Flame retardant compound and resin composition

Abstract

The embodiments of the present application provide a flame retardant compound and a resin composition. The flame retardant compound has a structural formula represented by formula (I). In 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, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted aryl, and a substituted or unsubstituted heteroaryl, and among R1, R2 and R3 linked to the same silicon atom, at least one is a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted aryl, or a substituted or unsubstituted heteroaryl. The flame retardant compound has a high flame retardant property, contains no halogen, is safe and environmentally friendly, can be uniformly mixed with various matrix resins to form a resin composition, and can also make a molded object of the resin composition have good transparency.

Description

Flame retardant compounds and resin compositions

[0001] This application claims priority to the Chinese patent application filed with the China Patent Office on January 3, 2024, with application number 202410024882.9 and application name “Flame Retardant Compounds and Resin Compositions”, the entire contents of which are incorporated by reference into this application. Technical Field

[0002] The embodiments of the present application relate to the technical field of flame retardants, and in particular to a flame retardant compound and a resin composition. Background Art

[0003] With technological advancements, synthetic polymers have gained widespread application in industrial manufacturing, engineering construction, and other fields. To enhance the flame retardancy of synthetic polymers, the industry typically adds flame retardants. However, currently used organic flame retardants are mostly halogen-containing, which release harmful gases during combustion. Furthermore, in some applications, such as light-transmitting communication devices, the resulting polymer molded products require high transparency, but existing flame retardants often significantly reduce this transparency. Summary of the Invention

[0004] 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 properties, is halogen-free, 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.

[0005] Specifically, a first aspect of the embodiments of the present application provides a flame retardant compound having a structural formula shown in formula (I):

[0006] In formula (I), R1, R2 and R3 are all halogen-free groups, and 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 at least one of R1, R2 and R3 attached to the same silicon atom 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 in the embodiment of the present application uses 1,3,5-tris(2-hydroxyethyl)isocyanurate as the parent core, and connects alkyl, cycloalkyl, alkenyl, aryl or heteroaryl substituted silane to the hydroxyl group of the parent core in the form of a silyl ether bond (Si-O). This special molecular structure design gives the flame retardant compound a low melting point and a high thermal decomposition temperature. The flame retardant compound can be used as a transparent flame retardant additive and uniformly mixed with various base resins to form a resin composition, so that the molded product of the resin composition has both high flame retardant properties and good transparency. In addition, the flame retardant compound is a halogen-free flame retardant, which can avoid the production of harmful substances during combustion and is safe and environmentally friendly.

[0008] The flame-retardant compound described in this application is a silicon-nitrogen flame-retardant additive that combines the excellent thermal stability, melt dripping resistance, and flame retardancy and smoke suppression properties of silicon-based flame retardants with the excellent flame-retardant effect of nitrogen-based flame retardants through expansion and thermal insulation. Specifically, silicon promotes the carbonization of polymer materials, creating a dense silicon-carbon layer that isolates combustibles from oxygen and effectively prevents secondary combustion caused by melt dripping of polymer materials.

[0009] In the embodiment 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. The raw materials of the groups with suitable carbon number are readily available and the structure is 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 anthracenyl group, a substituted or unsubstituted phenanthrenyl 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 spirofluorenyl group, and a substituted or unsubstituted binaphthylfluorenyl group. The aryl group can bring rigidity to the molecular structure of the flame retardant compound, thereby improving the flame retardant properties of the flame retardant compound.

[0011] In the embodiment of the present application, the substituted or unsubstituted heteroaryl group includes a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted benzopyrrolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted triazine group, or a substituted or unsubstituted xanthone group. The substituted or unsubstituted heteroaryl group may 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 properties of the flame retardant compound.

[0012] In the embodiments of the present application, the substituent groups on the substituted alkyl, substituted cycloalkyl, substituted alkenyl, substituted aryl, or substituted heteroaryl groups include one or more of a deuterium atom, a tritium atom, a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted aryl, or a substituted or unsubstituted heteroaryl group. The introduction of substituent groups not only allows for a wider variety of flame retardants, but also allows for fine-tuning of flame retardant properties to better meet different application requirements.

[0013] In the embodiment of the present application, in the formula (I), at least two of the three R1, R2 and R3 connected to the same silicon atom 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 the three R1, R2 and R3 connected to the same silicon atom to be 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 carbonization, obtain higher molecular bond energy, and better enable the flame retardant compound to have both high flame retardancy and good light transmittance.

[0014] In the embodiments of the present application, all 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. For example, in some embodiments of the present application, all R1, R2 and R3 in the formula (I) are substituted or unsubstituted alkyl. In some embodiments of the present application, all R1 and R2 in the formula (I) are substituted or unsubstituted alkyl, and all R3 are substituted or unsubstituted alkenyl. In some embodiments of the present application, all R1 and R2 in the formula (I) are substituted or unsubstituted alkyl, and all R3 are substituted or unsubstituted cycloalkyl. In some embodiments of the present application, all R1, R2 and R3 in the formula (I) are substituted or unsubstituted aryl. In some embodiments of the present application, all R1 and R2 in the formula (I) are substituted or unsubstituted alkyl, and all R3 are substituted or unsubstituted aryl. In some embodiments of the present application, all R1 and R2 in formula (I) are substituted or unsubstituted aryl groups, and all R3 are substituted or unsubstituted alkyl groups. In some embodiments of the present application, all R1 and R2 in formula (I) are substituted or unsubstituted aryl groups, and all R3 are substituted or unsubstituted alkenyl groups. By designing R1, R2 and R3 connected to the same silicon atom to be substituted or unsubstituted alkyl groups, substituted or unsubstituted cycloalkyl groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted aryl groups, or substituted or unsubstituted heteroaryl groups, the flame retardant compound can be better provided with both high flame retardancy 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 substituted or unsubstituted aryl groups, or a substituted or unsubstituted heteroaryl group. That is, an aromatic structure is introduced into the silicon atom of the flame retardant compound. The aromatic structure can bring rigidity to the molecular structure of the flame retardant compound, and generate π-π stacking between molecules, thereby improving the overall structural stability of the flame retardant compound; and the rearrangement reaction of the aromatic structure can promote the formation of a carbon layer with a conjugated aromatic structure in the polymer material at high temperature, which is conducive to further improving the flame retardant and anti-melting droplet properties. The multiple flame retardant mechanisms of nitrogen, silicon and aromatic structure play a synergistic role, which can make the flame retardant compound 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 flame retardant compound of the present application is a solid at room temperature, which facilitates storage and transportation. The flame retardant compound is a transparent liquid in a molten state. When added to the resin composition, the flame retardant compound can provide the resin composition molded article with better light transmittance, better melt mixing or good compatibility with other components in the resin composition, and enable the flame retardant compound to be evenly distributed in the resin composition system.

