Novel sulfonate, flame retardant, additive composition, resin composition, and molded article

Abstract

The first invention provides a novel sulfonate. The second invention provides: a flame retardant with which it is possible to achieve a molded article that has excellent flame retardancy and excellent appearance; an additive composition which contains the flame retardant; a resin composition; and a molded article.　The novel sulfonate according to the first invention is represented by general formula (1). (In general formula (1), R1, R2, and R3 each independently represent a hydrogen atom, a fluorine atom, or a chlorine atom, and at least two of R1, R2, and R3 each independently represent a fluorine atom or a chlorine atom. M represents a sodium atom, a potassium atom, or a cesium atom. However, the cases where all of R1, R2, and R3 are fluorine atoms, the cases where all of R1, R2, and R3 are chlorine atoms, the cases where two selected from among R1, R2, and R3 are fluorine atoms and the balance is a hydrogen atom, and M is a potassium atom, and the cases where two selected from R1, R2, and R3 are fluorine atoms and the balance is a chlorine atom, and M is a sodium atom are excluded.)　The flame retardant according to the second invention contains a sulfonate represented by general formula (2). (In general formula (2), Q1, Q2, and Q3 each independently represent a hydrogen atom or a halogen atom, and at least one of Q1, Q2, and Q3 represents a halogen atom. X represents an alkali metal or an alkaline earth metal. However, the cases where all of Q1, Q2, and Q3 are fluorine atoms are excluded.)

Description

Novel sulfonate, flame retardant, additive composition, resin composition, and molded article

[0001] The present invention relates to a novel sulfonate, a flame retardant, an additive composition, a resin composition, and a molded article.

[0002] Since sulfonates can be used in a variety of applications, novel sulfonates are being explored.

[0003] Furthermore, thermoplastic resins are excellent in ease of molding processability, appearance, economy, mechanical strength, and other physical and chemical properties, and are therefore used in a wide range of fields, such as electrical, electronic, and office equipment, precision machinery, automobile parts, building materials, and miscellaneous goods. In particular, in order to expand their applications to electrical, electronic, and office equipment, it is necessary to impart flame-retardant properties to thermoplastic resins, and this demand has been growing in recent years, leading to the development of various flame retardants.

[0004] Patent Documents 1 and 2 disclose perfluoroalkanesulfonic acid alkali metal salts as flame retardants, and state that perfluoroalkanesulfonic acid-based flame retardants exhibit high flame retardancy.

[0005] Special Publication No. 47-40445 Publication No. 54-32456

[0006] The first object of the present invention is to provide a novel sulfonate salt that can be used in various applications. In the conventional techniques described in Patent Documents 1 and 2, perfluoroalkanesulfonic acid-based flame retardants have a problem in compatibility with resins such as polycarbonate, and in particular, CF4 with a short alkyl chain is difficult to be used. ３ SO ３ When K is used, the polycarbonate resin composition or the cured product thereof becomes cloudy, which poses a second problem in terms of appearance.

[0007] The present inventors have discovered a novel sulfonate that can be used in a variety of applications, which is the first problem, and have completed the first invention. Furthermore, they have discovered that a flame retardant containing a specific sulfonate can solve the second problem, and have completed the second invention. That is, the first and second inventions can be described as follows.

[0008] The first invention can be represented by the following [1] to [4]: ​​[1] A sulfonate represented by the following general formula (1): (In general formula (1), R １ , R ２ , and R ３ each independently represents a hydrogen atom, a fluorine atom, or a chlorine atom; R １ , R ２ , and R ３ At least two of the groups independently represent a fluorine atom or a chlorine atom, and M represents a sodium atom, a potassium atom, or a cesium atom. １ , R ２ , and R ３ When all of are fluorine atoms, R １ , R ２ , and R ３ When all of are chlorine atoms, R １ , R ２ , and R ３ two selected from the group consisting of fluorine atoms and the remaining group consisting of hydrogen atoms, and M is a potassium atom; and R １ , R ２ , and R ３ [2] The sulfonate salt according to [1], selected from the following compounds: CF ２ ClSO ３ K.F. ２ ClSO ３ Cs CHFClSO ３ Na CHFClSO ３ K CHFClSO ３ CsCFCl ２ SO ３ NaCFCl ２ SO ３ KCFCl ２ SO ３ [3] A resin composition comprising a resin and the sulfonate salt according to [1] or [2]. [4] The resin composition according to [3], wherein the content of the sulfonate salt is 0.01 to 20 parts by mass per 100 parts by mass of the resin.

[0009] The second invention can be shown in the following [5] to

[16] . [5] A flame retardant containing a sulfonate represented by the following general formula (2): (In general formula (2), Q １ , Q ２ , and Q ３ each independently represents a hydrogen atom or a halogen atom; Q １ , Q ２ , and Q ３ At least one of the groups represents a halogen atom, and X represents an alkali metal or an alkaline earth metal. １ , Q ２ , and Q ３(Except when all of the above are fluorine atoms.) [6] The flame retardant according to [5], wherein the halogen atom is a fluorine atom, a chlorine atom, or a bromine atom. [7] The flame retardant according to [5] or [6], wherein the alkali metal is a sodium atom, a potassium atom, or a cesium atom, and the alkaline earth metal is a calcium atom, a strontium atom, a barium atom, or a magnesium atom. [8] The flame retardant according to any of [5] to [7], which is added to a resin containing one or more resins selected from the group consisting of polycarbonate resins and polyester resins. [9] An additive composition comprising the flame retardant according to any of [5] to [8], and at least one selected from an antioxidant, an ultraviolet absorber, and an anti-dripping agent.

[10] A resin composition comprising a resin, and the flame retardant according to any of [5] to [8].

[11] The resin composition according to

[10] , wherein the resin has a molecular structure containing an ester bond in the main chain.

[12] The resin composition according to

[11] , wherein the resin comprises one or more resins selected from the group consisting of polycarbonate resins and polyester resins.

[13] The resin composition according to any one of

[10] to

[12] , wherein the content of the flame retardant is 0.01 to 3 parts by mass per 100 parts by mass of the resin.

[14] The resin composition according to any one of

[10] to

[13] , further comprising glass fibers.

[15] The resin composition according to any one of

[10] to

[14] , further comprising at least one selected from the group consisting of an antioxidant, an ultraviolet absorber, and an anti-dripping agent.

[16] A molded article made of the resin composition according to any one of

[10] to

[15] .

[17] A method for using a sulfonate salt represented by the following general formula (2) as a flame retardant: (In general formula (2), Q １ , Q ２ , and Q ３ each independently represents a hydrogen atom or a halogen atom; Q １ , Q ２ , and Q ３ At least one of the groups represents a halogen atom, and X represents an alkali metal or an alkaline earth metal. １ , Q ２ , and Q３

[18] A method for producing a resin composition, comprising a step of mixing a resin with the flame retardant according to any one of [5] to [8].

[0010] According to the first invention, a novel sulfonate salt can be provided. Furthermore, according to the second invention, a flame retardant capable of producing a molded article having excellent appearance and flame retardancy, an additive composition containing the flame retardant, a resin composition, and a molded article can be provided. In other words, the flame retardant of the second invention has an excellent balance of these properties.

