Flame retardant compound and resin composition

Abstract

The embodiment of the invention provides a flame-retardant compound and a resin composition, the flame-retardant compound has a structural formula as shown in a formula (I): # imgabs0 #, in the formula (I), R1, R2 and R3 are all halogen-free groups; each of R1, R2 and R3 is independently selected from any one of a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group and a substituted or unsubstituted heteroaryl group, and R1, R2 and R3 are connected to the same silicon atom, and R1, R2 and R3 are independently selected from hydrogen atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted cycloalkyl groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted aryl groups and substituted or unsubstituted heteroaryl groups. And at least one is a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. The flame-retardant compound has high flame-retardant property, does not contain halogen, and is safe and environment-friendly; and the transparent resin composition can be uniformly mixed with various matrix resins to form the resin composition, and the molded product of the resin composition can have better transparency.

Description

Technical Field

[0001] The embodiments of the present application relate to the technical field of flame retardants, and particularly to a flame retardant compound and a resin composition. Background Art

[0002] With the progress of technology, synthetic polymer materials have been widely used in fields such as industrial manufacturing and engineering construction. To improve the flame retardant performance of synthetic polymer materials, the industry usually adds flame retardants to polymer materials. However, most of the currently used organic flame retardants are halogen-containing organic flame retardants, which have the problem of releasing harmful gases during combustion; in addition, in some application fields, such as communication devices with light transmission requirements, the final molded products of polymer materials need to have high transparency, while existing flame retardants will greatly reduce the transparency of the molded products. Summary of the Invention

[0003] In view of this, the embodiments of the present application provide a flame retardant compound and a resin composition. The flame retardant compound has high flame retardant performance, does not contain halogen, is safe and environmentally friendly; and can be uniformly mixed with various matrix resins to form a resin composition, and can also make the molded product of the resin composition have good transparency performance.

[0004] Specifically, in the first aspect of the embodiments of the present application, a flame retardant compound is provided. The flame retardant compound has a structural formula shown in formula (I):

[0005]

[0006] In formula (I), R1, R2, and R3 are all halogen-free groups. Each of R1, R2, and R3 independently selects any one of a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. Among R1, R2, and R3 connected to the same silicon atom, at least one is a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0007] The flame retardant compound provided by the embodiments of the present application uses 1,3,5-tris(2-hydroxyethyl) isocyanurate as the parent nucleus, and connects a silane substituted with an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, or a heteroaryl group to the hydroxyl group of the parent nucleus in the form of a silicon ether bond (Si-O). This special molecular structure design makes the flame retardant compound have a low melting point and a relatively high thermal decomposition temperature. The flame retardant compound can be used as a transparent flame retardant additive and uniformly mixed with various matrix resins to form a resin composition, so that the molded product of the resin composition has both high flame retardant performance and good transparency performance; and the flame retardant compound is a halogen-free flame retardant, which can avoid generating harmful substances during combustion and is safe and environmentally friendly.

[0008] The flame retardant compound of the present application is a flame retardant additive in a silicon-nitrogen system, possessing the excellent thermal stability, prevention of melt dripping, and flame retardant and smoke suppression properties of silicon-based flame retardants, as well as the excellent flame retardant effect exhibited by nitrogen-based flame retardants in terms of expansion and heat insulation. Specifically, silicon can promote the carbonization of polymer materials, forming a dense silicon-carbon layer that isolates flammable substances from oxygen and effectively prevents the molten dripping of polymer materials to form secondary combustion.

[0009] In the embodiments of the present application, the substituted or unsubstituted alkyl group is a substituted or unsubstituted C1-C30 alkyl group, the substituted or unsubstituted cycloalkyl group is a substituted or unsubstituted C3-C30 cycloalkyl group, the substituted or unsubstituted alkenyl group is a substituted or unsubstituted C2-C30 alkenyl group, the substituted or unsubstituted aryl group is a substituted or unsubstituted C6-C30 alkyl group, and the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted C2-C30 heteroaryl group. Group raw materials with suitable carbon atom numbers are easily available and the structures are controllable.

[0010] In the embodiments of the present application, the substituted or unsubstituted aryl group includes a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted binaphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted spirofluorene group, and a substituted or unsubstituted binaphthofluorenyl group. The aryl group can bring rigidity to the molecular structure of the flame retardant compound, which is beneficial to improving the flame retardant performance of the flame retardant compound.

[0011] In the embodiments of the present application, the substituted or unsubstituted heteroaryl group includes one of a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted benzopyrrolyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted triazinyl group, and a substituted or unsubstituted xanthenone group. The substituted or unsubstituted heteroaryl group can be connected to the silicon atom through a carbon atom or through a heteroatom. The heteroaryl group can bring rigidity to the molecular structure of the flame retardant compound, which is beneficial to improving the flame retardant performance of the flame retardant compound.

[0012] In the embodiments of the present application, the substituents on the substituted alkyl, substituted cycloalkyl, substituted alkenyl, substituted aryl, and substituted heteroaryl include one or more of deuterium atoms, tritium atoms, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl. The introduction of substituents can not only obtain a richer variety of flame retardants, but also achieve fine-tuning of the flame retardant properties to better meet different application requirements.

[0013] In the embodiments of the present application, in the formula (I), among R1, R2, and R3 connected to the same silicon atom, at least two of them independently selected from substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. Designing at least two of R1, R2, and R3 connected to the same silicon atom as substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl can increase the carbon-hydrogen ratio of the flame retardant compound molecules, facilitate carbon formation, obtain higher molecular bond energy, and better enable the flame retardant compound to have both high flame retardant performance and good light transmittance.

[0014] In the embodiments of the present application, all of R1, R2, and R3 in the formula (I) are independently selected from substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. Exemplarily, in some embodiments of the present application, all of R1, R2, and R3 in the formula (I) are substituted or unsubstituted alkyl. In some embodiments of the present application, all of R1 and R2 in the formula (I) are substituted or unsubstituted alkyl, and all of R3 are substituted or unsubstituted alkenyl. In some embodiments of the present application, all of R1 and R2 in the formula (I) are substituted or unsubstituted alkyl, and all of R3 are substituted or unsubstituted cycloalkyl. In some embodiments of the present application, all of R1, R2, and R3 in the formula (I) are substituted or unsubstituted aryl. In some embodiments of the present application, all of R1 and R2 in the formula (I) are substituted or unsubstituted alkyl, and all of R3 are substituted or unsubstituted aryl. In some embodiments of the present application, all of R1 and R2 in the formula (I) are substituted or unsubstituted aryl, and all of R3 are substituted or unsubstituted alkyl. In some embodiments of the present application, all of R1 and R2 in the formula (I) are substituted or unsubstituted aryl, and all of R3 are substituted or unsubstituted alkenyl. Designing all of R1, R2, and R3 connected to the same silicon atom as substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl can better enable the flame retardant compound to have both high flame retardant performance and good light transmittance.

[0015] In some embodiments of the present application, in formula (I), among R1, R2, and R3 connected to the same silicon atom, at least one is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. In some embodiments of the present application, in formula (I), among R1, R2, and R3 connected to the same silicon atom, at least two are a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. That is, an aromatic structure is introduced onto the silicon atom of the flame retardant compound, and the aromatic structure can bring rigidity to the molecular structure of the flame retardant compound, generating π-π stacking between molecules, thereby enhancing the overall structural stability of the flame retardant compound; moreover, the rearrangement reaction of the aromatic structure can promote the formation of a carbon layer with a conjugated aromatic structure in the high-temperature polymer material, which is beneficial to further improving the flame retardant and anti-dripping properties. The multiple flame retardant mechanisms of nitrogen, silicon, and the aromatic structure play a synergistic effect, enabling the flame retardant compound to have a more excellent flame retardant effect.

