JP2009270213A - Flame-retardant finishing agent for polyester-based fiber, flame-retardant polyester-based fiber using the same, and method for producing the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a flame-retardant finishing agent for a polyester-based fiber, obtained by reducing the amount of used phosphorus-based flame-retardant compound leaving problems on environmental safeguard, and capable of imparting flame-retardancy having excellent washing resistance to the polyester-based fiber. <P>SOLUTION: The flame-retardant finishing agent for the polyester-based fiber includes a diphenylsulfone-based compound (A) represented by general formula [1] and the organic phosphorus-based flame-retardant compound (B) as flame-retardant finishing components. (In the formula [1], R<SP>1</SP>, R<SP>2</SP>, R<SP>3</SP>and R<SP>4</SP>may be the same or different, and each a group selected from the group consisting of -H, -OH, -NH<SB>2</SB>, -COOH, -O(CH<SB>2</SB>CH<SB>2</SB>O)<SB>n</SB>H [n is an integer of 1-5],-CH<SB>2</SB>CH=CH<SB>2</SB>, -O-CH<SB>2</SB>CH=CH<SB>2</SB>, -OCH(CH<SB>3</SB>)CH<SB>3</SB>and -OCH<SB>2</SB>C<SB>6</SB>H<SB>5</SB>). <P>COPYRIGHT: (C)2010,JPO&INPIT

Description

  The present invention relates to a flame retardant processing agent used for flame retardant processing of polyester fibers, a method for producing flame retardant polyester fibers using the same, and flame retardant polyester fibers.

  Conventionally, flame-retardant processing of polyester fibers has been performed by infiltrating and fixing a halogen-based flame retardant compound typified by hexabromocyclododecane into the interior of the fiber by an immersion method or a thermosol method. However, polyester fiber that has been flame-retarded with a halogen-based flame retardant compound generates a gas harmful to the human body during combustion. Hexabromocyclododecane, which is a representative of the halogen-based flame retardant compound, is highly decomposable and highly resistant. Phosphorus-based flame retardant compounds have come to be used as flame retardant processing components in place of halogen-based flame retardant compounds because they are accumulative substances and are feared to be harmful to the natural environment.

  However, when a phosphorus-based flame retardant compound is applied to a polyester fiber, there is a problem in that the flame retardancy after washing tends to vary and stable flame retardancy cannot be obtained. Therefore, as a means for preventing the phosphorus-based flame retardant compound from falling off the polyester fiber due to washing, for example, JP-A-8-260351 (Patent Document 1) discloses a specific phosphorus compound and a water / oil repellent. A method for producing a polyester fiber having flame resistance and water repellency excellent in durability by applying a mixture with a functional agent such as polyurethane resin to a polyester fiber and heat-treating it at a temperature of 100 ° C. or higher Is disclosed.

However, even the flame-retardant polyester fiber obtained by this method is insufficient in terms of flame retardancy after washing and the like, and the regular polyester fiber which is particularly difficult to obtain flame retardancy and cationically possible. Most flame retardancy could not be imparted to the composite fiber with the dyed polyester fiber. Phosphorus flame retardant compounds are one of the causative substances of river eutrophication. Like halogen flame retardant compounds, phosphorus flame retardant compounds are used from the viewpoint of pollution prevention and environmental conservation. Substances to be reduced.
JP-A-8-260351

  The present invention has been made in view of the above-described problems of the prior art, suppresses the amount of phosphorus-based flame retardant compounds that remain problematic for environmental conservation, and is excellent in washing durability with respect to polyester fibers. A polyester system that can impart flame retardancy with excellent washing durability even for composite fibers of regular polyester fibers and cationic dyeable polyester fibers that are particularly difficult to flame retard. An object of the present invention is to provide a flame-retardant processing agent for fibers, a polyester fiber having flame retardancy excellent in washing durability, and a method for producing the same.

  As a result of intensive studies to achieve the above object, the present inventors have found that a specific diphenylsulfone compound does not have a flame retardant effect on a polyester fiber itself, but is an organic phosphorus compound. It has been found that the flame retardancy effect of the organophosphorus flame retardant compound is enhanced by the diphenyl sulfone compound when used in combination with the flame retardant compound, and the present invention has been completed.

  That is, the flame retardant processing agent for polyester fibers of the present invention has the following general formula [1]:

(In the formula [1], R ¹ , R ² , R ³ and R ⁴ may be the same or different, and are each —H, —OH, —NH ₂ , —COOH, —O (CH ₂ CH ₂ O). _n H [n is an integer of 1 to 5], —CH ₂ CH═CH ₂ , —O—CH ₂ CH═CH ₂ , —OCH (CH ₃ ) CH ₃ and —OCH ₂ C ₆ H ₅ Represents one to be selected.)
It contains the diphenyl sulfone type compound (A) represented by these, and an organophosphorus flame retardant compound (B) as a flame retardant processing component.

  The flame-retardant polyester fiber of the present invention is a polyester fiber, and the diphenylsulfone compound (A) and the organophosphorus flame-retardant compound fixed to the polyester fiber as a flame-retardant processing component. (B).

  Furthermore, the method for producing a flame retardant polyester fiber of the present invention comprises a step of bringing the flame retardant processing agent for a polyester fiber of the present invention into contact with a polyester fiber, and the diphenyl sulfone compound (A) and the above by heating. And a step of fixing the organophosphorus flame retardant compound (B) to the polyester fiber.

  In the present invention, the organophosphorus flame retardant compound (B) is a phosphoric acid ester represented by the following general formula [2], an aromatic phosphate represented by the following general formula [3], or the following general formula [ 4], a second aromatic phosphorus compound represented by the following general formula [6], an alkali metal salt of the second aromatic phosphorus compound, and an alkaline earth metal salt Aluminum salt, zinc salt and amine salt, phosphazene compound represented by the following general formula [8], first phosphoric acid amide compound represented by the following general formula [9], represented by the following general formula [10] At least one selected from the group consisting of a second phosphoramide compound represented by the following general formula [11], and a triphenylphosphine oxide represented by the following formula [12]. One phosphorus compound Preferred.

(In the formula [2], R ⁵ , R ⁶ and R ⁷ may be the same or different, and are each an alkyl group having 1 to 24 carbon atoms, an alkenyl group having 2 to 22 carbon atoms, or an oil having 5 to 6 carbon atoms. It represents one selected from the group consisting of a cyclic alkyl group and an aryl group which may have a substituent.)

(In the formula [3], R ⁸ , R ⁹ , R ¹⁰ and R ¹¹ may be the same or different and each represents an aryl group which may have a substituent, and R ¹² has 1 to 10 carbon atoms. And any one selected from the group consisting of an alkylene group and an arylene group which may have a substituent, and m represents an integer of 1 to 20.)