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

[0018] In the embodiment 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 low melting point, that is, it can be melted at a relatively low temperature, so it can be applied to various resin systems with processing temperatures higher than the melting point of the flame retardant compound, facilitating processing.

[0019] The second aspect of the embodiment of the present application provides a method for preparing the flame retardant compound of the first aspect, comprising:

[0020] 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).

[0021] Raw material A.

[0022] The preparation method provided in the embodiments of the present application has a simple process and can be used for large-scale production.

[0023] A third aspect of the present invention provides a resin composition comprising a base resin and a flame retardant, wherein the flame retardant comprises the flame retardant compound described in the first aspect of the present invention. The resin composition can be any resin composition product used to form a flame-retardant adhesive layer, film layer, solid part, or other product.

[0024] In the embodiment of the present application, the mass percentage of the flame retardant compound in the resin composition is 0.1%-45%. The addition of an appropriate amount of the flame retardant compound not only helps to improve the flame retardant properties of the resin composition as a whole, but also enables the matrix resin and other components in the resin composition to maintain a sufficient content to improve the overall performance of the resin composition. In particular, for resin compositions requiring transparency, the addition of an appropriate amount of the flame retardant compound can achieve excellent flame retardancy while also achieving excellent transparency.

[0025] In the embodiment of the present application, in the resin composition, the mass percentage of the base resin is 20%-99.9%. An appropriate amount of the base resin can provide basic performance requirements for the resin composition.

[0026] In an embodiment of the present application, the matrix resin includes a thermoplastic polymer elastomer, and the thermoplastic polymer elastomer includes one or more of SIS resin, SBS resin, SEBS resin, SEPS resin, thermoplastic polyolefin elastomer, thermoplastic styrene elastomer, and polyurethane thermoplastic elastomer.

[0027] In the embodiment of the present application, the resin composition further comprises one or more of a tackifying resin, a plasticizer, an antioxidant, an anti-ultraviolet agent, other flame retardants, a coupling agent, a cross-linking agent, and a softener. The addition of different additives can improve the overall performance of the resin composition.

[0028] In the embodiment of the present application, the other flame retardants include one or more of phosphorus-based flame retardants, halogen-based flame retardants, organosilicon flame retardants, inorganic flame retardants, and intumescent flame retardants.

[0029] In an embodiment of the present application, the resin composition has a melt viscosity of 8,000 to 20,000 centipoise seconds (CPS) at 175°C. A molded article of the resin composition having a thickness of 0.2 mm has a visible light transmittance of greater than or equal to 20%. The resin composition has a low melt viscosity, facilitating processing and molding operations. The molded article has a high visible light transmittance, effectively meeting application scenarios requiring transparency, such as transparent cables.

[0030] A fourth aspect of the present invention provides a molded article comprising a molded article of the resin composition described in the third aspect of the present invention. The molded article can have both high flame retardancy and good transparency.

[0031] The fifth aspect of the embodiments of the present application provides the use 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.

[0032] A sixth aspect of an embodiment of the present application provides a device, which comprises the flame retardant compound described in the first aspect, or a molded article of the resin composition described in the third aspect.

[0033] In an embodiment of the present application, the device includes a first component and a second component, and a bonding layer connected between the first component and the second component, and the bonding layer includes a molded product of the flame retardant compound or the resin composition.

[0034] In an embodiment 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 the flame retardant compound described in the first aspect, or a molded product of the resin composition described in the third aspect.

[0035] A seventh aspect of an embodiment of the present application provides a cable, comprising at least one optical fiber or at least one conductive wire, and a cable protective sheath wrapping the at least one optical fiber or at least one conductive wire, wherein the cable protective sheath comprises the flame retardant compound described in the first aspect, or a molded product of the resin composition described in the third aspect.

[0036] An embodiment of the present application further provides 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

[0037] FIG1 is a schematic diagram of a cross-sectional structure of a device 100 provided in one embodiment of the present application;

[0038] FIG2 is a schematic cross-sectional view of a device 100 according to another embodiment of the present application;

[0039] FIG3 is a schematic diagram of a cross-sectional structure of a cable 200 provided in one embodiment of the present application;

[0040] FIG4 is a schematic diagram of a cross-sectional structure of a cable 200 provided in another embodiment of the present application;

[0041] FIG5 is a DSC (Differential Scanning Calorimetry) curve of the flame retardant compound of formula (1);

[0042] Figure 6 is a thermogravimetric analysis curve of the flame retardant compound of formula (1);

[0043] FIG7 is a DSC (Differential Scanning Calorimetry) curve of the flame retardant compound of formula (2);

[0044] FIG8 is a thermogravimetric analysis curve of the flame retardant compound of formula (2). DETAILED DESCRIPTION

[0045] The embodiments of the present application will be described below with reference to the accompanying drawings.

