JPH0133596B2 - - Google Patents

Description

[Detailed description of the invention]

FIELD OF THE INVENTION The present invention relates to a textile product having superior permanent flame retardancy and to a method for producing the same. Efforts have been made to improve the combustion defects of textile products, whether synthetic or natural, and various proposals for improvement have been made. As a result, it has become possible to modify each type of synthetic fiber, such as polyester and nylon, as well as natural fibers, using specific flame retardants. However, such flame-retardant fiber products can now only be made of one type of fiber and have a flame retardancy that meets the standards set forth in the Fire Service Act. For example, for mixed products such as different types of synthetic fibers or synthetic fibers and natural fibers, it is not possible to impart a practical level of flame retardancy using such conventional techniques, and even if the optimum resistance of each of the mixed component fibers cannot be imparted, Faced with the fact that even with the use of retardant agents, it is no longer possible to meet the standards of the Fire Service Act, which were met by single retardants, there is an urgent need to consider ways to make flame retardant products in combination with these retardants. On the other hand, the conventional flame-retardant textile products mentioned above exhibit flame-retardant performance that meets the provisions of the Fire Service Act in the initial stage of practical use, but they cannot be used in the process of washing, dry cleaning, ironing, etc. As a result, the performance deteriorates, and the product eventually deviates from the standard. In view of the shortcomings of the prior art, the present inventors investigated a technique that can permanently impart flame retardancy to any fiber, regardless of the type of fiber. The inventors have discovered that a combination of a compound and a specific flame retardant achieves the above object, and have arrived at the present invention. That is, the gist of the present invention is as follows. (1) The surface of each single fiber constituting the textile product is coated with a coating consisting of a compound containing a triazine ring and having at least two polymerizable functional groups, and the coating is made of a compound containing phosphorus or Permanently flame-retardant fiber containing either nitrogen or halogen as an active ingredient and at least one kind of flame retardant that is dispersed with compatibility or affinity with the coating. product. (2) When making textile products flame retardant, a compound containing a triazine ring and at least two polymerizable functional groups is added to the surface of each single fiber by heat treatment in the presence of moisture. and applying at least one kind of flame retardant containing phosphorus, nitrogen, or halogen as an active ingredient and dispersing with compatibility or affinity with the film. A method for producing permanently flame-retardant textile products, characterized by performing a treatment that combines two steps: A method for producing permanently flame-retardant textile products characterized by the following: By adopting this technical configuration, it is possible to produce products made by mixing different types of fibers, which was previously impossible, as well as to produce products that are uniformly outstanding regardless of their type. It has the characteristics of being able to be modified to have flame retardancy, and compared to conventional technology, its durability can be maintained permanently, and it also has a significantly superior feel (flexibility). This is what we could have provided. Furthermore, the method of the present invention has the advantage that flame-retardant fiber products having such excellent performance can be easily and stably produced by extremely easy means. The textile products referred to in the present invention include natural fibers such as cotton, hemp, silk, and wool, synthetic fibers such as polyester, nylon, and acrylic, cellulose acetate,
The product may be made of any fiber, such as semi-synthetic fibers such as rayon, and the form of the product is not limited. Examples of the compound containing a triazine ring and having at least two polymerizable functional groups (hereinafter simply referred to as a triazine ring-containing compound) in the present invention include those represented by the following general formula. (In the formula, R ₀ to R ₂ : -H, -OH, -C ₆ H ₅ , -C _o0
H _2o0+1 (n ₀ : 1~10), −COOC _o1 H _2o1+1 (n ₁ : 1~
20), −CONR ₃ R ₄ , −NR ₃ R ₄ However, R ₃ , R ₄ : −H, −OH, −OC _o3 H _2o3+1 ,
−CH ₂ OC _o3 H _2o3+1 , −CH ₂ COOC _o3 H _2o3+1 (n ₃ :1
~20) −CH ₂ OH, −CH ₂ CH ₂ OH, −CONH ₂ , −
_{CONHCH 2 OH} , _{-O- ( X - O ) -o4 R 5} -CH ₅ , -C ₃ H ₇ More preferred compounds among the above general formulas are:
A compound in which R ₀ and R ₁ are -NR ₃ R ₄ , and among them, R ₂ is -CONR ₃ R ₄ and -NR ₃ R ₄ , and R ₃ and R ₄ are -CH ₂ OH, _{−CH2CH2OH ,}