[In the formula [4], R ¹³ is an alkyl group having 1 to 24 carbon atoms, an alkenyl group having 2 to 22 carbon atoms, a hydroxyalkyl group having 1 to 10 carbon atoms, an aralkyl group which may have a substituent, -OH group, an alkoxy group having 1 to 10 carbon atoms, an aralkyloxy group which may have a substituent, and the following general formula [5]:

(In the formula [5], R ¹⁴ represents one selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 24 carbon atoms, and an alicyclic alkyl group having 5 to 6 carbon atoms.)
Any one selected from the group consisting of groups represented by: ]

[In the formula [6], R ¹⁵ is an alkyl group having 1 to 24 carbon atoms, an alkenyl group having 2 to 22 carbon atoms, a hydroxyalkyl group having 1 to 10 carbon atoms, an aralkyl group which may have a substituent, -OH group, an alkoxy group having 1 to 10 carbon atoms, an aralkyloxy group which may have a substituent, and the following general formula [7]:

(In the formula [7], R ¹⁶ represents any one selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 24 carbon atoms, and an alicyclic alkyl group having 5 to 6 carbon atoms.)
Any one selected from the group consisting of groups represented by: ]

(In the formula [8], R ¹⁷ and R ¹⁸ may be the same or different, and each may have an alkyl group having 1 to 24 carbon atoms, an alkenyl group having 2 to 22 carbon atoms and an aryl group which may have a substituent. Represents any one selected from the group consisting of groups, and k represents an integer of 3 to 10.)

(In the formula [9], R ²¹ and R ²² may be the same or different and each represents an aryl group which may have a substituent, and R ¹⁹ and R ²⁰ may be the same or different, Each has a hydrogen atom, an alkyl group having 1 to 24 carbon atoms, an alkenyl group having 2 to 22 carbon atoms, an alicyclic alkyl group having 5 to 6 carbon atoms, an aryl group which may have a substituent, and a substituent. Represents any one selected from the group consisting of aralkyl groups which may optionally be present, and R ¹⁹ and R ²⁰ may be bonded to each other to form a ring together with the nitrogen atom bonded to the phosphorus atom.

(In the formula [10], R ²⁷ represents an aryl group which may have a substituent, and R ²³ , R ²⁴ , R ²⁵ and R ²⁶ may be the same or different, and each represents a hydrogen atom or a carbon number. An alkyl group having 1 to 24 carbon atoms, an alkenyl group having 2 to 22 carbon atoms, an alicyclic alkyl group having 5 to 6 carbon atoms, an aryl group which may have a substituent, and an aralkyl group which may have a substituent R ²³ and R ²⁴ or R ²⁵ and R ²⁶ may be bonded to each other to form a ring together with the nitrogen atom bonded to the phosphorus atom.

(In the formula [11], R ²⁸ , R ²⁹ , R ³⁰ , R ³¹ , R ³² and R ³³ may be the same or different, and each is a hydrogen atom, an alkyl group having 1 to 24 carbon atoms, or 2 to 2 carbon atoms. Represents any one selected from the group consisting of 22 alkenyl groups, C5-C6 alicyclic alkyl groups, optionally substituted aryl groups, and optionally substituted aralkyl groups. , R ²⁸ and R ²⁹ , R ³⁰ and R ³¹ , or R ³² and R ³³ may be bonded to each other to form a ring together with the nitrogen atom bonded to the phosphorus atom.)

  Moreover, in this invention, the compounding ratio (A: B) of the said diphenyl sulfone type compound (A) and the said organophosphorus type flame retardant compound (B) is 0.01: 1-1.25: 1 is preferable.

  According to the present invention, it is possible to suppress the amount of phosphorus-based flame retardant compound that remains a problem for environmental protection, and to impart flame retardancy excellent in washing durability to polyester fibers, in particular. Flame retardant agent for polyester fibers that can impart flame retardancy with excellent washing durability even to complex fibers of regular polyester fibers and cationic dyeable polyester fibers that are difficult to flame retardant, and excellent washing durability It is possible to provide a polyester fiber having flame retardancy and a method for producing the same.

  In addition, since the flame retardant processing agent for polyester fiber of the present invention does not contain a halogen atom, it is caused by the flame retardant processing agent when the flame retardant polyester fiber according to the present invention obtained by using it is discarded and incinerated. Dioxin generation is sufficiently prevented, which is preferable from the viewpoint of environmental protection and ecology.

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

  The flame retardant processing agent for polyester fibers of the present invention contains a specific diphenylsulfone compound (A) and an organophosphorus flame retardant compound (B) as flame retardant processing components, and the diphenyl sulfone compound The present inventors speculate that (A) functions as a flame retardant enhancing component of the organophosphorus flame retardant compound (B), which is a flame retardant component.

  The diphenylsulfone compound (A) according to the present invention is a compound represented by the following general formula [1].

In the general formula [1], R ¹ , R ² , R ³ , and R ⁴ may be the same or different and are each —H, —OH, —NH ₂ , —COOH, —O (CH ₂ CH ₂ O). _n H [n is an integer of 1 to 5], —CH ₂ CH═CH ₂ , —O—CH ₂ CH═CH ₂ , —OCH (CH ₃ ) CH ₃ and —OCH ₂ C ₆ H ₅ Represents one to be selected.

  Examples of the diphenylsulfone compound (A) according to the present invention include diphenylsulfone, 4,4′-dihydroxydiphenylsulfone, 2,4′-dihydroxydiphenylsulfone, 4,4′-diallyloxydiphenylsulfone, and 4-allyloxy. -4'-hydroxydiphenylsulfone, 4,4'-diisopropoxydiphenylsulfone, 4-isopropoxy-4'-hydroxydiphenylsulfone, 4,4'-dibenzyloxydiphenylsulfone, 4-benzyloxy-4'- Examples include hydroxydiphenyl sulfone, 3,3′-diallyl-4,4′-dihydroxydiphenyl sulfone, and bis [4- (hydroxyethoxy) phenyl] sulfone. Among these, 4,4'-diallyloxydiphenylsulfone can be preferably used because it tends to have a higher exhaustion amount to the fiber.

  The organophosphorus flame retardant compound (B) used in the present invention is not particularly limited, but is a phosphate represented by the general formula [2] described later; an aromatic represented by the general formula [3] described later. Phosphate; first aromatic phosphorus compound represented by general formula [4] described later; second aromatic phosphorus compound represented by general formula [6] described later; second aromatic phosphorus compound described later Alkali metal salt, alkaline earth metal salt, aluminum salt, zinc salt and amine salt; phosphazene compound represented by general formula [8] described later; first phosphoric acid amide represented by general formula [9] described later A compound; a second phosphoramide compound represented by general formula [10] described later; a third phosphoramide compound represented by general formula [11] described later; and a formula [12] described later. From triphenylphosphine oxide It is preferably at least one phosphorus compound selected from that group. These phosphorus compounds may be used alone or in combination of two or more.

  The phosphoric ester is a compound represented by the following general formula [2].