[0046] While the widespread adoption of 5G communications has increased transmission speeds, the increased heat generation also presents potential safety hazards. To ensure the safety of communication devices, the materials used in these devices must possess high flame retardancy. A common approach in the industry is to add flame retardants to the polymer materials used to manufacture these devices. However, the organic flame retardants currently used are mostly halogen-containing, which can release harmful gases upon combustion. Furthermore, with the development of communication devices, aesthetics and concealment have become crucial considerations in their application. To meet the aesthetic demands of various application scenarios, materials used in communication components often require high transparency. Furthermore, in some optical applications, transparency in the visible light band facilitates device processing and use. To ensure that the polymer materials used in communication devices possess both high flame retardancy and good transparency, thereby meeting both flame retardancy and transparency requirements, the present invention provides a flame retardant compound that is halogen-free, safe, and environmentally friendly. This compound can be uniformly mixed with various matrix resins to form a resin composition, and can also impart good transparency to molded articles from the resin composition.

[0047] The flame retardant compound provided in the embodiments of the present application has the structural formula shown in formula (I):

[0048] 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 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 at least one of R1, R2 and R3 attached to the same silicon atom 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.

[0049] The flame retardant compound provided in the embodiment of the present application uses 1,3,5-tris(2-hydroxyethyl)isocyanurate as the parent core, and connects alkyl, cycloalkyl, alkenyl, aryl or heteroaryl substituted silane to the hydroxyl group of the parent core in the form of a silyl ether bond (Si-O). This special molecular structure design gives the flame retardant compound a low melting point and a high thermal decomposition temperature. The flame retardant compound can be used as a flame retardant additive and uniformly mixed with various base resins to form a resin composition, so that the molded product of the resin composition has both high flame retardant properties and good transparency. In addition, the flame retardant compound is a halogen-free flame retardant, which can avoid the production of harmful substances during combustion and is safe and environmentally friendly.

[0050] The flame-retardant compound described in this application is a silicon-nitrogen flame-retardant additive that combines the excellent thermal stability, melt dripping resistance, and flame retardancy and smoke suppression properties of silicon-based flame retardants with the excellent flame-retardant effect of nitrogen-based flame retardants through expansion and thermal insulation. Specifically, silicon promotes the carbonization of polymer materials, creating a dense silicon-carbon layer that isolates combustibles from oxygen and effectively prevents secondary combustion caused by melt dripping of polymer materials.

[0051] In the embodiments of the present application, the three R1s in formula (I) may be the same or different groups, the three R2s may be the same or different groups, and the three R3s may 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.

[0052] In the embodiments of the present application, the substituent groups on the substituted alkyl, substituted cycloalkyl, substituted alkenyl, substituted aryl, and substituted heteroaryl groups include one or more of a deuterium atom, a tritium atom, a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted aryl, and a substituted or unsubstituted heteroaryl group. The introduction of substituent groups not only allows for a wider variety of flame retardants, but also allows for fine-tuning of flame retardant properties to better meet different application requirements.

[0053] In some embodiments of the present application, the substituted or unsubstituted alkyl group may be a substituted or unsubstituted C1-C30 alkyl group, or a substituted or unsubstituted C1-C20 alkyl group, specifically, for example, 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 may be a straight-chain alkyl group or a branched-chain alkyl group. For example, the substituted or unsubstituted C1 alkyl group is a substituted or unsubstituted methyl group, the substituted or unsubstituted C2 alkyl group is a substituted or unsubstituted ethyl group, the substituted or unsubstituted C3 alkyl group is a substituted or unsubstituted n-propyl group or isopropyl group, the substituted or unsubstituted C4 alkyl group is a substituted or unsubstituted n-butyl group, isobutyl group or tert-butyl group, and the same applies to other substituted or unsubstituted alkyl groups. In some embodiments of the present application, the substituted alkyl group may be a deuterated alkyl group or an aryl alkyl group. Deuterated alkyl groups may include, for example, deuterated methyl, deuterated ethyl, deuterated isopropyl, or deuterated tert-butyl; aryl alkyl groups may include, for example, benzyl or phenethyl. Substituted or unsubstituted alkyl groups for R1, R2, and R3 can impart molecular polarity to the flame retardant compound, adjusting the molecular polarity and enabling better mixing with various matrix resins.

[0054] In some embodiments of the present application, the substituted or unsubstituted cycloalkyl group may be a substituted or unsubstituted C3-C30 cycloalkyl group, or a substituted or unsubstituted C3-C20 cycloalkyl group, specifically, for example, a substituted or unsubstituted C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20 cycloalkyl group. For example, the substituted or unsubstituted C3 cycloalkyl group is a substituted or unsubstituted cyclopropyl group, the substituted or unsubstituted C5 cycloalkyl group is a substituted or unsubstituted cyclopentyl group, the substituted or unsubstituted C6 alkyl group is a substituted or unsubstituted cyclohexyl group, and the like for other substituted or unsubstituted cycloalkyl groups. The substituted cycloalkyl group may be, for example, a deuterated cyclopentyl group, a tritiated cyclopentyl group, a methyl-substituted cyclopentyl group, etc.

[0055] In some embodiments of the present application, the substituted or unsubstituted alkenyl group may be a substituted or unsubstituted C2-C30 alkenyl group, or a substituted or unsubstituted C2-C20 alkenyl group, specifically, for example, 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 may be a straight-chain alkenyl group or a branched-chain alkenyl group. For example, a substituted or unsubstituted C2 alkenyl group is a substituted or unsubstituted vinyl group, a substituted or unsubstituted C3 alkenyl group is a substituted or unsubstituted propenyl group, and the same applies to other substituted or unsubstituted alkenyl groups. R1, R2, and R3 being substituted or unsubstituted alkenyl groups can impart reactive properties to the flame retardant compound.