Compounds _-CONH2 , _-CONHCH2OH are preferred. Further, R ₀ to R ₂ are -NR ₃ R ₄ , and R ₃ and R ₄ are -H, -OC _o H _2o+1 , -CH ₂ OC _o H _2o+1 , (n=1 to 16) , -CH ₂ OH, -CH ₂ CH ₂ OH, -CONH ₂ , -CONHCH ₂ OH have the property of being able to form a film even when left in a wet state at room temperature, and are energy-saving. Measures and texture (flexibility)
This is extremely convenient from this point of view. In addition, in achieving the object of the present invention, diamine derivative compounds such as urea and thiourea, formalin, phenol compounds, triazone compounds, ethylene urea, glyoxal compounds,
A uron compound or the like can be used in combination, and for example, a coating made of an ethylene urea cocondensate, dimethylol urea cocondensate, dimethylol thiourea condensate, etc. with the compound represented by the above general formula is also effective. According to the present invention, the surface of each single fiber is coated with a coating made of such a compound, that is, it is coated in a cylindrical shape, and in particular, it is uniform and completely coated with no exposed fiber parts. The coated form is most preferred. From the standpoint of flame retardancy, there may be no problem even if there is a partial lack of coating as long as combustion does not propagate. The triazine ring-containing compound of the present invention can further improve wetting properties by selecting the type of polymerizable functional group depending on the type of target fiber, and improve film properties such as uniformity, coverage, and durability. It can be improved. In other words, in the case of fibers whose structural units are nitrogen-containing compounds, it is not necessary to select the functional group of the triazine ring-containing compound, but in the case of fibers whose structural units are composed of units other than nitrogen-containing compounds, such as polyester fibers, etc. is the general formula R ₀
~ By selecting a compound in which _R2 has an ester or ether functional group, the wetting properties can be further improved, and when the compound is polymerized on the fiber surface, the functional group between the compound and the fiber matrix can be further improved. The groups can partially induce chemical bonds, and the durability of the film can be significantly improved. A feature of the present invention is that the cylindrical coating made of such a compound contains at least one flame retardant containing phosphorus, nitrogen, or halogen as an active ingredient in a dispersed state. The present inventors have discovered that although a film made of the above compound alone cannot suppress combustion, by incorporating a flame retardant into the film, an extremely high flame retardant effect can be exhibited. Such flame retardants have the above-mentioned active ingredients,
In addition, an organic flame retardant that is dispersed with compatibility or affinity with the film (meaning non-reactive with the film; hereinafter simply referred to as a flame retardant) is applied. . Examples of such organic flame retardants include halogenated organic sulfur phosphorus compounds, organic phosphorus compounds, halogenated sulfur phosphorus compounds, organic phosphorus-zirconium complex salts, phosphorus-containing aminoplasts, sulfur-containing aminoplasts, organic phosphorus nitrogen compounds, and thiourea. Examples include compounds, halogenated organic phosphorus compounds, and the like. A specific example of such a flame retardant is shown below, but the invention is not limited thereto. (Here, R: phenyl group or halophenyl group,
(lower alkyl group or haloalkyl group). [Here, R: H, alkyl group, haloalkyl group, X: halogen, methylol compound] [Here, X: halogen R: alkylene group n, m: 1 to 2] All of these flame retardants have compatibility and affinity with the film made of the triazine ring-containing compound, and are Most of them are contained in dispersed form. Such flame retardants can be used alone or in combination of two or more. In the present invention, the flame retardant is contained in a film made of a triazine ring-containing compound, and may be contained in the form of being attached to the surface or back of the film, but at least It is essential that it be dispersed and contained within the film. That is, the flame retardant has the property of being transferred into the film and contained therein by dry heat treatment, and is further made uniform by the transfer into the film.
This dramatically improves the flame retardancy of the coating. Although such a coating is effective even if it is extremely thin, the thickness is preferably about 0.01 to 10 μm, and from the viewpoint of a high flame retardant effect, the thickness is about 0.05 μm or more, preferably about 0.5 to 3 μm. However, this coating thickness is a value including the thickness that penetrates into the fibers. Further, the amount of the compound deposited is 0.1 to 20%, preferably 0.2 to 10%, based on the weight of the fiber, in terms of nitrogen element, to achieve a sufficient effect. The amount of flame retardant contained in the permanently flame retardant fiber product of the present invention is 0.5 including the amount exhausted inside the fiber.