In the general formula [2], R ⁵ , R ⁶ and R ⁷ may be the same or different, and are each an alkyl group having 1 to 24 carbon atoms, an alkenyl group having 2 to 22 carbon atoms, or an oil having 5 to 6 carbon atoms. It represents one selected from the group consisting of a cyclic alkyl group and an aryl group which may have a substituent. Examples of the alkyl group having 1 to 24 carbon atoms include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, hexyl group, 2-ethylhexyl group, decyl group, dodecyl group, and 2-butyloctyl group. , 2-butyldecyl group, hexadecyl group, octadecyl group, 2-octyldecyl group, docosyl group and tetracosyl group, from the viewpoint of increasing the phosphorus content in the compound, an alkyl group having 1 to 10 carbon atoms is preferred. Examples of the alkenyl group having 2 to 22 carbon atoms include a vinyl group, 1-propenyl group, 2-propenyl group, isopropenyl group, 2-butenyl group, 2-pentenyl group, decenyl group, dodecenyl group, and tridecenyl group. , A hexadecenyl group, an octadecenyl group, an eicocenyl group, and a dococenyl group, and an alkenyl group having 2 to 6 carbon atoms is preferable from the viewpoint of increasing the phosphorus content in the compound. Furthermore, as a C5-C6 alicyclic alkyl group, a cyclopentyl group and a cyclohexyl group are mentioned, for example. In addition, examples of the aryl group which may have a substituent include a phenyl group, a tolyl group, a xylyl group, a cumenyl group, and a mesityl group. Examples of the substituent include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a t-butyl group, and a hydroxy group.

  Examples of such phosphate esters include trixyl phosphate, triphenyl phosphate, tolyl phosphate, tolyl diphenyl phosphate, tricumenyl phosphate, trimethyl phosphate, triethyl phosphate, tributyl phosphate, tri (2-ethylhexyl) phosphate. .

  The aromatic phosphate is a compound represented by the following general formula [3].

In the general formula [3], R ⁸ , R ⁹ , R ¹⁰ and R ¹¹ may be the same or different and each represents an aryl group which may have a substituent. Examples of the aryl group which may have a substituent include the same aryl groups as those optionally having a substituent as R ⁵ , R ⁶ and R ^{7 in} the general formula [2]. R ¹² represents any one selected from the group consisting of an alkylene group having 1 to 10 carbon atoms and an arylene group which may have a substituent. Examples of the alkylene group having 1 to 10 carbon atoms include a methylene group, an ethylene group, a trimethylene group, a propylene group, a tetramethylene group, a butylene group, a hexamethylene group, an octamethylene group, and a decamethylene group. Examples of the arylene group which may have a substituent include a phenylene group, a methylene bisphenylene group, a dimethylmethylene bisphenylene group, and a sulfone bisphenylene group. Examples of the substituent include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a t-butyl group, and a hydroxy group. Moreover, m represents the integer of 1-20.

  Examples of such aromatic phosphates include resorcinol bis (diphenyl phosphate), resorcinol bis (2,6-xylyl phosphate), resorcinol bis (ditolyl phosphate), bisphenol A bis (diphenyl phosphate), bisphenol A bis ( (Ditolyl phosphate), bisphenol S bis (diphenyl phosphate), bisphenol S bis (ditolyl phosphate).

  The first aromatic phosphorus compound is a compound represented by the following general formula [4].

In the general formula [4], R ¹³ is an alkyl group having 1 to 24 carbon atoms, an alkenyl group having 2 to 22 carbon atoms, a hydroxyalkyl group having 1 to 10 carbon atoms, an aralkyl group which may have a substituent, It represents one selected from the group consisting of an —OH group, an alkoxy group having 1 to 10 carbon atoms, an aralkyloxy group which may have a substituent, and a group represented by the following general formula [5].

Examples of the alkyl group having 1 to 24 carbon atoms and the alkenyl group having 2 to 22 carbon atoms include an alkyl group having 1 to 24 carbon atoms as R ⁵ , R ⁶ and R ^{7 in} the general formula [2], and 2 to 2 carbon atoms. The same thing as the 22 alkenyl group is mentioned. Examples of the C1-C10 hydroxyalkyl group include a hydroxymethyl group, a hydroxyethyl group, a hydroxybutyl group, a hydroxyhexyl group, a hydroxyoctyl group, and a hydroxydecyl group. Furthermore, examples of the aralkyl group which may have a substituent include a benzyl group, a 3-methylbenzyl group, a 4-methoxybenzyl group, and a 4-hydroxy-3,5-tertiarybutylbenzyl group. Examples of the substituent include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a t-butyl group, a methoxy group, an ethoxy group, and a hydroxy group. Moreover, as a C1-C10 alkoxy group, a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a hexyloxy group, an octyloxy group, a decyloxy group is mentioned. Furthermore, examples of the aralkyloxy group which may have a substituent include a benzyloxy group, a 3-methylbenzyloxy group, and a 4-methoxybenzyloxy group. Examples of the substituent include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a t-butyl group, a methoxy group, an ethoxy group, and a hydroxy group.

In General Formula [5], R ¹⁴ represents any one selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 24 carbon atoms, and an alicyclic alkyl group having 5 to 6 carbon atoms. Examples of the alkyl group having 1 to 24 carbon atoms and the alicyclic alkyl group having 5 to 6 carbon atoms include alkyl groups having 1 to 24 carbon atoms and carbon atoms as R ⁵ , R ⁶ and R ^{7 in} the general formula [2]. The same thing as the alicyclic alkyl group of several 5-6 is mentioned.

  Examples of such a first aromatic phosphorus compound include 10-methyl-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (compound A):

10-hydroxymethyl-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (compound B):

10-hydroxyethyl-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (compound C):

10-phenyl-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (compound D):

10-Benzyl-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (Compound E):

10- (p-methylbenzyl) -9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (compound F):

[3- (9,10-Dihydro-9-oxa-10-phosphaphenanthrene-10-oxide-10-yl) methyl] succinimide (Compound G):

N-ethyl [3- (9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide-10-yl) methyl] succinimide (Compound H):

N-phenyl [3- (9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide-10-yl) methyl] succinimide (Compound I):

Is mentioned.

  The second aromatic phosphorus compound is a compound represented by the following general formula [6].

In the general formula [6], R ¹⁵ is an alkyl group having 1 to 24 carbon atoms, an alkenyl group having 2 to 22 carbon atoms, a hydroxyalkyl group having 1 to 10 carbon atoms, an aralkyl group which may have a substituent, It represents one selected from the group consisting of an —OH group, an alkoxy group having 1 to 10 carbon atoms, an aralkyloxy group which may have a substituent, and a group represented by the following general formula [7].

Examples of the alkyl group having 1 to 24 carbon atoms and the alkenyl group having 2 to 22 carbon atoms include an alkyl group having 1 to 24 carbon atoms as R ⁵ , R ⁶ and R ^{7 in} the general formula [2] and 2 to 2 carbon atoms. The same thing as the 22 alkenyl group is mentioned. Moreover, as a C1-C10 hydroxyalkyl group, the aralkyl group which may have a substituent, the C1-C10 alkoxy group, and the aralkyloxy group which may have a substituent, general formula is shown. The hydroxyalkyl group having 1 to 10 carbon atoms as R ^{13 in} [4], an aralkyl group which may have a substituent, an alkoxy group having 1 to 10 carbon atoms and an aralkyl which may have a substituent The thing similar to an oxy group is mentioned.

