JP2006348443A - Flame retardant for polyester fiber - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a flame retardant for polyester fibers, which has excellent temporal emulsion stability and can impart flame retardancy having excellent durability to the polyester fibers. <P>SOLUTION: This flame retardant for the polyester fibers is characterized in that a phosphate represented by the general formula (1) [(p) is 1 or 2] is emulsified and dispersed in water with at least one surfactant selected from the group consisting of the following surfactants (x<SB>1</SB>) to (x<SB>3</SB>). The above-mentioned surfactants (x<SB>1</SB>) to (x<SB>3</SB>) are the surfactant (x<SB>1</SB>) of formula (2), the surfactant (x<SB>2</SB>) of formula (3), and the surfactant (x<SB>3</SB>) of formula (4). Therein, R<SB>1</SB>, R<SB>2</SB>, R<SB>3</SB>are each a 2 to 4C alkylene; (a), (b), (c) are each an integer of 1 to 200; (m), (n) and (s) are each an integer of 1 to 5; (k) is 1 or 2; Y is ammonium or the like. <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

  The present invention relates to a flame retardant processing agent that imparts flame resistance excellent in durability to polyester fibers and enables stable flame retardant processing.

  Conventionally, durable flame retardant processing of polyester fibers has been performed by infiltrating the interior of the fibers with an alicyclic halogen compound typified by hexabromocyclododecane in a dyeing bath or by a thermosol method. However, polyester fiber that has been flame-retardant processed with a halogen compound has a problem that it generates gases harmful to the human body during combustion, which may be harmful to the natural environment. Has come to be used. For example, JP-A-8-260351 (Patent Document 1) discloses a flame retardant polyester fiber in which a specific phosphorus compound and a functional agent are imparted to the fiber surface. Specific condensed phosphate esters are described. However, since the condensed phosphate ester described in Patent Document 1 is difficult to be stably emulsified in a dyeing bath, there is a problem that variation in flame retardancy occurs and stable flame retardancy cannot be obtained. there were.

  On the other hand, in order to stably emulsify in a dyeing bath, for example, JP-A-2000-328445 (Patent Document 2) emulsifies and disperses resorcinol bis (diphenyl phosphate) in the presence of a specific surfactant. A flame retardant processing method for polyester fiber is disclosed in which an emulsion is prepared and adsorbed onto the fiber simultaneously with dyeing. Japanese Patent Laid-Open No. 2002-88368 (Patent Document 3) discloses a flame retardant processing agent in which resorcinol bis (diphenyl phosphate) is emulsified and dispersed using a specific nonionic surfactant and / or anionic surfactant, and A flame retardant processing method is disclosed.

However, the flame retardant processing agent in which resorcinol bis (diphenyl phosphate) is emulsified and dispersed using the surfactants disclosed in these publications cannot always be said to have sufficient emulsion stability over time. In addition, the conventional flame-retardant polyester fibers produced using the flame-retardant processing agents disclosed in these publications are not necessarily sufficient in flame retardancy especially after washing.
JP-A-8-260351 JP 2000-328445 A JP 2002-88368 A

  The present invention has been made in view of the above-described problems of the prior art, and is a polyester fiber that has excellent emulsification stability over time and can impart flame resistance with excellent durability to the polyester fiber. It aims at providing the flame retardant finishing agent.

  As a result of intensive research to solve the above-mentioned problems, the present inventors have improved emulsification stability over time by emulsifying and dispersing using a specific surfactant as an emulsifying dispersant for a specific phosphate ester. The present inventors have found that a flame retardant processing agent capable of imparting excellent flame resistance with excellent durability to a polyester fiber can be obtained, and the present invention has been completed based on this finding.