[0016] In the embodiments of the present application, the flame retardant compound is a solid at room temperature and a transparent liquid in a molten state. The fact that the flame retardant compound of the present application is a solid at room temperature is convenient for storage and transportation. The fact that the flame retardant compound is a transparent liquid in a molten state can enable the molded article of the resin composition to obtain better light transmittance when it is added to the resin composition, and can also better achieve melt mixing or good compatibility with other components in the resin composition, enabling the flame retardant compound to be uniformly distributed in the resin composition system.

[0017] In the embodiments of the present application, the thermal decomposition temperature T d 90 of the flame retardant compound with a 10% weight loss is greater than 170 °C. The flame retardant compound of the present application has a relatively high thermal decomposition temperature and excellent heat resistance.

[0018] In the embodiments of the present application, the melting point of the flame retardant compound is less than 230 °C. The flame retardant compound of the present application has a relatively low melting point, that is, it can be melted at a relatively low temperature, so that it can be applicable to various resin systems with a processing temperature higher than the melting point of the flame retardant compound, facilitating processing.

[0019] In the second aspect of the embodiments of the present application, a preparation method of the flame retardant compound described in the first aspect is provided, including:

[0020] Reacting 1,3,5-tris(2-hydroxyethyl) isocyanurate with raw material A in the presence of imidazole to obtain a flame retardant compound having the structural formula shown in formula (I).

[0021]

[0022] Raw material A.

[0023] The preparation method provided by the embodiments of the present application has a simple process and can achieve large-scale production.

[0024] In the third aspect of the embodiments of the present application, a resin composition is provided, which includes a matrix resin and a flame retardant. The flame retardant includes the flame retardant compound described in the first aspect of the embodiments of the present application. This resin composition can be various resin composition products used for molding products such as adhesive layers, film layers, and solid parts with flame retardant requirements.

[0025] In the embodiments of the present application, in the resin composition, the mass percentage of the flame retardant compound is 0.1% - 45%. The addition of an appropriate amount of the flame retardant compound is beneficial to improving the overall flame retardant performance of the resin composition, and at the same time enables other components such as the matrix resin in the resin composition to maintain a sufficient content to improve the comprehensive performance of the resin composition. Especially for resin compositions with transparency requirements, the addition of an appropriate amount of the flame retardant compound can obtain excellent transparency while achieving excellent flame retardancy.

[0026] In the embodiments of the present application, in the resin composition, the mass percentage of the matrix resin is 20% - 99.9%. An appropriate amount of the matrix resin can provide basic performance requirements for the resin composition.

[0027] In the embodiments of the present application, the matrix resin includes a thermoplastic elastomer, and the thermoplastic elastomer includes one or more of SIS resin, SBS resin, SEBS resin, SEPS resin, thermoplastic polyolefin elastomer, thermoplastic styrene elastomer, and polyurethane thermoplastic elastomer.

[0028] In the embodiments of the present application, the resin composition further includes one or more of a tackifying resin, a plasticizer, an antioxidant, an anti-ultraviolet agent, other flame retardants, a coupling agent, a crosslinking agent, and a softening agent. The addition of different additives can improve the comprehensive performance of the resin composition.

[0029] In the embodiments of the present application, the other flame retardants include one or more of a phosphorus-based flame retardant, a halogen-based flame retardant, a silicone-based flame retardant, an inorganic flame retardant, and an intumescent flame retardant.

[0030] In the embodiments of the present application, the melt viscosity of the resin composition at 175°C is 8000 CPS - 20000 CPS (centipoise·second); the visible light transmittance of the molded article of the resin composition with a thickness of 0.2 mm is greater than or equal to 20%. The resin composition has a low melt viscosity, which is beneficial to processing and molding operations; the molded article of the resin composition has a high visible light transmittance, which can better meet the application scenarios with transparency requirements, such as transparent cables.

[0031] In the fourth aspect of the embodiments of the present application, a molded article is provided, which includes the molded article of the resin composition described in the third aspect of the embodiments of the present application. This molded article can have both high flame retardant performance and good transparency performance.

[0032] In the fifth aspect of the embodiments of the present application, there is provided an application of the flame retardant compound described in the first aspect or the resin composition described in the third aspect in adhesives, protective covers or protective layers for communication devices, cable protective covers or protective layers, and protective covers or protective layers for vehicles.

[0033] In the sixth aspect of the embodiments of the present application, there is provided a device, which includes a molded product of the flame retardant compound described in the first aspect or the resin composition described in the third aspect.

[0034] In the embodiments of the present application, the device includes a first component and a second component, and an adhesive layer connected between the first component and the second component, and the adhesive layer includes a molded product of the flame retardant compound or the resin composition.

[0035] In the embodiments of the present application, the device includes a device body and a protective cover or protective layer covering the device body, and the protective cover or protective layer contains a molded product of the flame retardant compound described in the first aspect or the resin composition described in the third aspect.

[0036] In the seventh aspect of the embodiments of the present application, there is provided a cable, which includes at least one optical fiber or at least one wire, and a cable protective cover wrapping the at least one optical fiber or at least one wire, and the cable protective cover contains a molded product of the flame retardant compound described in the first aspect or the resin composition described in the third aspect.

[0037] The embodiments of the present application further provide a communication system, which includes the device described in the sixth aspect or the cable described in the seventh aspect. BRIEF DESCRIPTION OF THE DRAWINGS

[0038] Figure 1 It is a schematic cross-sectional structure diagram of a device 100 provided by an embodiment of the present application;

[0039] Figure 2 It is a schematic cross-sectional structure diagram of a device 100 provided by another embodiment of the present application;

[0040] Figure 3 It is a schematic cross-sectional structure diagram of a cable 200 provided by an embodiment of the present application;

[0041] Figure 4 It is a schematic cross-sectional structure diagram of a cable 200 provided by another embodiment of the present application;

[0042] Figure 5 It is a DSC (Differential Scanning Calorimetry) curve of the flame retardant compound with the structure of formula (1);

[0043] Figure 6 Thermogravimetric analysis curve of the flame retardant compound with the structure of formula (1);

[0044] Figure 7 DSC (Differential Scanning Calorimetry) curve of the flame retardant compound with the structure of formula (2);

[0045] Figure 8 Thermogravimetric analysis curve of the flame retardant compound with the structure of formula (2). Detailed implementation manners

[0046] The embodiments of the present application will be described below with reference to the accompanying drawings in the embodiments of the present application.