A range of 10% owf, more preferably 2 to 10% owf.
If it is less than 0.5% owf, the flame retardant effect is weak, and if it exceeds 10% owf, the flame retardant property is improved more than necessary, but the texture becomes rough and hard. The film thickness and adhesion amount depend on the desired degree of flame retardancy and product characteristics such as texture (flexibility).
What is necessary is to determine its maximum value. The flame-retardant performance of the permanently flame-retardant fiber products of the present invention is extremely high, and the above-mentioned film thickness and adhesion amount can be reduced accordingly. Flame retardant textile products have the advantages that they can offer. The permanently flame retardant fiber products of the present invention are produced by a combination of two steps. One of the steps is to apply the triazine ring-containing compound to a textile product to form a coating. After the treatment, a solution or dispersion consisting of an aqueous medium containing the triazine ring-containing compound and a polymerization catalyst is applied. The amount of the triazine ring-containing compound contained in such a treatment liquid is 0.01 to 40% by weight, preferably 0.1 to 10% by weight.
If the content is less than 0.01% by weight, it will not be possible to form a film sufficient to exhibit the flame retardant effect, and if the content exceeds 40% by weight, the texture will be rough and hard. Although the flame retardance is improved more than necessary, it is not preferable as a material for ordinary clothing from the commercial value point of view, although it depends on the use. Next, the polymerization catalyst added to the treatment solution is as follows:
Acids such as inorganic acids or organic acids and their salts are applicable. Such inorganic acids include sulfuric acid,
Examples include sulfite, persulfuric acid, phosphoric acid, nitric acid, carbonic acid, hydrochloric acid, and phosphoric acid compounds in the ultra range. The organic acid is a compound having a carboxy group. For example, formic acid,
Aliphatic carboxylic acids such as acetic acid, olefin carboxylic acids such as acrylic acid and methacrylic acid, saturated dicarboxylic acids such as oxalic acid, malonic acid, and succinic acid, oxycarboxylic acids such as malic acid, citric acid, and tartaric acid, glumitanic acid, and asparagine. Examples include aminocarboxylic acids such as acids, unsaturated dicarboxylic acids such as maleic acid, itaconic acid, and methyl fumaric acid, and aromatic dicarboxylic acids such as phthalic acid and isophthalic acid, but are not particularly limited to the above-mentioned acids. The amount of such catalyst added is a normal catalyst amount,
For example, from 0.01 to 10% by weight, generally from 0.01 to 3% by weight. Any method such as dipping, spraying, coating, etc. may be used to apply the treatment liquid to the textile product, but the dipping method is simple. Next, the fiber product to be treated is heat-treated at a temperature above room temperature, preferably 40°C to 140°C, to cause the compound to undergo a polymerization reaction and form a film. At this time, it is important to perform the reaction in the presence of moisture. It is.
The water content greatly affects the performance of the membrane formed, and the reaction is usually carried out in an atmosphere with a relative humidity of 25% or more of the weight of the fibers or 40% or more. Of course, the heating reaction may be carried out while immersed in the treatment liquid. When heat treatment is performed in a separate process, heated steam (including saturated and unsaturated) or cold treatment, in which the product is immersed in the treatment liquid and left sealed, is used.