  That is, the flame retardant agent for polyester fibers of the present invention has the following general formula (1):

[In formula (1), p represents 1 or 2. ]
The phosphoric acid ester represented by the formula ( ₁ ) is characterized by being emulsified and dispersed in water using at least one surfactant selected from the group consisting of the following surfactants (x ₁ ) to (x ₃ ). It is what.
<Surfactant _(x 1)>
The following general formula (2):

[In Formula (2), R ₁ represents an alkylene group having 2 to 4 carbon atoms, a represents an integer of 1 to 200, and when a is 2 or more, R ₁ O may be the same or different. , When R ₁ O is 2 or more, it may be random addition or block addition, m represents an integer of 1 to 5, k represents 1 or 2, M represents a hydrogen atom, an alkali metal, an alkaline earth It represents at least one selected from the group consisting of metals, ammonium, alkylamines having 1 to 20 carbon atoms, and alkanolamines having 2 to 12 carbon atoms. ]
A compound represented by
<Surfactant _(x 2)>
The following general formula (3):

[In Formula (3), R ₂ represents an alkylene group having 2 to 4 carbon atoms, b represents an integer of 1 to 200, and when b is 2 or more, R ₂ O may be the same or different. In the case where two or more R ₂ Os are present, random addition or block addition may be used, and n represents an integer of 1 to 5. ]
A compound represented by
<Surfactant _(x 3)>
The following general formula (4):

[In Formula (4), R ₃ represents an alkylene group having 2 to 4 carbon atoms, c represents an integer of 1 to 200, and when c is 2 or more, R ₃ O may be the same or different. , When R ₃ O is 2 or more, it may be random addition or block addition, s represents an integer of 1 to 5, Y represents a hydrogen atom, an alkali metal, an alkaline earth metal, ammonium, 1 to C 1 It represents at least one selected from the group consisting of 20 alkylamines and alkanolamines having 2 to 12 carbon atoms. ]
A compound represented by

In the polyester fibers for flame retarding agent of the present invention, as the surfactant, it is preferable to use a surfactant (x _1).

Furthermore, in the flame retardant processing agent for polyester fibers of the present invention, it is preferable to use a surfactant (x ₁ ) and a surfactant (x ₂ ) as the surfactant.

In the polyester fibers for flame retarding agent of the present invention, as the surfactant, it is preferable to use a surfactant (x ₁₎ and surfactant (x _3).

  ADVANTAGE OF THE INVENTION According to this invention, it becomes possible to provide the flame retardant processing agent for polyester fibers which is excellent in the emulsification stability with time, and can provide the flame retardancy excellent in durability to the polyester fiber. . In addition, since the flame retardant processing agent for polyester fibers of the present invention does not contain a halogen atom, the generation of dioxins from the flame retardant processing agent is small even when the polyester fiber obtained by treatment is discarded and incinerated, thereby protecting the environment. It is also preferable from the viewpoint of ecology.

  Hereinafter, the flame retardant processing agent for polyester fibers of the present invention will be described in detail in line with preferred embodiments thereof.

The flame retardant processing agent for polyester fiber of the present invention is at least selected from the group consisting of surfactants (x ₁ ) to (x ₃ ) described later, wherein the phosphate ester represented by the general formula (1) described later. It is characterized by being emulsified and dispersed in water using one kind of surfactant.

  The phosphate ester used in the present invention has the following general formula (1):

It is a compound represented by these.

  In general formula (1), p represents 1 or 2. Examples of such phosphoric acid esters include diphenyl monoorthoxenyl phosphate and phenyl diorthoxenyl phosphate.

  Moreover, in the flame retardant processing agent for polyester fibers of the present invention, the content of such phosphate ester is preferably 20 to 90% by mass with respect to the total amount of solids in the flame retardant processing agent, It is more preferable that it is 30-70 mass%. If the content of such a phosphate ester is less than the lower limit, good flame retardancy that satisfies the durability tends to be obtained unless the amount of the flame retardant treatment is increased. On the other hand, the content exceeds the upper limit. In such a case, it becomes difficult to obtain the flame retardant finish as a liquid, and the handling tends to be difficult. Furthermore, the average particle diameter of the phosphoric acid ester emulsified dispersion in the flame retardant processing agent for polyester fibers of the present invention is preferably 2 μm or less from the viewpoint of easy adsorption and absorption to the polyester fibers. More preferably, it is 0.5 μm or less.

The surfactant used in the present invention is at least one selected from the group consisting of surfactants (x ₁ ) to (x ₃ ) described below.