[0056] In some embodiments of the present application, the substituted or unsubstituted aryl group may be a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C6-C20 aryl group, specifically, for example, 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, or C30 aryl group. The substituted or unsubstituted aryl group may be a monocyclic aryl group or a polycyclic aryl group, and the polycyclic aryl group may be a fused ring type or a non-fused ring type (such as biphenyls). Illustratively, the substituted or unsubstituted aryl group is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted binaphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted spirofluorenyl, or substituted or unsubstituted binaphthylfluorenyl. In some embodiments of the present application, the substituted aryl group may be a deuterated aryl group, an alkylaryl group, an alkylsilylaryl group, and the deuterated aryl group may be, for example, a deuterated phenyl group, a deuterated biphenyl group, or a deuterated naphthyl group; the alkylaryl group may be a substituted or unsubstituted aryl group selected from the group consisting of methyl, ethyl, isopropyl, and tert-butyl groups, specifically, a methyl-substituted phenyl group, an ethyl-substituted phenyl group, an isopropyl-substituted phenyl group, a tert-butyl-substituted phenyl group, a deuterated methyl-substituted phenyl group, a deuterated ethyl-substituted phenyl group, a deuterated isopropyl-substituted phenyl group, a deuterated tert-butyl-substituted phenyl group, a deuterated biphenyl group, Examples of the flame retardant include methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl, methyl-substituted naphthyl, ethyl-substituted naphthyl, isopropyl-substituted naphthyl, tert-butyl-substituted naphthyl, deuterated methyl-substituted naphthyl, deuterated ethyl-substituted naphthyl, deuterated isopropyl-substituted naphthyl, and deuterated tert-butyl-substituted naphthyl. Alkylsilylaryl groups may be, for example, trimethylsilyl-substituted phenyl. The aryl group can impart rigidity to the molecular structure of the flame retardant compound, thereby enhancing its flame retardant properties.

[0057] In some embodiments of the present application, the substituted or unsubstituted heteroaryl group may be a substituted or unsubstituted C2-C30 heteroaryl group, or a substituted or unsubstituted C2-C20 heteroaryl group; specifically, for example, it may be a substituted or unsubstituted C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, or C20 heteroaryl group. The substituted or unsubstituted heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. The heteroatoms in the heteroaryl group may be one or more of oxygen, nitrogen, and sulfur. Illustratively, the substituted or unsubstituted heteroaryl group includes a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted benzopyrrolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted triazinyl group, or a substituted or unsubstituted xanthone group. The substituted heteroaryl group may 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 methyl, ethyl, isopropyl, or tert-butyl substituted heteroaryl group, specifically a methyl substituted heteroaryl group (e.g., 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 linked to the silicon atom via a carbon atom or a heteroatom. The heteroaryl group can bring rigidity to the molecular structure of the flame retardant compound, which is beneficial for improving the flame retardant properties of the flame retardant compound.

[0058] 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 substituted or unsubstituted aryl groups, or a substituted or unsubstituted heteroaryl group. That is, an aromatic structure is introduced into the silicon atom of the flame retardant compound. The aromatic structure can bring rigidity to the molecular structure of the flame retardant compound, and generate π-π stacking between molecules, thereby improving the overall structural stability of the flame retardant compound; and the rearrangement reaction of the aromatic structure can promote the formation of a carbon layer with a conjugated aromatic structure in the polymer material at high temperature, which is conducive to further improving the flame retardant and anti-melting droplet properties. The multiple flame retardant mechanisms of nitrogen, silicon and aromatic structure play a synergistic role, which can make the flame retardant compound have a more excellent flame retardant effect.

[0059] In some embodiments of the present application, in formula (I), at least two of R1, R2, and R3 attached to the same silicon atom 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 to be 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 carbonization, obtain higher molecular bond energy, and better enable the flame retardant compound to have both high flame retardancy and good light transmittance.

[0060] In the embodiments of the present application, all 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 R1s in formula (I) may be the same or different groups, the three R2s may be the same or different groups, and the three R3s may be the same or different groups. For example, in some embodiments of the present application, all R1, R2 and R3 in formula (I) are substituted or unsubstituted alkyl. In some embodiments of the present application, all 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 R1 and 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 R1 and 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 R1, R2 and R3 in formula (I) are substituted or unsubstituted aryl. In some embodiments of the present application, all R1 and 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 R1 and 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 R1 and R2 in formula (I) are substituted or unsubstituted aryl, and all R3 are substituted or unsubstituted alkenyl. By designing R1, R2 and R3 connected to the same silicon atom to be substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, the flame retardant compound can be better provided with both high flame retardancy and good light transmittance.

[0061] In embodiments of the present application, all R1, R2, and R3 in formula (I) are substituted or unsubstituted alkyl groups, and at least one is a substituted or unsubstituted branched alkyl group. In some embodiments of the present application, in formula (I), at least one of R1, R2, and R3 attached to the same silicon atom is a substituted or unsubstituted branched alkyl group. Branched alkyl groups can improve the flame retardant properties of flame retardant compounds.

[0062] In some embodiments of the present application, the flame retardant compound has the structural formula shown in formula (1) to formula (11):

[0063] 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 flame retardant compound of the present application is a solid at room temperature, which facilitates storage and transportation. The flame retardant compound is a transparent liquid in a molten state. When added to the resin composition, the flame retardant compound can provide the resin composition molded article with improved light transmittance, better melt mixing or good compatibility with other components in the resin composition, and enable the flame retardant compound to be evenly distributed in the resin composition system.

[0064] In one embodiment of the present application, a flame retardant compound having a structure represented by formula (2) is added to a polyurethane resin system at a mass ratio of 10% to form a resin composition. The resin composition is maintained at 140° C. for 3 hours, and the resin composition becomes a transparent molten state.

[0065] In an embodiment 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 an embodiment of the present application, the melting point of the flame retardant compound is less than 180°C. In an embodiment 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 relatively low melting point, i.e., it can be melted at a relatively low temperature, so it can be applied to various resin systems having a processing temperature higher than the melting point of the flame retardant compound, thereby facilitating processing.