Batch method etc. can be adopted. The processing time varies somewhat depending on the type of compound and temperature conditions, but
Generally, at low temperatures (including room temperature) for 15 to 30 hours, 40℃
If it is more than that, it will be processed for about 0.5 to 180 minutes. Even if a treatment liquid consisting of the triazine ring-containing compound of the present invention is used, if the moisture content is less than the above range as in drying or dry heat treatment, the treatment liquid migrates on the fibers and aggregates. As a result, it is not possible to form a cylindrical film that completely covers each single fiber, and only a lump-like film is obtained. Another step is the step of applying the flame retardant. This step may be carried out before, during or after the step of forming the film. If the step of applying the flame retardant is before the film forming step, the flame retardant is attached to the fibers with some of it transferred into the fibers, and these flame retardants are attached to the fibers. It is transferred into the film by dry heat during soaping drying after formation and is contained in a dispersed form. In addition, when the flame retardant application step is performed after the flame retardant application step, the flame retardant is transferred from the film and contained in the film in a dispersed state by drying and dry heat treatment after application of the flame retardant, and further by soaping drying. In either method, the flame retardant is contained in the coating in a dispersed form. In addition, if the two steps are carried out simultaneously, it is contained in the film in a dispersed form from the beginning, and in this case, it also migrates into the fibers by dry heat treatment, and further migration occurs within the film, so that it is contained uniformly. be converted into That is, according to the present invention, as a result, the flame retardant is dispersed and contained within the coating, thereby dramatically improving the flame retardancy of the coating. Hereinafter, the method of applying the flame retardant will be specifically described. First, the method performed before and after the above-mentioned film forming step will be described. The treatment liquid contains the flame retardant at a concentration in the range of 50 to 800 g/preferably 80 to 600 g, but this concentration can be increased or decreased as necessary. Flame retardant active ingredient in treatment liquid 0.5~
It is preferable to adjust the content to 45% by weight, preferably 1 to 35% by weight. Water is usually used as the treatment liquid medium, but an organic solvent can be used if necessary. Furthermore, if necessary, various additives may be used in combination within a range that does not impede the object of the present invention. As a method for applying such a treatment liquid to a textile product, the means applied in the above-mentioned film forming step can be applied. In this case as well, the immersion method is simple and the paddo dry method is usually adopted. After immersion and drying, dry heat treatment is usually carried out at a temperature of 100°C or higher, preferably 140 to 200°C, and more preferably 160 to 180°C, for about 3 to 6 minutes. Next, a method of simultaneously performing the two steps of the present invention will be explained. In this method, a flame retardant is mixed and added to the treatment liquid in the film forming step, and the flame retardant may be added in a separate step. When mixing the flame retardant into the treatment liquid, the amount of the flame retardant can be varied over a fairly wide range, including cases in which the flame retardant is added in a smaller amount than the concentration range of the method in which the flame retardant is added in a separate process. Become. That is, the flame retardant active ingredient can be contained in the treatment liquid in an amount of 0.1 to 45% by weight, preferably 0.1 to 35% by weight. If the mixing amount is too small, the flame retardant effect will be small, and if the mixing amount is too large, film formation will be inhibited. In the present invention, the triazine ring-containing compound has a general formula in which R ₀ to _{R 2} are -NR ₃ R ₄ and R ₃ and R ₄ are -H, -OC _o H _2o+1 , -CH ₂ OC _o H _2o+1 , (n=1~
16), _-CH2OH , _-CH2OH , _-CONH2 , -
By selecting CONHCH ₂ OH, the heat treatment conditions for film formation can be set to room temperature, and film formation can be completed simply by leaving it in a state that retains moisture, which is extremely effective in terms of energy conservation. can be processed. Moreover, the textile products produced by this method have the advantage of being significantly more flexible than those produced by other processing methods. The permanently flame-retardant fiber products obtained in this way have extremely high flame retardancy compared to those made by conventional techniques,
Moreover, the washing resistance and dry cleaning resistance are dramatically improved. For example, the flame retardant effect is nine times greater under the same conditions of heat baking. This effect is due to the fact that the polymer made of the triazine ring-containing compound forms a uniform layer of film on the surface of each single fiber that makes up the product, and that film does not exhibit thermal properties that are completely different from the fiber matrix, that is, it does not exhibit a melting point. This was achieved for the first time through the synergistic effect of the property of carbonizing when the melting temperature is exceeded and the flame retardant effect of nitrogen, phosphorus, and halogens. The present invention will be further explained below with reference to examples.Example 1: 80% polyester, 20% cotton blended fabric (basis weight
250g/m ² ) by conventional methods, sintering, desizing, scouring,
Bleaching, heat setting, and dyeing are performed, and in the first step, a melamine resin is used to form a uniform cylindrical film on the fiber surface under the following conditions. Treatment bath composition Melamine resin Sumitex Resin M-3 (manufactured by Sumitomo Chemical) 7.0% Ammonium persulfate catalyst 0.3% Dispersant Megafac F-833 (manufactured by Dainippon Ink) 0.1% Water 92.6% Total 100.0% Pick up this resin liquid 80% %, and immediately use a hanging steamer to 100% R/H humidity.