The surfactant (x ₁ ) is a compound represented by the following general formula (2).

In the general formula (2), R ₁ represents an alkylene group having 2 to 4 carbon atoms. Examples of the alkylene group having 2 to 4 carbon atoms of R ₁ include an ethylene group, a propylene group, and a butylene group, and the stability of the emulsion of the phosphate ester represented by the general formula (1). From the viewpoint of (emulsion dispersibility of flame retardant processing agent), ethylene group and propylene group are preferable, and ethylene group is particularly preferable. Moreover, although a represents the integer of 1-200, it is an integer of 5-30 from a viewpoint of the stability (emulsification dispersibility of a flame-retardant processing agent) of the phosphate ester emulsion represented by the said General formula (1). More preferably. Even if the value of a is 0 or exceeds 200, the stability of the phosphate ester emulsion represented by the general formula (1) (emulsification stability of the flame retardant processing agent) becomes poor. Further, when a is 2 or more, R ₁ O may be the same or different, and when R ₁ O is 2 or more, random addition or block addition may be used. M represents an integer of 1 to 5, and k represents 1 or 2.

  Further, M represents at least one selected from the group consisting of a hydrogen atom, an alkali metal, an alkaline earth metal, ammonium, an alkylamine having 1 to 20 carbon atoms, and an alkanolamine having 2 to 12 carbon atoms. And as such an alkali metal, lithium, potassium, sodium, etc. are mentioned. Examples of such alkaline earth metals include calcium, magnesium, barium and the like. Furthermore, examples of the alkylamine having 1 to 20 carbon atoms include methylamine, ethylamine, propylamine, butylamine, octylamine, dodecylamine, hexadecylamine, octadecylamine, dimethylamine, diethylamine, and triethylamine. Examples of the alkanolamine having 2 to 12 carbon atoms include monoethanolamine, diethanolamine, and triethanolamine. Among these, M is ammonium and has 1 to 6 carbon atoms from the viewpoint of the stability of the emulsion of the phosphate ester represented by the general formula (1) (emulsion stability of the flame retardant processing agent) and flame retardancy. An alkylamine or an alkanolamine having 2 to 6 carbon atoms is preferable.

  As such a surfactant, for example, a compound obtained by adding alkylene oxide to styrenated phenol obtained by adding 1 to 5 mol of styrene to 1 mol of phenol, and a phosphorylating agent such as phosphoric anhydride and phosphorus oxychloride And salts of phosphoric acid monoesters or phosphoric acid diesters obtained by reacting. These are salts of a monoester alone, a salt of a diester alone, or a salt of a mixture of both, but generally a salt of a mixture of a monoester and a diester.

Surfactant (x ₂₎ is a compound represented by the following general formula (3).

In general formula (3), _{R 2} represents an alkylene group having 2 to 4 carbon atoms. Examples of the alkylene group having 2 to 4 carbon atoms of R ₂ include an ethylene group, a propylene group, and a butylene group. The stability of the phosphate ester emulsion represented by the general formula (1) is described below. From the viewpoint of (emulsion dispersibility of flame retardant processing agent), ethylene group and propylene group are preferable, and ethylene group is particularly preferable. In addition, b represents an integer of 1 to 200, but an integer of 5 to 30 from the viewpoint of the stability of the emulsion of the phosphate ester represented by the general formula (1) (emulsion dispersibility of the flame retardant processing agent). More preferably. Even if the value of b is 0 or exceeds 200, the stability of the emulsion of the phosphate ester represented by the general formula (1) (emulsification stability of the flame retardant processing agent) becomes poor. Furthermore, when b is 2 or more, R ₂ O may be the same or different, and when R ₂ O is 2 or more, random addition or block addition may be used. N represents an integer of 1 to 5.

  Examples of such a surfactant include a compound obtained by adding alkylene oxide to styrenated phenol obtained by adding 1 to 5 mol of styrene to 1 mol of phenol.

The surfactant (x ₃ ) is a compound represented by the following general formula (4).