[0011] Hereinafter, embodiments of the present invention will be described. For example, "1 to 10" means "1 or more" to "10 or less" unless otherwise specified. Hereinafter, the first invention will be described based on the first embodiment with reference to the drawings, and the second invention will be described based on the second embodiment with reference to the drawings.

[0012] First Embodiment [Sulfonate] The sulfonate of this embodiment is a novel compound represented by the following general formula (1).

[0013]

[0014] In general formula (1), R １ , R ２ , and R ３ each independently represents a hydrogen atom, a fluorine atom, or a chlorine atom; R １ , R ２ , and R ３ At least two of the above independently represent a fluorine atom or a chlorine atom, and M represents a sodium atom, a potassium atom, or a cesium atom.

[0015] R １ , R ２ , and R ３ When at least two of the groups independently represent a fluorine atom or a chlorine atom, specifically, R １ , R ２ , and R ３ Preferably, two selected from R are both fluorine atoms, both chlorine atoms, or a combination of fluorine and chlorine atoms.１ , R ２ , and R ３ When all of are fluorine atoms, R １ , R ２ , and R ３ Except when all of the above are chlorine atoms.

[0016] R １ , R ２ , and R ３ Specific examples of the combinations include the following combinations (1) to (4): (1) fluorine atom, fluorine atom, hydrogen atom (2) fluorine atom, fluorine atom, chlorine atom (3) fluorine atom, chlorine atom, hydrogen atom (4) fluorine atom, chlorine atom, chlorine atom However, R １ , R ２ , and R ３ two selected from the group consisting of fluorine atoms and the remaining group consisting of hydrogen atoms, and M is a potassium atom; and R １ , R ２ , and R ３ two selected from the group consisting of fluorine atoms and the remaining group consisting of chlorine atoms, and M is a sodium atom.

[0017] The sulfonate salt of the present embodiment contains one or more compounds selected from the compounds represented by the general formula (1).

[0018] Specifically, the sulfonate salt of the present embodiment can be selected from the following compounds, and one or more of them can be used in combination: CF ２ ClSO ３ K., C.F. ２ ClSO ３ Cs, CHFCISO ３ Na,CHFClSO ３ K, CHFClSO ３ Cs, CFCl ２ SO ３ Na, CFCl ２ SO ３ K, CFCl ２ SO ３ Cs

[0019] The novel sulfonate salt of the present embodiment can be used in various applications, for example, as a flame retardant, an antistatic agent, a precursor of a photoacid generator, a precursor of an ionic liquid, and the like.

[0020] [Method for Synthesizing Sulfonate] The method for synthesizing the sulfonate of this embodiment will be described with reference to the following reaction formula.

[0021]

[0022] First, 2-mercaptobenzothiazole sodium represented by the chemical formula (a) is reacted with BrCX ２ COONa (wherein each of the X's independently represents a fluorine atom or a chlorine atom) to synthesize a benzothiazole compound represented by general formula (b). １ , R ２ , and R ３ has the same meaning as in the general formula (1). The reaction can be carried out in a solvent. Examples of the solvent include dimethylformamide (DMF), carbon tetrachloride, and water. １ , R ２ , and R ３ The type of element can be selected.

[0023] The reaction can be carried out in an air atmosphere at a temperature of 20 to 80°C for 1 to 24 hours under a pressure of 0.05 to 0.15 MPa. By changing the molar ratio of carbon tetrachloride and sodium bromodifluoroacetate to sodium 2-mercaptobenzothiazole and the reaction conditions, R １ , R ２ , and R ３ The combination of hydrogen atoms, fluorine atoms, or chlorine atoms in can be varied.

[0024] Next, the obtained benzothiazole compound represented by general formula (b) is sulfonylated in the presence of ruthenium chloride, sodium periodate, and carbon tetrachloride in a mixed solvent of acetonitrile and water to synthesize a sulfonylbenzothiazole compound represented by general formula (c). １ , R ２ , and R ３has the same meaning as the general formula (1) above. The reaction can be carried out in an air atmosphere at a temperature of 0 to 50°C for 1 to 24 hours under a pressure of 0.05 to 0.15 MPaA.

[0025] Next, the obtained sulfonylbenzothiazole compound represented by general formula (c) is reacted with a metal t-butoxide (formula: t-BuOM (wherein M represents a sodium atom, a potassium atom, or a cesium atom)) in a methanol solvent to synthesize a sulfinate represented by general formula (d). １ , R ２ , and R ３ has the same meaning as the general formula (1) above. The reaction can be carried out in an air atmosphere at a temperature of 0 to 50°C for 1 to 24 hours under a pressure of 0.05 to 0.15 MPaA.

[0026] Finally, the obtained sulfinate represented by general formula (d) is sulfonated in ultrapure water in the presence of sodium tungstate hydrate and aqueous hydrogen peroxide to synthesize the sulfonate represented by general formula (1). The reaction can be carried out in an air atmosphere at a temperature of 0 to 50°C for 1 to 24 hours at a pressure of 0.05 to 0.15 MPaA.

[0027] By the synthesis method described above, a sulfonate represented by the general formula (1) can be obtained, and specifically, the following compound can be obtained: CF ２ ClSO ３ K., C.F. ２ ClSO ３ Cs, CHFCISO ３ Na,CHFClSO ３ K, CHFClSO ３ Cs, CFCl ２ SO ３ Na, CFCl ２ SO ３ K, CFCl ２ SO ３The above eight compounds, which are specific examples of the sulfonate salt represented by general formula (1) of this embodiment, can be synthesized by appropriately changing the raw materials and their amounts, as well as the reaction conditions, described in the above reaction formula. For example, M in general formula (1) can be a potassium atom, a cesium atom, or a sodium atom by using potassium tert-butoxide, cesium tert-butoxide, or sodium tert-butoxide as t-BuOM in the above reaction formula. In addition, for example, R in general formula (1) １ , R ２ , and R ３ is the molar ratio of carbon tetrachloride to sodium 2-mercaptobenzothiazole in the above reaction formula, ２ CO ２ By changing the molar ratio of Na and further the reaction conditions, the ratio of hydrogen atoms, fluorine atoms, or chlorine atoms introduced can be changed.

[0028] In each reaction step, after the synthesis of the target compound, a step of extracting the target compound and a step of washing the target compound can be carried out as appropriate.

[0029] [Resin Composition] The resin composition of the present embodiment contains a resin and the novel sulfonate represented by the general formula (1).