[0066] In the embodiment of the present application, the thermal decomposition temperature T of the flame retardant compound is 10% of the thermal weight loss. d 90 is greater than 170° C. In some embodiments of the present application, the thermal decomposition temperature T of the flame retardant compound when the thermal weight loss reaches 10% d 90 is greater than 180° C. In some embodiments of the present application, the thermal decomposition temperature T of the flame retardant compound when the thermal weight loss reaches 10% d 90 is greater than 200° C. In some embodiments of the present application, the thermal decomposition temperature T of the flame retardant compound at which the thermal weight loss is 10% d 90 is greater than 220° C. The flame retardant compound of the present application has a high thermal decomposition temperature and excellent heat resistance.

[0067] For the same flame retardant compound, its melting point is less than the thermal decomposition temperature T of 10% thermal weight loss.d 90.

[0068] The flame retardant compounds provided in the embodiments of the present application can be characterized and determined by combining techniques such as elemental analyzer, infrared spectroscopy, nuclear magnetic resonance spectroscopy, X-ray diffraction, and mass spectrometry to determine the molecular structure of the flame retardant compounds.

[0069] The present invention also provides a method for preparing the flame retardant compound, comprising:

[0070] 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).

[0071] Raw material A.

[0072] In some embodiments of the present application, the above preparation method specifically includes:

[0073] 1,3,5-tris(2-hydroxyethyl)isocyanurate was dissolved in an organic solvent and cooled to 0°C. Imidazole and raw material A were added in sequence. The reaction solution was heated to room temperature overnight. After the reaction was completed, the product was extracted and the obtained organic phase was dried and separated by column chromatography to obtain the target product.

[0074] The organic solvent may be, for example, N,N-dimethylformamide (DMF). After the reaction solution is heated to room temperature overnight, water may be added to the reaction solution to quench the reaction.

[0075] The preparation method provided in the embodiments of the present application has a simple process and can be used for large-scale production.

[0076] The flame-retardant compounds of the embodiments of the present application can be added as flame retardants to various organic systems requiring flame retardancy, and in particular, can be added as transparent flame retardants to organic systems requiring both flame retardancy and transparency. Furthermore, due to the excellent flame retardancy of the flame-retardant compounds of the embodiments of the present application, even a small amount of addition can achieve the required flame retardancy level, thereby further reducing the impact of the addition of the flame retardant compound on the transparency of the organic system and achieving even better transparency.

[0077] The present invention also provides a resin composition comprising a base resin and a flame retardant, wherein the flame retardant comprises the flame retardant compound described in the present invention. A flame retardant is an additive that prevents the resin from igniting or suppresses the spread of flames and is used for flame retardancy. The flame retardant compound described in the present invention is an additive flame retardant.

[0078] It can be understood that the resin composition can be various resin composition products used to be molded into adhesive layers, film layers, solid parts and other products with flame retardant requirements. The base resin can be selected according to actual application requirements, and the content of the base resin and the content of the flame retardant compound can also be selected according to actual needs.

[0079] 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 flame retardant compound is beneficial to improving the flame retardant properties of the resin composition as a whole, while enabling other components such as the matrix resin in the resin composition to maintain sufficient content to improve the comprehensive performance of the resin composition. In particular, for resin compositions with transparency requirements, the addition of an appropriate amount of flame retardant compound can better achieve excellent transparency while obtaining excellent flame retardancy.

[0080] In some embodiments of the present application, the mass percentage of the matrix resin in the resin composition 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%, or 99.9%.

[0081] In the embodiments of the present application, the matrix resin can be various resin materials having a melting point or processing temperature higher than the flame retardant compounds of the embodiments of the present application. In some embodiments, the matrix resin includes a thermoplastic polymer elastomer, and the thermoplastic polymer elastomer includes one or more of SIS resin, SBS resin, SEBS resin, SEPS resin, thermoplastic polyolefin elastomer, thermoplastic styrene elastomer, and polyurethane thermoplastic elastomer. SBS resin, i.e. 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 butadiene rubber (PB). SEBS resin is a saturated thermoplastic elastomer obtained by hydrogenation modification of SBS resin. After hydrogenation modification, it is resistant to oxidation, and its UV resistance and heat resistance are improved. SIS resin, i.e. styrene-isoprene-styrene. SEPS resin is a saturated thermoplastic elastomer obtained by hydrogenation modification of SIS resin. After hydrogenation modification, it is resistant to oxidation, and its UV resistance and heat resistance are improved. SIS resin, SBS resin, SEBS resin, and SEPS resin are all thermoplastic elastomers that exhibit rubber elasticity at room temperature and become plastic when heated. They can be used in tapes, hoses, cables, medical devices, and other fields.

[0082] In some embodiments of the present application, considering factors such as comprehensive performance and cost, the base resin may include two or more of SIS resin, SBS resin, SEBS resin, and SEPS resin. For example, the base resin includes SIS resin and SEBS resin, SIS resin and SBS resin, or SBS resin and SEPS resin.

[0083] According to actual needs, in some embodiments of the present application, the resin composition may further include one or more of a tackifying resin, a plasticizer, an antioxidant, an anti-ultraviolet agent, other flame retardants, a coupling agent, a cross-linking agent and a softener.

[0084] Wherein, tackifying resin can increase the viscosity of the system. Tackifying resin can be one or more of natural resin and petroleum resin. Petroleum resin can be aliphatic petroleum resin, alicyclic petroleum resin, aromatic petroleum resin, aliphatic / aromatic copolymer resin, hydrogenated petroleum resin. Aliphatic petroleum resin can be C5 aliphatic petroleum resin, alicyclic petroleum resin can be DCPD alicyclic petroleum resin (dicyclopentadiene), aromatic petroleum resin can be C9 aromatic petroleum resin, aliphatic / aromatic copolymer resin can be C5 / C9 aliphatic / aromatic copolymer petroleum resin, hydrogenated petroleum resin can be C5 hydrogenated petroleum resin, C9 hydrogenated petroleum resin, DCPD hydrogenated petroleum resin.

