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EP-4741472-A1 - FLAME RETARDANT COMPOUND, AND FLAME RETARDANT RESIN COMPOSITION AND PRODUCT USING SAME

EP4741472A1EP 4741472 A1EP4741472 A1EP 4741472A1EP-4741472-A1

Abstract

The present disclosure relates to a flame retardant compound of a novel structure with excellent flame retardancy properties and improved mechanical properties, and to a flame retardant resin composition and flame retardant products using the same.

Inventors

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

Assignees

  • LG Chem, Ltd.

Dates

Publication Date
20260513
Application Date
20250218

Claims (12)

  1. A flame retardant compound represented by the following chemical formula1: wherein, in Chemical Formula 1, R 1 and R 2 are the same or different from each other and are each independently hydrogen, a linear or branched alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, R 3 is hydrogen, a linear or branched alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, O, S, NR 2 , or the following Chemical Formula a, wherein, in the Chemical Formula a, Ra, Rb, and Rc are the same or different from each other and each independently is hydrogen, a linear or branched alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, O, S, or NR 2 , R 4 is hydrogen, a linear or branched alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, O, S, or NR 2 , wherein the alkyl group, aryl group, or heteroaryl group may include at least one carboxyl group, hydroxyl group, or amino group, R 3 and R 4 may form a ring with each other, M 1 is Zn, M 2 is one or more selected from the group consisting of metal and ammonium ions excluding Zn, m, n, x, and y are the same or different from each other and each independently is an integer from 0 to 5, p and q are integers of 1 or more.
  2. The flame retardant compound of claim 1, wherein in the Chemical Formula 1: R 1 and R 2 are the same or different, and are each independently a substituted or unsubstituted linear or branched alkyl group, or a substituted or unsubstituted aryl group, R 3 is an alkyl group, O, or the Chemical Formula a, R 4 is hydrogen, an alkyl group, or an aryl group, and R 3 and R 4 may together form a ring.
  3. The flame retardant compound of claim 2, wherein in the Chemical Formula 1: R 3 is a compound of the Chemical Formula a.
  4. The flame retardant compound of claim 1, wherein in the Chemical Formula 1: R 1 and R 2 are the same or different, and are each independently a substituted or unsubstituted linear or branched alkyl group, or a substituted or unsubstituted aryl group, R 3 is the Chemical Formula a, R 4 is hydrogen, or an alkyl group.
  5. The flame retardant compound of claim 1, wherein M 2 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.
  6. The flame retardant compound of claim 5, wherein M 2 is one or more selected from the group consisting of Al, Zn, Mg, Ca, and ammonium ions.
  7. The flame retardant compound of claim 1, wherein the flame retardant compound represented by the Chemical 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 10 wt% to 20 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 melt flow index (MFI) of 9 (g/10min) or more, measured according to the ISO 1133 method (220°C, 10kg).
  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. 10-2024-0033941, filed on March 11, 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 and mechanical properties of a polymer resin even when used in a relatively smaller amount than conventional compositions, 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. Therefore, there is a demand for the development of non-halogenated flame retardants suitable for increasing the flame retardancy of polymer resins. [DETAILED DESCRIPTION OF THE INVENTION] [TECHNICAL PROBLEM] It is an object of the present invention to provide a flame retardant compound capable of improving the flame retardant properties and mechanical properties of a polymer resin. 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 and R2 are the same or different from each other and are each independently hydrogen, a linear or branched alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,R3 is hydrogen, a linear or branched alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, O, S, NR2, or the following Chemical Formula a, wherein, in the Chemical Formula a,Ra, Rb, and Rc are the same or different from each other and each independently is hydrogen, a linear or branched alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, O, S, or NR2,R4 is hydrogen, a linear or branched alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, O, S, or NR2, wherein the alkyl group, aryl group, or heteroaryl group may include at least one carboxyl group, hydroxyl group, or amino group,R3 and R4 may form a ring with each other,M1 is Zn,M2 is one or more selected from the group consisting of metal and ammonium ions excluding Zn,m, n, x, and y are the same or different from each other and each independently is an integer from 0 to 5,p and q are integers of 1 or more. 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