[0047] The popularization of 5G communication has improved the communication transmission speed, but at the same time, the higher heat generation has brought more potential safety hazards. To ensure the use safety of communication devices, the relevant materials used in communication devices need to have high flame retardancy. The commonly used method in the industry is to add flame retardants to the polymer materials required for manufacturing communication devices. However, most of the currently used organic flame retardants are halogen-containing organic flame retardants, which have the problem of releasing harmful gases when burning. In addition, with the development of communication devices, aesthetics and concealment have also become an important part of applications. To adapt to the aesthetic requirements of multiple application scenarios, the corresponding materials of communication components often need to have good transparency. In addition, in some optical applications, the transparency in the visible light band will facilitate the processing and use of devices. To enable the polymer materials required for communication devices to have both high flame retardant performance and good transparency to simultaneously meet the requirements of flame retardancy and transparency, the embodiments of the present application provide a flame retardant compound, which has high flame retardant performance, does not contain halogen, is safe and environmentally friendly; and can be uniformly mixed with various matrix resins to form a resin composition, and can also make the molded product of the resin composition have good transparency.

[0048] The flame retardant compound provided by the embodiments of the present application has the structural formula shown in formula (I):

[0049]

[0050] In formula (I), R1, R2 and R3 are all halogen-free groups (i.e., groups that do not contain halogen), and each of R1, R2 and R3 independently selects any one of a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group, and among R1, R2 and R3 connected to the same silicon atom, at least one is a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.

[0051] The flame retardant compound provided by the embodiment of the present application uses 1,3,5-tris(2-hydroxyethyl)isocyanurate as the core, and connects silanes substituted with alkyl, cycloalkyl, alkenyl, aryl or heteroaryl groups to the hydroxyl groups of the core in the form of a silicon ether bond (Si-O). This special molecular structure design endows the flame retardant compound with a low melting point and a relatively high thermal decomposition temperature. The flame retardant compound can be used as a flame retardant additive to be uniformly mixed with various matrix resins to form a resin composition, so that the molded product of the resin composition has both high flame retardant performance and good transparency; and the flame retardant compound is a halogen-free flame retardant, which can avoid the generation of harmful substances during combustion, and is safe and environmentally friendly.

[0052] The flame retardant compound of the present application is a silicon-nitrogen system flame retardant additive, which combines the excellent thermal stability, anti-melt dripping and flame retardant and smoke suppression properties of silicon-based flame retardants, and the excellent flame retardant effect exhibited by nitrogen-based flame retardants in terms of expansion and heat insulation. Specifically, silicon elements can promote the carbonization of polymer materials, generate a dense silicon-carbon layer, isolate combustibles from oxygen, and effectively prevent the molten dripping of polymer materials to form secondary combustion.

[0053] In the embodiment of the present application, the three R1s in formula (I) can be the same or different groups, the three R2s can be the same or different groups, and the three R3s can be the same or different groups. In some embodiments, the three R1s in formula (I) are the same group, the three R2s are the same group, and the three R3s are the same group.

[0054] In the embodiment of the present application, the substituents on the substituted alkyl, substituted cycloalkyl, substituted alkenyl, substituted aryl, and substituted heteroaryl include one or more of deuterium atoms, tritium atoms, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl. The introduction of substituents can not only obtain a richer variety of flame retardants, but also achieve fine-tuning of the flame retardant performance to better meet different application requirements.

[0055] In some embodiments of the present application, the substituted or unsubstituted alkyl group can be a substituted or unsubstituted C1-C30 alkyl group, or a substituted or unsubstituted C1-C20 alkyl group. Specifically, for example, it can be a substituted or unsubstituted C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20 alkyl group. The alkyl group can be a straight-chain alkyl group or a branched-chain alkyl group. Exemplarily, the substituted or unsubstituted C1 alkyl group is the substituted or unsubstituted methyl group, the substituted or unsubstituted C2 alkyl group is the substituted or unsubstituted ethyl group, the substituted or unsubstituted C3 alkyl group is the substituted or unsubstituted n-propyl group or isopropyl group, the substituted or unsubstituted C4 alkyl group is the substituted or unsubstituted n-butyl group, isobutyl group or tert-butyl group, and so on for other substituted or unsubstituted alkyl groups. In some embodiments of the present application, the substituted alkyl group can be a deuterated alkyl group, an arylalkyl group. For example, the deuterated alkyl group can be deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl; the arylalkyl group can be benzyl, phenethyl, etc. That R1, R2, and R3 are substituted or unsubstituted alkyl groups can impart polarity to the flame retardant compound molecule, adjust the molecular polarity, and better achieve mixing with various matrix resins.

[0056] In some embodiments of the present application, the substituted or unsubstituted cycloalkyl group can be a substituted or unsubstituted C3-C30 cycloalkyl group, or a substituted or unsubstituted C3-C20 cycloalkyl group. Specifically, for example, it can be a substituted or unsubstituted C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20 cycloalkyl group. Exemplarily, the substituted or unsubstituted C3 cycloalkyl group is the substituted or unsubstituted cyclopropyl group, the substituted or unsubstituted C5 cycloalkyl group is the substituted or unsubstituted cyclopentyl group, the substituted or unsubstituted C6 alkyl group is the substituted or unsubstituted cyclohexyl group, and so on for other substituted or unsubstituted cycloalkyl groups. The substituted cycloalkyl group can be, for example, deuterated cyclopentyl, tritiated cyclopentyl, methyl-substituted cyclopentyl, etc.

[0057] In some embodiments of the present application, the substituted or unsubstituted alkenyl group can be a substituted or unsubstituted C2-C30 alkenyl group, or a substituted or unsubstituted C2-C20 alkenyl group. Specifically, for example, it can be a substituted or unsubstituted C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20 alkenyl group. The alkenyl group can be a straight-chain alkenyl group or a branched-chain alkenyl group. Exemplarily, the substituted or unsubstituted C2 alkenyl group is the substituted or unsubstituted vinyl group, the substituted or unsubstituted C3 alkenyl group is the substituted or unsubstituted propenyl group, and so on for other substituted or unsubstituted alkenyl groups. That R1, R2, and R3 are substituted or unsubstituted alkenyl groups can impart reactive activity to the flame retardant compound.

[0058] In some embodiments of the present application, the substituted or unsubstituted aryl group can be a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C6-C20 aryl group. Specifically, for example, it can be a substituted or unsubstituted C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30 aryl group. The substituted or unsubstituted aryl group can be a monocyclic aryl group or a polycyclic aryl group, and the polycyclic aryl group can be a fused-ring type or a non-fused-ring type (such as biphenyls). Exemplarily, the substituted or unsubstituted aryl group is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted binaphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted spirofluorene group, a substituted or unsubstituted binaphthofluorenyl group. In some embodiments of the present application, the substituted aryl group can be a deuterated aryl group, an alkylaryl group, an alkylsilylaryl group. The deuterated aryl group can be, for example, a deuterated phenyl group, a deuterated biphenyl group, a deuterated naphthyl group; the alkylaryl group can be an aryl group substituted with one or more of substituted or unsubstituted methyl, ethyl, isopropyl, tert-butyl, specifically, for example, a phenyl group substituted with methyl, a phenyl group substituted with ethyl, a phenyl group substituted with isopropyl, a phenyl group substituted with tert-butyl, a phenyl group substituted with deuterated methyl, a phenyl group substituted with deuterated ethyl, a phenyl group substituted with deuterated isopropyl, a phenyl group substituted with deuterated tert-butyl, a tritiated biphenyl group, a biphenyl group substituted with methyl, a biphenyl group substituted with ethyl, a biphenyl group substituted with isopropyl, a biphenyl group substituted with tert-butyl, a biphenyl group substituted with deuterated methyl, a biphenyl group substituted with deuterated ethyl, a biphenyl group substituted with deuterated isopropyl, a biphenyl group substituted with deuterated tert-butyl, a naphthyl group substituted with methyl, a naphthyl group substituted with ethyl, a naphthyl group substituted with isopropyl, a naphthyl group substituted with tert-butyl, a naphthyl group substituted with deuterated methyl, a naphthyl group substituted with deuterated ethyl, a naphthyl group substituted with deuterated isopropyl, a naphthyl group substituted with deuterated tert-butyl, etc.; the alkylsilylaryl group can be, for example, a phenyl group substituted with trimethylsilyl. The aryl group can bring rigidity to the molecular structure of the flame retardant compound, which is beneficial to improving the flame retardant performance of the flame retardant compound.