In the general formula [7], R ¹⁶ represents any one selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 24 carbon atoms, and an alicyclic alkyl group having 5 to 6 carbon atoms. Examples of the alkyl group having 1 to 24 carbon atoms and the alicyclic alkyl group having 5 to 6 carbon atoms include alkyl groups having 1 to 24 carbon atoms and carbon atoms as R ⁵ , R ⁶ and R ^{7 in} the general formula [2]. The same thing as the alicyclic alkyl group of several 5-6 is mentioned.

  As such a second aromatic phosphorus compound, for example, methyl (2'-hydroxy- [1,1'-biphenyl] -2-yl) phosphinic acid (compound J):

Hydroxymethyl (2'-hydroxy- [1,1'-biphenyl] -2-yl) phosphinic acid (Compound K):

Hydroxyethyl (2'-hydroxy- [1,1'-biphenyl] -2-yl) phosphinic acid (Compound L):

Phenyl (2'-hydroxy- [1,1'-biphenyl] -2-yl) phosphinic acid (Compound M):

Benzyl (2'-hydroxy- [1,1'-biphenyl] -2-yl) phosphinic acid (Compound N):

p-Methylbenzyl (2'-hydroxy- [1,1'-biphenyl] -2-yl) phosphinic acid (Compound O):

Succinimidomethyl- (2'-hydroxy- [1,1'-biphenyl] -2-yl) phosphinic acid (Compound P):

N-ethylsuccinimidomethyl- (2'-hydroxy- [1,1'-biphenyl] -2-yl) phosphinic acid (compound Q):

N-phenylsuccinimidomethyl (2'-hydroxy- [1,1'-biphenyl] -2-yl) phosphinic acid (compound R):

Is mentioned.

  The salt of the second aromatic phosphorus compound is an alkali metal salt, alkaline earth metal salt, aluminum salt, zinc salt or amine salt of the compound represented by the general formula [6]. And as these alkali metal salts, salts, such as lithium, sodium, potassium, are mentioned, for example. Moreover, as these alkaline-earth metal salts, salts, such as magnesium, calcium, barium, are mentioned, for example. Further, these amine salts include, for example, salts of primary amines such as ammonia, methylamine, ethylamine, propylamine, butylamine and allylamine; secondary amines such as dimethylamine, diethylamine, dipropylamine, dibutylamine and diallylamine. Salts of tertiary amines such as trimethylamine, triethylamine, tripropylamine, and tributylamine; salts of alkanolamines such as monoethanolamine, diethanolamine, and triethanolamine.

  Examples of such a salt of the second aromatic phosphorus compound include ammonium benzyl (2'-hydroxy- [1,1'-biphenyl] -2-yl) phosphinate (compound S):

Hydroxymethyl (2'-hydroxy- [1,1'-biphenyl] -2-yl) ammonium phosphinate (Compound T):

Hydroxyethyl (2'-hydroxy- [1,1'-biphenyl] -2-yl) aluminum phosphinate (Compound U):

Ammonium phenyl (2'-hydroxy- [1,1'-biphenyl] -2-yl) phosphinate (Compound V):

Ammonium benzyl (2'-hydroxy- [1,1'-biphenyl] -2-yl) phosphinate (Compound W):

Calcium p-methylbenzyl (2'-hydroxy- [1,1'-biphenyl] -2-yl) phosphinate (Compound X):

Succinimidomethyl- (2'-hydroxy- [1,1'-biphenyl] -2-yl) ammonium phosphinate (Compound Y):

N-ethylsuccinimidomethyl- (2'-hydroxy- [1,1'-biphenyl] -2-yl) ammonium phosphinate (compound Z):

N-phenylsuccinimidomethyl (2'-hydroxy- [1,1'-biphenyl] -2-yl) ammonium phosphinate (compound AA):

Is mentioned.

  The phosphazene compound is a compound represented by the following general formula [8].

In the general formula [8], R ¹⁷ and R ¹⁸ may be the same or different, and each may have an alkyl group having 1 to 24 carbon atoms, an alkenyl group having 2 to 22 carbon atoms, and an aryl group which may have a substituent. It represents one selected from the group consisting of groups. Examples of the alkyl group having 1 to 24 carbon atoms, the alkenyl group having 2 to 22 carbon atoms, and the aryl group which may have a substituent include carbon as R ⁵ , R ⁶ and R ^{7 in} the general formula [2]. The same thing as the aryl group which may have a C1-C22 alkyl group, a C2-C22 alkenyl group, and a substituent is mentioned. K represents an integer of 3 to 10.

  Examples of such phosphazene compounds include triphenoxytrimethoxycyclotriphosphazene, tetraphenoxytetramethoxycyclotetraphosphazene, and hexaphenoxyhexamethoxycyclohexaphosphazene.

  The first phosphoric acid amide compound is a compound represented by the following general formula [9].

In the general formula [9], R ²¹ and R ²² may be the same or different and each represents an aryl group which may have a substituent. Examples of the aryl group which may have a substituent include the same aryl groups as those optionally having a substituent as R ⁵ , R ⁶ and R ^{7 in} the general formula [2]. R ¹⁹ and R ²⁰ may be the same or different and are each a hydrogen atom, an alkyl group having 1 to 24 carbon atoms, an alkenyl group having 2 to 22 carbon atoms, an alicyclic alkyl group having 5 to 6 carbon atoms, and a substituent. Represents any one selected from the group consisting of an aryl group which may have a group and an aralkyl group which may have a substituent, and R ¹⁹ and R ²⁰ are bonded to each other and bonded to a phosphorus atom. A ring may be formed together with the nitrogen atom. Examples of the alkyl group having 1 to 24 carbon atoms, the alkenyl group having 2 to 22 carbon atoms, the alicyclic alkyl group having 5 to 6 carbon atoms and the aryl group which may have a substituent include those in the general formula [2]. R ⁵ , R ⁶ and R ⁷ as an alkyl group having 1 to 24 carbon atoms, an alkenyl group having 2 to 22 carbon atoms, an alicyclic alkyl group having 5 to 6 carbon atoms, and an aryl group optionally having a substituent The same thing is mentioned. Moreover, as an aralkyl group which may have a substituent, the same thing as the aralkyl group which may have a substituent as R < ¹³ > in General formula [4] is mentioned.

  Examples of such first phosphoric acid amide compounds include aminodiphenyl phosphate, methylaminodiphenyl phosphate, dimethylaminodiphenyl phosphate, ethylaminodiphenyl phosphate, diethylaminodiphenyl phosphate, propylaminodiphenyl phosphate, dipropylaminodiphenyl phosphate, octyl Amino diphenyl phosphate, diphenyl undecyl amino phosphate, cyclohexyl amino diphenyl phosphate, dicyclohexyl amino diphenyl phosphate, allyl amino diphenyl phosphate, anilino diphenyl phosphate, di-o-cresyl phenyl amino phosphate, diphenyl (methyl phenyl amino) phosphate, diphenyl ( Ethyl phenylami ) Phosphate, benzylamino diphenyl include morpholino diphenyl phosphate.