[0085] Plasticizers can weaken the forces between polymer molecules, reduce melting temperature and melt viscosity, and improve molding processability and the flexibility of resin composition products. Plasticizers can include naphthenic oil, hydroxy silicone oil, etc.

[0086] The antioxidant can improve the anti-oxidation performance of the resin composition, and the anti-ultraviolet agent can improve the ultraviolet resistance of the resin composition, thereby increasing the service life of the resin composition molding.

[0087] Other flame retardants refer to flame retardants other than the flame retardant compounds of the embodiments of the present application. Other flame retardants may be one or more of phosphorus flame retardants, halogen flame retardants, organosilicon flame retardants, inorganic flame retardants, and intumescent flame retardants. Among them, phosphorus flame retardants may be one or more of ammonium polyphosphate, phosphate ester flame retardants, and diethyl aluminum hypophosphite. Phosphate ester flame retardants may be, for example, triphenyl phosphate, tricresyl phosphate, propylphenyl phosphate, styrene butadiene phosphate, and toluene diphenyl phosphate. Halogen flame retardants may include decabromodiphenyl ether (DBDPO), tetrabromobisphenol A, bis(2,3-dialkylpropyl) ether (TBAB), octabromodiphenyl ether (OBDPO), brominated polystyrene, brominated epoxy, tetrabromobisphenol A carbonate oligomer, etc. Organosilicon flame retardants may include silicone oil, silicone resin, polysiloxane with functional groups, polycarbonate-siloxane copolymer acrylate-siloxane composite materials, and silicone gel, etc. Inorganic flame retardants can include aluminum hydroxide, magnesium hydroxide, expanded graphite, borates, aluminum oxalate, zinc sulfide, alumina trihydrate, boehmite, calcium carbonate, etc. Intumescent flame retardants are mainly composed of three parts: a carbonizing agent (carbon source), a carbonization catalyst (acid source), and an expansion agent (gas source). The carbonizing agent is a multifunctional substance rich in carbon, which can be pentaerythritol (PER) and its diacetyl, triacetyl, etc. The carbonization catalyst is a compound that can release an inorganic acid under heating conditions, for example, it can be ammonium polyphosphate (APP). The expansion agent is a compound that releases an inert gas when heated, which can be an ammonium and amide substance, such as urea, melamine, dicyandiamide and its derivatives. The above-mentioned other flame retardants can be used in combination with the flame retardant compounds of the present application embodiments as needed.

[0088] In an embodiment of the present application, the melt viscosity of the resin composition at 175° C. is 8,000 CPS to 20,000 CPS (centipoise seconds). In some embodiments, the melt viscosity of the resin composition is 8,000 CPS, 10,000 CPS, 11,000 CPS, 13,000 CPS, 15,000 CPS, 18,000 CPS, or 20,000 CPS. The resin composition has a lower melt viscosity, which facilitates processing and molding operations.

[0089] In an embodiment of the present application, a molded article of the resin composition having a thickness of 0.2 mm has a visible light (380 nm-760 nm) transmittance 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%, or 87%. The molded article of the resin composition has a high visible light transmittance, which can better meet application scenarios requiring transparency, such as transparent cables.

[0090] The embodiments of the present application also provide a molded article, including a molded article of the resin composition described above in the embodiments of the present application.

[0091] The present application also provides embodiments of the flame retardant compound or resin composition described above for use in adhesives, adhesive layers for communication devices, and protective covers or layers for vehicles. The resin composition can be used as an adhesive for directly bonding various components, or for bonding cables, devices, etc. to a carrier surface.

[0092] 1 and 2 , an embodiment of the present application further provides a device 100 comprising the flame retardant compound or a molded article of the resin composition. The device 100 may be any optical device, electronic device, optoelectronic device, communication device, or the like.

[0093] Referring to FIG. 1 , in some embodiments of the present application, a 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. Adhesive layer 103 includes a molded article of the aforementioned flame retardant compound or the aforementioned resin composition. Device 100 may be, for example, a spectrometer.

[0094] 2 , in some embodiments of the present application, a device 100 includes a device body 104 and a protective cover or layer 105 covering the device body 104. The protective cover or layer 105 includes the aforementioned flame retardant compound or a molded article of the aforementioned resin composition. Device 100 may be, for example, a router.

[0095] Referring to Figures 3 and 4, Figure 3 is a schematic cross-sectional view of a cable 200 according to one embodiment of the present application, and Figure 4 is a schematic cross-sectional view of a cable 200 according to another embodiment of the present application. The cable 200 provided in this embodiment of the present application includes at least one optical fiber or at least one wire 201, and a cable protective sheath 202 encasing the at least one optical fiber or at least one wire 201. The cable protective sheath 202 comprises the aforementioned flame retardant compound or a molded article of the aforementioned resin composition. The cable protective sheath is used to protect and support the optical fiber or wire, providing both protection and reinforcement.

[0096] In some embodiments of the present application, cable 200 is an optical cable. Cable 200 may include one or more optical fibers and a cable protective sheath surrounding the one or more optical fibers. An optical cable is a communication line used to transmit optical signals, with the optical fiber serving as the signal transmission medium. At the transmitting end, the optical cable converts the information to be transmitted into an electrical signal, which is then transmitted through a laser beam. The intensity of the light varies with the frequency of the electrical signal and is then transmitted through the optical fiber. At the receiving end, a detector receives the optical signal, converts it into an electrical signal, and then processes it to recover the original information.