In the general formula (4), _{R 3} represents an alkylene group having 2 to 4 carbon atoms. Examples of the alkylene group having 2 to 4 carbon atoms of R ₃ include an ethylene group, a propylene group, and a butylene group. The stability of the phosphate ester emulsion represented by the general formula (1) is described below. From the viewpoint of (emulsion dispersibility of flame retardant processing agent), ethylene group and propylene group are preferable, and ethylene group is particularly preferable. C represents an integer of 1 to 200, and is an integer of 5 to 30 from the viewpoint of the stability of the emulsion of the phosphate ester represented by the general formula (1) (emulsification dispersibility of the flame retardant processing agent). More preferably. Even if the value of c is 0 or exceeds 200, the stability of the emulsion of phosphate ester represented by the general formula (1) (emulsification stability of the flame retardant processing agent) becomes poor. Furthermore, when a is 2 or more, R ₃ O may be the same or different, and when R ₃ O is 2 or more, random addition or block addition may be used. M represents an integer of 1 to 5, and k represents 1 or 2.

  Y represents at least one selected from the group consisting of a hydrogen atom, an alkali metal, an alkaline earth metal, ammonium, an alkylamine having 1 to 20 carbon atoms, and an alkanolamine having 2 to 12 carbon atoms. And as such an alkali metal, alkaline-earth metal, ammonium, a C1-C20 alkylamine, and a C2-C12 alkanolamine, the alkali metal as M in general formula (2), alkaline-earth Examples thereof include the same metals, ammonium, alkylamines having 1 to 20 carbon atoms, and alkanolamines having 2 to 12 carbon atoms. Among these, from the viewpoints of the stability of the emulsion of the phosphate ester represented by the general formula (1) (emulsion stability of the flame retardant processing agent) and flame retardancy, Y is ammonium, and has 1 to 6 carbon atoms. An alkylamine or an alkanolamine having 2 to 6 carbon atoms is preferable.

  As such a surfactant, for example, a compound obtained by adding alkylene oxide to styrenated phenol obtained by adding 1 to 5 mol of styrene to 1 mol of phenol, and a sulfating agent such as chlorosulfonic acid or sulfamic acid are used. Examples thereof include a sulfate ester salt obtained by the reaction.

In the flame-retardant processing agent for polyester fibers of the present invention, _{one of the} surfactants (x ₁ ) to (x ₃ ) may be used alone, or two or more may be used in combination. The surfactant (x ₁ ) is not particularly limited, but from the viewpoint of stability of the phosphate ester emulsion represented by the general formula (1) (emulsion stability of the flame retardant processing agent) and flame retardancy. Is used alone or in combination of the surfactant (x ₁ ) and the surfactant (x ₂ ) or in combination of the surfactant (x ₁ ) and the surfactant (x ₃ ). Is preferred.

  Moreover, in the flame-retardant processing agent for polyester fibers of this invention, the usage-amount of the said surfactant is not restrict | limited in particular, However, 1-50 with respect to 100 mass parts of phosphate ester represented with the said General formula (1). It is preferable that it is a mass part, and it is more preferable that it is 1-30 mass parts. When the amount of the surfactant used is less than the lower limit, the stability of the flame retardant emulsion tends to be poor. On the other hand, when the amount exceeds the upper limit, it is represented by the general formula (1). There exists a tendency for the flame retardant property to fall because the adsorption rate of the phosphate ester to the polyester fiber is lowered.

Furthermore, the surfactant (x ₁ ) is more effective for the emulsifying dispersibility of the phosphate ester represented by the general formula (1) and the dispersibility of the dye as the amount used is larger. become large, to come out even negative effects during processing to polyester fibers by foaming, if used, phosphoric acid usage is represented by the general formula (1) of the surfactant (x ₁₎ It is preferable that it is 1-50 mass parts with respect to 100 mass parts of ester. The surfactant (x ₂ ) is more effective for the emulsifying dispersibility of the condensed phosphate ester represented by the general formula (1) as the amount used is larger, but the effect of slow dyeing is large, and the dyeing is performed. When used, the amount of the surfactant (x ₂ ) used is 1 with respect to 100 parts by mass of the phosphate ester represented by the general formula (1). It is preferable that it is -50 mass parts. Furthermore, the surfactant (x ₃ ) is more effective for the emulsifying dispersibility of the condensed phosphate ester represented by the general formula (1) as the amount used is larger. Therefore, when used, the amount of the surfactant (x ₃ ) used is 100 parts by mass of the phosphate ester represented by the general formula (1). It is preferable that it is 1-50 mass parts with respect to.