[0059] In some embodiments of the present application, the substituted or unsubstituted heteroaryl group can be a substituted or unsubstituted C2-C30 heteroaryl group, or a substituted or unsubstituted C2-C20 heteroaryl group; specifically, for example, it can be a substituted or unsubstituted C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20 heteroaryl group. The substituted or unsubstituted heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group. The heteroatoms in the heteroaryl group can include one or more of oxygen, nitrogen, and sulfur. Exemplarily, the substituted or unsubstituted heteroaryl group includes a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted benzopyrrolyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted xanthenone group. The substituted heteroaryl group can be a deuterated heteroaryl group, an alkyl heteroaryl group, or an alkylsilyl heteroaryl group. The substituted heteroaryl group can be, for example, a substituted or unsubstituted heteroaryl group substituted with one or more of methyl, ethyl, isopropyl, and tert-butyl. Specifically, for example, it is a methyl-substituted heteroaryl group (such as a methyl-substituted pyridyl group), an ethyl-substituted heteroaryl group, an isopropyl-substituted heteroaryl group, a tert-butyl-substituted heteroaryl group, a deuterated methyl-substituted heteroaryl group, a deuterated ethyl-substituted heteroaryl group, a deuterated isopropyl-substituted heteroaryl group, or a deuterated tert-butyl-substituted heteroaryl group. The substituted or unsubstituted heteroaryl group can be connected to the silicon atom through a carbon atom or through a heteroatom. The heteroaryl group can impart rigidity to the molecular structure of the flame retardant compound, which is beneficial to improving the flame retardancy of the flame retardant compound.

[0060] In some embodiments of the present application, in formula (I), among R1, R2, and R3 connected to the same silicon atom, at least one is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. In some embodiments of the present application, in formula (I), among R1, R2, and R3 connected to the same silicon atom, at least two are a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. That is, an aromatic structure is introduced onto the silicon atom of the flame retardant compound. The aromatic structure can impart rigidity to the molecular structure of the flame retardant compound, and π-π stacking occurs between molecules, thereby enhancing the overall structural stability of the flame retardant compound; moreover, the rearrangement reaction of the aromatic structure can promote the formation of a carbon layer with a conjugated aromatic structure in the high-temperature polymer material, which is beneficial to further improving the flame retardant and anti-dripping properties. The multiple flame retardant mechanisms of nitrogen, silicon, and the aromatic structure play a synergistic effect, enabling the flame retardant compound to have a more excellent flame retardant effect.

[0061] In some embodiments of the present application, in formula (I), among R1, R2, and R3 attached to the same silicon atom, at least two of them are independently selected from substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. Designing at least two of R1, R2, and R3 attached to the same silicon atom as substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl can increase the carbon-hydrogen ratio of the flame retardant compound molecule, facilitate carbon formation, obtain a higher molecular bond energy, and better enable the flame retardant compound to have both high flame retardant performance and good light transmittance.

[0062] In an embodiment of the present application, all of R1, R2, and R3 in formula (I) are independently selected from substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. The three R1 in formula (I) can be the same or different groups, the three R2 can be the same or different groups, and the three R3 can be the same or different groups. Exemplarily, in some embodiments of the present application, all of R1, R2, and R3 in formula (I) are substituted or unsubstituted alkyl. In some embodiments of the present application, all of R1, R2, and R3 in formula (I) are substituted or unsubstituted alkyl, and all R2 are substituted or unsubstituted branched alkyl. In some embodiments of the present application, all of R1, R2 in formula (I) are substituted or unsubstituted alkyl, and all R3 are substituted or unsubstituted alkenyl. In some embodiments of the present application, all of R1, R2 in formula (I) are substituted or unsubstituted alkyl, and all R3 are substituted or unsubstituted cycloalkyl. In some embodiments of the present application, all of R1, R2, and R3 in formula (I) are substituted or unsubstituted aryl. In some embodiments of the present application, all of R1, R2 in formula (I) are substituted or unsubstituted alkyl, and all R3 are substituted or unsubstituted aryl. In some embodiments of the present application, all of R1, R2 in formula (I) are substituted or unsubstituted aryl, and all R3 are substituted or unsubstituted alkyl. In some embodiments of the present application, all of R1, R2 in formula (I) are substituted or unsubstituted aryl, and all R3 are substituted or unsubstituted alkenyl. Designing all of R1, R2, and R3 attached to the same silicon atom as substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl can better enable the flame retardant compound to have both high flame retardant performance and good light transmittance.

[0063] In the embodiments of the present application, all R1, R2 and R3 in formula (I) are substituted or unsubstituted alkyl groups, and at least one of them is a substituted or unsubstituted branched alkyl group. In some embodiments of the present application, in formula (I), among R1, R2 and R3 connected to the same silicon atom, at least one of them is a substituted or unsubstituted branched alkyl group. The branched alkyl group is beneficial to improving the flame retardant performance of the flame retardant compound.

[0064] In some embodiments of the present application, the flame retardant compound has the structural formulas shown in formulas (1) to (11):

[0065]

[0066]

[0067] In the embodiments of the present application, the flame retardant compound is a solid at room temperature and a transparent liquid in the molten state. The fact that the flame retardant compound of the present application is a solid at room temperature is convenient for storage and transportation. The fact that the flame retardant compound is a transparent liquid in the molten state can enable the resin composition molding to obtain better light transmittance when it is added to the resin composition, and can also better achieve melting mixing or good compatibility with other components in the resin composition, so that the flame retardant compound can be evenly distributed in the resin composition system.

[0068] In an embodiment of the present application, a flame retardant compound having the structure shown in formula (2) is added to the polyurethane resin system at a mass ratio of 10% to form a resin composition, and the resin composition is maintained at 140 °C for 3 hours, and the resin composition becomes a transparent molten state.

[0069] In the embodiments of the present application, the melting point of the flame retardant compound is less than 230 °C. In some embodiments of the present application, the melting point of the flame retardant compound is less than 200 °C. In the embodiments of the present application, the melting point of the flame retardant compound is less than 180 °C. In the embodiments of the present application, the melting point of the flame retardant compound is less than 150 °C. The flame retardant compound of the present application has a lower melting point, that is, it can be melted at a lower temperature, so that it can be applicable to various resin systems with a processing temperature higher than the melting point of the flame retardant compound, which is convenient for processing.

[0070] In the embodiments of the present application, the thermal decomposition temperature T d 90 of the flame retardant compound with 10% thermal weight loss is greater than 170 °C. In some embodiments of the present application, the thermal decomposition temperature T d 90 of the flame retardant compound with 10% thermal weight loss is greater than 180 °C. In some embodiments of the present application, the thermal decomposition temperature T d 90 of the flame retardant compound with 10% thermal weight loss is greater than 200 °C. In some embodiments of the present application, the thermal decomposition temperature T d90 is greater than 220 °C. The flame retardant compound of the present application has a high thermal decomposition temperature and excellent heat resistance.

