Flame-retardant finishing agent for polyester-based synthetic fiber structures, flame-retardant polyester-based synthetic fiber structure, and method for flame-retardant finishing of polyester-based synthetic fiber structure

Abstract

Provided are: a flame-retardant finishing agent for polyester-based synthetic fiber structures, the agent having a reduced halogen content and being less likely to cause water stains; a flame-retardant polyester-based synthetic fiber structure; and a method for a flame-retardant finishing of a polyester-based synthetic fiber structure. The flame-retardant finishing agent for polyester-based synthetic fiber structures comprises a flame-retardant agent including at least one component selected from the group consisting of a first phosphoric acid ester compound represented by general formula (1) (in formula (1), R1, R2, and R3 each independently represent an alkyl group having 12-16 carbon atoms) and a second phosphoric acid ester compound represented by general formula (2) (in formula (2), R4 represents an alkyl group having 12-16 carbon atoms, and R5 represents an alkyl group having 12-16 carbon atoms or a hydrogen atom).

Description

Flame retardant agent for polyester synthetic fiber structures, flame retardant polyester synthetic fiber structures, and flame retardant processing method for polyester synthetic fiber structures

[0001] The present disclosure relates to a flame retardant agent for polyester-based synthetic fiber structures, a flame-retardant polyester-based synthetic fiber structure, and a method for flame-retarding a polyester-based synthetic fiber structure.

[0002] The flame retardant treatment of textile structures is carried out using flame retardants and processing methods suited to the textile material. Conventionally, polyester synthetic textile structures have been flame retarded by the padding method using water-soluble salts such as guanidine phosphate and carbamate phosphate as flame retardants (see, for example, Patent Document 1).

[0003] It is also known to flame-retard polyester synthetic fiber structures using halogen compounds by exhaustion or padding (see, for example, Patent Document 2).

[0004] JP 2002-38374 A JP 53-8840 A

[0005] However, when water-soluble salts are used as flame retardants, moisture absorption and release by flame-retardant polyester synthetic fiber structures can cause crystalline deposits on the surface of the fiber structure, and water adhesion to the surface of the fiber structure can cause ring stains, also known as edge stains. From the perspective of environmental impact, it is preferable that the flame retardant does not contain halogen compounds or that the amount used is small.

[0006] The present disclosure aims to provide a flame retardant for polyester-based synthetic fiber structures, a flame-retardant polyester-based synthetic fiber structure, and a method for flame-retarding a polyester-based synthetic fiber structure, which have a reduced halogen content and are less likely to cause smearing.

[0007] The flame retardant for a polyester synthetic fiber structure according to one embodiment of the present disclosure comprises a first phosphate ester compound represented by the following general formula (1) (wherein R １ , R ２ , R ３ each independently represents an alkyl group having 12 to 16 carbon atoms; and A second phosphate ester compound represented by the following general formula (2) (wherein R ４ is an alkyl group having 12 to 16 carbon atoms, R ５ represents an alkyl group having 12 to 16 carbon atoms or hydrogen. The flame retardant includes at least one selected from the group consisting of:

[0008] According to one embodiment of the present disclosure, there are provided a flame retardant for polyester-based synthetic fiber structures, a flame-retardant polyester-based synthetic fiber structure, and a flame-retardant processing method for polyester-based synthetic fiber structures, which have a reduced halogen content and are less likely to cause smearing.

[0009] Polyester synthetic fibers are hydrophobic synthetic fibers, and friction with sewing threads during machine sewing can damage the polyester synthetic fiber fabric and cause thread breakage. For this reason, to improve sewability, paraffin-based or silicone-based softeners are sometimes used as smoothing agents, or the padding method is used as a post-processing method to impart smoothness to polyester synthetic fibers.

[0010] Since such smoothing agents are flammable, the flame retardancy of polyester synthetic fibers to which the smoothing agents have been added is reduced. Therefore, in order to flame-retardantize polyester synthetic fibers to which the smoothing agents have been added, a larger amount of flame retardant must be used. This may also result in a deterioration in the texture of the polyester synthetic fibers.

[0011] If a flame retardant also functions as a smoothing agent, it is thought that the amount of smoothing agent added to polyester synthetic fibers to improve sewing properties can be reduced or the smoothing agent can be omitted. Furthermore, if the amount of smoothing agent used is reduced, the amount of flame retardant used can also be reduced. Based on this idea, the present inventors have devised a novel flame retardant for polyester synthetic fiber structures.

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

[0013] The flame retardant of the present disclosure can be used for flame retarding various fiber structures, and is particularly suitable for flame retarding polyester synthetic fiber structures. In this disclosure, polyester synthetic fiber structures refer to fibers containing at least polyester fibers, and fabrics containing such fibers, such as yarn, cotton, knitted / woven fabric, and nonwoven fabric. Preferably, the polyester synthetic fiber structures are polyester fibers, yarn, cotton, or fabrics such as knitted / woven fabric and nonwoven fabric made of polyester fibers. Furthermore, fabrics such as knitted / woven fabric and nonwoven fabric may be single-layered or may be laminates of two or more layers, or may be composites made of yarn, cotton, knitted / woven fabric, nonwoven fabric, etc.

[0014] Examples of the polyester fiber include polyethylene terephthalate, polytrimethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, polybutylene naphthalate, polyethylene terephthalate / isophthalate, polyethylene terephthalate / 5-sulfoisophthalate, polyethylene terephthalate / polyoxybenzoyl, polybutylene terephthalate / isophthalate, poly(D-lactic acid), poly(L-lactic acid), copolymers of D-lactic acid and L-lactic acid, copolymers of D-lactic acid and aliphatic hydroxycarboxylic acid, and L-lactic acid. copolymers of acids and aliphatic hydroxycarboxylic acids; polycaprolactones such as poly-ε-caprolactone (PCL); polyaliphatic hydroxycarboxylic acids such as polymalic acid, polyhydroxycarboxylic butyric acid, polyhydroxyvaleric acid, and β-hydroxybutyric acid (3HB)-3-hydroxyvaleric acid (3HV) random copolymers; and polyesters of glycols and aliphatic dicarboxylic acids such as polyethylene succinate (PES), polybutylene succinate (PBS), polybutylene adipate, and polybutylene succinate-adipate copolymers.

