Flame retardant processing agent, flame retardant synthetic fiber structure, and flame retardant processing method for synthetic fiber structure

Abstract

The flame retardant comprises a bifunctional monomer including at least one selected from the group consisting of a benzoxazine compound having a terminal structure represented by the following formula (1) at both terminals, a bisallylnadimide compound having a terminal structure represented by the following formula (2) at both terminals, and a bismaleimide compound having a terminal structure represented by the following formula (3) at both terminals, [Formula 1] TIFF0007652477000061.tif17170 [C2] TIFF0007652477000062.tif27170 [3] TIFF0007652477000063.tif26170 Thermoplastic resin, and

Description

[Technical field]

[0001] The present disclosure relates to a flame retardant processing agent, a flame retardant synthetic fiber structure, and a method for flame retarding a synthetic fiber structure. [Background technology]

[0002] In order to prevent fires in vehicles and buildings, it is preferable that interior materials such as seat fabrics, curtains, and wallpaper are flame-resistant. Flame retardants are used to make such interior materials flame-retardant. Conventionally, substances containing halogens or phosphorus have been widely used as flame retardants (for example, Patent Document 1).

[0003] In recent years, in order to reduce the environmental impact, various commercial products have been required to reduce the amount of halogens and phosphorus-containing substances used, or their use may be prohibited. In addition, while industrially usable phosphorus can be obtained from phosphate rock, there are only a limited number of countries that produce phosphate rock, and as a result, there are issues such as a lack of a stable supply of phosphorus and rising prices due to resource restrictions in producing countries. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] JP 2022-182867 A Summary of the Invention [Problem to be solved by the invention]

[0005] An object of the present disclosure is to provide a flame retardant processing agent, a flame retardant synthetic fiber structure, and a flame retardant processing method for a synthetic fiber structure, in which the content of substances containing halogens and phosphorus is reduced. [Means for solving the problem]

[0006] The flame retardant according to an embodiment of the present disclosure comprises a bifunctional monomer including at least one selected from the group consisting of a benzoxazine compound having a terminal structure represented by the following formula (1) at both ends, a bisallylnadimide compound having a terminal structure represented by the following formula (2) at both ends, and a bismaleimide compound having a terminal structure represented by the following formula (3) at both ends,

[0007] [ka]

[0008] [ka]

[0009] [ka]

[0010] and a thermoplastic resin. Effect of the Invention

[0011] According to one embodiment of the present disclosure, it is possible to obtain a flame retardant processing agent, a flame retardant synthetic fiber structure, and a flame retardant processing method for a synthetic fiber structure, in which the content of substances containing halogens and phosphorus is reduced. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0012] The following describes embodiments of the present disclosure. The present disclosure is not limited to the following embodiments, and appropriate design modifications can be made within the scope of the configuration of the present disclosure. The configurations described in the embodiments and modifications can be appropriately combined or modified within the scope of the gist of the present disclosure.

[0013] (First embodiment) The flame retardant of the present embodiment includes a bifunctional monomer and a thermoplastic resin. The flame retardant may further include at least one flame retardant selected from the group consisting of a nitrogen-based flame retardant and a phosphorus-based flame retardant as a flame retardant assistant.

[0014] The bifunctional monomer is a main component that functions as a flame retardant. The bifunctional monomer is a monomer of a thermosetting resin, and includes at least one selected from the group consisting of a benzoxazine compound and an imide compound. The imide compound is preferably a bisallylnadimide compound or a bismaleimide compound.

[0015] Specifically, the bifunctional monomer preferably has any one of the terminal structures represented by the following formulae (1) to (3) at both ends of the monomer skeleton.

[0016] [ka]

[0017] [ka]

[0018] [ka]

[0019] The bifunctional monomer having the terminal structure shown in formula (1) is a benzoxazine compound, and when burned, the six-membered ring containing NCO undergoes ring-opening polymerization to form polybenzoxazine. The bifunctional monomer having the terminal structure shown in formula (2) and formula (3) is a bisallylnadiimide compound and a bismaleimide compound, respectively, and when burned, the carbon-carbon double bond undergoes addition polymerization to form a polyimide. The bifunctional monomer preferably starts polymerization at a temperature of about 120°C or higher, and more preferably undergoes ring-opening polymerization or addition polymerization at a temperature of 150°C or higher and 270°C or lower. The bifunctional monomer is polymerized by the heat during combustion to form a thermosetting resin. Furthermore, the thermosetting resin is carbonized by the heat. This makes it possible to suppress the transfer of heat to the synthetic fiber structure, which is the flame-retardant processed product, the decomposition of the synthetic fiber structure, and the diffusion of combustible gases due to the decomposition. In addition, since two new bonds are formed at each end of the monomer during polymerization, it is easy to form a three-dimensional skeleton.

[0020] The bifunctional monomer is not particularly limited in monomer skeleton as long as it has the terminal structure shown in formulas (1) to (3), and may have a skeleton containing carbon, nitrogen and oxygen. From the viewpoint of reducing the environmental load, it is preferable that the monomer skeleton does not contain halogen atoms and phosphorus atoms. The terminal structure shown in formulas (1) to (3) does not contain halogen and phosphorus.

[0021] The connector of the monomer skeleton preferably contains a benzene ring. Here, the connector of the monomer skeleton refers to the portion of the bifunctional monomer excluding the terminal structures represented by formulae (1) to (3).

[0022] By including a benzene ring in the monomer skeleton, the rigidity of the polymer skeleton is increased, making the polymer less likely to soften when heated. In addition, the proportion of hydrogen in the polymer can be reduced, making the polymer more likely to be carbonized when burned.

[0023] The number of carbon atoms in the connector of the monomer skeleton is preferably, for example, 6 or more and 30 or less. If the number of carbon atoms is 6 or more, the connector of the monomer skeleton is likely to contain a benzene ring. In addition, if the number of carbon atoms in the connector of the monomer skeleton exceeds 30, the ratio of the monomer skeleton portion to both terminal structures increases, so that when a polymer is formed, the degree of polymerization becomes relatively small even with the same molecular weight. This makes it difficult to form a dense three-dimensional structure during combustion.

[0024] The bifunctional monomer may be various compounds as long as it satisfies the above conditions. Such bifunctional monomers are available on the market. For example, a commercially available benzoxazine compound may be a compound represented by the following formula (4).

[0025] [ka]

[0026] The bisallylnadimide compound may be a compound represented by the following formula (5) or (6).

[0027] [ka]

[0028] [ka]

[0029] The bismaleimide compound may be a compound represented by the following formula (7) to formula (12).

[0030] [ka]

[0031] [ka]

[0032] [ka]

[0033] [ka] [ka]

[0034] [ka]

[0035] The bismaleimide compound may be bis(3-ethyl-5-methyl-4-maleimidophenyl)methane represented by the following formula (13). [ka]

[0036] In general, it is preferable that the flame retardant processing has a small effect on the appearance of the processed object. Specifically, it is preferable that the effect on the hue and tone of the appearance of the processed object is small. For example, "bispentabromophenylethane" described in Patent Document 1 is a yellow powder, and depending on the concentration used, it may impair the appearance design of the flame retardant processed fabric.