In the present invention, the method for emulsifying and dispersing the phosphate ester represented by the general formula (1) is not particularly limited. For example, (i) the phosphate ester represented by the general formula (1) and the above-mentioned By gradually adding water thereto while stirring the surfactant (x ₁ ), and optionally the surfactant (x ₂ ) and / or the mixture containing the surfactant (x ₃ ). , A method of emulsifying and dispersing the phosphate ester represented by the general formula (1), (ii) the phosphate ester represented by the general formula (1) and the surfactant (x ₁ ), and optionally A mixture of the surfactant (x ₂ ) and / or the surfactant (x ₃ ) with water is emulsified and dispersed using an emulsifier / disperser such as a homogenizer, and is represented by the general formula (1). Emulsify and disperse the phosphate ester The method and the like.

  The polyester fiber that can impart flame retardancy using the flame retardant for polyester fiber of the present invention is not particularly limited. For example, regular polyester fiber, cationic dyeable polyester fiber, regenerated polyester fiber, or these Examples include yarns with two or more kinds of polyester fibers, tows, tops, casks, woven fabrics, knitted fabrics, non-woven fabrics, and ropes. Furthermore, these polyester fibers and natural fibers such as cotton, hemp, silk and wool; semi-synthetic fibers such as rayon and acetate; synthetic fibers such as nylon, acrylic and polyamide; carbon fibers, glass fibers, ceramic fibers, asbestos fibers, Examples thereof include inorganic fibers such as metal fibers; or yarns, tows, tops, casks, woven fabrics, knitted fabrics, non-woven fabrics, and ropes obtained by blending with fibers composed of two or more of these.

  When imparting flame retardancy to the polyester fiber using the flame retardant for polyester fiber of the present invention, the amount of the phosphate ester represented by the general formula (1) imparted to the polyester fiber is particularly limited. In general, the adsorption rate of the phosphate ester to the polyester fiber is 0.1 to 30% o.d. w. f. Is preferably 0.3 to 25% o. w. f. It is more preferable that Phosphate ester adsorption rate of 0.1% o.d. w. f. If it is less than the range, sufficient flame retardancy stabilizing effect tends not to be exhibited. On the other hand, the higher the phosphate ester adsorption rate, the greater the effect of stabilizing the flame retardancy, but the phosphate ester adsorption rate is 30% o. w. f. Exceeding the value tends to cause a significant change in texture and to cause powdering.

  The method for imparting flame retardancy to the polyester fiber using the flame retardant for polyester fiber of the present invention is not particularly limited. For example, it is difficult for the polyester fiber by dipping, padding, spraying, coating, printing or the like. A method of imparting flammability can be mentioned.

  For example, when flame-retardant processing is performed by dipping, the polyester fiber is immersed in the flame-retardant processing agent for polyester fiber at a temperature in the range of 90 ° C to 150 ° C, preferably 110 ° C to 140 ° C for about 10 to 60 minutes. Then, the flame retardant processing agent may be adsorbed and absorbed. If the heat treatment temperature is less than the lower limit, the flame retardant processing agent is not sufficiently absorbed and the flame retardancy tends to be insufficient. On the other hand, if the upper limit is exceeded, the polyester fiber tends to change or become brittle. At this time, dyeing can be performed simultaneously with the flame retardant processing using a disperse dye or a fluorescent dye simultaneously with the flame retardant processing agent.