[0015] The polymer may be a copolymer with a functional compound such as a flame retardant, or may be blended with a functional compound such as an antibacterial agent during polymerization of the polymer or during spinning.

[0016] Flame-retardant polyester synthetic fiber structures that have been flame-retarded with the flame retardant agent of the present disclosure are suitable for use in, for example, seats, seat covers, curtains, wallpaper, ceiling cloth, carpets, drop curtains, architectural protection sheets, tents, canvas, etc.

[0017] (First embodiment) The flame retardant for a polyester synthetic fiber structure of this embodiment comprises a flame retardant. The flame retardant contains at least one compound selected from the group consisting of a first phosphate ester compound represented by the following general formula (1) and a second phosphate ester compound represented by the following general formula (2). It is preferable that the first phosphate ester compound and the second phosphate ester compound do not contain a halogen. Here, in formula (1), R １ , R ２ , R ３ each independently represents an alkyl group having 12 to 16 carbon atoms, and in formula (2), R ４ is an alkyl group having 12 to 16 carbon atoms, R ５ represents an alkyl group having 12 to 16 carbon atoms or hydrogen.

[0018] Specifically, R １ , R ２ , R ３ , R ４ , R ５ is a linear or branched alkyl group having 12 to 16 carbon atoms. ５ may be hydrogen. The linear alkyl group having 12 to 16 carbon atoms is a dodecane group, a tridecane group, a tetradecane group, a pentadecane group, or a hexadecane group, and does not contain an unsaturated bond. The branched alkyl group having 12 to 16 carbon atoms may have one or more side chains at any position, as long as it has 12 to 16 carbon atoms. There is also no particular limitation on the number of carbon atoms in the side chain. For example, the branched alkyl group having 12 to 16 carbon atoms may be an isododecane group, an isotridecane group, an isotetradecane group, an isopentadecane group, an isohexadecane group, a 2-butyloctyl group, or a 2-hexyldecyl group.

[0019] In general formula (1), R １ , R ２ , R ３may all be the same alkyl group, or two may be the same and one may be different from the other two, or three may be different from each other. ４ , R ５ may be the same or different alkyl groups, and R ５ may be hydrogen.

[0020] The first phosphate ester compound represented by general formula (1) is a phosphate triester, and the second phosphate ester compound represented by general formula (2) is a phosphate monoester or a phosphate diester. The flame retardant contains at least one compound selected from the group consisting of the first phosphate ester compound represented by general formula (1) and the second phosphate ester compound represented by general formula (2). The flame retardant may contain two or more different first phosphate ester compounds. Similarly, the flame retardant may contain two or more different second phosphate ester compounds.

[0021] The first phosphate ester compound and the second phosphate ester compound plasticize the polyester synthetic fiber structure during combustion, improving dripping properties. In addition, metaphosphoric acid is produced by thermal decomposition, and polymetaphosphoric acid is produced by dehydration condensation. １ From R ５ The alkyl groups represented by the formula (I) also polymerize, forming a carbonized layer. These turn into char, which contributes to the flame retardancy of polyester synthetic fiber structures.

[0022] The first phosphate ester compound represented by the general formula (1) and the second phosphate ester compound represented by the general formula (2) are R １ From R ５ The alkyl group represented by the formula (I) has 12 to 16 carbon atoms, and is therefore oil-soluble and hardly dissolves in water. Therefore, even if water adheres to the surface of the polyester synthetic fiber structure, the flame retardant is hardly dissolved in water, and adhesion is unlikely to occur.

[0023] Also, R １ From R ５When the alkyl group represented by R is a linear alkyl group, the melting points of the first phosphate ester compound and the second phosphate ester compound are higher than room temperature, and the first phosphate ester compound and the second phosphate ester compound are solid at room temperature. １ From R ５ Since the first phosphate ester compound and the second phosphate ester compound are hydrocarbons with a large number of carbon atoms, they exhibit lubricity similar to that of paraffin. Therefore, by flame retarding the polyester synthetic fiber structure using the flame retardant agent of this embodiment, the polyester synthetic fiber structure can also be prevented from breaking.

[0024] R １ From R ５ When the alkyl group represented by R is a branched alkyl group, the melting points of the first phosphate ester compound and the second phosphate ester compound are １ From R ５ The alkyl group represented by R is a straight-chain alkyl group, and the alkyl group generally becomes liquid at room temperature. １ From R ５ Since R is a hydrocarbon with a large carbon number, it exhibits a certain degree of lubricity, like liquid paraffin. Therefore, by carrying out flame retardant processing using the flame retardant processing agent of this embodiment, polyester-based synthetic fiber structures can also exhibit the effect of preventing thread breakage. １ From R ５ The first phosphate ester compound and the second phosphate ester compound in which the alkyl group represented by the formula (I) is a branched alkyl group are industrially readily available and inexpensive, and are therefore advantageous in terms of the production costs of the flame retardant.

[0025] More specifically, in general formula (1), R １ , R ２ , R ３ are linear dodecyl groups, the melting point of tridodecyl phosphate is about 35°C, and R １ , R ２ , R ３ are linear hexadecyl groups, the melting point of trihexadecyl phosphate is about 62°C. ４is a dodecyl group, and R ５ is hydrogen, the melting point of monododecyl phosphate is about 39°C, ４ is a hexadecyl group, and R ５ is hydrogen, the melting point of monohexadecyl phosphate is about 71°C. ４ and R ５ is a hexadecyl group, the melting point of dihexadecyl phosphate is about 74° C. Thus, the first phosphate ester compound is １ , R ２ , R ３ is a linear alkyl group having 12 to 16 carbon atoms, the second phosphate ester compound is solid at room temperature, and ４ , R ５ If is a linear alkyl group having 12 to 16 carbon atoms, it is a solid at room temperature.

[0026] As described above, if the flame retardant is solid at room temperature, it can provide a higher effect of preventing thread breakage. On the other hand, from the viewpoint of the stability of the flame retardant in the flame retardant processing agent when left standing and uniformity when diluted, it may be preferable for the flame retardant to be liquid. Furthermore, flame retardants that are liquid at room temperature are generally easy to obtain and inexpensive. For this reason, the flame retardant may contain two or more first phosphate ester compounds and / or second phosphate ester compounds with different melting points. This makes it possible to adjust the melting point of the flame retardant and improve the stability and dispersibility of the flame retardant in the flame retardant processing agent.