[0037] Since benzoxazine compounds and imide compounds are generally colored, when a synthetic fiber structure is flame-retarded using the flame-retardant processing agent described above, the color of the flame-retardant synthetic fiber structure may change.

[0038] In contrast, the bifunctional monomer represented by formula (13) is a white to pale yellow solid at room temperature, which reduces the change in appearance of the synthetic fiber structure that has been flame-retarded, and can be used to suitably flame-retard various single- or multi-colored synthetic fiber structures without impairing their appearance.

[0039] The compounds represented by the above formulas (4) to (13) are commercially available or can be synthesized by known reactions. For example, the compound represented by formula (4) is sold by Shikoku Kasei Kogyo Co., Ltd. under the name "Pd-type benzoxazine." The compound represented by formula (7) is sold by Daiwa Kasei Kogyo Co., Ltd. under the trade name "BMI-1000."

[0040] In this way, the bifunctional monomer may contain at least one selected from the group consisting of a benzoxazine compound having the terminal structure represented by formula (1) at both ends, a bisallylnadimide compound having the terminal structure represented by formula (2) at both ends, and a bismaleimide compound having the terminal structure represented by formula (3) at both ends. For example, one selected from the bifunctional monomers represented by formulas (4) to (13), or two or more arbitrarily selected from them, can be used as the flame retardant.

[0041] The bifunctional monomer is dispersed in the flame retardant in the form of particles. The particle size of the bifunctional monomer is preferably, for example, about 0.3 μm or more and 20 μm or less. In general, when a synthetic fiber structure is flame retarded by post-processing, the particle size of the flame retardant used affects the flame retardant performance imparted to the synthetic fiber structure by the processing, and the smaller the particle size, the higher the flame retardant performance that can be imparted to the synthetic fiber structure.

[0042] The thermoplastic resin acts as an adhesive to hold the bifunctional monomer to the synthetic fiber structure to be flame retarded, and also functions as a char-forming aid during combustion.

[0043] The thermoplastic resin preferably contains a carbon double bond (C=C) excluding a benzene ring. Specifically, the thermoplastic resin preferably contains at least one selected from the group consisting of acrylic resins (polymethacrylic acid esters, polyacrylic acid esters, acrylic styrenes), vinyl acetate resins (polyvinyl acetate), ethylene vinyl acetate resins (poly(ethylene-co-vinyl acetate)), and acrylic vinyl acetate resins (poly(acrylic acid-co-vinyl acetate)). These thermoplastic resins contain unreacted carbon-carbon double bonds derived from the monomers used as raw materials. When the bifunctional monomer is polymerized by heating, the active species also reacts with the double bonds contained in the thermoplastic resin, causing the bifunctional monomer to form a three-dimensional skeleton polymer containing the thermoplastic resin. As a result, the polymer forms char without melting, suppressing the combustion of the synthetic fiber structure.

[0044] In the flame retardant of this embodiment, the ratio of the bifunctional monomer to the thermoplastic resin can be determined according to the types of bifunctional monomer and thermoplastic resin selected, the types of elements constituting the synthetic fiber structure to be flame retarded, the fiber structure, the flame retardancy required depending on the application of the synthetic fiber structure, etc. For example, the flame retardant of this embodiment preferably contains the bifunctional monomer in a ratio of 12 parts by weight to 560 parts by weight, more preferably 50 parts by weight to 500 parts by weight, and even more preferably 100 parts by weight to 400 parts by weight, per 100 parts by weight of the thermoplastic resin.

[0045] The flame retardant of the present embodiment may further contain at least one of a nitrogen-based flame retardant and a phosphorus-based flame retardant as a flame retardant assistant.

[0046] The nitrogen-based flame retardant generates nitrogen gas at a temperature in the range of 200° C. to 300° C., and suppresses combustion of synthetic fiber structures. Specifically, the nitrogen-based flame retardant includes at least one member selected from the group consisting of melamine, melamine cyanurate, benzoguanamine, and melamine sulfate.

[0047] The phosphorus-based flame retardant may be any of those commonly available, such as triphenyl phosphate, naphthyl diphenyl phosphate, biphenyl diphenyl phosphate, tricresyl phosphate, trixylenyl phosphate, anilinodiphenyl phosphate, triphenylphosphine oxide, resorcinol bis(di-2,6-xylenyl phosphate), resorcinol bis(diphenyl phosphate), hydroquinone bis(di-2,6-xylenyl phosphate), 4,4'-biphenol bis(di-2,6-xylenyl phosphate), 4,4'-biphenol bis(diphenyl phosphite), phosphate), 4,4'-biphenol bis(dicresyl phosphate), bisphenol A bis(diphenyl phosphate), bisphenol A bis(dicresyl phosphate), 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, 2,2'-(ethylene bisimino)bis(5,5-dimethyl-1,3,2-dioxaphosphorinane-2-oxide), biphenyl neopentyl phosphate, phosphoric acid, ammonium polyphosphate, amide phosphoric acid, guanidine phosphate, melamine phosphate, guanylurea phosphate, etc., and the phosphorus content is preferably 9% or more. For example, it is preferably at least one selected from the group consisting of ammonium polyphosphate, anilinodiphenyl phosphate, resorcinol bis(di-2,6-xylenyl phosphate), and melamine phosphate.

[0048] When the flame retardant contains a nitrogen-based flame retardant, it is preferable that the difunctional monomer is 18 to 560 parts by weight and the nitrogen-based flame retardant is 18 to 1600 parts by weight per 100 parts by weight of the thermoplastic resin, and more preferable that the difunctional monomer is 100 to 400 parts by weight and the nitrogen-based flame retardant is 240 to 1000 parts by weight per 100 parts by weight of the thermoplastic resin. When the flame retardant contains a phosphorus-based flame retardant, it is preferable that the difunctional monomer is 12 to 560 parts by weight and the phosphorus-based flame retardant is 12 to 1600 parts by weight per 100 parts by weight of the thermoplastic resin, and more preferable that the difunctional monomer is 100 to 400 parts by weight and the phosphorus-based flame retardant is 100 to 1000 parts by weight per 100 parts by weight of the thermoplastic resin.

[0049] The flame retardant of the present embodiment further contains a surfactant and a dispersion medium, the thermoplastic resin is emulsified in the dispersion medium, and the bifunctional monomer is dispersed in the dispersion medium.

[0050] The surfactant may be a nonionic surfactant, an anionic surfactant, or a combination thereof. The amount of the surfactant added is, for example, 1 to 5 parts by weight based on 100 parts by weight of the bifunctional monomer.

[0051] Examples of nonionic surfactants include polyoxyalkylene-type nonionic surfactants such as higher alcohol alkylene oxide adducts, alkylphenol alkylene oxide adducts, fatty acid alkylene oxide adducts, polyhydric alcohol aliphatic ester alkylene oxide adducts, higher alkylamine alkylene oxide adducts, fatty acid amide alkylene oxide adducts, polyoxyalkylene styrenated phenyl ethers, and polyoxyalkylene benzyl phenyl ethers; and polyhydric alcohol-type nonionic surfactants such as alkyl glycoxides and sucrose fatty acid esters.