[0097] In some embodiments of the present application, the cable 200 is an electrical cable, and the cable 200 includes one or more wires and a cable protective sheath wrapping the one or more wires.

[0098] In some embodiments of the present application, the cable 200 is a photoelectric hybrid cable, and the cable 200 includes one or more conductors, one or more optical fibers, and a cable protective sheath that wraps the one or more conductors and the one or more optical fibers.

[0099] In the embodiment of the present application, the cable protective cover 202 is partially or entirely made of the resin composition described above in the embodiment of the present application.

[0100] The cable in the embodiment of the present application can achieve flame retardancy and transparency at the same time by using the above-mentioned resin composition in the embodiment of the present application to prepare the cable protective cover, thereby improving the safety and convenience of cable use, and providing a basis for the application of cables in military fields, medical fields (such as medical equipment such as endoscopes), construction fields (such as multi-functional integration of lighting, music, etc.), transportation fields (such as multi-functional integration of in-vehicle entertainment, navigation, safety, etc.), industrial fields (such as machine vision, laser cutting, etc.) and other fields.

[0101] An embodiment of the present application further provides a communication system, which includes the above-mentioned device or cable.

[0102] The embodiments of the present application are further described below with reference to a number of embodiments.

[0103] Example 1

[0104] Preparation of flame retardant compound 1 having the structure of formula (1):

[0105] 1,3,5-Tris(2-hydroxyethyl)isocyanurate (1 g, 3.831 mmol) was dissolved in 10 mL of N,N-dimethylformamide (DMF) and cooled to 0°C. Imidazole (1.302 g, 19.155 mmol, 5 eq) and tert-butyldimethylsilyl chloride (2.30 g, 15.324 mmol, 4 eq) were added sequentially. The reaction solution was warmed to room temperature overnight. 10 mL of water was added to the reaction solution to quench the reaction. Ethyl acetate (20 mL) was then added to extract the product three times. The organic phases were mixed, dried, and spin-dried to obtain an oily crude product. The target product (2.2 g, 3.642 mmol) was obtained by column chromatography with a yield of 95% as an off-white solid. NMR results of the target product: 1H NMR (400 MHz, CDCl3) δ4.06 (t, J = 6.3 Hz, 6H), 3.82 (t, J = 6.3 Hz, 6H), 0.89 (s, 27H), 0.07 (s, 18H).

[0106] The above reaction formula is as follows:

[0107] Example 2

[0108] Preparation of flame retardant compound 2 having the structure of formula (2):

[0109] 11,3,5-Tris(2-hydroxyethyl)isocyanurate (1 g, 3.831 mmol) was dissolved in 10 mL of DMF and cooled to 0°C. Imidazole (1.302 g, 19.155 mmol, 5 eq) and tert-butyldiphenylsilyl chloride (4.212 g, 15.324 mmol, 4 eq) were added sequentially. The reaction solution was warmed to room temperature overnight. 10 mL of water was added to the reaction solution to quench the reaction. Ethyl acetate (20 mL) was then added to extract the product three times. The organic phases were mixed, dried, and spin-dried to obtain a milky white solid crude product. The target product was then separated by column chromatography with a yield of 99% as a white solid. NMR results of the target product: 1H NMR (400 MHz, CDCl3) δ7.63 (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).

[0110] The above reaction formula is as follows:

[0111] Example 3

[0112] Preparation of resin composition:

[0113] The flame retardant compound 2 having the structure of formula (2) is prepared into a resin composition 1 with a base resin, a tackifying resin, a plasticizer, an antioxidant, an anti-ultraviolet agent and other flame retardants. The component ratio of the resin composition 1 is shown in Table 1.

[0114] Example 4

[0115] Preparation of resin composition:

[0116] The flame retardant compound 2 having the structure of formula (2) is prepared into a resin composition 2 with a base resin, a tackifying resin, a plasticizer, an antioxidant, an anti-ultraviolet agent and other flame retardants. The component ratio of the resin composition 2 is shown in Table 1.

[0117] Example 5

[0118] Preparation of resin composition:

[0119] The flame retardant compound 1 having the structure of formula (1) is prepared into a resin composition 3 with a base resin, a tackifying resin, a plasticizer, an antioxidant, an anti-ultraviolet agent and other flame retardants. The component ratio of the resin composition 3 is shown in Table 1.

[0120] Comparative Example 1

[0121] The same base resin, tackifying resin, plasticizer, antioxidant, and anti-ultraviolet agent as those in Example 1 were prepared into a resin composition. The composition ratio of the resin composition is shown in Table 1.

[0122] Comparative Example 2

[0123] The same base resin, tackifying resin, plasticizer, antioxidant, anti-ultraviolet agent and commercial flame retardant as those in Example 1 were prepared into a resin composition. The composition ratio of the resin composition is shown in Table 1.

[0124] The flame retardant compound 1 having the structure of formula (1) prepared in Example 1 and the flame retardant compound 2 having the structure of formula (2) prepared in Example 2 were tested by differential scanning calorimetry (DSC), and the test results are shown in Figures 5 and 7; the flame retardant compound 1 having the structure of formula (1) prepared in Example 1 and the flame retardant compound 2 having the structure of formula (2) prepared in Example 2 were tested by thermogravimetric analyzer (TGA), and the test results are shown in Figures 6 and 8.

[0125] Figure 5 is a DSC curve of the flame retardant compound 1 having the structure of formula (1). Figure 5 shows that the flame retardant compound has a relatively low melting temperature, with an endothermic peak Tm of 56.7°C, corresponding to the melting or phase change process of the sample. Figure 6 is a thermogravimetric analysis curve of the flame retardant compound 1 having the structure of formula (1). Figure 6 shows that the flame retardant compound has a relatively high thermal decomposition temperature, with a thermal decomposition temperature Td(90%) of 232°C. Td(90%) is the temperature at which the sample loses 10% of its weight upon heating.