[0027] The first phosphate ester compound may be at least one selected from the group consisting of tridodecyl phosphate, tritridecyl phosphate, tritetradecyl phosphate, tripentadecyl phosphate, trihexadecyl phosphate, and triisotridecyl phosphate.

[0028] The second phosphate ester compound may be at least one selected from the group consisting of dodecan-1-yl dihydrogen phosphate, tridecan-1-yl dihydrogen phosphate, tetradecan-1-yl dihydrogen phosphate, pentadecan-1-yl dihydrogen phosphate, hexadecan-1-yl dihydrogen phosphate, didodecan-1-yl hydrogen phosphate, ditridecan-1-yl hydrogen phosphate, ditetradecan-1-yl hydrogen phosphate, dipentadecan-1-yl hydrogen phosphate, dihexadecan-1-yl hydrogen phosphate, isotridecan-1-yl dihydrogen phosphate, and diisotridecan-1-yl hydrogen phosphate.

[0029] The amount of phosphorus atoms in the flame retardant is preferably 4.0% or more and 11.7% or less. If the amount of phosphorus atoms is less than 4.0%, the flame retardant effect of the flame retardant may not be sufficiently obtained. From the viewpoint of the flame retardant effect, there is no particular upper limit to the amount of phosphorus atoms in the flame retardant. R of the phosphate ester compound represented by general formula (1) and general formula (2) １ , R ２ , R ３ , R ４ , R ５ When is an alkyl group having 12 to 16 carbon atoms, the maximum atomic weight that can be taken is 11.7%.

[0030] The first phosphate ester compound and / or the second phosphate ester compound may be R １ , R ２ , R ３ , R ４ , R ５ The greater the number of carbon atoms in R and the greater the number of linear alkyl groups, the higher the melting point and the greater the effect of preventing thread breakage. １ , R ２ , R ３ , R ４ , R ５The larger the number of carbon atoms in the first phosphate ester compound and / or the second phosphate ester compound, the smaller the amount of phosphorus atoms in the first phosphate ester compound and / or the second phosphate ester compound. Therefore, it is preferable to include two or more different first phosphate ester compounds and / or second phosphate ester compounds in the flame retardant so that the amount of phosphorus atoms in the flame retardant falls within the above-mentioned range and the desired effect of preventing yarn breakage can be obtained.

[0031] The flame retardant of this embodiment further contains a surfactant, and the flame retardant is dispersed in water by the surfactant. If the flame retardant is liquid, the flame retardant is emulsified in water by an emulsifier. In this disclosure, the surfactant and the emulsifier are referred to as surfactants without distinction.

[0032] The surfactant may be a nonionic surfactant, an anionic surfactant, or a combination thereof. The amount of surfactant added is preferably 10 to 25 parts by weight per 100 parts by weight of the flame retardant. If the amount of surfactant added is more than 25 parts by weight, the abrasion resistance of the resulting flame-retardant polyester synthetic fiber structure may decrease, and smearing may occur. If the amount of surfactant added is less than 10 parts by weight, the flame retardant may not be emulsified or dispersed in water.

[0033] As a nonionic surfactant that can be used in the flame retardant of the present disclosure, for example, a compound represented by the following general formula (3) is preferably used. ６ is a linear alkyl group, a branched alkyl group, or an alkylphenyl group having 8 to 30 carbon atoms; A １ O is an oxyethylene group and / or an oxypropylene group, a is 0 or , and b is an integer of 1 to 100.

[0034] In addition, as the anionic surfactant, sulfonates such as higher alcohol sulfates, sulfate ester salts, alkylbenzene sulfonates, and alkylnaphthalene sulfonates, alkali metal salts and ammonium salts of polyoxyalkylene styrenated phenyl ether sulfonates, and alkali metal salts and ammonium salts of bis(polyoxyalkylene styrenated phenyl ether) succinate sulfonates are preferably used.

[0035] The flame retardant of the present embodiment may further contain, in addition to the above surfactants, an anionic surfactant, a nonionic surfactant, or a cationic surfactant other than those described above, as necessary.

[0036] Examples of anionic surfactants other than those mentioned above include sulfate salts such as higher alkyl ether sulfate salts and sulfated fatty acid ester salts, higher alcohol phosphate salts, and alkylene oxide adduct phosphate salts of higher alcohols.Alkanolamines such as triethanolamine may also be used.

[0037] Examples of nonionic surfactants other than those mentioned above include polyoxyalkylene surfactants such as polyhydric alcohol aliphatic ester alkylene oxide adducts, higher alkylamine alkylene oxide adducts, and fatty acid amide alkylene oxide adducts, as well as polyhydric alcohol surfactants such as alkylglycoxides and sucrose fatty acid esters.

[0038] Examples of cationic surfactants include alkylamine salts, quaternary ammonium salts, polyoxyethylene alkylamine salts, and polyethylene polyamine derivatives.

[0039] These other anionic surfactants, nonionic surfactants and cationic surfactants may be used alone or in combination of two or more.

[0040] Water is used as the dispersion medium for the flame retardant. If necessary, the flame retardant may further contain an organic solvent such as alcohol. Examples of organic solvents include alcohols such as methanol and ethanol, aromatic hydrocarbons such as toluene, xylene, and alkylnaphthalene, ketones such as acetone and methyl ethyl ketone, ethers such as dioxane and ethyl cellosolve, amides such as dimethylformamide, sulfoxides such as dimethyl sulfoxide, and halogenated hydrocarbons such as methylene chloride and chloroform. Preferred examples of the organic solvent include water-soluble organic solvents such as alcohols such as methanol, ethers such as acetone and ethyl cellosolve, amides such as dimethylformamide, and sulfoxides such as dimethyl sulfoxide. If necessary, two or more of these organic solvents may be used in combination.

[0041] The flame retardant of this embodiment may further contain a pH adjuster. The second phosphate ester compound is a phosphate monoester or phosphate diester, and is acidic due to the presence of a hydroxyl group. Therefore, when a flame retardant processing agent containing the second phosphate ester compound is used to flame retard a polyester synthetic fiber structure, the low pH may damage the polyester synthetic fiber structure or the flame retardant processing equipment. In such cases, the flame retardant processing agent may further contain a pH adjuster. The pH adjuster may be any alkaline substance, and preferred examples include organic amines and ammonia.