[0052] Examples of the anionic surfactant include sulfate salts such as higher alcohol sulfate salts, higher alkyl ether sulfate salts, sulfated fatty acid ester salts, sulfate salts of styrenated phenol alkylene oxide adducts, and the like; phosphate salts such as phosphate salts of styrenated phenol alkylene oxide adducts, sulfonates such as alkylbenzene sulfonates, alkylnaphthalene sulfonates, and salts of bis(styrenated phenyl ether alkylene oxide adduct) succinate sulfonates, higher alcohol phosphate salts, and higher alcohol alkylene oxide adduct phosphate salts.

[0053] Water is usually used as the dispersion medium. However, if necessary, an organic solvent such as alcohol may be used as the dispersion medium. Examples of the organic solvent include ketones such as acetone and methyl ethyl ketone, alcohols such as methyl alcohol and ethyl alcohol, glycols such as ethylene glycol and propylene glycol, ethers such as dioxane, alkylene glycol alkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, and ethylene glycol monoisobutyl ether, amides such as dimethylformamide, sulfoxides such as dimethyl sulfoxide, and halogenated hydrocarbons such as methylene chloride and chloroform. These organic solvents may be used alone or in combination of two or more types as necessary. Furthermore, an organic solvent and water may be mixed and used.

[0054] The flame retardant of the present embodiment may contain, as necessary, protective colloids such as polyvinyl alcohol, methyl cellulose, carboxymethyl cellulose, starch paste, and preservatives to enhance its storage stability, as long as the performance of the flame retardant is not impaired. Furthermore, the flame retardant of the present embodiment may further contain materials that contribute to functions other than the flame retardant processing. For example, the flame retardant may contain an ultraviolet absorber, an antioxidant, and the like to enhance light fastness.

[0055] The flame retardant of the present embodiment is obtained by mixing the above-mentioned raw materials with a dispersion medium. Specifically, the bifunctional monomer, the flame retardant auxiliary selected as necessary, and the surfactant are weighed, and these raw materials are mixed with the dispersion medium. Next, the bifunctional monomer is microparticulated using a wet grinder to obtain a slurry, which is then mixed with a thermoplastic resin emulsion to obtain the flame retardant.

[0056] According to this embodiment, when the synthetic fiber structure processed with the flame retardant burns, the bifunctional monomer is polymerized by heat to form a thermosetting resin. Furthermore, the thermosetting resin is carbonized by heat. This makes it possible to suppress the transfer of heat to the synthetic fiber structure, which is the workpiece, the decomposition of the synthetic fiber structure, and the diffusion of combustible gases due to the decomposition. Furthermore, since the connecting hand of the bifunctional monomer contains a benzene ring, the rigidity of the skeleton of the thermosetting resin is increased and it becomes difficult to soften by heat. Furthermore, the proportion of hydrogen in the thermosetting resin can be reduced, making it easier for the thermosetting resin generated during combustion to be carbonized.

[0057] In addition, since the bifunctional monomer does not contain halogen or phosphorus, the halogen and phosphorus content in the flame retardant processing agent of this embodiment and in synthetic fiber structures flame retarded using the flame retardant processing agent of this embodiment can be reduced.

[0058] The thermoplastic resin attaches the bifunctional monomer to the synthetic fiber structure during the flame retardant treatment. In addition, since the thermoplastic resin has a carbon double bond, when the bifunctional monomer polymerizes by heating, it also reacts with the thermoplastic resin. This allows the bifunctional monomer to form bonds with the thermoplastic resin, making it easier for the polymer to form a three-dimensional skeleton. As a result, the polymer forms char without melting, suppressing the combustion of the synthetic fiber structure.

[0059] Furthermore, by including a flame retardant auxiliary in the flame retardant processing agent, it becomes possible to more reliably impart flame retardancy to various synthetic fiber structures.

[0060] In addition, the bifunctional monomer represented by formula (13) is a white or pale yellow solid, so that it can reduce the change in appearance of the synthetic fiber structure due to the flame retardant treatment. Since the bifunctional monomer does not contain halogen or phosphorus, it can reduce the halogen and phosphorus contents in the flame retardant treatment agent of this embodiment and in the synthetic fiber structure flame retarded with the flame retardant treatment agent of this embodiment.

[0061] Second embodiment DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Embodiments of flame retardant synthetic fiber structures and methods for flame retarding synthetic fiber structures are described.

[0062] The flame-retardant synthetic fiber structure of the present embodiment includes a synthetic fiber structure, a bifunctional monomer, and a thermoplastic resin.

[0063] The synthetic fiber structure is at least one selected from the group consisting of polyester fiber, acrylic fiber, and vinylon fiber, and refers to yarn, cotton, and fabrics such as knitted fabrics and nonwoven fabrics.

[0064] The flame-retardant synthetic fiber structure of this embodiment, which is flame-retarded using these fibers, is suitable for use in, for example, seat covers, seat covers, curtains, roll blinds, pleated blinds, wallpaper, ceiling cloth, carpets, drop curtains, architectural protection sheets, tents, canvas, clothing such as uniforms, aprons, and the like.

[0065] The bifunctional monomer and the thermoplastic resin are the flame retardant processing agents described in the first embodiment, and are fixed to the synthetic fiber structure. More specifically, the thermoplastic resin is adhered to the synthetic fiber structure, covering at least a portion of the particles of the bifunctional monomer.

[0066] The flame-retardant synthetic fiber structure of this embodiment can be obtained by flame-retarding a synthetic fiber structure using the flame retardant processing agent of the first embodiment to impart flame retardancy.

[0067] There are no particular limitations on the method of flame retardation, and for example, a flame retardant bifunctional monomer and a thermoplastic resin can be applied to a synthetic fiber structure by padding, spraying, coating, textile printing, screen printing, or the like, and then heat-treated at a temperature of 100°C to 200°C, thereby fixing the bifunctional monomer to the synthetic fiber structure with the thermoplastic resin as a binder. In the above process, the flame retardant is applied in an amount of 50 g / m2 to the synthetic fiber structure. 2 More than 100g / m 2 It is preferable to add it in the following ratio.

[0068] When flame retarding is performed using the padding method, a synthetic fiber structure is immersed in the flame retardant processing agent of the first embodiment, and the synthetic fiber structure containing the flame retardant processing agent is squeezed with a mangle or the like so that the above-mentioned adhesion amount is achieved. After that, the synthetic fiber structure is heated, for example, at a temperature in the range of 100°C to 200°C, preferably 150°C to 190°C, for several seconds to several minutes to evaporate the dispersion medium and fix the bifunctional monomer to the synthetic fiber structure using the thermoplastic resin as a binder.

[0069] The flame-retardant synthetic fiber structure of this embodiment may be treated with other functional finishing agents by mixing with a flame retardant processing agent or after flame retardant processing with a flame retardant processing agent. Examples of other functional finishing agents include hard finishing agents, softening agents, antistatic agents, water and oil repellents, texture adjusters, and SR agents.

[0070] According to the flame-retardant synthetic fiber structure and the flame-retardant processing method for a synthetic fiber structure of this embodiment, it is possible to obtain a flame-retardant synthetic fiber structure that does not contain halogens or phosphorus or has a low content of halogens and phosphorus, as described in the first embodiment. In addition, it is possible to effectively suppress the combustion of the synthetic fiber structure.