  The second phosphoric acid amide compound is a compound represented by the following general formula [10].

In the general formula [10], R ²⁷ represents an aryl group which may have a substituent. Examples of the aryl group which may have a substituent include the same aryl groups as those optionally having a substituent as R ⁵ , R ⁶ and R ^{7 in} the general formula [2]. R ²³ , R ²⁴ , R ²⁵ and R ²⁶ may be the same or different and each is a hydrogen atom, an alkyl group having 1 to 24 carbon atoms, an alkenyl group having 2 to 22 carbon atoms, or an alicyclic ring having 5 to 6 carbon atoms. Represents any one selected from the group consisting of an alkyl group, an aryl group optionally having substituent (s), and an aralkyl group optionally having substituent (s), wherein R ²³ and R ²⁴ or R ²⁵ and R ²⁶ are A ring may be formed together with the nitrogen atom bonded to each other and bonded to the phosphorus atom. Examples of the alkyl group having 1 to 24 carbon atoms, the alkenyl group having 2 to 22 carbon atoms, the alicyclic alkyl group having 5 to 6 carbon atoms and the aryl group which may have a substituent include those in the general formula [2]. R ⁵ , R ⁶ and R ⁷ as an alkyl group having 1 to 24 carbon atoms, an alkenyl group having 2 to 22 carbon atoms, an alicyclic alkyl group having 5 to 6 carbon atoms, and an aryl group optionally having a substituent The same thing is mentioned. Moreover, as an aralkyl group which may have a substituent, the same thing as the aralkyl group which may have a substituent as R < ¹³ > in General formula [4] is mentioned.

  Examples of such second phosphoric acid amide compounds include diaminophenyl phosphate, aminomethylaminophenyl phosphate, bis (methylamino) phenyl phosphate, aminoethylaminophenyl phosphate, bis (ethylamino) phenyl phosphate, and aminopropylamino. Phenyl phosphate, bis (propylamino) phenyl phosphate, aminooctylaminophenyl phosphate, aminoundecylaminophenyl phosphate, aminocyclohexylaminophenyl phosphate, biscyclohexylaminophenyl phosphate, bisallylaminophenyl phosphate, aminoanilinophenyl phosphate, dianilino Phenyl phosphate, anilinomethylaminophenyl phosphate, ethyl Mino phenylamino phenyl phosphate, bis-benzyl-aminophenyl phosphate include di-morpholinophenyl phosphate.

  The third phosphoric acid amide compound is a compound represented by the following general formula [11].

In the general formula [11], R ²⁸ , R ²⁹ , R ³⁰ , R ³¹ , R ³² and R ³³ may be the same or different, and each is a hydrogen atom, an alkyl group having 1 to 24 carbon atoms, or 2 to 2 carbon atoms. Represents any one selected from the group consisting of 22 alkenyl groups, C5-C6 alicyclic alkyl groups, optionally substituted aryl groups, and optionally substituted aralkyl groups. , R ²⁸ and R ²⁹ , R ³⁰ and R ³¹ , or R ³² and R ³³ may be bonded to each other to form a ring together with the nitrogen atom bonded to the phosphorus atom. Examples of the alkyl group having 1 to 24 carbon atoms, the alkenyl group having 2 to 22 carbon atoms, the alicyclic alkyl group having 5 to 6 carbon atoms and the aryl group which may have a substituent include those in the general formula [2]. R ⁵ , R ⁶ and R ⁷ as an alkyl group having 1 to 24 carbon atoms, an alkenyl group having 2 to 22 carbon atoms, an alicyclic alkyl group having 5 to 6 carbon atoms, and an aryl group optionally having a substituent The same thing is mentioned. Moreover, as an aralkyl group which may have a substituent, the same thing as the aralkyl group which may have a substituent as R < ¹³ > in General formula [4] is mentioned.

  Examples of such third phosphoric acid amide compounds include triaminophosphate, diaminomethylaminophosphate, bis (methylamino) aminophosphate, diaminoethylaminophosphate, bis (ethylamino) aminophosphate, diaminopropylaminophosphate, Bis (propylamino) aminophosphate, diaminooctylaminophosphate, diaminoundecylaminophosphate, diaminocyclohexylaminophosphate, tricyclohexylaminophosphate, aminobisallylaminophosphate, diaminoanilinophosphate, trianilinophosphate, bisanilinomethylamino Phosphate, bisanilinoethylaminophosphate, tribenzylaminophosphate, tripiperi Nohosufeto and the like.

  The triphenylphosphine oxide is a compound represented by the following formula [12]. Such triphenylphosphine oxide may contain triphenylphosphine or the like as an impurity as long as the effects of the present invention are not affected.

  The flame retardant component in the flame retardant for polyester fiber of the present invention, that is, the blending ratio of the diphenylsulfone compound (A) and the organophosphorus flame retardant compound (B) is a mass ratio of (A (Mass) :( mass of B) = 0.01: 1 to 1.25: 1 is preferable, and 0.25: 1 to 0.75: 1 is more preferable. When the blending ratio of the diphenylsulfone compound (A) is less than the lower limit, the flame-retardant washing durability obtained tends to be lowered, and on the other hand, the flame-retardant washing durability obtained even when the upper limit is exceeded. Tend to decrease.

  The flame retardant processing agent for polyester fiber of the present invention may contain the flame retardant processing component, and the solvent to be used is not particularly limited, but water is preferably used from the viewpoint of environmental considerations. In that case, the flame retardant processing component is preferably emulsified or dispersed in water, and a surfactant is more preferably used for emulsification or dispersion.

  Examples of such surfactants include nonionic surfactants and anionic surfactants. Such a nonionic surfactant is not particularly limited, and examples thereof include polyoxyalkylene ether, polyoxyalkylene alkyl ether, polyoxyalkylene aryl ether, and polyoxyalkylene alkyl polyhydric alcohol ether.

  Further, such an anionic surfactant is not particularly limited, and examples thereof include alkylbenzene sulfonate, α-olefin sulfonate, polyoxyalkylene ether sulfate, polyoxyalkylene alkyl ether sulfate, and polyoxyalkylene aryl. Ether sulfate, polyoxyalkylene alkyl polyhydric alcohol ether sulfate, sulfate of alcohol sulfate; polyoxyalkylene ether phosphate, polyoxyalkylene alkyl ether phosphate, polyoxyalkylene aryl ether phosphate, polyoxy Mention may be made of phosphate esters such as alkylene alkyl polyhydric alcohol ether phosphates and alcohol phosphates, and salts thereof. Examples of the salt include alkali metal salts and amine salts. Examples of the alkali metal salts include lithium, sodium, and potassium salts. Examples of amine salts include salts of primary amines such as ammonia, methylamine, ethylamine, propylamine, butylamine and allylamine; salts of secondary amines such as dimethylamine, diethylamine, dipropylamine, dibutylamine and diallylamine. A salt of a tertiary amine such as trimethylamine, triethylamine, tripropylamine or tributylamine; a salt of an alkanolamine such as monoethanolamine, diethanolamine or triethanolamine; These nonionic surfactants and anionic surfactants may be used alone or in combination of two or more.