[0042] The flame retardant of this embodiment may further contain a wax. As described above, according to the flame retardant of this embodiment, the first phosphate ester compound and / or the second phosphate ester compound contained in the flame retardant have the effect of preventing thread breakage. However, if the flame retardant's effect of preventing thread breakage is insufficient or if further improvement in thread breakage prevention is desired, a wax may be added to the flame retardant. This allows a wax other than the flame retardant to be applied to the polyester synthetic fiber structure during flame retardation. Even if the flame retardant's effect of preventing thread breakage is insufficient, the thread breakage prevention effect can be further improved without a separate thread breakage prevention treatment. Examples of waxes that can be used to prevent thread breakage include paraffin wax (115°F wax, 130°F wax, 155°F wax), isoparaffin wax, and waxes with melting points of approximately 40°C or higher. Waxes are naturally derived waxes, and when added to flame retardant agents, they may reduce the flame retardant effect compared to paraffin. Therefore, when wax is added to a flame retardant, it is preferable to increase the amount of flame retardant added so as to obtain a sufficient flame retardant effect.

[0043] The flame retardant of this embodiment may further contain other additives such as a dispersant and a stabilizer. For example, the flame retardant may further contain a protective colloid such as polyvinyl alcohol, methyl cellulose, carboxymethyl cellulose, or starch paste to improve storage stability. The flame retardant may also further contain a flame retardant aid to improve flame retardancy, an ultraviolet absorber to improve lightfastness, an antioxidant, or the like. The flame retardant may also further contain a conventionally known flame retardant.

[0044] The flame retardant of this embodiment is obtained by mixing the above-mentioned raw materials with a dispersion medium. Specifically, the flame retardant, optionally selected surfactant, pH adjuster, and wax are weighed, and these raw materials are mixed with the dispersion medium. Next, the flame retardant is emulsified in the dispersion medium using a propeller agitator, homomixer, homogenizer, or high-pressure emulsifying device, or the flame retardant is pulverized and micronized using a wet pulverizer, thereby dispersing the flame retardant in the dispersion medium, thereby obtaining the flame retardant.

[0045] Commercially available products can be used as raw materials. Alternatively, the first phosphate ester compound and / or the second phosphate ester compound can be prepared by synthesis. For example, among the second phosphate ester compounds, a phosphate monoester compound can be obtained by reacting phosphoric anhydride with an alcohol, as disclosed in Japanese Patent Publication No. 41-14416, and a phosphate diester compound can be obtained by reacting phosphoric anhydride with an alcohol, as disclosed in Japanese Patent Application Laid-Open No. 59-13791. Furthermore, a phosphate triester, which is the first phosphate ester compound, can be obtained by reacting phosphorus oxychloride (phosphoryl chloride) with a higher alcohol having 12 to 16 carbon atoms in an appropriate organic solvent in the presence of trimethylamine or the like.

[0046] According to this embodiment, the flame retardant contains a phosphate ester compound represented by general formula (1) or (2), which reduces the solubility in water. Therefore, polyester synthetic fiber structures flame-retarded with the flame retardant of this embodiment are suppressed from forming a gap. In addition, the R １ ~R ５ is an alkyl group having 12 to 16 carbon atoms (R ５ Since the flame retardant has lubricity, the flame-retardant polyester synthetic fiber structure has the effect of suppressing thread breakage during sewing. １ ~R ５ is a straight chain alkyl group (R ５may be hydrogen.) By using the flame retardant, the flame retardant becomes solid at room temperature and exhibits the same effects as wax. Therefore, polyester-based synthetic fiber structures flame-retarded with the flame retardant of this embodiment can exhibit a higher thread breakage prevention effect compared to conventionally known flame retardant treatments. Furthermore, since the polyester-based synthetic fiber structure exhibits the thread breakage prevention effect without the need for a separate wax, it is possible to avoid the increase in flammability of polyester-based synthetic fiber structures due to the addition of wax, and to achieve a high flame retardancy effect even with a reduced amount of flame retardant added. Furthermore, because the flame retardant does not contain halogen, the flame retardant of this embodiment has a low impact on the environment.

[0047] Second Embodiment A flame-retardant polyester-based synthetic fiber structure and a flame-retardant processing method for a polyester-based synthetic fiber structure will be described. The flame-retardant polyester-based synthetic fiber structure of this embodiment comprises a polyester-based synthetic fiber structure and a flame retardant supported on the polyester-based synthetic fiber structure.

[0048] The types and characteristics of polyester-based synthetic fibers and fiber structures to be flame-retardant treated have been described above, as have the uses of polyester-based synthetic fiber structures.

[0049] As described in the first embodiment, the flame retardant contains at least one compound selected from the group consisting of a first phosphate ester compound represented by general formula (1) and a second phosphate ester compound represented by general formula (2).

[0050] The amount of flame retardant attached to a polyester synthetic fiber structure is preferably 0.1 to 10% by weight (% owf) of the polyester synthetic fiber structure, and more preferably 0.5 to 5% by weight. The amount of attachment is even more preferably 0.5 to 3% by weight. If the amount of attachment is less than 0.1% by weight, it may not be possible to impart sufficient flame retardancy to the polyester synthetic fiber structure. Furthermore, if the amount of attachment exceeds 10% by weight, problems such as the texture of the polyester synthetic fiber structure becoming rough and hard after flame retardant processing may occur. The appropriate amount of attachment depends on the phosphorus atom weight of the flame retardant.

[0051] The flame-retardant polyester-based synthetic fiber structure of this embodiment may further contain a wax supported on the polyester-based synthetic fiber structure. When the polyester-based synthetic fiber structure contains wax, the polyester-based synthetic fiber structure can be more reliably provided with a thread breakage prevention effect, even if the flame retardant is liquid at room temperature. Furthermore, since the wax can be applied to the polyester-based synthetic fiber structure during flame retardant processing, a separate thread breakage prevention treatment is not required, thereby improving the productivity of the flame-retardant polyester-based synthetic fiber structure.