[0071] In addition, since the bifunctional monomer represented by formula (13) is a white to pale yellow solid at room temperature, even if a synthetic fiber structure having a multicolored design or pattern is flame-retarded, the color tone of the design or pattern does not change. Therefore, the flame-retardant agent of this embodiment can be used for flame-retarding various single-color or multicolored synthetic fiber structures.

[0072] (Examples 1 to 10) In order to confirm the effects of the first and second embodiments, flame retardant processing agents were prepared at various compounding ratios, and synthetic fiber structures were flame-retarded using the prepared flame retardant processing agents, and the properties of the resulting flame-retardant synthetic fiber structures were evaluated. 1. Sample preparation and evaluation method (1) Preparation of flame retardant The following raw materials were used to prepare the flame retardant.

[0073] [Table 1]

[0074] As the dispersant, 2 parts by weight of polyoxyethylene distyrenated phenyl ether was used per 100 parts by weight of the bifunctional monomer. Water was used as the dispersion medium. As shown in each of the following examples, a bifunctional monomer was selected, weighed, mixed with water and a dispersant, and micronized to an average particle size of 1.0 μm or less using a wet grinder. The resulting slurry was mixed with a thermoplastic resin emulsion to obtain a flame retardant. The parts of the thermoplastic resin, flame retardant, and flame retardant assistant in the table are the solid content ratio in the slurry. (2) Fabrication of flame-retardant synthetic fiber structures The following fabrics were used for the synthetic fiber construction:

[0075] [Table 2]

[0076] The padding method was used to apply flame retardancy to a synthetic fiber structure. The synthetic fiber structure was immersed in the prepared flame retardant, and the synthetic fiber structure containing the flame retardant was squeezed with a mangle or the like so that the weight of the flame retardant after drying was the specified amount of adhesion. The synthetic fiber structure was then held at a temperature of 130°C for 5 minutes to evaporate the dispersion medium, and the flame retardant was fixed to the synthetic fiber structure using the thermoplastic resin as a binder, resulting in a flame-retardant synthetic fiber structure. (3) Evaluation The flame retardancy, texture and adhesion were evaluated.

[0077] Flame retardancy: A horizontal burning test was conducted in accordance with Federal Motor Vehicle Safety Standard No. 302 (FMVSS 302). Samples that self-extinguish within a burning distance of 50 mm (self-extinguishing) and samples with a burning rate of 100 mm / min or less (slow burning) were judged as passing (P), and samples with a burning rate of more than 100 mm / min were judged as failing (F).

[0078] Adhesion: Cellophane tape was applied to a flame-retardant synthetic fiber structure, and the cellophane tape was peeled off to evaluate the adhesion of the flame retardant. No powdering was judged as pass (P), and powdering was judged as fail (F).

[0079] Texture: Based on the A method (45° cantilever method) described in 8.21 (bending resistance) of JIS L 1096:2010 "Fabric testing methods for woven and knitted fabrics", 8.21.1, a test piece of 2cm x 15cm in the vertical direction was prepared and placed on a horizontal table with a 45° inclination, and the test piece was slid and the scale was read when the center point of one end of the test piece came into contact with the inclined surface, and the evaluation was performed. Test pieces of 100mm or less were judged as pass (P), and test pieces over 100mm were judged as fail (F). 2. Examples and Results [Example 1] As shown in Table 3, polyester fiber was used as the synthetic fiber structure, acrylic resin (solid concentration 45%) was used as the thermoplastic resin, Pd-type benzoxazine was used as the flame retardant, and melamine was used as the flame retardant assistant, and these were mixed in various compounding ratios to prepare a flame retardant processing agent. Furthermore, the prepared flame retardant processing agent was used to flame-retard the synthetic fiber structure, and a flame-retardant synthetic fiber structure was obtained.

[0080] [Table 3]

[0081] As shown by "NA" in Table 3, samples 1-5, 1-8, and 1-11 were not subjected to the combustion test because the texture of the flame-retardant synthetic fiber structure or the adhesion of the flame-retardant processing agent did not meet the requirements.

[0082] As shown in samples 1-1 and 1-3, the burning rate of the thermoplastic resin alone, or the thermoplastic resin and the flame retardant synergist alone, is high, and almost no flame retardant effect is obtained. On the other hand, as shown in sample 1-2, the burning rate is reduced by combining the thermoplastic resin with the flame retardant, and it is understood that the Pd-type benzoxazine functions as a flame retardant. As shown in samples 1-4, 1-7, and 1-9, the burning rate of the thermoplastic resin combined with the flame retardant and the flame retardant synergist can be reduced, and a flame retardant effect can be obtained at a level of slow flame or self-extinguishing.

[0083] From the results of Example 1, it can be seen that by adding 18 parts by weight or more of the flame retardant and the flame retardant assistant, respectively, a flame retardant effect of more than flame retardancy can be obtained. As the amount of the flame retardant and the flame retardant assistant added increases, the flame retardant effect increases. However, if the amount of these added is too large, the texture of the processed flame retardant synthetic fiber structure deteriorates and the adhesiveness decreases. Specifically, from a comparison between Sample 1-7 and Sample 1-8, it can be seen that the texture deteriorates when the amount of the flame retardant added exceeds 560 parts by weight. Also, from a comparison between Sample 1-10 and Sample 1-11, it can be seen that the adhesiveness decreases when the amount of the flame retardant assistant added exceeds 1600 parts by weight, and the components of the flame retardant processing agent, such as the thermoplastic resin, the flame retardant, and the flame retardant assistant, tend to fall off from the flame retardant synthetic fiber structure.

[0084] In addition, the amount of flame retardant applied to the synthetic fiber structure also affects the flame retardant effect and texture. 2 In the above cases, a sufficient flame retardant effect can be obtained, and it can be seen that the flame retardant effect increases as the adhesion amount increases. On the other hand, from sample 1-5, when the adhesion amount was 100 g / m 2 It can be seen that the texture deteriorates when the temperature exceeds this value. [Examples 2, 3, and 4] In Example 2, a flame retardant was prepared using polyester fiber as the synthetic fiber structure, acrylic resin (solid concentration 45%), ethylene vinyl acetate resin (solid concentration 55%), urethane resin (solid concentration 50%), and polyester resin (solid concentration 25%) as thermoplastic resins, Pd-type benzoxazine as the flame retardant, and melamine, melamine cyanurate, benzoguanamine, melamine sulfate, melem (2,5,8-triaminoheptazine), and melon (polymeric carbon nitride) as flame retardant assistants, as shown in Table 4. The synthetic fiber structure was then flame-retarded using the prepared flame retardant to obtain a flame-retardant synthetic fiber structure.

[0085] [Table 4]

[0086] As Example 3, as shown in Table 5, a flame retardant processing agent was prepared in the same manner as in Example 2, except that acrylic fibers were used as the synthetic fiber structure, and a flame-retardant synthetic fiber structure was obtained.

[0087] [Table 5]

[0088] As Example 4, as shown in Table 6, a flame retardant processing agent was prepared in the same manner as in Example 2, except that vinylon fiber was used as the synthetic fiber structure, and a flame-retardant synthetic fiber structure was obtained.

