least one of aliphatic isocyanate, polymethyl methacrylate, polycarbonate, polyamide, polymethyl methacrylate, fluorine/silicon-modified 45 polyacrylic acid, and polyisocyanate/polythioether; preferably, the article of manufacture is an automotive paint comprising a cathodic electrodeposition primer and a coating compounded therewith; the electrodeposition primer or the coating compounded therewith comprises a resin coating material and the compound according to any one of claims 1-5; the cathodic electrodeposition primer coating takes an epoxy resin as a matrix, and the cathodic electrodeposition primer coating further comprises a polyester resin, a polyurethane resin, an epoxy/polyester hybrid resin, an acrylic resin, a polysiloxane resin, an amino acrylic resin, a hydroxyl acrylic resin, a polysiloxane-modified resin, and an epoxy-modified resin.
10. 10. Use of the compound according to any one of claims 1-4, as an ultraviolet absorber.
11. 11. Use of the composition according to claim 5, as an ultraviolet absorber.
12. 12. Use of the polymer material according to claim 7 as an ultraviolet absorber.
13. 13. An article of manufacture comprising the composition according to claim 5.
14. 14. An article of manufacture comprising the polymer material according to claim 7.
15. 15. The article of manufacture according to claim 13 or 14, wherein the article of manufacture is selected from an epoxy resin-based article of manufacture and composite articles of manufacture thereof, a polyethylene naphthalate-based article of manufacture, an optical adhesive, an optical element, an optical film, an optical lens, an anti-blue light article of manufacture, a reflective sheet and a conformable marking sheet, a vehicle window and a film thereof, a vehicle paint protection film, an automotive paint, a solar control film, a solar reflector, a reflective printed label, a UV absorbing glass and a glass coating material, an electrochromic device, a film/a glazing, a windshield, or a middle layer; preferably, the article of manufacture is an epoxy-reinforced carbon fiber composite material comprising an epoxy-reinforced carbon fiber and an outer layer coating thereof; the coating comprises a resin coating material and the compound according to any one of claims 1-4; the coating material is preferably selected from at least one of an amino acrylic resin coating material, a hydroxyl acrylic resin coating 46 material, a polyester resin coating material, a polyurethane acrylate coating material, a polyurethane resin coating material, an epoxy-modified resin coating material, and a polysiloxane-modified resin coating material; preferably, the article of manufacture is an optical film or an optical element comprising a coating material resin substrate and the compound according to any one of claims 1-4; the resin substrate is preferably selected from at least one of cellulose triacetate, polycarbonate, polyacrylate, polyethylene naphthalate, polyethylene terephthalate, polyvinyl alcohol, polymethyl methacrylate, polycyclopentene, polyimide, polystyrene and derivatives thereof, an epoxy resin, polyurethane, and polysilane; preferably, the article of manufacture is an anti-blue light lens comprising a resin substrate and the compound according to any one of claims 1-4; the resin substrate is preferably selected from at least one of aliphatic isocyanate, polymethyl methacrylate, polycarbonate, polyamide, polymethyl methacrylate, fluorine/silicon-modified polyacrylic acid, and polyisocyanate/polythioether; preferably, the article of manufacture is an automotive paint comprising a cathodic electrodeposition primer and a coating compounded therewith; the electrodeposition primer or the coating compounded therewith comprises a resin coating material and the compound according to any one of claims 1-5; the cathodic electrodeposition primer coating takes an epoxy resin as a matrix, and the cathodic electrodeposition primer coating further comprises a polyester resin, a polyurethane resin, an epoxy/polyester hybrid resin, an acrylic resin, a polysiloxane resin, an amino acrylic resin, a hydroxyl acrylic resin, a polysiloxane-modified resin, and an epoxy-modified resin 47

Description