[0052] Alternatively, the flame-retardant polyester-based synthetic fiber structure of this embodiment may not contain wax. If the flame retardant is solid at room temperature, the flame retardant can sufficiently prevent thread breakage. Therefore, a separate treatment to prevent thread breakage is not required, and the productivity of the flame-retardant polyester-based synthetic fiber structure can be improved. Furthermore, because flammable wax is not added to the polyester-based synthetic fiber structure, the amount of flame retardant to be added to make the polyester-based synthetic fiber structure flame-retardant can be reduced, thereby achieving effects such as improving the texture of the polyester-based synthetic fiber structure.

[0053] The flame-retardant polyester synthetic fiber structure of this embodiment can be obtained by subjecting a polyester synthetic fiber structure to flame retardancy as a post-processing step using the flame retardant agent of the first embodiment.

[0054] For example, the flame retardant of the first embodiment is diluted with water to prepare a processing liquid, which preferably contains the flame retardant in the range of 0.5 to 5.0 wt %.

[0055] There are no limitations on the post-processing method, and various processing methods can be used. For example, a flame retardant is applied to a polyester synthetic fiber structure, dried, and then heat-treated at a temperature of 100°C to 170°C for 1 to 5 minutes to support and fix the flame retardant to the polyester synthetic fiber structure. For example, padding, spraying, coating, etc. can be used as post-processing.

[0056] Alternatively, an exhaustion method using a dyeing machine may be used for flame retardant treatment. For example, a package dyeing machine such as a jet dyeing machine, beam dyeing machine, or cheese dyeing machine may be used to immerse a polyester synthetic fiber structure in a flame retardant treatment agent or a diluted treatment solution thereof, and the polyester synthetic fiber structure may be treated in the bath at a temperature of 100 to 140°C to allow the flame retardant to be absorbed into the fiber. In this case, the flame retardant treatment may be carried out before, simultaneously with, or after dyeing the polyester synthetic fiber structure.

[0057] In the flame-retardant treatment method for polyester synthetic fiber structures of this embodiment, a treatment with other functional finishing agents may be carried out by mixing with a flame-retardant agent, or before or after the flame-retardant treatment with the flame-retardant agent. Examples of other functional finishing agents include hardening agents, softeners, antistatic agents, water and oil repellents, texture adjusters, and SR agents.

[0058] According to this embodiment, as described in the first embodiment, the resulting flame-retardant polyester-based synthetic fiber structure can be prevented from having seams, and thread breakage during sewing of the flame-retardant polyester-based synthetic fiber structure can be prevented.

[0059] (Example) In order to confirm the effects of the first and second embodiments, flame retardant agents were prepared at various blend ratios, and polyester synthetic fiber structures were flame-retarded using the prepared flame retardant agents, and the properties of the resulting flame-retardant polyester synthetic fiber structures were evaluated. 1. Sample Preparation and Evaluation Method

[0060] (1) Preparation of Flame Retardant Agents Commercially available raw materials were used to prepare the flame retardant agents. Some of the flame retardants were prepared according to the synthesis method described in the first embodiment.

[0061] Flame retardants Samples 1 to 17 were prepared. Table 1 shows the phosphate ester compounds used as flame retardants and their compounding ratios for each sample. For flame retardants containing two types of second phosphate ester compounds, the two types of second phosphate ester compounds are shown as Second Phosphate Ester A and Second Phosphate Ester B. Table 1 also shows the phosphorus atom content in the flame retardant and the melting point of the flame retardant. When a flame retardant contains two or more types of phosphate ester compounds, the phosphorus atom content is the phosphorus atom content relative to the total flame retardant, and the melting point is the melting point of the flame retardant as a mixture. Flame retardants that are liquid at room temperature are marked as "liquid." Wax was also added to the flame retardants of Samples 13 to 17.

[0062] The surfactant (emulsifier) ​​used was at least one selected from polyoxyethylene sorbitan monolaurate, polyoxyethylene stearyl ether, sodium salt of sulfonated bis(polyoxyalkylene styrenated phenyl ether) succinate, triethanolamine, and sodium t-butylnaphthalene sulfonate. The stabilizer used was xanthan gum. Each flame retardant sample was prepared by mixing 20 parts by weight of flame retardant, 75 parts by weight of water, and the remaining 5 parts by weight of surfactant and stabilizer in 100 parts by weight of the flame retardant, using a wet propeller mixer or wet grinder, so that the phosphorus content in the flame retardant was approximately 1-2%.

[0063] For comparison, samples of flame retardants containing flame retardants different from the flame retardant used in the flame retardant of the first embodiment were prepared. As shown in Table 2, the flame retardants were sample 21 containing monoguanidine phosphate and diguanidine phosphate, sample 22 containing resorcinol bis(di-2,6-xylenyl phosphate), sample 23 containing diphenyl-N-phenylphosphoramidate, and sample 24 containing a compound represented by general formula (1) where R １ , R ２ , R ３ Each of the groups contained octadecenyl (having 18 carbon atoms). Sample 24 was prepared in the same manner as samples 1-17.

[0064]

[0065]

[0066] (2) Preparation of flame-retardant synthetic fiber structure The flame-retardant finishing agents of Samples 1 to 17 and Samples 21 to 24 were diluted with water, and the resulting finishing solution was applied to a polyester jersey knit fabric (basis weight 280 g / m) made of black dope-dyed yarn. ２ ) by a padding method and dried at 150°C for 3 minutes to obtain a flame-retardant polyester-based synthetic fiber structure. The flame-retardant polyester-based synthetic fiber structures obtained using the flame retardant processing agents of Samples 1 to 17 and Samples 21 to 24 are referred to as the flame-retardant polyester-based synthetic fiber structures of Samples 1 to 17 and Samples 21 to 24, respectively.

[0067] Tables 3 and 4 show the amounts of flame retardant attached to the resulting flame-retardant polyester synthetic fiber structures. Samples 1-1 and 1-2, 2-1, 2-2, and 2-3, 7-1 and 7-2, and 24-1 and 24-2 were prepared by varying the amount of flame retardant attached to Sample 1, Sample 2, Sample 7, and Sample 24. Samples 27-1 and 27-2 were also prepared by using only a wax-based thread breakage prevention treatment without any flame retardant treatment, and Sample 28 was also prepared by using neither a flame retardant treatment nor a thread breakage prevention treatment.

