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EP-4741471-A1 - FLAME RETARDANT COMPOUND, AND FLAME RETARDANT RESIN COMPOSITION AND FLAME RETARDANT PRODUCT USING SAME

EP4741471A1EP 4741471 A1EP4741471 A1EP 4741471A1EP-4741471-A1

Abstract

The present disclosure relates to a flame retardant compound having a novel structure capable of exhibiting excellent flame retardant properties, mechanical properties, and heat resistance, and a flame retardant resin composition and a flame retardant product using same.

Inventors

  • HWANG, BYUNGHEE
  • IM, Seoyoung
  • JANG, Hanbit
  • LEE, HOYONG

Assignees

  • LG Chem, Ltd.

Dates

Publication Date
20260513
Application Date
20241217

Claims (12)

  1. A flame retardant compound represented by the following chemical formula1: wherein, in Chemical Formula 1, R 1 is a substituted or unsubstituted linear or branched alkylene group, a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group, O, S, or N, R 2 and R 3 are the same or different from each other, and are each independently hydrogen, a hydroxyl group, a substituted or unsubstituted linear or branched alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, R 4 and R 5 are the same or different from each other, and are each independently a substituted or unsubstituted linear or branched alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, M is one or more selected from the group consisting of metal and ammonium ions, n, m, x, and y are the same or different from each other, and are each independently an integer from 1 to 5.
  2. The flame retardant compound of claim 1, wherein in the Chemical Formula 1: R 1 is a substituted or unsubstituted linear or branched alkylene group having 1 to 20 carbon atoms, O, or N, R 2 and R 3 are the same or different from each other and are each independently a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, R 4 and R 5 are the same or different from each other and are each independently a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  3. The flame retardant compound of claim 1, wherein in the Chemical Formula 1: R 1 is an unsubstituted linear or branched alkylene group having 1 to 20 carbon atoms, or O, R 2 and R 3 are the same or different from each other and are each independently an unsubstituted alkyl group having 1 to 20 carbon atoms, R 4 and R 5 are the same or different from each other and are each independently an unsubstituted linear alkyl group having 1 to 20 carbon atoms or an unsubstituted aryl group having 6 to 20 carbon atoms.
  4. The flame retardant compound of claim 1, wherein the M is one or more selected from the group consisting of Mg, Ca, Al, Sb, Sn, Ge, Ti, Zn, Fe, Zr, Ce, Bi, Sr, Mn, Li, Na, K, and ammonium ions.
  5. The flame retardant compound of claim 4, wherein the M is one or more selected from the group consisting of Al, Zn, Mg, Ca, and ammonium ions.
  6. The flame retardant compound of claim 1, wherein the flame retardant compound represented by Formula 1 is a coordination compound between ligands, which include one or more selected from the group consisting of the first ligand represented by the following Chemical Formula 2 and one or more selected from the group consisting of the second ligand represented by the following Chemical Formula 3; and a central metal element M: wherein, in Chemical Formulas 2 to 3, the definitions of R 1 to R 5 , x, y, n, and m are the same as those described in claim 1.
  7. The flame retardant compound of claim 1, wherein the flame retardant compound represented by Formula 1 includes any one selected from the compounds of the following structural formulas:
  8. A flame retardant resin composition comprising the flame retardant compound of claim 1; and a binder resin.
  9. The flame retardant resin composition of claim 8, wherein the binder resin comprises a polyester, or a polyamide.
  10. The flame retardant resin composition of claim 8, wherein the content of the flame retardant compound is from 1 wt% to 30 wt% based on the total weight of the solids in the flame retardant resin composition.
  11. The flame retardant resin composition of claim 8, wherein the flame retardant resin composition has a 5% weight loss thermal decomposition temperature (T 5% ) of 400°C or more by thermogravimetric analysis (TGA).
  12. A flame retardant product comprising the flame-retardant resin composition of claim 8.

Description

[TECHNICAL FIELD] Cross-Reference to Related Applications This application claims priority to and the benefit of Korean Patent Application No. 10-2024-0004832, filed on January 11, 2024 and Korean Patent Application No. 10-2024-0187366, filed on December 16, 2024, with the Korean Intellectual Property Office, the disclosures of which are incorporated herein by reference in their entirety. The present disclosure relates to a flame retardant compound, a flame retardant resin composition, and a flame retardant product using the same. More specifically, it relates to a flame retardant compound capable of improving the flame retardant properties, mechanical properties, and heat resistance of a polymer resin, and to a flame retardant resin composition and a flame retardant product using the same. [BACKGROUND OF ART] Resins used in electrical/electronic products and office equipment must satisfy flame retardant standards to ensure the fire safety of electrical/electronic products. There are methods for imparting flame retardancy, such as polymerizing by including a flame-retardant monomer, and mixing a flame retardant or flame-retardant auxiliary with the produced resin. The flame retardants include halogenated flame retardants, as well as non-halogen flame retardants such as phosphorus-based, nitrogen-based, and hydroxide-based flame retardants. The flame-retardant auxiliaries include antimony compounds, silicon-based compounds, and zinc-based compounds etc. The halogenated flame retardants are the most common since they have higher flame retardant efficiency compared to non-halogen flame retardants and can maintain the mechanical properties of the resin, among which brominated flame retardants are particularly effective. However, if the resin is processed by adding the brominated flame retardant, the high temperatures and pressures generated during processing reduce thermal stability, causing decomposition, and as a result, corrosive and toxic gases are produced, which negatively affect both the working environment and human body. To avoid these problems, a method of using non-halogenated flame retardants is available, among which the method of using non-halogenated flame retardant compounds is widely employed. However, as non-halogenated flame retardant compounds have lower flame-retardant efficiency compared to halogenated flame retardants, there is a disadvantage that an excessive amount of non-halogenated flame retardant compounds must be added, and in the case of a thermoplastic resin composition that is incapable of generating a char due to the principle of phosphorus-based flame retardant systems, it is difficult to exhibit sufficient flame retardancy. Furthermore, conventional methods do not satisfy the desired levels of mechanical properties and heat resistance. Therefore, there is a demand for the development of non-halogenated flame retardants that are suitable for increasing flame retardancy while maintaining the excellent mechanical properties and heat resistance of polymer resins. [DETAILED DESCRIPTION OF THE INVENTION] [TECHNICAL PROBLEM] It is an object of the present disclosure to provide a flame retardant compound capable of ensuring excellent flame retardant properties of the polymer resin, while improving both the mechanical properties and the heat resistance. It is another object of the present disclosure to provide a flame retardant resin composition comprising the flame retardant compound. It is another object of the present disclosure to provide a flame retardant product comprising the flame retardant resin composition. [Technical Solution] In this specification, there is provided a flame retardant compound represented by the following Chemical Formula 1: wherein, in Chemical Formula 1, R1 is a substituted or unsubstituted linear or branched alkylene group, a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group, O, S, or N,R2 and R3 are the same or different from each other, and are each independently hydrogen, a hydroxyl group, a substituted or unsubstituted linear or branched alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,R4 and R5 are the same or different from each other, and are each independently a substituted or unsubstituted linear or branched alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,M is one or more selected from the group consisting of metal and ammonium ions,n, m, x, and y are the same or different from each other, and each independently is an integer from 1 to 5. In addition, in this specification, there is provided a flame retardant resin composition comprising the flame retardant compound and a binder resin. Further, in this specification, there is provided a flame retardant product comprising the flame retardant resin composition. Hereinafter, the flame retardant compound, and the flame retardant resin compo