[0071] For the same flame retardant compound, its melting point is less than the thermal decomposition temperature T at 10% weight loss d 90.

[0072] The flame retardant compound provided by the embodiment of the present application can be characterized and its molecular structure determined by combining techniques such as elemental analyzer, infrared spectroscopy, nuclear magnetic resonance spectroscopy, X-ray diffraction, and mass spectrometry.

[0073] The embodiment of the present application also provides a preparation method of the above-mentioned flame retardant compound, including:

[0074] React 1,3,5-tris(2-hydroxyethyl)isocyanurate with raw material A in the presence of imidazole to obtain a flame retardant compound with the structural formula shown in formula (I),

[0075]

[0076] Raw material A.

[0077] In some embodiments of the present application, the above preparation method specifically includes:

[0078] Dissolve 1,3,5-tris(2-hydroxyethyl)isocyanurate in an organic solvent, cool to 0 °C, then add imidazole and raw material A in sequence, raise the temperature of the reaction solution to room temperature and let it react overnight. After the reaction is completed, extract the product, and dry and subject the obtained organic phase to column chromatography separation to obtain the target product.

[0079] The organic solvent can be, for example, N,N-dimethylformamide (DMF). After the temperature of the reaction solution is raised to room temperature and it reacts overnight, water can be added to the reaction solution to quench the reaction.

[0080] The preparation method provided by the embodiment of the present application has a simple process and can be scaled up for production.

[0081] The flame retardant compound of the embodiment of the present application can be added as a flame retardant to various organic systems with flame retardant requirements, especially as a transparent flame retardant to organic systems with both flame retardant and transparency requirements. Moreover, due to the excellent flame retardancy of the flame retardant compound of the embodiment of the present application, a small amount of addition can meet the required flame retardant grade requirements, thereby being able to better reduce the impact of the addition of the flame retardant compound on the transparency of the organic system and obtaining more excellent transparency.

[0082] The embodiments of the present application also provide a resin composition, which includes a matrix resin and a flame retardant. The flame retardant includes the flame retardant compound described above in the embodiments of the present application. A flame retardant is an auxiliary agent that can prevent the resin from being ignited or inhibit the spread of flames and is used for flame retardancy. The flame retardant compound of the embodiments of the present application is an additive flame retardant.

[0083] It can be understood that the resin composition can be various resin composition products for forming products such as a bonding layer, a film layer, a solid part, etc. with flame retardant requirements. The matrix resin can be selected according to actual application needs, and the content of the matrix resin and the content of the flame retardant compound can also be selected according to actual needs.

[0084] In some embodiments of the present application, in the resin composition, the mass percentage of the flame retardant compound is 0.1%-45%. In some embodiments, the mass percentage of the flame retardant compound is 1%-30%. In some embodiments, the mass percentage of the flame retardant compound is 5%-20%. Exemplarily, the mass percentage of the flame retardant compound is 0.1%, 1%, 3%, 5%, 8%, 10%, 12%, 15%, 20%, 25%, 30%, 35%, 40%, 45%. The addition of an appropriate amount of the flame retardant compound is beneficial to improving the overall flame retardant performance of the resin composition, and at the same time can keep other components such as the matrix resin in the resin composition at a sufficient content to improve the comprehensive performance of the resin composition. Especially for resin compositions with transparency requirements, the addition of an appropriate amount of the flame retardant compound can better obtain excellent transparency while obtaining excellent flame retardancy.

[0085] In some embodiments of the present application, in the resin composition, the mass percentage of the matrix resin is 20%-99.9%. In some embodiments, the mass percentage of the matrix resin is 40%-70%. Exemplarily, the mass percentage of the matrix resin is 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, 99%, 99.9%.

[0086] In the embodiments of the present application, the matrix resin can be various resin materials with a melting point or processing temperature higher than that of the flame retardant compounds in the embodiments of the present application. In some embodiments, the matrix resin includes thermoplastic elastomers, and the thermoplastic elastomers include one or more of SIS resin, SBS resin, SEBS resin, SEPS resin, thermoplastic polyolefin elastomer, thermoplastic styrene elastomer, and polyurethane thermoplastic elastomer. SBS resin, namely styrene-butadiene-styrene, also known as thermoplastic styrene-butadiene rubber, has both the good solubility and thermoplasticity of polystyrene (PS) and the good flexibility and resilience of cis-butadiene rubber (PB). SEBS resin is a saturated thermoplastic elastomer obtained by hydrogenating and modifying SBS resin. After hydrogenation modification, its oxidation resistance, ultraviolet resistance, and heat resistance are improved. SIS resin, namely styrene-isoprene-styrene. SEPS resin is a saturated thermoplastic elastomer obtained by hydrogenating and modifying SIS resin. After hydrogenation modification, its oxidation resistance, ultraviolet resistance, and heat resistance are improved. SIS resin, SBS resin, SEBS resin, and SEPS resin are all thermoplastic elastomers, showing rubber elasticity at room temperature and plasticity when heated, and can be used in fields such as tapes, hoses, cables, and medical devices.

[0087] In some embodiments of the present application, considering factors such as comprehensive performance and cost, the matrix resin can be two or more of SIS resin, SBS resin, SEBS resin, and SEPS resin. Exemplarily, the matrix resin includes SIS resin and SEBS resin, SIS resin and SBS resin, SBS resin and SEPS resin.

[0088] According to actual needs, in some embodiments of the present application, the resin composition may further include one or more of tackifying resin, plasticizer, antioxidant, ultraviolet absorber, other flame retardants, coupling agent, crosslinking agent, and softening agent.

[0089] Among them, the tackifying resin can increase the viscosity of the system. The tackifying resin can be one or more of natural resin and petroleum resin. The petroleum resin can be aliphatic petroleum resin, alicyclic petroleum resin, aromatic petroleum resin, aliphatic / aromatic copolymer resin, and hydrogenated petroleum resin. The aliphatic petroleum resin can be C5 aliphatic petroleum resin, the alicyclic petroleum resin can be DCPD alicyclic petroleum resin (dicyclopentadiene), the aromatic petroleum resin can be C9 aromatic petroleum resin, the aliphatic / aromatic copolymer resin can be C5 / C9 aliphatic / aromatic copolymer petroleum resin, and the hydrogenated petroleum resin can be C5 hydrogenated petroleum resin, C9 hydrogenated petroleum resin, and DCPD hydrogenated petroleum resin.

[0090] Plasticizers can weaken the intermolecular forces of polymer molecules, lower the melting temperature and melt viscosity, and improve the molding processability and flexibility of resin composition products. The plasticizer can include naphthenic oil, hydroxyl silicone oil, etc.

[0091] Antioxidants can enhance the antioxidant performance of the resin composition, and ultraviolet stabilizers can enhance the ultraviolet light resistance of the resin composition, thereby increasing the service life of the molded resin composition.