Steam treatment at a temperature of 105°C for 3 minutes. Then soap, wash with water and dry. As a second step, the film was treated with a flame retardant under the following conditions to disperse and contain the flame retardant in the film. Treatment liquid composition Flame retardant Phosphorus-containing aminoplast 41.3% Formalin scavenger Dicyacydiamide 4.6% Crosslinking agent Sumitex Resin M-3 (manufactured by Sumitomo Chemical)
1.0% Tear strength reduction inhibitor D-1710 (polyethylene softener, Dai-ichi Kogyo)
1.9% Softener Elasfinish E-200 (manufactured by Dai-ichi Kogyo) 1.0% Catalyst Sumitex Accelerator KX (manufactured by Sumitomo Chemical) 0.5% Water 49.7% Total 100.0% Pick up the adjustment solution with the above composition at 100%, and 140% Dry for 2 minutes at °C. Thereafter, it was subjected to dry heat treatment at 160°C for 3 minutes in a hot full type baking device. Then soaped and dried. Comparative Example 1 Same as Example 1. However, the first step is omitted. Comparative Example 2 Same as Example 1. However, the second step is omitted. The flame retardance of Example 1, Comparative Example 1, Comparative Example 2, and untreated fabrics are shown in Table 1. As shown in Table 2, Example 1 shows better flame retardancy than Comparative Example 1 even after washing and dry cleaning five times each.

【table】

[Table] Example 2 A blended fabric of 65% polyester and 35% rayon (basis weight 230 g/m ² ) was dyed in the same manner as in Example 1, and the first
The process was processed. Next, as a second step, flame retardant processing was performed under the following conditions. Treatment bath composition Flame retardant Pyrovatex CP (organic phosphorus compound, Ciba-Geigy
43.0% Cross-linking agent Sumitex Resin M-3 (manufactured by Sumitomo Chemical) 6.0% Non-ionic activator Megafuc F-833 (manufactured by Dainippon Ink)
0.1% Catalyst Magnesium chloride 1.0% Acid Phosphoric acid (85%) 0.2% Water 49.7% Total 100.0% Pick up the above composition at 85% and dry at 140°C for 2 minutes. Thereafter, it was processed at 165° C. for 5 minutes in a hot full type baking device.
Then soaped and dried. Comparative Example 3 Same as Example 2. However, the first step is omitted. Comparative Example 4 Same as Example 2. However, the second step is omitted. The flame retardance of Example 2, Example 3, Comparative Example 4, and untreated fabric is shown in Table 3.

[Table] Example 3 80% polyester, 20% cotton blended fabric (basis weight 250
g/m ² ) was dyed in the same manner as in Example 1. Thereafter, as a first step, the fabric was treated with the flame retardant used in the second step of Example 1. Treatment liquid composition Flame retardant Phosphorus-containing aminoplast 41.3% Formalin scavenger dicyandiamide 4.6% Crosslinking agent Sumitex Resin M-3 (manufactured by Sumitomo Chemical)
1.0% Tear strength reduction inhibitor D-1710 (polyethylene softener Daiichi Kogyo) 1.9% Softener Elasfinish E-200 (Daiichi Kogyo) 1.0% Catalyst Sumitex Accelerator (Sumitomo Chemical) 0.5% Water 49.7% Total 100.0% Pick up the adjustment solution with the above composition at 100% and dry at 140℃ for 2 minutes. Thereafter, it was subjected to dry heat treatment at 160° C. for 3 minutes in a hot-fluid baking device. Then soaped and dried. As a second step, a cylindrical film of melamine resin was formed on the fiber surface under the conditions of the first step of Example 1. Treatment bath composition Melamine resin Sumitex Resin M-3 (manufactured by Sumitomo Chemical) 7.0% Catalyst Ammonium persulfate 0.3% Dispersion liquid Megafutsuku F-833 (manufactured by Dainippon Ink) 0.1% Water 92.6% Total 100.0% Pick up this resin liquid to 80% Immediately heat to 100% R/H using a hanging type steamer.
Steam treatment at a temperature of 105°C for 3 minutes. Then soap, wash with water and dry. As a result of measuring flame retardancy,
Similar results to Example 1 were obtained. Example 4 100% polyester short fiber fabric (basis weight 200g/
m ² ) by a conventional method, and the first dye was dyed in the same manner as in Example 1.