[0030] The novel sulfonate salt of this embodiment can be used in various applications. For example, the novel sulfonate salt can be used as a flame retardant due to its excellent flame retardant performance, and can also be used as an antistatic agent due to its excellent antistatic performance. When the novel sulfonate salt of this embodiment is used as a flame retardant, it can be used in combination with known flame retardants such as known sulfonates, silicone-based flame retardants, and phosphoric acid-based flame retardants. That is, the flame retardant containing the novel sulfonate salt of this embodiment may further contain a known flame retardant. Known sulfonates include potassium trifluoromethanesulfonate (CF ３ SO ３ K), cesium trifluoromethanesulfonate (CF ３ SO ３ Cs), potassium perfluorobutanesulfonate (C４ F ９ SO ３ K), cesium perfluorobutanesulfonate (C ４ F ９ SO ３ Examples of the silicone flame retardant include silicone oil, silicone rubber, and silicone resin. Examples of the phosphoric acid flame retardant include organic phosphorus flame retardants such as triphenyl phosphate, tricresyl phosphate, diphenyl cresyl phosphate, and tris(tribromoneopentyl)phosphate, and inorganic phosphorus flame retardants such as red phosphorus, phosphorus trichloride, phosphorus pentachloride, and ammonium polyphosphate.

[0031] Furthermore, since the novel sulfonate of the present embodiment has excellent antistatic properties, the novel sulfonate can be used as an antistatic agent. The antistatic agent containing the novel sulfonate can include conventionally known antistatic agents.

[0032] The novel sulfonate salt of the present embodiment can be used for various applications, and the type of resin is not particularly limited, and known resins can be used depending on the application.

[0033] Examples of the resin include thermoplastic resins and thermosetting resins. Examples of the thermoplastic resin include olefin resins such as polyethylene resins and polypropylene resins, poly(meth)acrylate resins, polystyrene resins, styrene-acrylonitrile resins, acrylonitrile-butadiene-styrene resins, polyvinyl chloride resins, polyvinylidene chloride resins, polyvinyl acetate resins, polyvinyl butyral resins, ethylene-vinyl acetate copolymers, ethylene-vinyl alcohol resins, polyethylene terephthalate resins, polybutylene terephthalate resins, polyester resins, polyacetal resins, polyamide resins, polycarbonate resins, polyurethane resins, and polyphenylene sulfide resins.

[0034] Examples of thermosetting resins include epoxy resins, melamine resins, unsaturated polyester resins, phenolic resins, urea resins, alkyd resins, thermosetting polyimide resins, urethane resins, and thiourethane resins.

[0035] When the sulfonate salt of the present embodiment is used as a flame retardant, it can be suitably used in a polycarbonate resin or the like as the resin.

[0036] When the sulfonate salt of the present embodiment is used as an antistatic agent, it can be suitably used in resins such as olefin-based resins, polystyrene-based resins, styrene-acrylonitrile-based resins, acrylonitrile-butadiene-styrene-based resins, polyvinyl chloride-based resins, polyethylene terephthalate resins, polybutylene terephthalate resins, polyester-based resins, epoxy resins, melamine resins, and phenolic resins.

[0037] Molded articles obtained from resin compositions containing the novel sulfonate salts of this embodiment have excellent appearance (transparency) and can be suitably used for optical components. That is, the resin composition of this embodiment can be used as a resin composition for optical components containing a resin and the novel sulfonate salt represented by the general formula (1). The molded articles preferably have excellent haze and total light transmittance.

[0038] In the resin composition of the present embodiment, the content of the sulfonate may be 0.01 parts by mass to 20 parts by mass relative to 100 parts by mass of the resin. The content of the sulfonate can be adjusted depending on the application of the resin composition.

[0039] When the sulfonate salt of this embodiment is used as a flame retardant, the content of the sulfonate salt can be preferably 0.01 to 3 parts by mass, more preferably 0.05 to 2 parts by mass, and even more preferably 0.07 to 1 part by mass, relative to 100 parts by mass of the resin. Within this range, a molded product with excellent flame retardancy can be obtained.

[0040] When the sulfonate of this embodiment is used as an antistatic agent, the content of the sulfonate can be preferably 0.01 to 3 parts by mass, more preferably 0.05 to 2 parts by mass, and even more preferably 0.07 to 1 part by mass, relative to 100 parts by mass of the resin. Within this range, a molded product with excellent antistatic performance can be obtained.

[0041] (Other Components) The resin composition of the present embodiment may further contain various components depending on its application. For example, when the sulfonate salt of the present embodiment is used as a flame retardant, the resin composition may further contain an antioxidant, an ultraviolet absorber, an anti-dripping agent, an antistatic agent, a flame retardant aid, an anti-fogging agent, an anti-blocking agent, a release agent, a flow improver, a plasticizer, a dispersant, an antibacterial agent, a surfactant, a compatibilizer, a chelating agent, etc.

[0042] Furthermore, when the sulfonate salt of the present embodiment is used as an antistatic agent, the resin composition may further contain an antioxidant, an ultraviolet absorber, an antifogging agent, an antiblocking agent, a release agent, a flow improver, a plasticizer, a dispersant, an antibacterial agent, a surfactant, a compatibilizer, a chelating agent, or the like.

[0043] (Method for preparing resin composition) The resin composition of this embodiment can be obtained by mixing using a conventionally known method. When a thermoplastic resin is used as the resin, it can be melt-kneaded and processed into various shapes such as pellets.

[0044] [Molded Article] A molded article can be obtained from the resin composition of this embodiment. Examples of molding methods include injection molding, extrusion molding, blow molding, sintering molding, compression molding, and transfer molding.

[0045] [Uses] The molded article containing the sulfonate salt of the present embodiment can be used in a variety of applications, for example, in applications requiring flame retardancy or antistatic properties.

[0046] Specific examples of applications requiring flame retardancy include electrical and electronic equipment, office automation equipment, information terminal equipment, machine parts, home appliances, optical parts, vehicle parts, building materials, various containers, and lighting equipment.

[0047] Specific examples of applications requiring antistatic performance include electrical and electronic devices, office automation equipment, information terminal equipment, machine parts, home appliances, optical parts, interior and exterior vehicle materials, building materials, various containers, semiconductor encapsulation materials, LED encapsulation materials, bottles, and various films.

[0048] The molded article obtained from the resin composition containing the novel sulfonate salt of this embodiment has excellent appearance and can be suitably used for optical components. That is, in this embodiment, the resin composition can be used as an optical component.

[0049] Second Embodiment [Flame Retardant] The flame retardant of this embodiment contains a sulfonate represented by the following general formula (2). A flame retardant containing such a sulfonate can provide a molded article that is excellent in flame retardancy and total light transmittance, and therefore excellent in transparency and appearance. In other words, a molded article with an excellent balance of these properties can be obtained. The flame retardant of this embodiment is preferably also excellent in haze, and can provide a molded article with an excellent appearance.

[0050]

[0051] In general formula (2), Q １ , Q ２ , and Q ３ each independently represents a hydrogen atom or a halogen atom; Q １ , Q ２ , and Q ３ At least one of represents a halogen atom. Examples of the halogen atom include a fluorine atom, a chlorine atom, and a bromine atom.

[0052] Q １ , Q ２ , and Q ３ At least one of Q represents a halogen atom, and preferably at least two of Q represent halogen atoms. This allows a molded article to be obtained that is superior in flame retardancy and appearance. １ , Q ２ , and Q ３ Excluding the case where all of the above are fluorine atoms.