[0089] [Table 6]

[0090] From Tables 4, 5, and 6, it can be seen that when the synthetic fiber structure is made of acrylic fiber or vinylon fiber, as in the case of polyester fiber, by combining a thermoplastic resin, a flame retardant, and a flame retardant assistant, a flame-retardant synthetic fiber structure with a flame-retardant or self-extinguishing effect can be obtained. It was also found that the same flame-retardant effect as with acrylic resin can be obtained when ethylene vinyl acetate resin is used as the thermoplastic resin.

[0091] On the other hand, as shown in samples 2-3 and 2-4, when urethane resin and polyester resin were used as the thermoplastic resin, sufficient flame retardant effect could not be obtained. Since these thermoplastic resins do not contain carbon double bonds, it is considered that the formation of polymers containing thermoplastic resins did not progress because Pd-type benzoxazine hardly reacted with the thermoplastic resin when it was polymerized.

[0092] It was found that the same flame retardant effect could be obtained by using nitrogen-based flame retardants other than melamine, such as melamine cyanurate, benzoguanamine, and melamine sulfate, as flame retardant synergists. On the other hand, melem and melon are nitrogen-based flame retardants, but even when these flame retardant synergists are used, sufficient flame retardant effect cannot be obtained. This is thought to be because melem and melon are molecules with relatively large molecular weights and have high decomposition temperatures, so at the temperature at which Pd-type benzoxazine polymerizes due to combustion, melem and melon hardly decompose and no nitrogen gas is generated. [Example 5] As shown in Table 7, a flame retardant was prepared using polyester fiber as the synthetic fiber structure, acrylic resin (solid concentration 45%) and acrylic vinyl chloride resin (solid concentration 43%) as the thermoplastic resin, Pd-type benzoxazine as the flame retardant, and melamine, ammonium polyphosphate, anilinodiphenyl phosphate, resorcinol bis(di-2,6-xylenyl phosphate), and melamine phosphate as the flame retardant assistants. The flame retardant was then used to flame-retard the synthetic fiber structure, to obtain a flame-retardant synthetic fiber structure.

[0093] [Table 7]

[0094] From Table 7, it was found that when a phosphorus-based flame retardant is used as a flame retardant assistant, the same flame retardant effect can be obtained as when a nitrogen-based flame retardant is used. In particular, when a phosphorus-based flame retardant is used, as shown in sample 5-5, a flame retardant effect with a slow flame retardancy can be obtained even when the amount of Pd-type benzoxazine added is 12 parts by weight. Also, as shown in sample 5-2, when the amount of flame retardant applied is 42 g / m 2 Even if the temperature is reduced to as low as 100° C., sufficient flame retardant effect can be obtained.

[0095] Furthermore, as shown in Sample 5-6, when an acrylic vinyl chloride resin is used, a similar flame retardant effect can be obtained even when the amount of Pd-type benzoxazine added is 14 parts by weight.

[0096] Thus, halogen and phosphorus are effective elements in terms of flame retardancy. Therefore, in the case where the total amount of halogen and / or phosphorus used can be reduced by replacing a part of the conventional flame retardant containing halogen and / or phosphorus with the bifunctional monomer and thermoplastic resin of the present disclosure, it is also useful to apply the flame retardant of the present disclosure in such an embodiment. [Example 6] As shown in Table 8, a flame retardant was prepared using polyester fiber as the synthetic fiber structure, acrylic resin (solid concentration 45%) as the thermoplastic resin, 4,4'-diphenylmethane bismaleimide as the flame retardant, and melamine, melamine cyanurate, benzoguanamine, and melamine sulfate as flame retardant assistants. The synthetic fiber structure was then flame-retarded using the prepared flame retardant to obtain a flame-retardant synthetic fiber structure.

[0097] [Table 8]

[0098] As shown in Table 8, even when 4,4'-diphenylmethane bismaleimide is used as a flame retardant, it is possible to obtain a flame retardant agent having excellent flame retardant effect by combining a thermoplastic resin with a flame retardant assistant, as in the case of Pd-type benzoxazine. In particular, as shown in sample 6-2, it is found that when 4,4'-diphenylmethane bismaleimide is used, a flame retardant effect of more than flame retardancy can be obtained by adding 15 parts by weight or more of each of the flame retardant and the flame retardant assistant. As shown in sample 6-8, when 4,4'-diphenylmethane bismaleimide is not used and the flame retardant agent contains only a thermoplastic resin and a flame retardant assistant, a sufficient flame retardant effect cannot be obtained.

[0099] As in Example 1, from the viewpoint of texture, it is considered preferable that the amount of flame retardant added is 560 parts by weight or less. Also, from the viewpoint of adhesion, it is considered preferable that the amount of flame retardant auxiliary added is 1600 parts by weight or less. Also, as in Example 1, the same flame retardant effect can be obtained by using melamine cyanurate, benzoguanamine, or melamine sulfate as the flame retardant auxiliary. [Example 7] As shown in Table 9, a flame retardant was prepared using polyester fiber, acrylic fiber, and vinylon fiber as the synthetic fiber structure, acrylic resin (solid concentration 45%), ethylene vinyl acetate resin (solid concentration 55%), and acrylic vinyl chloride resin (solid concentration 43%) as the thermoplastic resin, 4,4'-diphenylmethane bismaleimide as the flame retardant, and melamine, melamine cyanurate, benzoguanamine, melamine sulfate, and ammonium polyphosphate as the flame retardant assistants. The synthetic fiber structure was then flame-retarded using the prepared flame retardant to obtain a flame-retardant synthetic fiber structure.

[0100] [Table 9]

[0101] It was found that when 4,4'-diphenylmethane bismaleimide was used as a flame retardant, it was possible to impart a flame retardant effect of more than just flame retardancy to polyester fibers, acrylic fibers, and vinylon fibers, just like Pd-type benzoxazine. It was also found that a flame retardant effect was achieved when ethylene vinyl acetate resin or acrylic vinyl chloride resin was used as the thermoplastic resin, and when melamine, melamine cyanurate, benzoguanamine, melamine sulfate, or ammonium polyphosphate was used as the flame retardant assistant. As shown in samples 7-3 and 7-4, when the thermoplastic resin contains halogen or the flame retardant assistant contains phosphorus, the amount of 4,4'-diphenylmethane bismaleimide added can be reduced. [Examples 8, 9, and 10] As Example 8, as shown in Table 10, a flame retardant processing agent was prepared using polyester fiber as the synthetic fiber structure, acrylic resin (solid content concentration 45%) as the thermoplastic resin, Pd-type benzoxazine and 4,4'-diphenylmethane bismaleimide as the flame retardants, and no flame retardant assistant. Furthermore, the prepared flame retardant processing agent was used to flame-retard the synthetic fiber structure to obtain a flame-retardant synthetic fiber structure. Only the combustion test of the obtained flame-retardant synthetic fiber structure was performed.

[0102] [Table 10]

[0103] As Example 9, as shown in Table 11, a flame retardant processing agent was prepared in the same manner as in Example 8, except that acrylic fibers were used as the synthetic fiber structure, and a flame-retardant synthetic fiber structure was obtained.

[0104] [Table 11]

[0105] As Example 10, as shown in Table 12, a flame retardant processing agent was prepared in the same manner as in Example 8, except that vinylon fiber was used as the synthetic fiber structure, and a flame-retardant synthetic fiber structure was obtained.