  In particular, when a surfactant having an aromatic substituent is used, an emulsion or dispersion having excellent storage stability tends to be obtained. It is preferable to use an ionic surfactant) or a sulfate ester salt or phosphate ester salt (anionic surfactant) of an alkylene oxide adduct of styrenated phenol.

  Although the usage-amount of such surfactant is not restrict | limited in particular, It is preferable that it is about 1-50 mass parts with respect to 100 mass parts of total amounts of the said flame-retardant processing component, and is about 1-30 mass parts. Is more preferable. If the amount of such a surfactant used is less than the lower limit, the stability of the resulting flame retardant processing emulsion tends to be poor, whereas if the upper limit is exceeded, the flame retardant processing component fibers are added. There is a tendency for the flame retardance to decrease due to a decrease in the amount of adhesion.

  Furthermore, in the flame-retardant finishing agent for polyester fibers of the present invention, a protective colloid agent can be used in combination as long as the performance is not impaired. Examples of such protective colloid agents include polyvinyl alcohol, carboxymethyl cellulose, and starch.

  The content of the flame retardant processing component in the flame retardant processing agent for polyester fibers of the present invention is not particularly limited, but is preferably about 20 to 90% by mass with respect to the total mass of the flame retardant processing agent, 25 More preferably, it is about ˜60 mass%. If the content of the flame retardant component is less than the lower limit, there is a tendency that good flame retardancy satisfying the durability cannot be obtained unless the treatment amount of the flame retardant is increased. When it exceeds, it will become difficult to obtain a flame retardant processing agent as a liquid, and handling will tend to be difficult. In addition, the flame retardant processing agent of this invention can be used as it is or suitably diluted according to the application | coating method etc. which are employ | adopted when performing a flame retardant processing to a polyester fiber so that it may mention later.

  In the present invention, the method for emulsifying or dispersing the flame retardant processing component is not particularly limited, and examples of the method for emulsifying include phase inversion emulsification using a homomixer. Examples of the dispersion method include a wet dispersion method using a bead mill using glass beads.

  Furthermore, it is preferable that it is 0.01-1 micrometer as an average particle diameter of the emulsification or dispersion of the said flame-retardant processing component in the flame-retardant processing agent for polyester-type fibers of this invention. When the average particle size of the emulsified or dispersed product exceeds the upper limit, it becomes difficult to penetrate into the polyester fiber and the like, and sufficient flame retardancy tends to be hardly exhibited.

  In addition, although the flame retardant processing agent for polyester fibers of the present invention may be an emulsion or dispersion in which the diphenylsulfone compound (A) and the organophosphorus flame retardant compound (B) are mixed. A kit of an emulsification or dispersion containing the diphenylsulfone compound (A) and an emulsification or dispersion containing the organophosphorus flame retardant compound (B) may be used.

  Next, the manufacturing method of the flame-retardant polyester fiber of this invention is demonstrated.

  The method for producing a flame-retardant polyester fiber according to the present invention comprises a step of bringing a polyester fiber into contact with the above-mentioned flame retardant processing agent for polyester fiber according to the present invention, and heating the diphenyl sulfone compound (A) and the organic. A step of fixing the phosphorus-based flame retardant compound (B) to the polyester fiber.

  Although it does not specifically limit as a polyester-type fiber used by this invention, For example, a regular polyester fiber, a cation dyeable polyester fiber, a regenerated polyester fiber, or the polyester fiber which consists of these 2 or more types is mentioned. In addition, such 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 and asbestos fibers In addition, inorganic fibers such as metal fibers; or composite fibers obtained by blending with fibers composed of two or more of these may be used as polyester fibers. Furthermore, it does not restrict | limit especially as a form of the polyester-type fiber used by this invention, Forms, such as a thread | yarn, a tow, a top, a casserole, a woven fabric, a knitted fabric, a nonwoven fabric, a rope, may be sufficient.

  First, the process of bringing the flame retardant finish into contact with the polyester fiber will be described. This step is a method in which the flame retardant processing agent is brought into contact with and adhered to the polyester fiber that is the material to be treated, such as dipping method, padding method, spray method, coating method (coating method, printing method), etc. The flame retardant agent can be brought into contact with the polyester fiber by a method.

  In addition, when using the emulsification or dispersion in which the diphenylsulfone compound (A) and the organophosphorus flame retardant compound (B) are mixed as the flame retardant processing agent for polyester fiber of the present invention, It is diluted as appropriate and used as a treatment liquid. Moreover, the emulsification or dispersion containing the said diphenyl sulfone type compound (A) and the emulsification or dispersion containing the said organophosphorus flame retardant compound (B) as a flame retardant processing agent for polyester fiber of this invention When using a kit, it is preferable to mix in advance and use it as a treatment liquid. However, each emulsification or dispersion is used as a treatment liquid sequentially (the order may be any of A → B and B → A) or simultaneously. You may make it contact with a polyester-type fiber.

  Moreover, when using an immersion method, the polyester-type fiber can be immersed in the process liquid containing the said flame-retardant processing agent, and the said flame-retardant processing agent can be made to adhere to a polyester-type fiber. In addition, the dyeing and the step of attaching the flame retardant processing agent can be simultaneously performed using a disperse dye or a fluorescent dye simultaneously with the flame retardant processing agent. In this case, for example, a liquid dyeing machine, a beam dyeing machine, or a cheese dyeing machine can be used.

  Further, in the case of using a coating method, the flame retardant finishing agent adjusted to a viscosity suitable for treatment may be used, and the liquid containing the flame retardant finishing agent is foamed to form the polyester fiber. You may use the foam processing coating method made to adhere to. According to such a foam processing coating, the required amount of liquid containing the flame retardant processing agent can be adhered to the polyester fiber, and thus the energy and time required for drying can be greatly reduced, and The flame retardant finish can be used without waste. Although it does not restrict | limit especially as a viscosity modifier for adjusting to the viscosity suitable for a process, For example, polyvinyl alcohol, methylcellulose, propylcellulose, carboxymethylcellulose, hydroxyethylcellulose, xanthan gum, starch paste etc. are mentioned. In this case, for example, an air doctor coater, blade coater, rod coater, knife coater, squeeze coater, reverse coater, transfer coater, gravure coater, kiss roll coater, cast coater, curtain coater, and calendar coater can be used. .

  Moreover, when using a spray method, the air spray which sprays the process liquid containing the said flame-retardant processing agent in a mist form with compressed air, and the air spray of a hydraulic atomization system can be used, for example. Furthermore, when using the printing method, for example, a roller printing machine, a flat screen printing machine, and a rotary screen printing machine can be used.

  Next, the process of fixing the flame retardant processing component to the polyester fiber by heating will be described. This step is a heat treatment step in which the polyester fiber to which the flame retardant processing agent is attached is heat treated to fix (exhaust) the flame retardant processing component to the polyester fiber, and the step of attaching the flame retardant processing agent ( The heat treatment step may be performed after the attachment step), or the adhesion step and the heat treatment step may be performed simultaneously.