  Furthermore, when flame retardant processing is performed by padding, spraying, coating or printing, a polyester fiber flame retardant is attached to the polyester fiber, followed by dry heat treatment and saturated atmospheric steam. It can heat-process by steaming heat processing, such as a process, a heating steam process, and a high pressure steam process. In both the dry heat treatment and the steam heat treatment, the heat treatment temperature is usually in the range of 110 ° C to 210 ° C, preferably in the range of 160 ° C to 210 ° C. When the heat treatment temperature is less than the lower limit, the flame retardant processing agent is not sufficiently absorbed, and the flame retardancy tends to be insufficient, whereas when the upper limit is exceeded, discoloration and embrittlement of the polyester fibers tend to occur. is there.

  In addition, when flame-retardant processing is performed by coating, a polyester fiber flame-retardant processing agent adjusted to a viscosity suitable for processing may be used as a liquid for flame-retardant processing, or flame-retardant processing is performed. Flame retardant processing may be performed by foam processing coating in which the liquid is foamed and adhered to the polyester fiber. According to the foam processing coating, it is possible to apply a necessary amount of foamed flame retardant processing liquid to the polyester fiber, so that the energy and time required for drying can be greatly reduced, and the liquid to be flame retardant processed The entire amount can be used without waste. Furthermore, the viscosity modifier used to adjust the viscosity suitable for processing is not particularly limited, and examples thereof include polyvinyl alcohol, methyl cellulose, propyl cellulose, carboxymethyl cellulose, hydroxyethyl cellulose, xanthan gum, and starch paste. . Moreover, when performing a flame-retardant process by dipping, a liquid dyeing machine, a beam dyeing machine, and a cheese dyeing machine can be used, for example. Furthermore, when flame-retardant processing is performed by spraying, for example, an air spray that sprays a liquid that is flame-retardant processed with compressed air in a mist form, or a hydraulic atomization type air spray can be used. In the case of flame retardant processing by coating, for example, air doctor coater, blade coater, rod coater, knife coater, squeeze coater, reverse coater, transfer coater, gravure coater, kiss roll coater, cast coater, curtain coater, A coating using a calendar coater or the like can be used. Furthermore, when flame-retardant processing is performed by printing, for example, printing using a roller printing machine, a flat screen printing machine, or a rotary screen printing machine can be used.

  Furthermore, in the method of imparting flame retardancy to the polyester fiber described above, after performing the heat treatment step, the polyester fiber is soaped by an ordinary known method, and does not firmly adhere to the polyester fiber, It is preferable to remove the phosphate ester that does not penetrate and is only attached to the surface. Examples of the cleaning agent used in such a soaping process include ordinary anionic, nonionic, and amphoteric surfactants and detergents containing these.

  In addition to the flame retardant processing agent, other conventionally used fiber processing agents can be used in combination with the flame retardant processing agent to the extent that flame retardancy is not impaired. Examples of such fiber processing agents include antistatic agents, water and oil repellents, antifouling agents, hard finishes, texture modifiers, softeners, antibacterial agents, water absorbing agents, antislip agents, and light fastness. An improver is mentioned.

  EXAMPLES Hereinafter, the present invention will be described in more detail with reference to examples and comparative examples, but the present invention is not limited to these examples. In addition, the emulsion stability of the flame retardant processing agent for polyester fibers and the flame retardance of polyester fibers were evaluated by the following methods, respectively.

(1) Evaluation of Emulsification Stability of Flame Retardant for Polyester Fiber 300 mL of the obtained flame retardant was put in a glass bottle, sealed, and stored at 45 ° C. for 30 days. The state of the flame retardant after 30 days was observed to evaluate the emulsion stability. When there is no separation, it is judged as “stable”, when there is a very small amount of separation as “separation (low)”, and when there is clear separation (separation of 10% or more of the total amount), it is judged as “separation (large)” did.

(2) Flame retardancy of polyester fiber The flame retardant polyester fiber obtained was used as a sample without washing and washing. Further, as a sample after washing and washing with water, a sample obtained by washing and washing flame-retardant polyester fiber according to JIS L 1091 was used. Furthermore, as a sample after dry cleaning, a flame-retardant polyester fiber dry-cleaned according to JIS L 1018 was used. Using these samples, the flame retardancy of the polyester fibers was evaluated by the following method.

(I) 45 ° Micro Burner Method Flame retardancy was evaluated according to the A-1 method described in JIS L 1091. In addition, the case where it was within 3 seconds of afterflame time was determined as the pass ((circle)), and the case other than that was determined as the disqualification (x).