[0106] [Table 12]

[0107] As shown in Table 10, it was found that by using Pd-type benzoxazine or 4,4'-diphenylmethane bismaleimide as a flame retardant and adding a thermoplastic resin, it is possible to impart flame retardancy of a level equal to or higher than that of a retardant to polyester fibers, even without the use of a flame retardant assistant. As shown in Table 12, it was found that adding 2160 parts by weight of Pd-type benzoxazine to vinylon fibers can impart flame retardancy at a level equal to that of a retardant, although the texture will be deteriorated. Also, as shown in Table 11, it was found that adding 2160 parts by weight of Pd-type benzoxazine or 4,4'-diphenylmethane bismaleimide to acrylic fibers can achieve a burning rate of about 100 mm / min.

[0108] These findings demonstrate that even if a flame retardant processing agent does not contain a flame retardant auxiliary, it is possible to impart flame retardancy to synthetic fiber structures.

[0109] Example 11 In order to confirm the effects of the first and second embodiments when the compound of formula (13) is used, a flame retardant processing agent was prepared, and a synthetic fiber structure was flame-retarded using the prepared flame retardant processing agent, and the properties of the obtained flame-retardant synthetic fiber structure were evaluated.

[0110] 1. Sample preparation and evaluation method (1) Preparation of flame retardant The following raw materials were used to prepare the flame retardant. [Table 13]

[0111] As the flame retardant, in addition to the bismaleimide represented by formula (13) in the first embodiment, a bismaleimide represented by formula (7) and a Pd-type benzoxazine represented by formula (4) were used as a reference example. [ka] [ka]

[0112] Bismaleimide represented by formula (7) is also a bifunctional monomer, and forms polyimide by addition polymerization of the carbon-carbon double bond of the five-membered ring during combustion. Pd-type benzoxazine represented by formula (4) is also a bifunctional monomer, and forms polybenzoxazine by ring-opening polymerization of the six-membered ring containing NCO during combustion.

[0113] The dispersant used was polyoxyethylene distyrenated phenyl ether in an amount of 2 parts by weight per 100 parts by weight of the bifunctional monomer, and water was used as the dispersion medium.

[0114] The raw materials were added in the ratios shown in Table 14 to produce flame retardants, Samples 11-1 to 11-8. Specifically, a bifunctional monomer of any one of formulas (13), (7), or (4) was selected, weighed, mixed with water and a dispersant, and micronized using a wet grinder. The resulting slurry was mixed with a thermoplastic resin emulsion (solid concentration 45%) and a flame retardant synergist to produce flame retardants, Samples 11-3, 11-4, and 11-5. The parts of (A) thermoplastic resin, (B) flame retardant, and (C) flame retardant synergist in the table are the solids ratios in the slurry.

[0115] The flame retardant processing agents of Samples 11-1 and 11-2 do not contain a flame retardant but contain a thermoplastic resin and a flame retardant assistant, while the flame retardant processing agents of Samples 11-6, 11-7, and 11-8 do not contain a flame retardant assistant but contain a thermoplastic resin and a flame retardant.

[0116] (2) Fabrication of flame-retardant synthetic fiber structures As a synthetic fiber structure, the basis weight is 230g / m 2 White polyester double pique was used.

[0117] The synthetic fiber structure was flame-retarded using the padding method. The synthetic fiber structure was immersed in the prepared flame retardant, and the synthetic fiber structure containing the flame retardant was squeezed with a mangle or the like so that the dried weight of the flame retardant would be the adhesion amount shown in Table 2. The synthetic fiber structure was then held at a temperature of 130°C for 5 minutes to evaporate the dispersion medium, and the flame retardant was fixed to the synthetic fiber structure using the thermoplastic resin as a binder, to obtain a flame-retardant synthetic fiber structure. The synthetic fiber structures flame-retarded using the flame retardants of Samples 11-1 to 11-8 are similarly referred to as Samples 11-1 to 11-8.

[0118] (3) Combustion testing and evaluation A horizontal burn test was conducted in accordance with Federal Motor Vehicle Safety Standard No. 302 (FMVSS 302). Samples with a burn rate of 100 mm / min or less (slow burn) were judged as passing (P), and samples with a burn rate of more than 100 mm / min were judged as failing (F). The measurement results and the judgment results are shown in Table 14.

[0119] (4) Measurement of color difference of synthetic fiber structures before and after flame retardant treatment Using a spectrophotometer CM-600d (Konica Minolta, Inc.), the L of synthetic fiber structures before and after flame retardant treatment was measured. * , a * , b * The value of L * The value is called the brightness index, and the larger the value, the brighter it is, and the smaller the value, the darker it is. * Value and b * The value represents the hue and saturation and is called the chromaticity index. * The more positive the value, the more reddish the color becomes, and the more negative the value, the more greenish the color becomes. * The more positive the value, the more yellowish the color becomes, and the more negative the value, the more blueish the color becomes. * , a * , b * The difference in values ​​is ΔL * , Δa * , Δb * Then, the color difference ΔE = [(ΔL * ) 2 +(Δa *) 2 +(Δb * ) 2 ] 1 / 2 The larger the ΔE value, the greater the color change before and after the flame retardant treatment, and the greater the influence of the coloring caused by the flame retardant treatment agent. Samples with a ΔE value of 6 or less were judged as pass (P), and samples with a ΔE value of more than 6 were judged as fail (F). The measurement results and judgment results are shown in Table 14.

[0120] [Table 14]

[0121] 2.Results (1) Flame retardancy The results of Samples 11-1 and 11-2 show that a sufficient flame retardant effect cannot be obtained by using only a thermoplastic resin and a phosphorus-based flame retardant as a flame retardant assistant.

[0122] On the other hand, the results of samples 11-3 to 11-8 show that the flame-retardant synthetic fiber structures made using the flame retardant containing any one of the flame retardants of formula (13), (7), or (4) have a flame retardant effect of retarding flames. In addition, when the amount of the flame retardant added is 560 parts by weight, the flame retardant exhibits a sufficient flame retardant effect even if it does not contain a flame retardant auxiliary.

[0123] (2) Color difference As shown in Samples 11-1 and 11-2 in Table 14, when a synthetic fiber structure is flame retarded with a flame retardant processing agent that does not contain a flame retardant, the color difference ΔE of the synthetic fiber structure before and after the flame retardant processing is less than 6. This indicates that the flame retardant synergist is a white powder and has almost no effect on the color tone of the synthetic fiber structure.

[0124] When flame retarding is performed using the flame retardant of sample 11-3 containing 12 parts by weight of the bismaleimide represented by formula (13), the color difference ΔE of the synthetic fiber structure before and after the flame retarding is 6 or less. This shows that the flame retardant represented by formula (13) also has almost no effect on the color tone of the synthetic fiber structure. In addition, in sample 11-6, the flame retardant contains 560 parts by weight of the bismaleimide represented by formula (13), but similarly the color difference ΔE of the synthetic fiber structure before and after the flame retarding is 6 or less. Therefore, it was found that the flame retardant of this embodiment hardly changes the color tone of the synthetic fiber structure to be processed within the range of the amount of the flame retardant added that can exhibit excellent functions as a flame retardant.