[0053] Q １ , Q ２ , and Q ３ When at least two of the groups represent halogen atoms, Q １ , Q ２ , and Q ３ Specifically, two selected from the above may be all fluorine atoms, all chlorine atoms, all bromine atoms, a combination of fluorine atoms and chlorine atoms, a combination of fluorine atoms and bromine atoms, or a combination of chlorine atoms and bromine atoms, and preferably all fluorine atoms, all chlorine atoms, or a combination of fluorine atoms and chlorine atoms. This allows for the production of a molded product with better flame retardancy and appearance.

[0054] Q １ , Q ２ , and Q ３ When at least one of represents a halogen atom, the following combinations (a) to (i) can be specifically mentioned, and combinations (a) and (d) to (i) are preferred. These combinations enable the production of molded articles with superior flame retardancy and appearance. (a) fluorine atom, hydrogen atom, hydrogen atom (b) chlorine atom, hydrogen atom, hydrogen atom (c) bromine atom, hydrogen atom, hydrogen atom (d) fluorine atom, fluorine atom, hydrogen atom (e) fluorine atom, fluorine atom, chlorine atom (f) fluorine atom, chlorine atom, hydrogen atom (g) fluorine atom, chlorine atom, chlorine atom (h) fluorine atom, fluorine atom, bromine atom (i) chlorine atom, chlorine atom, hydrogen atom (j) chlorine atom, chlorine atom, chlorine atom

[0055] X represents an alkali metal or alkaline earth metal. Examples of alkali metals include sodium, potassium, and cesium atoms. Examples of alkaline earth metals include calcium, strontium, barium, and magnesium atoms.

[0056] In the present embodiment, X in general formula (2) is more preferably a sodium atom, a potassium atom, or a cesium atom, which allows for the production of a molded article with better flame retardancy and appearance.

[0057] The sulfonate contained in the flame retardant of this embodiment includes one or more compounds selected from the compounds represented by the general formula (2).

[0058] Specific examples of the compound represented by the general formula (2) include the following compounds, and one or more selected from these may be used in combination: CF ２ ClSO ３ Na, CF ２ ClSO ３ K., C.F. ２ ClSO ３ Cs, CHFCISO ３ Na,CHFClSO ３ K, CHFClSO ３ Cs, CFCl ２ SO ３ Na, CFCl ２ SO ３ K, CFCl ２ SO ３ Cs, CF ２ HSO ３ Na, CF ２ HSO ３ K., C.F. ２ HSO ３ Cs, CFH ２ SO ３ Na, CFH ２ SO ３ K., C.F.H. ２ SO ３ Cs, CF ２ BrSO ３ Na, CF ２ BrSO ３ K., C.F. ２ BrSO ３ Cs, CHCl ２ SO ３ Na, CHCl ２ SO ３ K, CHCl ２ SO ３ Cs, CCl ３ SO ３ Na, CCl ３ SO ３ K, CCl ３ SO ３ Cs

[0059] By using a flame retardant containing a sulfonate selected from these, a molded article having excellent flame retardancy and appearance can be obtained.

[0060] In this embodiment, the average particle size of the flame retardant (sulfonate) is preferably 100 μm or less, more preferably 0.1 to 90 μm, and even more preferably 0.5 to 70 μm. The average particle size (median size) can be measured using, for example, a laser diffraction / scattering particle size distribution analyzer.

[0061] The flame retardant of the present embodiment may contain, in addition to the sulfonate represented by the general formula (2), a known flame retardant such as a known sulfonate-based flame retardant, a silicone-based flame retardant, or a phosphoric acid-based flame retardant. Examples of known sulfonate salts include potassium trifluoromethanesulfonate (CF ３ SO ３ K), cesium trifluoromethanesulfonate (CF ３ SO ３ Cs), potassium perfluorobutanesulfonate (C ４ F ９ SO ３ K), cesium perfluorobutanesulfonate (C ４ F ９ SO ３ Examples of the silicone flame retardant include silicone oil, silicone rubber, and silicone resin. Examples of the phosphoric acid flame retardant include organic phosphorus flame retardants such as triphenyl phosphate, tricresyl phosphate, diphenyl cresyl phosphate, and tris(tribromoneopentyl)phosphate, and inorganic phosphorus flame retardants such as red phosphorus, phosphorus trichloride, phosphorus pentachloride, and ammonium polyphosphate.

[0062] [Additive composition] The additive composition of the present embodiment contains a flame retardant and at least one selected from an antioxidant, an ultraviolet absorber, and an anti-dripping agent. As the flame retardant contained in the additive composition of the present embodiment, a flame retardant containing a sulfonate represented by the general formula (2) can be used.

[0063] The flame retardant can be contained in an amount of preferably 1 to 95 parts by mass, more preferably 2 to 90 parts by mass, and even more preferably 5 to 80 parts by mass per 100 parts by mass of the additive composition of this embodiment. By containing the flame retardant in the additive composition of this embodiment in this range, a molded article with excellent flame retardancy can be obtained.

[0064] (Antioxidant) Examples of the antioxidant include phenol-based antioxidants, thioether-based antioxidants, and phosphorus-based antioxidants. Among these, phenol-based antioxidants and thioether-based antioxidants are preferred, and thioether-based antioxidants are particularly preferred. These antioxidants may be used alone or in combination of two or more.

[0065] Examples of phenolic antioxidants include 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione, 4,4',4'-(1-methylpropanyl-3-ylidene)tris(6-tert-butyl-m-cresol), 6,6'-di-tert-butyl-4,4'-butylidene-di-m-cresol, and octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate. nate, pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], 3,9-bis{2-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionyloxy]-1,1-dimethylethyl}-2,4,8,10-tetraoxaspiro[5.5]undecene, 1,3,5-tris(3,5-di-tert-butyl-4-hydroxyphenylmethyl)-2,4,6-trimethylbenzene, and the like.

[0066] Examples of the thioether antioxidant include 2,2-bis({[3-(dodecylthio)propionyl]oxy}methyl)-1,3-propanediyl bis[3-(dodecylthio)propionate] and di(tridecyl)3,3′-thiodipropionate.

[0067] Examples of phosphorus-based antioxidants include 3,9-bis(octadecyloxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5,5]undecene, 3,9-bis(2,6-di-tert-butyl-4-methylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5,5]undecene, 2,2'-methylenebis(4,6-di-tert-butylphenyl)-2-ethylhexyl phosphite, tris(2,4-di-tert-butylphenyl)phosphite, tris(nonylphenyl)phosphite, tetra-C １２－１５ -alkyl(propane-2,2-diylbis(4,1-phenylene))bis(phosphite), 2-ethylhexyldiphenyl phosphite, isodecyldiphenyl phosphite, triisodecyl phosphite, triphenyl phosphite, and the like.

[0068] These antioxidants may be commercially available products or synthesized products. Examples of commercially available products include Adeka STAB (manufactured by Adeka Corporation): AO-20, AO-30, AO-40, AO-50, AO-50F, AO-60, AO-60G, AO-80, AO-330, AO-412S, AO-503, PEP-8, PEP-8W, PEP-36, PEP-36A, HP-10, 2112, 2112RG, 1178, 1500, C, 135A, 3010, and TPP.