(Ii) Coil method (flame contact test)
Flame retardancy was evaluated according to the D method described in JIS L 1091. In addition, the case where the number of times of flame contact was 3 times or more was determined to be acceptable (◯), and the other cases were determined to be unacceptable (x).

Example 1
First, a mixture of 40 g of diphenyl monoorthoxenyl phosphate and 20 g of a 50 mass% aqueous solution of a phosphoric ester ammonium salt of a 15 mol adduct of tristyrenated phenol with ethylene oxide (monoester: diester = 1: 1) was stirred. While gradually adding 40 g of water, the mixture was emulsified and dispersed to obtain a flame retardant finish for polyester fibers. About the obtained flame retardant processing agent for polyester fibers, the average particle size of the emulsion was measured using a laser diffraction particle size distribution analyzer [LA-920: manufactured by Horiba, Ltd.]. It was. Moreover, the emulsion stability of the obtained flame retardant for polyester fiber was “stable”.

Next, a weft original regular polyester 100% by mass undyed cloth with a basis weight of 220 g / m ² was used with a disperse dye [C.I. I. Disperse
Blue 56] 1% o. w. f. Dispersion leveling agent [Nikka Sun Salt RM-340E: manufactured by Nikka Chemical Co., Ltd.] 0.5 g / L, 80% by mass acetic acid 0.3 mL / L and polyester fiber flame retardant 15% o. w. f. In the dye bath containing No. 1, the mixture was treated for 30 minutes under conditions of a bath ratio of 1:15 and a temperature of 130 ° C. Next, using an aqueous solution containing 2 g / L of a soaping agent [Escudo FRN: manufactured by Nikka Chemical Co., Ltd.] and 1 g / L of caustic soda, it is soaped at 80 ° C. for 20 minutes, dried at 170 ° C. for 1 minute, and flame retardant -Resistant polyester fibers were obtained.

(Example 2)
In a mixture of 40 g of diphenyl monoorthoxenyl phosphate, 4 g of an ethylene oxide 10 mol adduct of tristyrenated phenol, and 10 g of a 50 mass% aqueous solution of a phosphoric ester ammonium salt of an ethylene oxide 15 mol adduct of tristyrenated phenol While stirring, 36 g of water was gradually added and emulsified and dispersed to obtain a flame retardant polyester fiber in the same manner as in Example 1, except that a flame retardant finish for polyester fiber was obtained. In addition, the average particle diameter of the emulsion of the flame retardant processing agent for polyester fibers obtained was 0.2 μm. Moreover, the emulsion stability of the obtained flame retardant for polyester fiber was “stable”.

(Example 3)
40 g of diphenyl monoorthoxenyl phosphate, 8 g of a 50% by weight aqueous solution of ammonium sulfate ester of tristyrenated phenol ethylene oxide 15 mol adduct, and ammonium phosphate ester of tristyrenated phenol ethylene oxide 15 mol adduct Flame retardant polyester fiber in the same manner as in Example 1 except that 32 g of water was gradually added to a mixture with 10 g of a 50% by weight aqueous solution and emulsified and dispersed to obtain a flame retardant processing agent for polyester fiber. Got. In addition, the average particle diameter of the emulsion of the flame retardant processing agent for polyester fibers obtained was 0.2 μm. Moreover, the emulsion stability of the obtained flame retardant for polyester fiber was “stable”.

Example 4
40 g of water is gradually added with stirring to a mixture of 40 g of phenyl diorxoxenyl phosphate and 20 g of a 50% by weight aqueous solution of ammonium sulfate of 10 mol adduct of tristyrenated phenol, and the mixture is emulsified and dispersed. A flame retardant polyester fiber was obtained in the same manner as in Example 1 except that the flame retardant finish for polyester fiber was obtained. In addition, the average particle diameter of the emulsion of the obtained flame retardant processing agent for polyester fibers was 0.3 μm. Moreover, the emulsion stability of the obtained flame retardant for polyester fiber was “stable”.