[0068] (3) Evaluation A combustion test, a flammability test, and a thread breakage test were carried out.

[0069] Flammability test: A horizontal flame test was conducted in accordance with Federal Motor Vehicle Safety Standard No. 302 (FMVSS 302). Fabrics that self-extinguished within a burning distance of 50 mm in both the longitudinal and transverse directions were rated as "self-extinguishing," while fabrics with burning rates of 100 mm / min or less and greater than 100 mm / min were rated as "slow-burning" and "easy-burning," respectively. The lower of the two test results was used as the overall rating.

[0070] Evaluation of staining: A flame-retardant treated fabric was placed on top of urethane foam, and 5 mL of pure water and boiling water were dropped onto the surface. After 24 hours, the surface of the sample was observed, and samples that showed no ring stains or staining were judged to pass (Good, indicated by "G"), and samples that showed ring stains or staining were judged to fail (Fail, indicated by "F").

[0071] Yarn breakage evaluation: A polyester jersey knit fabric (weight 280 g / m) with a width of 10 cm and a length of 30 cm was used. ２ Two pieces of fabric were stacked on top of each other and sewn together lengthwise with polyester thread (Teijin Tetron sewing thread No. 8) at a stitch pitch of 3 mm and a sewing machine revolution speed of 2000 rpm using an industrial sewing machine (STH-8BLD-3, manufactured by Seiko Sewing Machine Co., Ltd.) equipped with a #21 ball point needle. The sewn portion was observed, and the number of places where thread breakage occurred was counted.

[0072] The results are shown in Tables 3 and 4.

[0073]

[0074]

[0075] 2. Results and Discussion As shown in Table 1, the phosphorus atom amounts of the first and second phosphate ester compounds used as flame retardants were R １ , R ２ , R ３ are each a hexadecyl group, the lowest is 4% by weight, and R ４ is a dodecyl group, and R ５ When is hydrogen, the amount of phosphorus atoms is the largest, 11.7 wt %.

[0076] As shown in Samples 2-1 to 2-3 in Table 3, when the phosphorus atom content of the flame retardant is low, the flame retardant performance can be improved by increasing the attachment amount (3.0% owf). On the other hand, as shown in Sample 3 in Table 3, when the phosphorus atom content of the flame retardant is high, the flame retardant performance becomes self-extinguishing even when the attachment amount is low (0.5% owf).

[0077] As shown in Samples 24-1 and 24-2 in Table 4, R in general formula (1) １ , R ２ , R ３ When the carbon number is greater than 16, the phosphorus atom content of the flame retardant is less than 4% by weight. Therefore, even if the amount of the flame retardant is increased to 3.2% by weight, it is not possible to obtain flame retardancy beyond retardancy.

[0078] These findings indicate that a flame retardant containing at least one compound selected from the group consisting of a first phosphate ester compound represented by general formula (1) and a second phosphate ester compound represented by general formula (2) can provide a halogen-free flame retardant that exhibits sufficient flame retardancy.

[0079] Furthermore, as shown in Samples 21 and 22 in Table 4, when conventional guanidine phosphate or resorcinol bis(di-2,6-xylenyl phosphate) is used as a flame retardant, there is a possibility of nicking. In contrast, as shown in Samples 1-1 to 17 in Table 3, when the first phosphate ester compound or the second phosphate ester compound is used as a flame retardant, it is clear that nicking can be effectively suppressed.

[0080] R of Sample 1, Sample 2, Sample 3, and Sample 9 in Table 1 １ , R ２ , R ３ , R ４ When R is a linear alkyl group having 12 to 16 carbon atoms, the first phosphate ester and the second phosphate ester compound become solid at room temperature. ４ and R ５ The examples in which R is a linear alkyl group are not included in Samples 1 to 17, but ５ is hydrogen, R ４ If R is a linear alkyl group, the second phosphate ester is solid at room temperature. ４ and R ５ Even if the alkyl group is a straight chain alkyl group, the second phosphate ester compound becomes a solid at room temperature.

[0081] On the other hand, as shown in Samples 4 and 12, R １ , R ２ , R ３ , R ４ , R ５When the second phosphate ester compound is a branched alkyl group, the melting point is lowered and the flame retardant becomes a liquid at room temperature. The second phosphate ester compound is a monoester or diester and has a higher phosphorus atom content than the first phosphate ester compound. Therefore, the flame retardant can adjust the phosphorus atom content by including the first phosphate ester compound and the second phosphate ester compound. At this time, the melting point can also be changed.

[0082] As shown in Table 3, in the flame-retardant polyester-based synthetic fiber structures of Samples 1-1 to 9, Sample 11, and Sample 12, thread breakage was suppressed to five or fewer locations. In contrast, in Samples 21 to 23, which used a conventional flame retardant, thread breakage occurred in ten or more locations, and even in the polyester-based synthetic fiber structures that were not flame-retarded, thread breakage occurred in eight locations. Therefore, it can be seen that the flame-retardant processing agent of this embodiment, whether the flame retardant is liquid or solid, can prevent thread breakage in the resulting flame-retardant polyester-based synthetic fiber structures, without the need for a wax-based thread breakage prevention treatment.

[0083] Furthermore, a comparison of Sample 2 with Samples 4 and 12 reveals that a solid flame retardant can provide a higher thread breakage prevention effect than a liquid flame retardant. Furthermore, a comparison of Sample 4 with Sample 10 reveals that adding wax to the flame retardant can also further enhance the thread breakage prevention effect.

[0084] As shown in Sample 10 and Samples 14 to 17 in Table 3, when wax is added to a flame retardant, paraffin is preferable to wax from the viewpoint of flame retardancy. Alternatively, when wax is added to a flame retardant, it is preferable to increase the amount of flame retardant attached compared to when paraffin is used in order to enhance flame retardancy. For example, a comparison of Samples 2-1 and 2-3, or Samples 7-1 and 7-2, shows that increasing the amount of flame retardant attached by about two times can improve the flame retardancy rating of a polyester synthetic fiber structure from flammable to self-extinguishing.

[0085] Furthermore, from the viewpoint of preventing thread breakage, it is preferable that the melting point of the paraffin is high, and it is more preferable that the melting point is about 56°C (130°F) or higher.