ULTRAVIOLET ABSORBER AND USE THEREOF Technical field [0001] The present invention belongs to the field of light stabilizers, and specifically: relates to ultraviolet absorbers. Background [0002] Polymer materials are indispensable basic materials in many facets of life and society, and the issue of time stability of the polymer materials inevitably affects their usability, causing shortened service life and a waste of resources. The factors causing stability issues over time of polymers are mainly light and heat, among which ultraviolet rays in natural sunlight have a great influence on the long-acting performance of the polymers. At present, the prevention of outdoor photoaging is mainly solved by adding light stabilizers. Such light stabilizers include ultraviolet absorbers and hindered amine light stabilizers. With the gradual penetration and extension of polymer materials from general-purpose and basic materials to special functional materials, some special application scenarios have emerged in the anti-aging of polymer materials, and traditional light stabilizers can no longer fully meet the needs. [0003] Although traditional ultraviolet absorbers have a relatively full coverage in most of ultraviolet regions (wavelength 280-400 nm), the absorption efficiency at wavelengths above 380 nm is significantly reduced. When ultraviolet absorbers are applied to application fields with special requirements in the aspect of a long wave (redshift region), the traditional ultraviolet absorbers are not as useful to meet the desired requirements. [0004] Carbon fibers are an emerging material of great interest. At present, carbon fiber reinforced epoxy resin composite materials are the most widely used carbon fiber reinforced materials (CFRMs) having the highest comprehensive indexes such as strength, modulus, etc. However, epoxy resins are themselves susceptible to damage by ultraviolet rays and visible light below 420 nm, causing degradation, and thus affecting their performance. Ultraviolet absorbers with high absorption efficiency at 380-420 nm 1    can effectively protect such materials. [0005] Polyethylene naphthalate (PEN) is a polymer material with excellent comprehensive properties such as chemical stability, mechanical properties, heat resistance, etc., and has relatively good application prospects in the fields of optical elements and the like. However, ultraviolet rays at 360-400 nm are prone to causing damage to PEN and composite materials containing PEN, resulting in material degradation. [0006] In addition, there are some fields that require special shielding requirements for light in the wavelength range of 360-430 nm. For example, special polarizers are required to absorb ultraviolet rays in the wavelength range of 380 nm and below as completely as possible or at least 75-85% of the ultraviolet rays, while transmitting ultraviolet rays above 410 nm as much as possible, for example, transmitting at least greater than 95% of the ultraviolet rays. Still other glass coatings and films, such as those used in automotive front windshields and special architectural glasses, are required to shield ultraviolet rays below 400 nm as much as possible to meet the higher health requirements of people exposed to such environments. In order to meet such requirements, the ultraviolet absorbers must be red shifted to a higher wavelength, so as to meet the requirement of better absorption efficiency in the of 380-410 nm region. For another example, optical lenses, display screen devices, etc. are required to have relatively high absorption for high-energy blue light in the waveband of 400 nm-445 nm, thereby protecting the vision health of users of electronic products. [0007] In this field, there is an urgent need for an ultraviolet absorber that not only has a good absorption effect on most of ultraviolet regions (280-400 nm), but also keeps a good absorption effect on light with a wavelength above 380 nm, particularly light in a redshifted spectral region. Summary [0008] According to the present invention, thioether or sulfonyl is introduced into the conventional benzotriazole absorber, so that the cut-off wavelength of the conventional 2    benzotriazole absorber is red-shifted from 400-410 nm to a long-wave direction up to 430 nm. In addition, by selecting a proper alkyl chain segment, the compound with the novel structure is ensured to have proper melting point and solubility, as well as better system compatibility, making it applicable to a variety of material systems. [0009] One aspect of the present invention provides a compound having a structure represented by formula (I) or formula (II), (I) (II) [0010] , C1-C20 linear or branched alkyl, R2 is selected from C1-C8 linear or branched alkyl, and n is selected from an integer of 1-3. [0011] In some embodiments, in formula (I) and formula (II), R1 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, n-heptyl, n-o