(Comparative Example 1)
40 g of water was gradually added to a mixture of 40 g of resorcinol bis (diphenyl phosphate) and 20 g of a 50 mass% aqueous solution of ammonium sulfate 15 mol adduct of tristyrenated phenol with stirring, and the mixture was emulsified and dispersed. A comparative flame-retardant polyester fiber was obtained in the same manner as in Example 1 except that a flame-retardant processing agent for comparative polyester fiber was obtained. In addition, the average particle diameter of the emulsion of the flame retardant processing agent for comparative polyester fibers obtained was 0.6 μm. Moreover, the emulsification stability of the obtained flame retardant processing agent for a polyester fiber for comparison was “separation (low)”.

  About each flame-retardant polyester fiber obtained in Examples 1-4 and Comparative Example 1, the flame retardance was evaluated. The obtained results are shown in Table 1.

  As is apparent from the results shown in Table 1, flame retardancy obtained in Examples 1 to 4 in which 100% by mass of a regular polyester undyed fabric was treated with the flame retardant for polyester fiber of the present invention. The polyester fiber has excellent flame retardancy. In particular, the polyester fiber of the present invention also has excellent flame retardancy for a sample without water washing, a sample after washing with water, and a sample after dry cleaning. It was confirmed that the flame retardant having excellent durability was imparted to the polyester fiber by the flame retardant finishing agent. In addition, as described above, the flame retardant processing agent for polyester fibers of the present invention has a small average particle size of the emulsion, and is excellent in the emulsion stability over time of the flame retardant without separation after 30 days. It could be confirmed.

As described above, according to the present invention, it is possible to provide a flame retardant processing agent that has excellent emulsification stability over time and can impart flame resistance with excellent durability to polyester fibers. It becomes possible.

Claims (4)

The following general formula (1):

[In formula (1), p represents 1 or 2. ]
The phosphoric acid ester represented by the formula ( ₁ ) is characterized by being emulsified and dispersed in water using at least one surfactant selected from the group consisting of the following surfactants (x ₁ ) to (x ₃ ). A flame retardant for polyester fiber.
<Surfactant _(x 1)>
The following general formula (2):

[In Formula (2), R ₁ represents an alkylene group having 2 to 4 carbon atoms, a represents an integer of 1 to 200, and when a is 2 or more, R ₁ O may be the same or different. , When R ₁ O is 2 or more, it may be random addition or block addition, m represents an integer of 1 to 5, k represents 1 or 2, M represents a hydrogen atom, an alkali metal, an alkaline earth It represents at least one selected from the group consisting of metals, ammonium, alkylamines having 1 to 20 carbon atoms, and alkanolamines having 2 to 12 carbon atoms. ]
A compound represented by
<Surfactant _(x 2)>
The following general formula (3):

[In Formula (3), R ₂ represents an alkylene group having 2 to 4 carbon atoms, b represents an integer of 1 to 200, and when b is 2 or more, R ₂ O may be the same or different. In the case where two or more R ₂ Os are present, random addition or block addition may be used, and n represents an integer of 1 to 5. ]
A compound represented by
<Surfactant _(x 3)>
The following general formula (4):

[In Formula (4), R ₃ represents an alkylene group having 2 to 4 carbon atoms, c represents an integer of 1 to 200, and when c is 2 or more, R ₃ O may be the same or different. , When R ₃ O is 2 or more, it may be random addition or block addition, s represents an integer of 1 to 5, Y represents a hydrogen atom, an alkali metal, an alkaline earth metal, ammonium, 1 to C 1 It represents at least one selected from the group consisting of 20 alkylamines and alkanolamines having 2 to 12 carbon atoms. ]
A compound represented by The flame retardant processing agent for polyester fibers according to claim 1, wherein a surfactant (x ₁ ) is used as the surfactant. The flame retardant processing agent for polyester fibers according to claim 1, wherein a surfactant (x ₁ ) and a surfactant (x ₂ ) are used as the surfactant. The flame retardant processing agent for polyester fibers according to claim 1, wherein a surfactant (x ₁ ) and a surfactant (x ₃ ) are used as the surfactant.