[0069] The antioxidant can be contained in an amount of preferably 1 to 95 parts by mass, more preferably 2 to 90 parts by mass, and even more preferably 5 to 80 parts by mass per 100 parts by mass of the additive composition of this embodiment. By containing the antioxidant in the additive composition of this embodiment in this range, a molded article can be obtained in which the occurrence of coloring, cloudiness, oxidative degradation, etc. is suppressed.

[0070] (Ultraviolet Absorber) Examples of the ultraviolet absorber include benzotriazole derivatives such as 2-(2'-hydroxy-5'-methylphenyl)benzotriazole, 2-(2'-hydroxy-3',5'-di-tert-butylphenyl)benzotriazole, 2-(2'-hydroxy-3'-tert-butyl-5'-methylphenyl)-5-chlorobenzotriazole, 2-(2'-hydroxy-3',5'-di-tert-butylphenyl)-5-chlorobenzotriazole, and 2-(2'-hydroxy-3',5'-di-tert-amylphenyl)benzotriazole, and Examples of suitable benzophenone derivatives include benzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-octoxybenzophenone, 2-hydroxy-4-dodecyloxybenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, and 2-hydroxy-4-methoxy-5-sulfobenzophenone, as well as cyanoacrylate derivatives such as 2-ethylhexyl-2-cyano-3,3'-diphenylacrylate and ethyl-2-cyano-3,3'-diphenylacrylate. A specific example is TINUVIN 327 (manufactured by Ciba-Geigy).

[0071] The ultraviolet absorber can be contained in an amount of preferably 1 to 95 parts by mass, more preferably 2 to 90 parts by mass, and even more preferably 5 to 80 parts by mass per 100 parts by mass of the additive composition of this embodiment. By containing the ultraviolet absorber in the additive composition of this embodiment in this range, a molded article in which deterioration is suppressed can be obtained.

[0072] (Anti-drip agent) As the anti-drip agent (anti-drip agent), a fluoropolymer is preferably used. Examples of the fluoropolymer include fluoroolefin resins, which are polymers (including copolymers) containing a fluoroethylene structure. Specific examples include difluoroethylene resins, tetrafluoroethylene resins, tetrafluoroethylene / hexafluoropropylene resins, and tetrafluoroethylene / perfluoroalkyl vinyl ether resins.

[0073] The anti-dripping agent can be contained in an amount of preferably 1 to 95 parts by mass, more preferably 2 to 90 parts by mass, and even more preferably 5 to 80 parts by mass per 100 parts by mass of the additive composition of this embodiment. By containing the anti-dripping agent in this range in the additive composition of this embodiment, it is possible to suppress the resin from dropping from a burned molded article and prevent the spread of fire.

[0074] (Other Components) The additive composition of the present embodiment may contain, as other components, an antistatic agent, a flame retardant aid, an antifogging agent, an antiblocking agent, a release agent, a flow improver, a plasticizer, a dispersant, an antibacterial agent, a surfactant, a compatibilizer, a chelating agent, and the like.

[0075] (Method for Preparing Additive Composition) The additive composition of this embodiment can be prepared by mixing the above-described components using a conventionally known method, for example, using a Banbury mixer, a kneader, or the like.

[0076] [Resin Composition] The resin composition of the present embodiment includes a resin and a flame retardant. The flame retardant included in the resin composition of the present embodiment is a flame retardant containing a sulfonate salt represented by the general formula (2).

[0077] The resin composition of this embodiment preferably contains the flame retardant in an amount of 0.01 to 2 mass%, more preferably 0.03 to 1.5 mass%, and even more preferably 0.05 to 1 mass%, based on 100 mass% of the resin. The content of the flame retardant is preferably 0.01 to 3 mass parts, more preferably 0.05 to 2 mass parts, and even more preferably 0.07 to 1 mass part, based on 100 mass parts of the resin.

[0078] By including the flame retardant in the above range, a molded article having excellent flame retardancy and appearance can be obtained, in other words, an excellent balance of these properties.

[0079] (Resin) The resin contained in the resin composition of the present embodiment is not particularly limited, and any known resin can be used as long as it can achieve the effects of the present invention.

[0080] In this embodiment, the resin may have a molecular structure containing an ester bond in the main chain, and the molecular structure contains at least an ester bond as a group (divalent group) formed as a bond connecting adjacent structural units.

[0081] Examples of the resin having a molecular structure containing an ester bond in the main chain include polycarbonate resins and polyester resins, and these can be used alone or in combination of two or more.

[0082] (Polycarbonate Resin) Examples of the polycarbonate resin include aliphatic polycarbonate resins and aromatic polycarbonate resins. From the viewpoints of affinity with flame retardants and the impact resistance and heat resistance of molded articles obtained from the resin composition, it is preferable to use aromatic polycarbonate resins.

[0083] Specifically, the aromatic polycarbonate resin is an aromatic polycarbonate polymer or copolymer obtained by reacting an aromatic dihydroxy compound, which is a dihydric phenol, with phosgene or a carbonic acid diester.

[0084] Examples of aromatic dihydroxy compounds include 2,2-bis(4-hydroxyphenyl)propane (i.e., bisphenol A), 2,2-bis(3-methyl-4-hydroxyphenyl)propane (i.e., bisphenol C), tetramethylbisphenol A, α,α'-bis(4-hydroxyphenyl)-p-diisopropylbenzene, hydroquinone, resorcinol, and 4,4'-dihydroxydiphenyl.

[0085] Preferred examples of aromatic polycarbonate resins include polycarbonate resins containing bisphenol A as the aromatic dihydroxy compound or a combination of bisphenol A and another aromatic dihydroxy compound, and polycarbonate resins containing bisphenol C or a combination of bisphenol C and another aromatic dihydroxy compound (particularly bisphenol A).

[0086] The polycarbonate resin may be a homopolymer consisting of one type of repeating unit, or a copolymer having two or more types of repeating units. In this case, the copolymer may be a random copolymer, a block copolymer, or any other copolymerization form. The polycarbonate resin may be a resin whose polymer chain has a linear molecular structure or a branched structure.

[0087] The polycarbonate resin can be contained in an amount of preferably 30 to 99.8% by mass, more preferably 40 to 99.8% by mass, and even more preferably 50 to 99.8% by mass, based on 100% by mass of the resin composition of this embodiment.

[0088] By including the polycarbonate resin in the above range, a molded article having excellent flame retardancy and appearance can be obtained, in other words, an excellent balance of these properties.

[0089] (Polyester Resin) Examples of polyester resins include aliphatic polyesters and aromatic polyesters, and condensation polymers of polyhydric alcohols and polycarboxylic acids can also be used.

[0090] Examples of polycarboxylic acids include aliphatic dicarboxylic acids such as oxalic acid, malonic acid, maleic acid, fumaric acid, citraconic acid, itaconic acid, glutaconic acid, succinic acid, alkenylsuccinic acid, adipic acid, and sebacic acid; alicyclic dicarboxylic acids such as cyclohexanedicarboxylic acid; aromatic dicarboxylic acids such as terephthalic acid, isophthalic acid, phthalic acid, and naphthalenedicarboxylic acid; and anhydrides thereof. The polycarboxylic acids may be used alone or in combination of two or more selected from these.