[0125] In contrast, as shown in samples 11-4, 11-5, 11-7, and 11-8, when a flame retardant containing the flame retardant represented by formula (7) or formula (4) was used, the color difference ΔE of the synthetic fiber structure before and after the flame retardant treatment exceeded 6, indicating a large change in color tone. * This is believed to be due to the fact that the flame retardants represented by formula (7) or formula (4) are yellow in color.

[0126] Even when visually observed, the synthetic fiber structures after the flame retardant treatment of Samples 11-1 to 11-3, and 11-6 were almost white, while the synthetic fiber structures after the flame retardant treatment of Samples 11-4, 11-5, 11-7, and 11-8 were yellow.

[0127] These results show that when flame retarding is performed using the flame retardant processing agents of the present embodiment, ie, Samples 11-3 and 11-6, changes in the appearance of the flame-retardant synthetic fiber structure can be reduced.

[0128] These results demonstrate that the flame retardant processing agent and the flame retardant processing method for synthetic fiber structures of the present embodiment can improve the flame retardancy of the synthetic fiber structures and reduce changes in the appearance of the synthetic fiber structures.

[0129] Thus, it has been found that the flame retardant processing agent of the present disclosure can impart flame retardancy to synthetic fiber structures while reducing the amounts of halogens and phosphorus used, or without using halogens or phosphorus.

[0130] The flame retardant processing agent, flame retardant synthetic fiber structure, and flame retardant processing method for a synthetic fiber structure of the present disclosure can also be explained as follows.

[0131] The flame retardant according to the first aspect includes a bifunctional monomer containing at least one selected from the group consisting of benzoxazine compounds and imide compounds, and a thermoplastic resin. According to the first aspect, the bifunctional monomer is polymerized during combustion. At this time, the bifunctional monomer also reacts with the thermoplastic resin to form a thermosetting polymer with a three-dimensional structure. Therefore, the polymer forms char without melting, suppressing the burning of the fiber.

[0132] In the flame retardant according to the second aspect, in the first aspect, the bifunctional monomer may include a bisallylnadimide compound or a bismaleimide compound.

[0133] The flame retardant according to the third aspect is the flame retardant according to the first aspect, wherein the bifunctional monomer is represented by the following formulas (1) to (3):

[0134] [ka]

[0135] [ka]

[0136] [ka]

[0137] The monomer skeleton may have any one of the terminal structures represented by the following formula (I):

[0138] In other words, the flame retardant according to the third aspect may contain a bifunctional monomer including at least one selected from the group consisting of a benzoxazine compound having a terminal structure represented by formula (1) at both terminals, a bisallylnadimide compound having a terminal structure represented by formula (2) at both terminals, and a bismaleimide compound having a terminal structure represented by formula (3) at both terminals, and a thermoplastic resin.

[0139] The flame retardant according to the fourth aspect may be the third aspect, in which the connecting part of the monomer skeleton contains a benzene ring. By containing the benzene ring, the polymer skeleton has rigidity and is less likely to melt during combustion. In addition, the proportion of hydrogen can be reduced, making it easier to generate char.

[0140] The flame retardant according to the fifth aspect may be such that, in the third aspect, the number of carbon atoms in the connecting portion of the monomer skeleton is 6 or more and 30 or less.

[0141] In the flame retardant according to the sixth aspect, in the third aspect, the benzoxazine compound is represented by the following formula (4):

[0142] [ka]

[0143] The compound may be represented by the formula:

[0144] In the flame retardant according to the seventh aspect, in the third aspect, the bisallylnadimide compound is represented by the following formula (5) or (6):

[0145] [ka]

[0146] [ka]

[0147] The compound may be represented by the formula:

[0148] In the flame retardant according to the eighth aspect, in the third aspect, the bismaleimide compound is represented by the following formula (7) to formula (13):

[0149] [ka]

[0150] [ka]

[0151] [ka]

[0152] [ka]

[0153] [ka]

[0154] [ka] [ka]

[0155] The compound may be represented by the formula:

[0156] In other words, the flame retardant according to the eighth configuration may be the third configuration, in which the benzoxazine compound is a Pd-type benzoxazine represented by formula (4), the bisallylnadimide compound is at least one selected from the group consisting of compounds represented by formulas (5) and (6), and the bismaleimide compound is at least one selected from the group consisting of compounds represented by formulas (7) to (13).

[0157] The flame retardant according to the ninth aspect is A bifunctional monomer represented by the following formula (13): [ka] and a thermoplastic resin.

[0158] According to the ninth aspect, when a synthetic fiber structure treated with a flame retardant is burned, the bifunctional monomer is polymerized by heat. At this time, the bifunctional monomer also reacts with the thermoplastic resin to form a thermosetting polymer with a three-dimensional structure. Therefore, the polymer forms char without melting, suppressing the burning of the fiber. In addition, since the bifunctional monomer is a white or pale yellow solid, it is possible to reduce the change in appearance of the synthetic fiber structure caused by the flame retardant treatment. The flame retardant according to the tenth aspect is any one of the first to ninth aspects, in which the thermoplastic resin may contain at least one selected from the group consisting of acrylic resin, vinyl acetate resin, ethylene vinyl acetate resin, and acrylic vinyl acetate resin. When the thermoplastic resin contains a double bond derived from the monomer, it is easy to form a bond with the thermoplastic resin during polymerization of the bifunctional monomer to form a three-dimensional skeleton. As a result, char is formed without melting, suppressing the burning of the fiber.

[0159] The flame retardant according to an eleventh aspect may further contain a nitrogen-based flame retardant in any one of the first to tenth aspects. By containing a nitrogen-based flame retardant, the flame retardant effect of the thermosetting resin can be supplemented.

[0160] A flame retardant according to a twelfth aspect is the eleventh aspect, wherein the nitrogen-based flame retardant includes at least one selected from the group consisting of melamine, melamine cyanurate, benzoguanamine, and melamine sulfate.

[0161] The flame retardant processing agent according to the thirteenth configuration may contain, in the twelfth configuration, a bifunctional monomer in an amount of 18 parts by weight or more and 560 parts by weight or less and a nitrogen-based flame retardant in an amount of 18 parts by weight or more and 1,600 parts by weight or less per 100 parts by weight of thermoplastic resin.

[0162] The flame retardant processing agent according to the fourteenth aspect may further contain a phosphorus-based flame retardant in any one of the first to tenth aspects. By containing a phosphorus-based flame retardant, the flame retardant effect of the thermosetting resin can be supplemented. In addition, it is possible to reduce the amount of bifunctional monomer added, and the amount of phosphorus-based flame retardant can also be reduced, so that the texture when flame retardant processing is performed can be further improved.

[0163] The flame retardant according to the fifteenth aspect is the fourteenth aspect, wherein the phosphorus-based flame retardant is selected from the group consisting of triphenyl phosphate, naphthyl diphenyl phosphate, biphenyl diphenyl phosphate, tricresyl phosphate, trixylenyl phosphate, anilino diphenyl phosphate, triphenylphosphine oxide, resorcinol bis(di-2,6-xylenyl phosphate), resorcinol bis(diphenyl phosphate), hydroquinone bis(di-2,6-xylenyl phosphate), 4,4'-biphenol bis(di-2,6-xylenyl phosphate), 4,4'-biphenol bis(diphenyl phosphate), The phosphate buffer may contain at least one selected from the group consisting of 4,4'-biphenol bis(dicresyl phosphate), bisphenol A bis(diphenyl phosphate), bisphenol A bis(dicresyl phosphate), 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, 2,2'-(ethylene bisimino)bis(5,5-dimethyl-1,3,2-dioxaphosphorinane-2-oxide), biphenyl neopentyl phosphate, phosphoric acid, ammonium polyphosphate, amide phosphoric acid, guanidine phosphate, melamine phosphate, guanylurea phosphate, and the like.