[0092] Other flame retardants refer to flame retardants other than the flame retardant compounds in the embodiments of the present application. The other flame retardants can include one or more of phosphorus-based flame retardants, halogen-based flame retardants, silicone-based flame retardants, inorganic flame retardants, and intumescent flame retardants. Among them, the phosphorus-based flame retardants can include one or more of ammonium polyphosphate, phosphate ester flame retardants, and aluminum diethyl phosphinate. The phosphate ester flame retardants can be, for example, triphenyl phosphate, tricresyl phosphate, propylphenyl phosphate, styrene-butadiene phosphate, and tolyldiphenyl phosphate. The halogen-based flame retardants can include decabromodiphenyl ether (DBDPO), tetrabromobisphenol A, bis(2,3-dibromopropyl) ether (TBAB), octabromodiphenyl ether (OBDPO), brominated polystyrene, brominated epoxy, and tetrabromobisphenol A carbonate oligomer. The silicone-based flame retardants can include silicone oil, silicone resin, functional group-containing polysiloxane, polycarbonate-silicone copolymer acrylate-silicone composite material, and silicone gel. The inorganic flame retardants can include aluminum hydroxide, magnesium hydroxide, expanded graphite, borate, aluminum oxalate, zinc sulfide, aluminum trihydrate, boehmite, calcium carbonate, etc. The intumescent flame retardant mainly consists of three parts: a charring agent (carbon source), a charring catalyst (acid source), and an expanding agent (gas source). The charring agent is a carbon-rich polyfunctional substance, which can be pentaerythritol (PER) and its diacetal, triacetal, etc. The charring catalyst is a compound that can release inorganic acid under heating conditions, such as ammonium polyphosphate (APP). The expanding agent is a compound that releases inert gas when heated, which can be ammonium and amide substances, such as urea, melamine, dicyandiamide, and their derivatives. The above-mentioned other flame retardants can be used in combination with the flame retardant compounds in the embodiments of the present application as needed.

[0093] In the embodiments of the present application, the melt viscosity of the resin composition at 175 °C is 8000 CPS - 20000 CPS (centipoise·second). In some embodiments, the melt viscosity of the resin composition is 8000 CPS, 10000 CPS, 11000 CPS, 13000 CPS, 15000 CPS, 18000 CPS, 20000 CPS. The resin composition has a lower melt viscosity, which is beneficial to the processing and molding operations.

[0094] In the embodiments of the present application, the visible light (380 nm - 760 nm) transmittance of the molded article of the resin composition with a thickness of 0.2 mm is greater than or equal to 20%. In some embodiments, the visible light (380 nm - 760 nm) transmittance of the molded article of the resin composition is, for example, 20%, 23%, 25%, 30%, 33%, 35%, 40%, 50%, 60%, 70%, 80%, 85%, 87%. The molded article of the resin composition has a high visible light transmittance and can better meet the application scenarios with transparency requirements, such as transparent cables.

[0095] The embodiments of the present application further provide a molded article, including the molded article of the resin composition in the above embodiments of the present application.

[0096] The embodiments of the present application further provide the application of the above flame retardant compound or the above resin composition in adhesives, adhesive layers for communication devices, protective sleeves or protective layers for vehicles. The resin composition can be used as an adhesive for directly bonding various components, or for bonding cables, devices, etc. to the surface of a carrier.

[0097] See Figure 1 and Figure 2 , the embodiments of the present application further provide a device 100, which includes the above flame retardant compound or the molded article of the above resin composition. The device 100 can be various optical devices, electronic devices, optoelectronic devices, communication devices, etc.

[0098] See Figure 1 , in some embodiments of the present application, the device 100 includes a first component 101 and a second component 102, and an adhesive layer 103 connected between the first component 101 and the second component 102. The adhesive layer 103 includes the above flame retardant compound or the molded article of the above resin composition. The device 100 can be, for example, an optical splitter, etc.

[0099] See Figure 2 , in some embodiments of the present application, the device 100 includes a device body 104 and a protective sleeve or protective layer 105 covering the device body 104. The protective sleeve or protective layer 105 includes the above flame retardant compound or the molded article of the above resin composition. The device 100 can be, for example, a router, etc.

[0100] See Figure 3 and Figure 4 , Figure 3 is a schematic cross-sectional structure diagram of a cable 200 provided in an embodiment of the present application, Figure 4Schematic cross-sectional structure diagram of the cable 200 provided by another embodiment of the present application. The cable 200 provided by the embodiment of the present application includes at least one optical fiber or at least one wire 201, and a cable protective sleeve 202 that wraps the at least one optical fiber or the at least one wire 201. The cable protective sleeve 202 contains the above-mentioned flame retardant compound or a molded article of the above-mentioned resin composition. The cable protective sleeve is used to protect and support the optical fiber or the wire, playing a role of protection and reinforcement.

[0101] In some embodiments of the present application, the cable 200 is an optical cable. The cable 200 may include one or more optical fibers and a cable protective sleeve that wraps the one or more optical fibers. An optical cable is a communication line used to realize optical signal transmission, and the optical fiber is the signal transmission medium. At the transmitting end of the optical cable, the information to be transmitted is converted into an electrical signal, and then transmitted to the laser beam through a laser. The intensity of the light changes with the frequency of the electrical signal and is transmitted through the optical fiber. At the receiving end, the detector receives the optical signal and converts it into an electrical signal, and restores the original information after processing.

[0102] In some embodiments of the present application, the cable 200 is a cable. The cable 200 includes one or more wires and a cable protective sleeve that wraps the one or more wires.

[0103] In some embodiments of the present application, the cable 200 is a hybrid fiber-optic and electrical cable. The cable 200 includes one or more wires, one or more optical fibers, and a cable protective sleeve that wraps the one or more wires and the one or more optical fibers.

[0104] In the embodiment of the present application, part or all of the cable protective sleeve 202 is made of the resin composition described above in the embodiment of the present application.

[0105] For the cable in the embodiment of the present application, by using the resin composition described above in the embodiment of the present application to prepare the cable protective sleeve, flame retardancy and transparency can be achieved simultaneously, improving the use safety and convenience of the cable, and providing a basis for the application of the cable in fields such as the military field, the medical field (such as medical devices like endoscopes), the construction field (such as multi-functional integration of lighting, music, etc.), the transportation field (such as multi-functional integration of in-vehicle entertainment, navigation, safety, etc.), and the industrial field (such as machine vision, laser cutting, etc.).

[0106] The embodiment of the present application also provides a communication system, which includes the above-mentioned device or cable.

[0107] The embodiments of the present application will be further described below with multiple examples.

[0108] Example 1

[0109] Preparation of the flame retardant compound 1 having the structure of formula (1):

[0110] Dissolve 1,3,5-tris(2-hydroxyethyl)isocyanurate (1 g, 3.831 mmol) in 10 mL of N,N-dimethylformamide (DMF). After cooling to 0 °C, add imidazole (1.302 g, 19.155 mmol, 5 eq) and tert-butyldimethylsilyl chloride (2.30 g, 15.324 mmol, 4 eq) successively. Let the reaction mixture warm to room temperature overnight. Add 10 mL of water to the reaction mixture to quench the reaction, then extract the product 3 times with ethyl acetate (20 mL). Combine the organic phases, dry, and concentrate by rotary evaporation to obtain a crude oily product. Further purification by column chromatography gives the target product (2.2 g, 3.642 mmol) with a yield of 95%, which is a grayish-white solid. The NMR results of the target product are as follows: 1H NMR (400 MHz, CDCl3) δ 4.06 (t, J = 6.3 Hz, 6H), 3.82 (t, J = 6.3 Hz, 6H), 0.89 (s, 27H), 0.07 (s, 18H).