[0091] Examples of polyhydric alcohols include aliphatic diols such as ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, butanediol, hexanediol, and neopentyl glycol; alicyclic diols such as cyclohexanediol, cyclohexanedimethanol, and hydrogenated bisphenol A; and aromatic diols such as ethylene oxide adducts of bisphenol A and propylene oxide adducts of bisphenol A. Polyhydric alcohols may be used singly or in combination of two or more selected from these. Trivalent or higher carboxylic acids having a crosslinked or branched structure, or trivalent or higher polyhydric alcohols having a crosslinked or branched structure, may also be used in combination with the polycarboxylic acids and dicarboxylic acids.

[0092] Examples of the aliphatic polyester resin include poly(ε-caprolactone), polyenantholactone, polycaprylolactone, polybutylene adipate, polyethylene adipate, polybutylene succinate, and polybutylene succinate adipate.

[0093] Examples of aromatic polyester resins include polyethylene terephthalate resin, polybutylene terephthalate resin, polyhexamethylene terephthalate resin, polyethylene naphthalate resin, polybutylene naphthalate resin, and butanediol terephthalate-polytetramethylene glycol copolymer.

[0094] The polyester resin may be contained in an amount of preferably 30 to 98% by mass, more preferably 40 to 90% by mass, and even more preferably 50 to 80% by mass, based on 100% by mass of the resin composition of this embodiment. By containing the polyester resin in this range, a molded article with excellent flame retardancy and appearance can be obtained. In other words, the balance of these properties is excellent.

[0095] The molded article obtained from the resin composition containing the flame retardant of this embodiment is excellent in transparency, haze, and total light transmittance, and therefore can be suitably used for optical components. That is, the resin composition of this embodiment can be used as a resin composition for optical components containing a resin and the flame retardant.

[0096] (Glass Fiber) The resin composition of the present embodiment may further contain glass fiber. Examples of glass fiber include those made of E-glass, C-glass, S-glass, D-glass, ECR-glass, A-glass, and AR-glass. Among these, E-glass or S-glass is particularly preferred.

[0097] The fiber diameter of the glass fiber is not particularly limited, but can be 3 to 20 μm, for example. Considering the production cost per unit mass of glass fiber, a diameter of 3 μm or more is preferable. Furthermore, from the viewpoint of the strength of the resulting molded article, a diameter of 20 μm or less is preferable. More preferable upper limits can be 16 μm and 13 μm, and more preferable lower limits can be 6 μm and 9 μm. These upper and lower limits can be combined as desired.

[0098] The resin composition of this embodiment preferably contains the glass fiber in an amount of 5 to 70% by mass, more preferably 10 to 60% by mass, and even more preferably 20 to 50% by mass, based on 100% by mass of the resin composition. By containing the glass fiber in this range, the resin composition has excellent handleability and the obtained molded article has excellent mechanical strength.

[0099] The resin composition of the present embodiment preferably contains silica particles in addition to the glass fibers, which provides the resulting molded article with better flame retardancy and mechanical strength.

[0100] (Antioxidant, UV absorber, and anti-dripping agent) The resin composition of the present embodiment may further contain at least one selected from an antioxidant, an UV absorber, and an anti-dripping agent. As the antioxidant, the UV absorber, and the anti-dripping agent, the same ones as those contained in the additive composition described above can be used.

[0101] The antioxidant may be contained in an amount of preferably 0.01 to 10% by mass, more preferably 0.05 to 5% by mass, and even more preferably 0.1 to 3% by mass, based on 100% by mass of the resin composition of this embodiment. By containing the antioxidant in this range, a molded product can be obtained in which the occurrence of coloring, cloudiness, oxidative degradation, etc. is suppressed.

[0102] The ultraviolet absorber may be contained in an amount of preferably 0.01 to 10% by mass, more preferably 0.05 to 5% by mass, and even more preferably 0.1 to 3% by mass, based on 100% by mass of the resin composition of this embodiment. By containing the ultraviolet absorber in this range, a molded product in which deterioration is suppressed can be obtained.

[0103] The anti-dripping agent may be contained in an amount of preferably 0.01 to 10% by mass, more preferably 0.05 to 5% by mass, and even more preferably 0.1 to 3% by mass, based on 100% by mass of the resin composition of this embodiment. By containing the anti-dripping agent in this range, it is possible to suppress the resin from dropping from the burned molded body and prevent the fire from spreading.

[0104] (Other Components) The resin composition of the present embodiment may contain, as other components, an antistatic agent, a flame retardant aid, an antifogging agent, an antiblocking agent, a release agent, a flow improver, a plasticizer, a dispersant, an antibacterial agent, a surfactant, a compatibilizer, a chelating agent, or the like.

[0105] (Method for preparing resin composition) The resin composition of this embodiment can be melt-kneaded and processed into various shapes. Examples of the melt-kneading method include methods using a batch kneader such as a Brabender, a Banbury mixer, a Henschel mixer, a helical rotor, a roll, a single-screw extruder, a twin-screw extruder, etc. The melt-kneading temperature is selected from a temperature range in which the resin melts but the other components do not decompose.

[0106] The melt-kneaded resin composition can then be processed into various shapes, such as a method of extruding the melt-kneaded product into a strand shape and forming it into pellets, a method of hot-cutting or underwater-cutting the molten mixture into pellets, a method of extruding the product into a sheet shape and cutting it, or a method of extruding the product into a block shape and pulverizing it into a powder shape.

[0107] [Molded Article] A molded article can be obtained from the resin composition of this embodiment. Examples of molding methods include injection molding, extrusion molding, blow molding, and sinter molding.

[0108] [Uses] The molded article of the present embodiment can be used in a wide range of applications requiring flame retardancy, such as electrical and electronic devices, office automation equipment, information terminal equipment, machine parts, home appliances, optical parts, vehicle parts, building materials, various containers, and lighting equipment.

[0109] The molded article obtained from the resin composition containing the flame retardant of this embodiment is excellent in transparency, haze, and total light transmittance, and therefore can be suitably used for optical parts. That is, in this embodiment, the molded article can be used as an optical part made of the resin composition.

[0110] Although the embodiments of the present invention have been described above, these are merely examples of the present invention, and various configurations other than those described above can be adopted as long as they do not impair the effects of the present invention.

[0111] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples.

[0112] Example A Example a1 As shown in the following reaction formula, potassium chlorodifluoromethanesulfonate (CF ２ ClSO ３K) was synthesized. Specifically, this was done as follows. <Synthesis of potassium chlorodifluoromethanesulfinate of formula (iv) below> The raw material, 2-((chlorodifluoromethyl)sulfonyl)benzo[d]thiazole, was synthesized under the reaction conditions described in Scheme 5D on page 9 of the paper (Cell Reports Physical Science, 2, 100394, 2021). 2-((chlorodifluoromethyl)sulfonyl)benzo[d]thiazole of formula (iii) (31.4 g, 110.8 mmol), methanol (87.1 g), and potassium tert-butoxide / 20% methanol solution (14.9 g, 133.0 mmol) were charged into a 0.5 L two-necked recovery flask and stirred at room temperature for 3 hours. The reaction solution was washed with heptane, and the methanol solvent was then distilled off at less than 30 hPaA and a bath temperature of 50°C to obtain crude crystals. The crude crystals were washed with a toluene / methyl tert-butyl ether mixed solvent and then dried under conditions of less than 2 kPaA and a bath temperature of 50°C, thereby obtaining potassium chlorodifluoromethanesulfinate of formula (iv) (21.0 g, 89.5 mmol, purity 80.5%, step yield 81%, overall yield 46%).