[0164] The flame retardant processing agent according to the sixteenth configuration may be the fifteenth configuration, and may contain a bifunctional monomer in an amount of 12 parts by weight or more and 560 parts by weight or less and a phosphorus-based flame retardant in an amount of 12 parts by weight or more and 1,600 parts by weight or less per 100 parts by weight of thermoplastic resin.

[0165] A flame retardant agent according to a seventeenth aspect is any one of the first to sixteenth aspects, further comprising a surfactant and water, wherein the thermoplastic resin is emulsified in the water and the bifunctional monomer is dispersed in the water.

[0166] The flame-retardant synthetic fiber structure of the 18th configuration comprises a synthetic fiber structure, and a thermoplastic resin and a bifunctional monomer contained in the flame retardant processing agent of any one of the 1st to 17th configurations, the thermoplastic resin and the bifunctional monomer being fixed to the synthetic fiber structure.

[0167] A flame-retardant synthetic fiber structure according to a nineteenth aspect is the eighteenth aspect, wherein the synthetic fiber structure includes at least one fiber selected from the group consisting of polyester fiber, acrylic fiber, and vinylon fiber.

[0168] A flame retardant processing method for a synthetic fiber structure in accordance with a twentieth aspect comprises carrying a thermoplastic resin and a bifunctional monomer, which are any one of the flame retardant processing agents in accordance with the first to seventeenth aspects, on a synthetic fiber structure, and heating the synthetic fiber structure to fix the bifunctional monomer to the synthetic fiber structure using the thermoplastic resin as a binder.

[0169] The flame retardant processing method for a synthetic fiber structure according to the twenty-first aspect of the present invention is the twentieth aspect, in which a flame retardant is applied to the synthetic fiber structure at a rate of 50 g / m 2 More than 100g / m 2 The following proportions may be given:

[0170] The flame retardant processing method for synthetic fiber structures according to a twenty-second aspect is the twentieth or twenty-first aspect, wherein the synthetic fiber structure may contain at least one fiber selected from the group consisting of polyester fibers, acrylic fibers, and vinylon fibers. [Industrial Applicability]

[0171] The flame retardant processing agent, flame retardant synthetic fiber structure, and method for flame retarding a synthetic fiber structure of the present disclosure are suitable for flame retarding synthetic fiber structures used in a variety of applications.

Claims

1. a bifunctional monomer including at least one selected from the group consisting of a benzoxazine compound having a terminal structure represented by the following formula (1) at both terminals, a bisallylnadimide compound having a terminal structure represented by the following formula (2) at both terminals, and a bismaleimide compound having a terminal structure represented by the following formula (3) at both terminals; 【Chemistry 1】 【Chemistry 2】 【Chemistry 3】 A flame retardant processing agent comprising: a thermoplastic resin.

2. The flame retardant according to claim 1 , wherein a connecting arm of the monomer skeleton of the bifunctional monomer contains a benzene ring.

3. The flame retardant according to claim 1, wherein the number of carbon atoms in the connecting portion of the monomer skeleton of the bifunctional monomer is 6 or more and 30 or less.

4. The benzoxazine compound is represented by the following formula (4): 【Chemistry 4】 The bisallylnadimide compound is a Pd-type benzoxazine represented by the following formula (5) and formula (6): 【Chemistry 5】 【Chemistry 6】 The bismaleimide compound is at least one selected from the group consisting of compounds represented by the following formulas (7) to (13): 【Chemistry 7】 【Chemistry 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 2. The flame retardant according to claim 1, which is at least one selected from the group consisting of compounds represented by the following formula:

5. The bifunctional monomer is represented by the following formula (13): 【Chemistry 13】 The flame retardant according to claim 1 , comprising the bismaleimide compound represented by the formula:

6. 2. The flame retardant according to claim 1, wherein the thermoplastic resin comprises at least one resin selected from the group consisting of an acrylic resin, a vinyl acetate resin, an ethylene vinyl acetate resin, and an acrylic vinyl acetate resin.

7. The flame retardant processing agent according to claim 1 , further comprising a nitrogen-based flame retardant.

8. The flame retardant according to claim 7, wherein the nitrogen-based flame retardant comprises at least one selected from the group consisting of melamine, melamine cyanurate, benzoguanamine, and melamine sulfate.

9. The flame retardant processing agent according to claim 8, comprising 18 parts by weight or more and 560 parts by weight or less of the bifunctional monomer and 18 parts by weight or more and 1600 parts by weight or less of the nitrogen-based flame retardant, relative to 100 parts by weight of the thermoplastic resin.

10. The flame retardant according to claim 1, further comprising a phosphorus-based flame retardant.

11. The flame retardant according to claim 10, wherein the phosphorus-based flame retardant has a phosphorus content of 9% or more in the molecule.

12. The flame retardant processing agent according to claim 11, comprising the bifunctional monomer in an amount of 12 parts by weight or more and 560 parts by weight or less and the phosphorus-based flame retardant in an amount of 12 parts by weight or more and 1600 parts by weight or less, relative to 100 parts by weight of the thermoplastic resin.

13. 2. The flame retardant according to claim 1, further comprising a surfactant and water, wherein the thermoplastic resin is emulsified in the water and the bifunctional monomer is dispersed in the water.

14. 2. The flame retardant according to claim 1, comprising a bifunctional monomer containing at least one member selected from the group consisting of benzoxazine compounds and imide compounds, and a thermoplastic resin.

15. A flame-retardant synthetic fiber structure comprising: a synthetic fiber structure; and the thermoplastic resin and the bifunctional monomer contained in the flame retardant processing agent according to any one of claims 1 to 14, the thermoplastic resin and the bifunctional monomer being fixed to the synthetic fiber structure.

16. 16. The flame-retardant synthetic fiber structure according to claim 15, wherein the synthetic fiber structure comprises at least one fiber selected from the group consisting of polyester fiber, acrylic fiber, and vinylon fiber.

17. 15. A flame retardant processing method for a synthetic fiber structure, comprising carrying the thermoplastic resin and the bifunctional monomer contained in the flame retardant processing agent according to claim 1 on a synthetic fiber structure, and heating the synthetic fiber structure to fix the bifunctional monomer to the synthetic fiber structure using the thermoplastic resin as a binder.

18. The flame retardant is applied to the synthetic fiber structure at a rate of 50 g / m. ２ More than 100g / m ２ The method for flame retardant treatment of synthetic fiber structures according to claim 17, wherein the flame retardant is applied in the following ratio:

19. 18. The method for flame retardant treatment of a synthetic fiber structure according to claim 17, wherein the synthetic fiber structure comprises at least one fiber selected from the group consisting of polyester fiber, acrylic fiber, and vinylon fiber.

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