[0086] As described above, the flame retardant agent for polyester synthetic fiber structures, the flame retardant polyester synthetic fiber structure, and the flame retardant processing method for polyester synthetic fiber structures of the present embodiment can impart excellent flame retardancy to the polyester synthetic fiber structure and also prevent thread breakage during sewing.

[0087] The flame retardant agent for polyester-based synthetic fiber structures, the flame-retardant polyester-based synthetic fiber structure, and the flame-retardant processing method for polyester-based synthetic fiber structures of the present disclosure can also be explained as follows.

[0088] The flame retardant for polyester synthetic fiber structures according to the first aspect of the present invention comprises a first phosphate ester compound represented by the following general formula (1) (wherein R １ , R ２ , R ３ each independently represents an alkyl group having 12 to 16 carbon atoms; and A second phosphate ester compound represented by the following general formula (2) (wherein R ４ is an alkyl group having 12 to 16 carbon atoms, R ５ represents an alkyl group having 12 to 16 carbon atoms or hydrogen. According to the first aspect, the flame retardant includes at least one selected from the group consisting of R １ ~R ５ is an alkyl group with a large number of carbon atoms (R ５ may be hydrogen.) Therefore, the solubility in water is reduced, and adhesion is suppressed.

[0089] The flame retardant for polyester synthetic fiber structures according to the second aspect may have a phosphorus atom content of 4.0% or more and 11.7% or less in the first aspect. A phosphorus atom content of 4.0% or more can provide excellent flame retardancy.

[0090] The flame retardant for polyester synthetic fiber structures according to the third aspect of the present invention is the flame retardant for polyester synthetic fiber structures according to the first aspect of the present invention, wherein the R １ , R ２ , R ３、 R ４ and R ５At least one of the alkyl groups may be a straight-chain alkyl group having 12 to 16 carbon atoms. The straight-chain alkyl group allows the phosphate ester compound to become solid at room temperature, thereby preventing the fibers from breaking during sewing. This eliminates the need to separately apply a smoothing agent to the fiber structure to improve the sewability.

[0091] The flame retardant for polyester synthetic fiber structures according to the fourth aspect of the present invention is the flame retardant for polyester synthetic fiber structures according to the first aspect of the present invention, wherein the R １ , R ２ , R ３、 R ４ and R ５ At least one of the alkyl groups may be a branched alkyl group having a carbon number of 12 to 16. By using a branched alkyl group, the raw materials are inexpensive, and the production cost can be reduced.

[0092] The flame retardant for polyester synthetic fiber structures according to the fifth aspect may be the flame retardant of the first aspect, wherein the melting point of the flame retardant is 35°C or higher. Since the flame retardant is solid at room temperature, the flame retardant also functions as a wax during flame retardation, thereby suppressing thread breakage. Since there is no need to apply a separate wax to the fiber, the effectiveness of the flame retardant can be enhanced.

[0093] The flame retardant for polyester synthetic fiber structures according to a sixth aspect is the flame retardant for polyester synthetic fiber structures according to the first aspect, wherein the flame retardant contains the first phosphate ester compound, and the R １ , R ２ , R ３ may each independently be a linear alkyl group having 12 to 16 carbon atoms. １ , R ２ , R ３ is a linear alkyl group having 12 to 16 carbon atoms, the flame retardant becomes solid at room temperature.

[0094] A seventh aspect of the flame retardant for polyester synthetic fiber structures is the first aspect, wherein the flame retardant contains the first phosphate ester compound and the second phosphate ester compound. Since the second phosphate ester compound has a higher phosphorus content than the first phosphate ester compound, the inclusion of the second phosphate ester compound can enhance the flame retardant effect. Linearization of the alkyl group of the first phosphate ester also contributes to preventing yarn breakage.

[0095] The flame retardant for polyester-based synthetic fiber structures according to an eighth aspect is the first aspect, wherein the first phosphate ester compound is at least one selected from the group consisting of tridodecyl phosphate, tritridecyl phosphate, tritetradecyl phosphate, tripentadecyl phosphate, trihexadecyl phosphate, and triisotridecyl phosphate.

[0096] A ninth aspect of the flame retardant for polyester synthetic fiber structures is the first aspect, wherein the second phosphate ester compound is at least one compound selected from the group consisting of dodecan-1-yl dihydrogen phosphate, tridecan-1-yl dihydrogen phosphate, tetradecan-1-yl dihydrogen phosphate, pentadecan-1-yl dihydrogen phosphate, hexadecan-1-yl dihydrogen phosphate, didodecan-1-yl hydrogen phosphate, ditridecan-1-yl hydrogen phosphate, ditetradecan-1-yl hydrogen phosphate, dipentadecan-1-yl hydrogen phosphate, dihexadecan-1-yl hydrogen phosphate, isotridecan-1-yl dihydrogen phosphate, and diisotridecan-1-yl hydrogen phosphate.

[0097] The flame retardant for polyester synthetic fiber structures according to a tenth aspect is the first aspect, further comprising a nonionic surfactant and / or anionic surfactant and water, and the flame retardant may be dispersed or emulsified in the water.

[0098] The flame retardant for polyester-based synthetic fiber structures according to an eleventh aspect is the first aspect, further comprising a pH adjuster containing at least one selected from the group consisting of ammonia and alkanolamines, and the flame retardant may also contain the second phosphate ester compound.

[0099] The flame retardant for the polyester synthetic fiber structure according to the twelfth aspect may further contain wax in the first aspect. Because the flame retardant contains paraffin, there is no need for a separate thread breakage prevention treatment.

[0100] A flame retardant for polyester synthetic fiber structures according to a thirteenth aspect is the twelfth aspect, wherein the wax is paraffin.

[0101] A flame-retardant polyester-based synthetic fiber structure according to a fourteenth aspect includes a polyester-based synthetic fiber structure and the flame retardant contained in the flame retardant treatment agent for polyester-based synthetic fiber structures according to any one of the first to thirteenth aspects, the flame retardant being supported on the polyester-based synthetic fiber structure. This configuration reduces the occurrence of edging in the flame-retardant polyester-based synthetic fiber structure compared to when a water-soluble salt such as guanidine phosphate is used. When the phosphate ester compound is solid, it also has the effect of preventing thread breakage.