[0113] <Synthesis of potassium chlorodifluoromethanesulfonate of the following formula (v)> The obtained potassium chlorodifluoromethanesulfinate (2.2 g, 11.5 mmol), ultrapure water (23.0 g), sodium tungstate dihydrate (151.7 mg, 0.5 mmol), and hydrogen peroxide solution (1.7 g, 15.0 mmol) were charged into a 0.5 L two-necked eggplant flask and stirred at room temperature for 2 hours. The reaction solution was concentrated at less than 10 hPaA and a bath temperature of 40 ° C., and the target substance in the slurry was extracted with methanol. The solvent was distilled off from the methanol extract at less than 30 hPaA and a bath temperature of 50 ° C., and the obtained crystals were dried under conditions of less than 2 kPaA and a bath temperature of 50 ° C. to obtain potassium chlorodifluoromethanesulfonate of formula (v) (2.2 g, 9.8 mmol, purity 92%, step yield 85%, overall yield 39%). １９ F-NMR (-62.1ppm), １３ C-NMR (126.4, t, J C-H =332Hz) DART-MS ([M-K] － =165.0, [2M-K] －= 368.9)

[0114] [Example a2] Cesium chlorodifluoromethanesulfonate (CF) was synthesized under the same conditions as in Example a1, except that cesium tert-butoxide was used instead of potassium tert-butoxide. ２ ClSO ３ Cs) was synthesized. １９ F-NMR (-62.1ppm), １３ C-NMR (126.5, t, J C-H =331Hz) DART-MS ([MCs] － =165.0, [2M-Cs] － = 462.9)

[0115] Examples A-1 to A-3, Comparative Examples A-1 to A-4 Preparation of pellets The components shown in Tables 1 and 3 below were prepared. Next, using a 25 mm diameter co-rotating twin-screw extruder (manufactured by Parker Corporation, product name: HK25D (41D)), the components were melt-kneaded at a cylinder temperature of 280°C to the contents shown in Tables 1 and 3, to obtain various pellets (resin compositions). Details of the components used are as follows:

[0116] (Polycarbonate resin) Mitsubishi Engineering Plastics Corporation, product name: Iupilon H-2000

[0117] (Sulfonate) Potassium chlorodifluoromethanesulfonate (CF ２ ClSO ３ K): Synthesized in Example a1 Potassium trifluoromethanesulfonate (CF ３ SO ３ K): Manufactured by Synquest Laboratories, Inc.

[0118] (Anti-drip agent) Polytetrafluoroethylene (PTFE): Polyflon MPA FA-500H manufactured by Daikin Industries, Ltd.

[0119] <Production of Flat Plate> The obtained pellets were dried at 120°C for 6 hours using a dryer. Next, a compression molding machine (manufactured by The Japan Steel Works, Ltd., product name: J100ADS-110U) was used to obtain flat plates (test pieces) measuring 127 mm x 13 mm x 3.1 mm thick at a molding temperature of 280°C and a mold temperature of 85°C. The obtained test pieces were used to perform the following measurements and tests, and the obtained results are shown in Table 1.

[0120] <Evaluation: Total Light Transmittance> The total light transmittance of the test piece was measured using HZ-V3 manufactured by Suga Test Instruments Co., Ltd.

[0121] <Evaluation: Haze> The haze of the test piece was measured using COH7700 manufactured by Nippon Denshoku Industries Co., Ltd. The evaluation was based on the following criteria. (Evaluation criteria) A: |(H ０ )-(H ｘ ) | ≦ 5% B: 5% < | (H ０ )-(H ｘ )|≦30% C: More than 30%<|(H ０ )-(H ｘ ) | (H ０ ): Haze value (%) of Comparative Example A-2 containing no sulfonate (H ｘ ): Haze value (%) of each test piece of Example A-1 and Comparative Example A-1

[0122] <Evaluation: Visibility of transmitted image> The obtained test piece (3.1 mm thick) was placed on top of characters (black print with a width of 0.5 mm), and the readability of the characters was visually confirmed from above the test piece, and the visibility of the transmitted image was evaluated according to the following criteria: (Evaluation criteria) A: Characters can be clearly read B: Characters can be read, although their outlines are slightly blurred or slightly unclear C: Characters cannot be read

[0123]

[0124] As shown in Table 1, the molded article containing the novel sulfonate of the present invention exhibited a total light transmittance and haze equivalent to those of polycarbonate resin containing no additive, and furthermore, had superior visibility of the transmitted image compared to conventionally known potassium trifluoromethanesulfonate. Thus, by using the novel sulfonate of the present invention, a molded article having a clearer appearance than conventional ones, i.e., an appearance with excellent transparency, could be obtained.

[0125] The flame retardancy of the test specimens of Examples A-2 and A-3 and Comparative Examples A-3 and A-4, each containing a drop prevention agent, was evaluated, and the results are shown in Table 3. <Evaluation: Flame Retardancy> The flame retardancy of the test specimens was measured under the following test conditions in accordance with UL94-V. (Test Conditions) At room temperature of 23°C and humidity of 50%, the burning time was determined after the first and second 10-second exposure to flame. In addition, the test specimens were observed for ignition of cotton placed 300 mm below the test specimens, and for combustion reaching the clamp. The UL94-V criteria were as shown in Table 2 below.

[0126]

[0127]

[0128] As shown in Table 3, molded articles containing the novel sulfonate salt of the present invention exhibited excellent flame retardancy in practical formulations. The results in Tables 1 and 3 demonstrate that the novel sulfonate salt of the present invention has a better balance of appearance (transparency) and flame retardancy than conventional salts, and can be suitably used as a flame retardant.

[0129] <Example B> [Examples B-1 to B-2, Comparative Examples B-1 to B-3] <Preparation of pellets> The components shown in Tables 4 and 6 below were prepared. Next, using a 25 mm diameter co-rotating twin-screw extruder (manufactured by Parker Corporation, product name: HK25D (41D)), the components were melt-kneaded at a cylinder temperature of 280°C to the contents shown in Tables 4 and 6, to obtain various pellets (resin compositions). Details of the components used are as follows.

[0130] (Polycarbonate resin) ・Polycarbonate resin A: Novarex M7027BF manufactured by Mitsubishi Engineering Plastics ・Polycarbonate resin B: Iupilon H-4000 manufactured by Mitsubishi Engineering Plastics

[0131] (Sulfonate) Potassium chlorodifluoromethanesulfonate (CF ２ ClSO ３ K): Synthesized in Example a1 Potassium trifluoromethanesulfonate (CF ３ SO ３ K): Manufactured by Synquest Laboratories, Inc.