[0111] The above reaction formula is as follows:

[0112]

[0113] Example 2

[0114] Preparation of the flame retardant compound 2 with the structure of formula (2):

[0115] Dissolve 1,3,5-tris(2-hydroxyethyl)isocyanurate (1 g, 3.831 mmol) in 10 mL of DMF. After cooling to 0 °C, add imidazole (1.302 g, 19.155 mmol, 5 eq) and tert-butyldiphenylchlorosilane (4.212 g, 15.324 mmol, 4 eq) successively. Let the reaction mixture warm to room temperature overnight. Add 10 mL of water to the reaction mixture to quench the reaction, then extract the product 3 times with ethyl acetate (20 mL). Combine the organic phases, dry, and concentrate by rotary evaporation to obtain a crude milky-white solid product. Further purification by column chromatography gives the target product with a yield of 99%, which is a white solid. The NMR results of the target product are as follows: 1H NMR (400 MHz, CDCl3) δ 7.63 (d, J = 6.7 Hz, 10H), 7.42 (t, J = 7.3 Hz, 10H), 7.36 (t, J = 7.2 Hz, 10H), 3.99 (t, J = 6.0 Hz, 6H), 3.84 (t, J = 5.9 Hz, 6H), 1.02 (s, 27H).

[0116] The above reaction formula is as follows:

[0117]

[0118] Example 3

[0119] Preparation of resin composition:

[0120] The flame retardant compound 2 with the structure of formula (2) is prepared into resin composition 1 together with the matrix resin, tackifying resin, plasticizer, antioxidant, ultraviolet light absorber and other flame retardants. The component ratios of resin composition 1 are shown in Table 1.

[0121] Example 4

[0122] Preparation of resin composition:

[0123] The flame retardant compound 2 with the structure of formula (2) is prepared into resin composition 2 together with the matrix resin, tackifying resin, plasticizer, antioxidant, ultraviolet light absorber and other flame retardants. The component ratios of resin composition 2 are shown in Table 1.

[0124] Example 5

[0125] Preparation of resin composition:

[0126] The flame retardant compound 1 with the structure of formula (1) is prepared into resin composition 3 together with the matrix resin, tackifying resin, plasticizer, antioxidant, ultraviolet light absorber and other flame retardants. The component ratios of resin composition 3 are shown in Table 1.

[0127] Comparative Example 1

[0128] The same matrix resin, tackifying resin, plasticizer, antioxidant and ultraviolet light absorber as in Example 1 are prepared into a resin composition. The component ratios of the resin composition are shown in Table 1.

[0129] Comparative Example 2

[0130] The same matrix resin, tackifying resin, plasticizer, antioxidant, ultraviolet light absorber and commercial flame retardant as in Example 1 are prepared into a resin composition. The component ratios of the resin composition are shown in Table 1.

[0131] The flame retardant compound 1 with the structure of formula (1) prepared in Example 1 and the flame retardant compound 2 with the structure of formula (2) prepared in Example 2 are tested by differential scanning calorimetry (DSC, Differential Scanning Calorimetry), and the test results are as Figure 5 and Figure 7 shown; the flame retardant compound 1 with the structure of formula (1) prepared in Example 1 and the flame retardant compound 2 with the structure of formula (2) prepared in Example 2 are tested by a thermogravimetric analyzer (TGA, Thermal Gravimetric Analyzer), and the test results are as Figure 6 and Figure 8 shown.

[0132] Among them, Figure 5DSC curve of flame retardant compound 1 with the structure of formula (1), from Figure 5 it can be seen that this flame retardant compound has a relatively low melting temperature, the endothermic peak Tm is 56.7 °C, and Tm corresponds to the melting or phase change process of the sample. Figure 6 TG curve of flame retardant compound 1 with the structure of formula (1), from Figure 6 it can be seen that this flame retardant compound has a relatively high thermal decomposition temperature, the thermal decomposition temperature Td(90%) is 232 °C, and Td(90%) is the temperature when the sample loses 10% of its weight upon heating.

[0133] Figure 7 DSC curve of flame retardant compound 2 with the structure of formula (2), from Figure 7 it can be seen that this flame retardant compound has a relatively low melting temperature, the endothermic peak Tm is 113.6 °C, and Tm corresponds to the melting or phase change process of the sample. Figure 8 TG curve of flame retardant compound 2 with the structure of formula (2), from Figure 8 it can be seen that this flame retardant compound has a relatively high thermal decomposition temperature, the thermal decomposition temperature Td(90%) is 372.5 °C, and Td(90%) is the temperature when the sample loses 10% of its weight upon heating.

[0134] From Figure 5 and Figure 7 it can be seen that the flame retardant compound 1 with the structure of formula (1) in Example 1 and the flame retardant compound 2 with the structure of formula (2) in Example 2 have relatively high thermal decomposition temperatures, and the high-temperature region of the TG curve is relatively flat, indicating that the heat resistance of the material is good and it is suitable to be used as a flame retardant additive. From Figures 6 to 8 it can be seen that compared with the flame retardant compound 1 in Example 1, the flame retardant compound 2 in Example 2 has a higher melting point and thermal decomposition temperature, and better flame retardant performance.

[0135] The resin compositions or their molded articles of Examples 3 to 5, Comparative Example 1 and Comparative Example 2 were subjected to the following performance tests, and the test results are shown in Table 1:

[0136] Light transmittance: Tested in accordance with the standard of GB / T 2410-2008, with a thickness of 0.2 mm.

[0137] Melt viscosity: Tested in accordance with the standard of ASTM D1238.

[0138] Softening point: Tested in accordance with the standard of ASTM D6493.

[0139] Flame retardant level: The flame retardant level, i.e., the flame retardant rating, refers to the combustion performance level of materials in a fire and is tested according to the UL94-HB standard, ANSI / UL-94-1985. V0 grade, V-2 grade, and HB grade in Table 1 refer to UL-94 V0 grade, V-2 grade, and HB grade. The flame retardant level decreases gradually from V-0, V-1, V-2 to HB, and the higher the flame retardant level, the better the flame retardant performance.

[0140] 180° peel strength (N / 25mm): The 180° peel strength on the surface of PET (polyethylene terephthalate) is tested according to the GB 2792-2014 standard.

[0141] Table 1

[0142]

[0143] Note: The percentages of each component in Table 1 are the mass percentages of the component in the resin composition, and " / " indicates that the addition amount is 0.

[0144] It can be seen from the results in Table 1 that the resin compositions of Example 3 and Example 4 added with the flame retardant compound 2 of the present application embodiment have a flame retardant level reaching V-0 grade, have improved light transmittance, and suitable melt viscosity and peel strength. Compared with the resin composition of Comparative Example 1 without a flame retardant component, its flame retardant level is improved from HB to V-0, and the flame retardant performance is significantly improved. Compared with the resin composition of Comparative Example 2 added with only an existing flame retardant without adding the flame retardant compound 2 of the present application embodiment, the light transmittance of its molded product is significantly improved. The resin composition of Example 5 added with the flame retardant compound 1 of the present application embodiment can reach V-2 grade in flame retardant level and has good light transmittance. Compared with the resin composition of Comparative Example 1 without a flame retardant component, its flame retardant level is improved from HB to V-2, and the flame retardant performance is significantly improved. Moreover, compared with the resin composition of Comparative Example 2 added with only an existing flame retardant without adding the flame retardant compound 1 of the present application embodiment, the light transmittance of its molded product is significantly improved.