  In addition, when performing such a heat treatment step after performing the adhesion step, the polyester fiber to which the flame retardant processing agent is adhered is subjected to a dry heat treatment, a saturated normal pressure steam treatment, a heating steam treatment, a high pressure steam treatment, and the like. It can be heat-treated by steaming. In such heat treatment, the heat treatment temperature is preferably in the range of 110 ° C to 210 ° C, and more preferably in the range of 160 ° C to 210 ° C. If the heat treatment temperature is less than the lower limit, the flame-retardant processing component is not sufficiently fixed to the polyester fiber, and the flame retardancy tends to be insufficient due to the dropping of the flame-retardant processing component in the next step, When the above upper limit is exceeded, discoloration and embrittlement of the polyester fibers tend to occur. In such a heat treatment, the treatment time is preferably in the range of 10 seconds to 10 minutes. When the heat treatment time is less than the lower limit, the flame-retardant processing component is not sufficiently fixed to the polyester fiber, and the flame-retardant property tends to be insufficient due to the dropping of the flame-retardant processing component in the next step, When the above upper limit is exceeded, discoloration and embrittlement of the polyester fibers tend to occur.

  In addition, the polyester fiber to which the flame retardant finish is adhered can be heat-treated in the bath. The heat treatment in the bath is a treatment for fixing (exhausting) the flame-retardant processing component to the polyester fiber in a dye bath or a bath not containing a dye. In such bath heat treatment, the heat treatment temperature is preferably in the range of 90 to 150 ° C, more preferably in the range of 110 ° C to 140 ° C. When the heat treatment temperature in the bath is less than the lower limit, the flame-retardant processing components are not exhausted sufficiently, and the flame retardancy tends to be insufficient. On the other hand, when the upper limit is exceeded, the polyester fiber changes or becomes brittle. Tend to happen. In such a heat treatment in a bath, the treatment time is preferably in the range of 10 minutes to 60 minutes. When the heat treatment time is less than the lower limit, exhaust of the flame-retardant processing component to the polyester fiber is insufficient, and the flame retardancy tends to be insufficient due to the dropping of the flame-retardant processing component in the next step, On the other hand, when the upper limit is exceeded, embrittlement of the polyester fiber tends to occur. Furthermore, in such a heat treatment in a bath, for example, a liquid dyeing machine, a beam dyeing machine, a cheese dyeing machine, or the like can be used. In addition, the dry heat treatment or steam heat treatment described above and the above-described heat treatment in bath can be combined. By carrying out a combination of these treatments, it is possible to more reliably exhaust the flame-retardant processing component to the polyester fiber, and to obtain a flame-retardant polyester fiber having more excellent durability. is there.

  Moreover, when performing such a heat treatment step simultaneously with the adhesion step, while immersing the polyester fiber in the treatment liquid containing the flame retardant processing agent to adhere the flame retardant processing agent to the polyester fiber, Heat treatment can be performed while simultaneously performing dyeing and adhesion of the flame retardant using a disperse dye or a fluorescent dye simultaneously with the flame retardant. Such heat treatment conditions (treatment temperature and treatment time) may be the same as those in the heat treatment in the bath.

  In the method for producing a flame-retardant polyester fiber of the present invention described above, the amount of the flame-retardant processing component imparted to the polyester fiber is not particularly limited, but usually the flame-retardant with respect to the polyester fiber. The fixing amount of the processing component (total exhaust amount of the diphenylsulfone compound (A) and the organophosphorus flame retardant compound (B)) is 0.5 to 30 before processing, that is, with respect to the mass of the fiber to be processed. % O. w. f. (On weight of fiber), preferably 1.5 to 20% o. w. f. It is more preferable that If the amount of fixing of the flame-retardant processing component is less than the lower limit, sufficient flame retardancy tends to be difficult to be expressed, while if the upper limit is exceeded, the flame-retardant processing component cannot be exhausted into the fiber, A large amount adheres to the fiber surface and tends to cause problems such as a decrease in texture and powdering on the fiber surface.

  Furthermore, in the method for producing a flame-retardant polyester fiber according to the present invention, after the heat treatment step, the polyester fiber is soaped by an ordinary known method to adhere to the surface without being fixed to the polyester fiber. It is preferable to remove the flame-retardant processing component that is simply being processed. As the cleaning agent used in such soaping treatment, a cleaning agent that is usually used for reduction cleaning of polyester fiber dyed products can be used. For example, anionic, nonionic, amphoteric surfactants and these Formulated detergents can be used.

  Moreover, in the manufacturing method of the flame-retardant polyester fiber of the present invention, in addition to the flame-retardant processing agent, other conventionally used fiber processing agents are used in combination so as not to impair the flame retardancy. You can also. 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.

  The flame-retardant polyester fiber of the present invention includes the above-described polyester fiber and the above-mentioned flame-retardant processing component fixed (exhausted) to the polyester fiber, that is, the diphenylsulfone compound (A) and the organic. It comprises a phosphorus-based flame retardant compound (B). Such a flame-retardant polyester fiber of the present invention has excellent flame retardancy, and the flame retardancy is excellent in washing durability, particularly dry cleaning durability.

  EXAMPLES Hereinafter, although this invention is demonstrated more concretely based on an Example and a comparative example, this invention is not limited to a following example. In addition, the following fabric was used as a polyester fiber which is a to-be-processed material, and the flame retardance (washing durability) of the polyester fiber processed with the flame-retardant processing agent was evaluated with the following method.

(1) Polyester fiber Using a regular polyester fiber of 84 dtex 36 filaments made of full dull polyester fiber (containing 3.5% by mass of titanium oxide) as warp, and a 167 dtex 48 filament polyester fiber made of black original polyester fiber as weft Polyester which is a material to be treated by scouring a woven fabric having a density of 360 / 2.54 cm × 100 / 2.54 cm and having a double-sided satin weave by a conventional method and pre-setting. A system fiber fabric was obtained.

(2) Evaluation of flame retardancy (washing durability) of polyester fiber As a sample without washing with water, polyester fiber treated with a flame retardant was used as it was ("no washing"). Further, as a sample after washing with water, a polyester fiber treated with a flame retardant was washed 5 times according to the method (flame retardancy) described in JIS L 1091 (“5 times of washing”). "). Further, as a sample after dry cleaning, a polyester fiber treated with a flame retardant processing agent was used 5 times dry-cleaned according to the method (flame retardant) described in JIS L 1018 ("DC 5 times"). . Using these samples, the flame retardancy (washing durability) of the polyester fibers was evaluated by the following method.

(i) 45 ° micro burner method (afterflame test)
Residual flame time [seconds] was measured according to the A-1 method described in JIS L 1091 to evaluate flame retardancy.

(Ii) Coil method (flame contact test)
In accordance with the D method described in JIS L 1091, the number of times of flame contact [times] was measured three times each to evaluate flame retardancy.