[0126] Figure 7 is a DSC curve of the flame retardant compound 2 having the structure of formula (2). As shown in Figure 7, the flame retardant compound has a low melting temperature, with an endothermic peak Tm of 113.6°C, corresponding to the melting or phase change process of the sample. Figure 8 is a thermogravimetric analysis curve of the flame retardant compound 2 having the structure of formula (2). As shown in Figure 8, the flame retardant compound has a high thermal decomposition temperature, with a thermal decomposition temperature Td(90%) of 372.5°C. Td(90%) is the temperature at which the sample loses 10% of its weight due to heat.

[0127] As shown in Figures 5 and 7, flame retardant compound 1 having the structure of formula (1) in Example 1 and flame retardant compound 2 having the structure of formula (2) in Example 2 have higher thermal decomposition temperatures, and the high temperature region of the thermogravimetric analysis curve is relatively flat, indicating that the materials have good heat resistance and are suitable for use as flame retardant additives. As shown in Figures 6 to 8, flame retardant compound 2 in Example 2 has a higher melting point and thermal decomposition temperature than flame retardant compound 1 in Example 1, and has better flame retardant properties.

[0128] The resin compositions or their molded articles of Examples 3 to 5, Comparative Examples 1 and 2 were subjected to the following performance tests. The test results are shown in Table 1:

[0129] Light transmittance: tested in accordance with GB / T 2410-2008 standard, thickness is 0.2mm.

[0130] Melt viscosity: tested according to ASTM D1238.

[0131] Softening point: tested according to ASTM D6493 standard.

[0132] Flame retardancy rating: Flame retardancy rating refers to a material's combustion performance in a fire. It is tested according to the UL94-HB standard, ANSI / UL-94-1985. The V0, V-2, and HB grades in Table 1 refer to the UL-94 V0, V-2, and HB grades. Flame retardancy levels decrease from V-0, V-1, V-2, and HB, with higher grades indicating improved flame retardancy.

[0133] 180° Peel Force (N / 25mm): The 180° peel force on the PET (polyethylene terephthalate) surface is tested in accordance with GB 2792-2014.

[0134] Table 1

[0135] 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.

[0136] As can be seen from the results in Table 1, the flame retardant grade of the resin composition of Example 3 and Example 4, to which the flame retardant compound 2 of the embodiment of the present application is added, reaches V-0, and has improved light transmittance, as well as suitable melt viscosity and peel strength. Compared with the resin composition of Comparative Example 1 in which no flame retardant component is added, the flame retardant grade is increased from HB to V-0, and the flame retardant performance is significantly improved. Compared with the resin composition of Comparative Example 2 in which only the existing flame retardant is added but no flame retardant compound 2 of the embodiment of the present application is added, the light transmittance of the molded article is significantly improved. The flame retardant grade of the resin composition of Example 5 in which the flame retardant compound 1 of the embodiment of the present application is added can reach V-2, and has good light transmittance. Compared with the resin composition of Comparative Example 1 in which no flame retardant component is added, the flame retardant grade is increased from HB to V-2, and the flame retardant performance is significantly improved. Compared with the resin composition of Comparative Example 2 in which only the existing flame retardant is added but no flame retardant compound 1 of the embodiment of the present application is added, the light transmittance of the molded article is significantly improved.

[0137] In addition, the resin composition of Example 3 is added with a phenyl-containing flame retardant compound 2, and the resin composition of Example 5 is added with a non-phenyl-containing flame retardant compound 1. By comparing Example 3 and Example 5, it can be seen that the phenyl-containing flame retardant compound 2 can better improve the flame retardant properties of the resin composition, improve the peel strength, and thereby improve the safety and reliability of the application of the resin composition, while also enabling the resin composition to have a certain light transmittance after molding; and the non-phenyl-containing flame retardant compound 1 is beneficial for the resin composition to obtain a higher light transmittance, and can also achieve a certain flame retardant level and peel strength.

[0138] It should be understood that the first, second and various numerical numbers involved in this document are only distinguished for the convenience of description and are not intended to limit the scope of this application.

[0139] In this application, "and / or" describes the relationship between related objects, indicating that three possible relationships exist. For example, "A and / or B" can mean: A exists alone, A and B exist simultaneously, and B exists alone. A and B can be singular or plural. The character " / " generally indicates that the related objects are in an "or" relationship.

[0140] In this application, "at least one" means one or more, and "more than one" means two or more. "At least one of the following" or similar expressions refers 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 all mean: a, b, c, ab (i.e., a and b), ac, bc, or abc, where a, b, and c can be single or multiple.

[0141] 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, which means that the value of a can be between 0.5 and 15, and includes the endpoint values ​​0.5 and 15.

[0142] It should be understood that in the various embodiments of the present application, the size of the serial numbers of the above-mentioned processes does not mean 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 on the implementation process of the embodiments of the present 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 from 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 anthracenyl 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 from 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 from 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 of the flame retardant compound with 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 the flame retardant compound according to any one of claims 1-10, characterized in that, Comprising: 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, Comprising a matrix resin and a flame retardant, and the flame retardant comprises the flame retardant compound according to any one of claims 1-10.

13. The resin composition according to claim 12, characterized in that, 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 12-14, 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 elastomer, and polyurethane 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 to 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 molded article, characterized in that, A molded article comprising the resin composition according to any one of claims 12-19.

21. The use 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 a communication device, a protective cover or a protective layer for a vehicle.

22. A device, characterized in that, The device comprises the flame retardant compound according to any one of claims 1-10, or a molded article comprising 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 comprises 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 protective cover or a protective layer covering the device body, and the protective cover or the protective layer comprises 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 protective sleeve wrapping the at least one optical fiber or at least one wire, and the cable protective sleeve comprises the flame retardant compound according to any one of claims 1-10, or a molded article comprising the resin composition according to any one of claims 12-19.

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

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