I processed the process. Next, as a second step, flame retardant processing was performed under the following conditions. Treatment bath composition Flame retardant Vicol No. 400 (organic nitrogen-containing phosphorus compound manufactured by Daikyo Chemical) 40.0% Hard finishing agent Sumitex Resin M-3 (manufactured by Sumitomo Chemical)
1.0% Catalyst Sumitex Accelerator ACX (manufactured by Sumitomo Chemical) 0.2% Water 58.8% Total 100.0% Pick up the adjustment solution with the above composition at 70% and dry at 140℃ for 2 minutes. Thereafter, it was treated at 160° C. for 3 minutes in a hot-fluid baking device.
Then soaped and dried. Comparative Example 5 Same as Example 4. However, the first step is omitted. Comparative Example 6 Same as Example 4. However, the second step is omitted. As a result of measuring flame retardancy, the same results as in Example 1 were obtained. Example 5 100% polyamide long fiber fabric (basis weight 200g/m ² )
Relaxation scouring, heat setting, and dyeing were carried out using conventional methods, and the first step was treatment using a triazine compound. Treatment liquid composition Triazine compound [In the triazine ring-containing compound of the above general formula]
R ₀ is C ₂ H ₅ and R ₁ to R ₄ are all -CH ₂ OH] 4.0% Ammonium persulfate 0.2% Megafac F-833 (manufactured by Dainippon Ink Co., Ltd.)
0.2% Water 95.6% Total 100.0% This aqueous solution was padded with a pick-up of 70% and steamed for 2 minutes at 103° C. with a humidity of 100% R.H. using a Hanking type steamer. Next, it was soaped and washed with water. As a second step, flame retardant processing was performed under the following conditions. Treatment liquid composition Flame retardant Vigor NA-7 (sulfur-containing nitrogen compound,
Daikyo Chemical Co., Ltd.) 20.0% Catalyst Sumitox Accelerator (Sumitomo Chemical Co., Ltd.)
2.0% Water 78.0% Total 100.0% The adjustment solution having the above composition was padded with a 70% pick-up, dried at 120°C for 2 minutes, and then subjected to dry heat treatment at 160°C for 40 seconds in a tenter. Comparative Example 7 Same as Example 5. However, the first step is omitted. Comparative Example 8 Same as Example 5. However, the second step is omitted. As a result of measuring flame retardancy, the same results as in Example 1 were obtained. Comparative Example 9 Same as Comparative Example 1. However, cross-linking agent (Sumitex
The amount of RE esin M-3) used was 8%. The texture of this fabric is much harder than that of Example 1, and the results of the micro-burner test and flame contact test after processing, washing, and cleaning are all the same as Comparative Example 1. It was only a matter of degree. Furthermore, when this fabric was observed under an electron microscope, it was found that the resin aggregated at the weave lines and intersections of fibers and was intermittently attached in lumps, indicating that the resin liquid had migrated during drying and dry heat treatment. . Observation of the cross section of the fiber revealed that there were scattered areas where resin was partially attached. On the other hand, the fabric of Example 1 had almost the same texture and softness as the untreated fabric, and when its fiber cross section was observed under an electron microscope, it was found that each single fiber constituting the fabric was made of the resin. It was completely covered in a cylindrical shape. Comparative Example 10 Same as Example 1. However, the heat treatment in the first step was drying at 100°C for 10 minutes, followed by dry heat treatment at 140°C for 5 minutes. The obtained fabric was very hard, similar to Comparative Example 9.
The flame retardant performance was also at the same level as Comparative Example 9, with no difference. Furthermore, when the fibers constituting this fabric were observed using an electron microscope, they showed the same fiber structure as Comparative Example 9, with lumpy resin scattered and fixed.

Claims (1)

[Scope of Claims] 1. The surface of each single fiber constituting the textile product is coated with a film consisting of a compound containing a triazine ring and having at least two polymerizable functional groups, and The film is characterized in that it contains phosphorus, nitrogen, or halogen as an active ingredient, and at least one kind of flame retardant that is dispersed with compatibility or affinity with the film. Permanently flame retardant textile products. 2. When making textile products flame retardant, a compound containing a triazine ring and at least two polymerizable functional groups is added, and the surface of each single fiber is coated by heat treatment in the presence of moisture. and a step of applying at least one kind of flame retardant containing phosphorus, nitrogen, or halogen as an active ingredient and dispersing with compatibility or affinity with the film. A method for producing permanently flame-retardant textile products, which is characterized by performing a treatment that combines two steps.