[0145] In addition, the resin composition of Example 3 added with the phenyl-containing flame retardant compound 2, and the resin composition of Example 5 added with the non-phenyl-containing flame retardant compound 1. Comparing Example 3 and Example 5, it can be seen that the phenyl-containing flame retardant compound 2 can better improve the flame retardant performance of the resin composition, improve the peel strength, and thus improve the safety and reliability of the application of the resin composition. At the same time, it can also make the resin composition have a certain light transmittance after molding; while the non-phenyl-containing flame retardant compound 1 is beneficial to making the resin composition obtain a higher light transmittance, and can also reach a certain flame retardant level and peel strength.

[0146] It should be understood that the first, second, and various numerical numbers involved herein are only for the convenience of description and do not limit the scope of the present application.

[0147] In this application, "and / or" describes the relationship between associated objects, indicating that there can be three relationships. For example, A and / or B can represent: A exists alone, A and B exist simultaneously, or B exists alone, where A and B can be singular or plural. The character " / " generally indicates that the associated objects before and after are in an "or" relationship.

[0148] In this application, "at least one" means one or more, and "a plurality" means two or more. "At least one of the following" or its similar expressions refer to any combination of these items, including any combination of single items or plural items. For example, "at least one of a, b, or c", or "at least one of a, b, and c" can both represent: a, b, c, a - b (i.e., a and b), a - c, b - c, or a - b - c, where a, b, and c can be single or multiple respectively.

[0149] In this application, "-" represents a range value, including the endpoint values at both ends. For example, the value of a can be 0.5 - 15, indicating that the value of a can be between 0.5 and 15, and includes the endpoint values 0.5 and 15.

[0150] It should be understood that in various embodiments of this application, the magnitudes of the sequence numbers of the above processes do not imply the order of execution. Some or all of the steps can be executed in parallel or sequentially. The execution order of each process should be determined by its function and internal logic, and should not constitute any limitation to the implementation process of the embodiments of this application.

Claims

1. A flame retardant compound, characterized in that, The flame retardant compound has a structural formula shown in formula (I): In formula (I), R1, R2 and R3 are all halogen-free groups, and each of R1, R2 and R3 independently selects any one of a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. Among R1, R2 and R3 connected to the same silicon atom, at least one is a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

2. The flame retardant compound according to claim 1, characterized in that, The substituted or unsubstituted alkyl group is a substituted or unsubstituted C1-C30 alkyl group, the substituted or unsubstituted cycloalkyl group is a substituted or unsubstituted C3-C30 cycloalkyl group, the substituted or unsubstituted alkenyl group is a substituted or unsubstituted C2-C30 alkenyl group, the substituted or unsubstituted aryl group is a substituted or unsubstituted C6-C30 alkyl group, and the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted C2-C30 heteroaryl group.

3. The flame retardant compound according to claim 1 or 2, characterized in that, The substituted or unsubstituted aryl group includes a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted binaphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted spirofluorene group, and a substituted or unsubstituted binaphthofluorenyl group.

4. The flame retardant compound according to claim 1 or 2, characterized in that, The substituted or unsubstituted heteroaryl group includes a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted benzopyrrolyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted triazinyl group, and a substituted or unsubstituted xanthenone group.

5. The flame retardant compound according to any one of claims 1-4, characterized in that, The substituents on the substituted alkyl group, substituted cycloalkyl group, substituted alkenyl group, substituted aryl group, and substituted heteroaryl group include one or more of a deuterium atom, a tritium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group.

6. The flame retardant compound according to any one of claims 1-5, characterized in that, In formula (I), among R1, R2 and R3 connected to the same silicon atom, at least two independently select a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

7. The flame retardant compound according to any one of claims 1-6, characterized in that, All of R1, R2 and R3 in formula (I) independently select a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

8. The flame retardant compound according to any one of claims 1-7, characterized in that, The flame retardant compound is a solid at room temperature and a transparent liquid in a molten state.

9. The flame retardant compound according to any one of claims 1-8, characterized in that, The thermal decomposition temperature T at which the flame retardant compound has a 10% weight loss d 90 is greater than 170 °C.

10. The flame retardant compound according to any one of claims 1-9, characterized in that, The melting point of the flame retardant compound is less than 230 °C.

11. The method for preparing a flame retardant compound according to any one of claims 1-10, characterized in that, Including: 1,3,5-tris(2-hydroxyethyl) isocyanurate and raw material A are reacted in the presence of imidazole to obtain a flame retardant compound having the structural formula shown in formula (I).

12. A resin composition, characterized in that, It includes a matrix resin and a flame retardant, and the flame retardant includes the flame retardant compound according to any one of claims 1-10.

13. The resin composition according to claim 12, wherein In the resin composition, the mass percentage of the flame retardant compound is 0.1%-45%.

14. The resin composition according to claim 12 or 13, characterized in that, In the resin composition, the mass percentage of the matrix resin is 20%-99.9%.

15. The resin composition according to any one of claims 12 to 14, characterized in that, The matrix resin includes a thermoplastic elastomer, and the thermoplastic elastomer includes one or more of SIS resin, SBS resin, SEBS resin, SEPS resin, thermoplastic polyolefin elastomer, thermoplastic styrene-based elastomer, and polyurethane-based thermoplastic elastomer.

16. The resin composition according to any one of claims 12 to 15, characterized in that, The resin composition further includes one or more of a tackifying resin, a plasticizer, an antioxidant, an anti-ultraviolet agent, other flame retardants, a coupling agent, a crosslinking agent, and a softening agent.

17. The resin composition according to claim 16, wherein The other flame retardants include one or more of a phosphorus-based flame retardant, a halogen-based flame retardant, a silicone-based flame retardant, an inorganic flame retardant, and an intumescent flame retardant.

18. The resin composition according to any one of claims 12 - 17, characterized in that, The melt viscosity of the resin composition at 175°C is 8000 CPS - 20000 CPS.

19. The resin composition according to any one of claims 12-18, characterized in that, The visible light transmittance of the molded article of the resin composition with a thickness of 0.2 mm is greater than or equal to 20%.

20. A formed article, characterized in that, A molded article including the resin composition according to any one of claims 12-19.

21. The application of the flame retardant compound according to any one of claims 1-10, or the resin composition according to any one of claims 12-19 in a binder, an adhesive layer for communication devices, a vehicle protection cover or a protective layer.

22. A device, characterized in that, The device contains the flame retardant compound according to any one of claims 1-10, or a molded article containing the resin composition according to any one of claims 12-19.

23. The device according to claim 22, characterized in that, The device includes a first component and a second component, and an adhesive layer connected between the first component and the second component, and the adhesive layer contains the flame retardant compound or the molded article of the resin composition.

24. The device according to claim 22, wherein, The device includes a device body and a protection cover or a protective layer covering the device body, and the protection cover or the protective layer contains the flame retardant compound or the molded article of the resin composition.

25. A cable, characterized in that, It includes at least one optical fiber or at least one wire, and a cable protection sleeve wrapping the at least one optical fiber or at least one wire, and the cable protection sleeve contains the flame retardant compound according to any one of claims 1-10, or a molded article containing the resin composition according to any one of claims 12-19.

26. A communication system, characterized in that, The communication system includes the device according to any one of claims 22-24 or the cable according to claim 25.

Images