[0102] A flame retardant for a polyester synthetic fiber structure according to a fifteenth aspect comprises a polyester synthetic fiber structure and the flame retardant contained in the flame retardant for a polyester synthetic fiber structure according to any one of the first to eleventh aspects, the flame retardant being supported on the polyester synthetic fiber structure, and does not contain wax. Because the flame retardant does not contain paraffin, which has the effect of preventing thread breakage, the amount of phosphate ester compound added can be reduced, and the texture of the fiber structure can be improved.

[0103] A flame retardant processing method for polyester-based synthetic fiber structures according to a sixteenth aspect comprises carrying a flame retardant processing agent for polyester-based synthetic fiber structures described in any one of the first to thirteenth aspects on a polyester-based synthetic fiber structure.

[0104] A seventeenth aspect of the flame retardant processing method for polyester-based synthetic fiber structures is the sixteenth aspect, wherein a flame retardant is applied to the polyester-based synthetic fiber structure in a proportion of 0.1% by weight or more and 10% by weight or less.

[0105] The flame retardant processing method for polyester-based synthetic fiber structures according to an eighteenth aspect may be the sixteenth aspect, in which the polyester-based synthetic fiber structure is supported with at least one type of phosphate ester compound, and then the polyester-based synthetic fiber structure is heat-treated at a temperature of 100°C to 170°C.

[0106] The flame retardant agent for polyester synthetic fiber structures, the flame retardant polyester synthetic fiber structure, and the flame retardant processing method for polyester synthetic fiber structures of the present disclosure are suitable for use in polyester synthetic fiber structures for a variety of applications.

Claims

1. A first phosphate ester compound represented by the following general formula (1) (in formula (1), R １ , R ２ , R ３ independently represent an alkyl group having 12 to 16 carbon atoms), and a second phosphate ester compound represented by the following general formula (2) (in formula (2), R ４ is an alkyl group having 12 to 16 carbon atoms, R ５ represents an alkyl group having 12 to 16 carbon atoms or hydrogen). A flame retardant processing agent for a polyester synthetic fiber structure comprising at least one selected from the group consisting of 2. The flame retardant processing agent for a polyester synthetic fiber structure according to claim 1, wherein the phosphorus atomic weight in the flame retardant is 4.0% or more and 11.7% or less.

3. The R １ , R ２ , R ３、 R ４ and R ５ At least one of which is a linear alkyl group having 12 to 16 carbon atoms, the flame retardant processing agent for the polyester synthetic fiber structure according to claim 1.

4. The above R １ , R ２ , R ３、 R ４ and R ５ At least one of them is a branched alkyl group having 12 to 16 carbon atoms, and the flame retardant processing agent for the polyester synthetic fiber structure according to claim 1.

5. The flame retardant processing agent for a polyester synthetic fiber structure according to claim 1, wherein the melting point of the flame retardant is 35°C or higher.

6. The flame retardant contains the first phosphate ester compound, and the R １ , R ２ , R ３ are each independently a linear alkyl group having 12 to 16 carbon atoms. The flame retardant finishing agent for the polyester synthetic fiber structure according to claim 1.

7. The flame retardant processing agent for a polyester synthetic fiber structure according to claim 1, wherein the flame retardant contains the first phosphate ester compound and the second phosphate ester.

8. The flame retardant processing agent for a polyester synthetic fiber structure according to claim 1, wherein the first phosphate ester compound is at least one selected from the group consisting of tridodecyl phosphate, tritridecyl phosphate, tritetradecyl phosphate, tripentadecyl phosphate, trihexadecyl phosphate, and triisotridecyl phosphate.

9. The flame retardant processing agent for a polyester synthetic fiber structure according to claim 1, wherein the second phosphate ester compound is at least one selected from the group consisting of dodecan-1-yl dihydrogen phosphate, tridecan-1-yl dihydrogen phosphate, tetradecan-1-yl dihydrogen phosphate, pentadecan-1-yl dihydrogen phosphate, hexadecan-1-yl dihydrogen phosphate, didodecan-1-yl hydrogen phosphate, ditridecan-1-yl hydrogen phosphate, ditetradecan-1-yl hydrogen phosphate, dipentadecan-1-yl hydrogen phosphate, dihexadecan-1-yl hydrogen phosphate, isotridecan-1-yl dihydrogen phosphate, and diisotridecan-1-yl hydrogen phosphate.

10. The flame retardant processing agent for a polyester synthetic fiber structure according to claim 1, further comprising a nonionic surfactant and / or an anionic surfactant and water, wherein the flame retardant is dispersed or emulsified in the water.

11. The flame retardant processing agent for a polyester synthetic fiber structure according to claim 1, further comprising a pH adjuster containing at least one selected from the group consisting of ammonia and alkanolamine, and the flame retardant contains the second phosphate ester compound.

12. The flame retardant processing agent for a polyester synthetic fiber structure according to claim 4, further comprising wax.

13. The flame retardant finishing agent for a polyester synthetic fiber structure according to claim 12, wherein the wax is paraffin.

14. A flame-retardant polyester synthetic fiber structure comprising: a polyester synthetic fiber structure; and the flame retardant contained in the flame retardant finishing agent for a polyester synthetic fiber structure according to any one of claims 1 to 13, wherein the flame retardant is supported on the polyester synthetic fiber structure.

15. A flame-retardant polyester synthetic fiber structure comprising: a polyester synthetic fiber structure; and the flame retardant contained in the flame retardant finishing agent for a polyester synthetic fiber structure according to any one of claims 1 to 11, wherein the flame retardant is supported on the polyester synthetic fiber structure and does not contain wax.

16. A method for flame-retardant finishing of a polyester synthetic fiber structure, comprising loading the polyester synthetic fiber structure with the flame retardant by using the flame retardant finishing agent for a polyester synthetic fiber structure according to any one of claims 1 to 13.

17. The method for flame-retardant finishing of a polyester synthetic fiber structure according to claim 16, wherein the flame retardant is applied to the polyester synthetic fiber structure at a ratio of 0.1% by weight or more and 10% by weight or less.

18. The method for flame-retardant finishing of a polyester synthetic fiber structure according to claim 16, wherein after loading the polyester synthetic fiber structure with the at least one phosphoric acid ester compound, the polyester synthetic fiber structure is heat-treated at a temperature of 100°C to 170°C.

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