[0132] (Release agent) Pentaerythritol tetrastearate: manufactured by Tokyo Chemical Industry Co., Ltd. Octadecyl stearate: manufactured by Tokyo Chemical Industry Co., Ltd.

[0133] <Production of Plate> The obtained pellets were dried at 120°C for 6 hours using a dryer. Next, a compression molding machine (manufactured by The Japan Steel Works, Ltd., product name: J100ADS-110U) was used to obtain a plate (test piece) measuring 127 mm x 13 mm x 3.1 mm thick at a molding temperature of 280°C and a mold temperature of 85°C. The obtained test piece was used to perform the following measurements and tests, and the obtained evaluation results are shown in Table 4.

[0134] <Evaluation: Total Light Transmittance> The total light transmittance of the test piece was measured using HZ-V3 manufactured by Suga Test Instruments Co., Ltd.

[0135] <Evaluation: Haze> The haze of the test piece was measured using COH7700 manufactured by Nippon Denshoku Industries Co., Ltd. (Evaluation criteria) A: |(H ０ )-(H ｘ ) | ≦ 5% B: 5% < | (H ０ )-(H ｘ )|≦30% C: More than 30%<|(H ０ )-(H ｘ ) | (H ０ ): Haze value (%) of Comparative Example B-2 containing no sulfonate (H ｘ ): Haze value (%) of each test piece of Example B-1 and Comparative Example B-1

[0136] <Evaluation: Visibility of transmitted image> The obtained test piece (3.1 mm thick) was placed on top of characters (black print with a width of 0.5 mm), and the readability of the characters was visually confirmed from above the test piece, and the visibility of the transmitted image was evaluated according to the following criteria: (Evaluation criteria) A: Characters can be clearly read B: Characters can be read, although their outlines are slightly blurred or slightly unclear C: Characters cannot be read

[0137]

[0138] As shown in Table 4, the molded article containing the novel sulfonate of the present invention exhibited a total light transmittance equivalent to that of a polycarbonate resin to which no sulfonate had been added, and furthermore, compared with the conventionally known potassium trifluoromethanesulfonate, the molded article had improved haze and excellent visibility of the transmitted image. Thus, by using the novel sulfonate of the present invention, a molded article having a clearer appearance than conventional ones, i.e., an appearance having excellent transparency, can be obtained.

[0139] The test specimens of Example B-2 and Comparative Examples B-2 and B-3 were evaluated for flame retardancy, and the results are shown in Table 6. <Evaluation: Flame Retardancy> The flame retardancy of the test specimens was measured under the following test conditions in accordance with UL94-V. (Test Conditions) At room temperature of 23°C and humidity of 50%, the burning times were determined after the first and second 10-second exposure to flame. In addition, the test specimens were observed for ignition of cotton placed 300 mm below the test specimens and for combustion reaching the clamp. The UL94-V criteria were as shown in Table 5 below.

[0140]

[0141]

[0142] As shown in Table 6, molded articles containing the flame retardant of the present invention had higher total light transmittance and also showed excellent flame retardancy in practical formulations compared to molded articles containing conventionally known flame retardants. The results in Tables 4 and 6 demonstrate that the novel sulfonate salt of the present invention has a better balance of appearance (transparency) and flame retardancy than conventional salts, and can be suitably used as a flame retardant.

[0143] This application claims priority based on Japanese Patent Application No. 2024-108469, filed July 4, 2024, the disclosure of which is incorporated herein by reference in its entirety.

Claims

1. A sulfonate represented by the following general formula (1): (In general formula (1), R １ , R ２ , and R ３ each independently represents a hydrogen atom, a fluorine atom, or a chlorine atom; R １ , R ２ , and R ３ At least two of the groups independently represent a fluorine atom or a chlorine atom, and M represents a sodium atom, a potassium atom, or a cesium atom. １ , R ２ , and R ３ When all of are fluorine atoms, R １ , R ２ , and R ３ When all of are chlorine atoms, R １ , R ２ , and R ３ two selected from the group consisting of fluorine atoms and the remaining group consisting of hydrogen atoms, and M is a potassium atom; and R １ , R ２ , and R ３ two selected from the group consisting of fluorine atoms and the remaining group consisting of chlorine atoms, and M is a sodium atom.

2. The sulfonate salt of claim 1, selected from the following compounds: CF ２ ClSO ３ K.F. ２ ClSO ３ Cs CHFClSO ３ Na CHFClSO ３ K CHFClSO ３ CsCFCl ２ SO ３ NaCFCl ２ SO ３ KCFCl ２ SO ３ Cs 3. A resin composition comprising: a resin; and the sulfonate salt according to claim 1 or 2.

4. The resin composition according to claim 3, wherein the content of the sulfonate is 0.01 to 20 parts by mass per 100 parts by mass of the resin.

5. A flame retardant containing a sulfonate salt represented by the following general formula (2): (In general formula (2), Q １ , Q ２ , and Q ３ each independently represents a hydrogen atom or a halogen atom; Q １ , Q ２ , and Q ３ At least one of the groups represents a halogen atom, and X represents an alkali metal or an alkaline earth metal. １ , Q ２ , and Q ３ Except when all of are fluorine atoms.) 6. The flame retardant according to claim 5, wherein the halogen atom is a fluorine atom, a chlorine atom, or a bromine atom.

7. The flame retardant according to claim 5, wherein the alkali metal is a sodium atom, a potassium atom, or a cesium atom, and the alkaline earth metal is a calcium atom, a strontium atom, a barium atom, or a magnesium atom.

8. The flame retardant according to claim 5, which is added to a resin containing one or more resins selected from the group consisting of polycarbonate resins and polyester resins.

9. An additive composition comprising the flame retardant according to any one of claims 5 to 8 and at least one selected from the group consisting of an antioxidant, an ultraviolet absorber, and an anti-dripping agent.

10. A resin composition comprising: a resin; and the flame retardant according to any one of claims 5 to 8.

11. The resin composition according to claim 10, wherein the resin has a molecular structure containing an ester bond in the main chain.

12. The resin composition according to claim 11, wherein the resin comprises one or more resins selected from the group consisting of polycarbonate resins and polyester resins.

13. The resin composition according to claim 10, wherein the content of the flame retardant is 0.01 to 3 parts by mass per 100 parts by mass of the resin.

14. The resin composition according to claim 10, further comprising glass fibers.

15. The resin composition according to claim 10, further comprising at least one selected from the group consisting of an antioxidant, an ultraviolet absorber, and an anti-dripping agent.

16. A molded article made from the resin composition according to claim 10.

17. A method for using a sulfonate salt represented by the following general formula (2) as a flame retardant: (In general formula (2), Q １ , Q ２ , and Q ３ each independently represents a hydrogen atom or a halogen atom; Q １ , Q ２ , and Q ３ At least one of the groups represents a halogen atom, and X represents an alkali metal or an alkaline earth metal. １ , Q ２ , and Q ３ Except when all of are fluorine atoms.) 18. A method for producing a resin composition, comprising the step of mixing a resin with the flame retardant according to any one of claims 5 to 8.

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