<Preparation of emulsified dispersion of flame retardant component I (diphenylsulfone compound)>
40 parts by mass of 4,4′-diallyloxydiphenylsulfone (flame retardant processing component I) and 4 parts by mass of a sulfate ester ammonium salt of 10 moles of ethylene oxide adduct of tristyrenated phenol are emulsified and dispersed in 56 parts by mass of water. It was.

<Preparation of emulsified dispersion of flame retardant processing component II (diphenylsulfone compound)>
40 parts by mass of 2,4′-dihydroxydiphenylsulfone (flame retardant processing component II) and 4 parts by mass of an ammonium sulfate ester ammonium salt adduct of tristyrenated phenol with 10 mol of ethylene oxide were emulsified and dispersed in 56 parts by mass of water. .

<Preparation of emulsified dispersion of flame retardant component III (diphenylpropane compound)>
40 parts by mass of 4,4′-dihydroxydiphenylpropane (flame retardant component III) and 4 parts by mass of an ammonium sulfate ester ammonium salt adduct of 10 mol of tristyrenated phenol were emulsified and dispersed in 56 parts by mass of water. .

<Preparation of emulsified dispersion of flame retardant processing component IV (organic phosphorus-based flame retardant compound)>
40 parts by mass of biphenyl diphenyl phosphate (flame retardant processing component IV) and 4 parts by mass of ammonium sulfate ester ammonium salt of adduct of 10 moles of tristyrenated phenol were emulsified and dispersed in 56 parts by mass of water.

<Preparation of emulsified dispersion of flame retardant processing component V (organophosphorus flame retardant compound)>
40 parts by mass of resorcinol bis (diphenyl phosphate) (flame retardant processing component V) and 4 parts by mass of an ammonium sulfate ester ammonium salt adduct of 10 mol of tristyrenated phenol were emulsified and dispersed in 56 parts by mass of water.

<Preparation of emulsified dispersion of flame retardant processing component VI (organophosphorus flame retardant compound)>
40 parts by mass of 10-benzyl-9,10-dihydroxy-9-oxa-10-phosphaphenanthrene-10-oxide (flame retardant processing component VI) and ammonium sulfate ester adduct of tristyrenated phenol with 10 moles of ethylene oxide 4 parts by mass of the salt was emulsified and dispersed in 56 parts by mass of water.

<Preparation of emulsified dispersion of flame retardant processed component VII (organic phosphorus flame retardant compound)>
40 parts by mass of phenoxymethoxyphosphazene (flame retardant processing component VII) and 4 parts by mass of ammonium sulfate ester ammonium salt adduct of tristyrenated phenol with 10 mol of ethylene oxide were emulsified and dispersed in 56 parts by mass of water.

<Preparation of emulsified dispersion of flame retardant component VIII (organic phosphorus flame retardant compound)>
40 parts by mass of anilinodiphenyl phosphate (flame retardant component VIII) and 4 parts by mass of ammonium sulfate ester ammonium salt of 10 mol adduct of tristyrenated phenol were emulsified and dispersed in 56 parts by mass of water.

<Preparation of emulsified dispersion of flame retardant component IX (organic phosphorus flame retardant compound)>
Forty parts by mass of triphenylphosphine oxide (flame retardant component IX) and 4 parts by mass of ammonium sulfate ester ammonium adduct of tristyrenated phenol with 10 mol of ethylene oxide were emulsified and dispersed in 56 parts by mass of water.

Example 1
A mini-color dyeing machine [manufactured by Tecsum Giken Co., Ltd.] is used for the polyester fiber fabric as the material to be treated, and the following composition:
(i) Disperse dye [CI Disperse Blue 56] 1% o.w.f.,
(ii) Dispersing leveling agent [Nikka Sun Salt RM-340E, manufactured by Nikka Chemical Co., Ltd.] 0.5 g / L,
(iii) 80% by mass acetic acid 0.3 mL / L, and
(iv) The total amount of flame retardant component I and flame retardant component IV is 5% o. w. f. And a flame retardant processing agent in which the emulsified dispersion is mixed so that the blending ratio (I / IV) is 0.65 / 1 by mass ratio,
For 30 minutes under the conditions of a bath ratio of 1:15 and a temperature of 130 ° C. Next, with respect to the polyester fiber subjected to the above treatment, 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 is used at 80 ° C. for 20 minutes. The soaping process was performed, and it dried at 170 degreeC for 1 minute, and obtained the flame-retardant polyester fiber used as a sample.

(Example 2)
As the flame retardant processing agent, the total amount of the flame retardant processing component I and the flame retardant processing component V is 5% o. w. f. Thus, it was difficult to prepare a sample in the same manner as in Example 1 except that the flame retardant processing agent in which the emulsified dispersion was mixed so that the mixing ratio (I / V) was 0.65 / 1 in mass ratio was used. A flammable polyester fiber was obtained.

(Example 3)
As the flame retardant, the total amount of flame retardant component I and flame retardant component VI is 5% o. w. f. Thus, it was difficult to prepare a sample in the same manner as in Example 1 except that the flame retardant processing agent mixed with the emulsified dispersion was used so that the blending ratio (I / VI) was 0.01 / 1. A flammable polyester fiber was obtained.

Example 4
As the flame retardant processing agent, the total amount of the flame retardant processing component I and the flame retardant processing component VI is 1.25% o. w. f. Thus, it was difficult to prepare a sample in the same manner as in Example 1 except that the flame retardant processing agent mixed with the emulsified dispersion was used so that the blending ratio (I / VI) was 0.65 / 1. A flammable polyester fiber was obtained.

(Example 5)
As the flame retardant, the total amount of flame retardant component I and flame retardant component VI is 5% o. w. f. Thus, it was difficult to prepare a sample in the same manner as in Example 1 except that the flame retardant processing agent mixed with the emulsified dispersion was used so that the blending ratio (I / VI) was 0.65 / 1. A flammable polyester fiber was obtained.

(Example 6)
As the flame retardant processing agent, the total amount of the flame retardant processing component I and the flame retardant processing component VI is 25% o. w. f. Thus, it was difficult to prepare a sample in the same manner as in Example 1 except that the flame retardant processing agent mixed with the emulsified dispersion was used so that the blending ratio (I / VI) was 0.65 / 1. A flammable polyester fiber was obtained.

(Example 7)
As the flame retardant processing agent, the total amount of the flame retardant processing component I and the flame retardant processing component VI is 50% o. w. f. Thus, it was difficult to prepare a sample in the same manner as in Example 1 except that the flame retardant processing agent mixed with the emulsified dispersion was used so that the blending ratio (I / VI) was 0.65 / 1. A flammable polyester fiber was obtained.

(Example 8)
As the flame retardant processing agent, the total amount of the flame retardant processing component I and the flame retardant processing component VI is 75% o. w. f. Thus, it was difficult to prepare a sample in the same manner as in Example 1 except that the flame retardant processing agent mixed with the emulsified dispersion was used so that the blending ratio (I / VI) was 0.65 / 1. A flammable polyester fiber was obtained.

Example 9
As the flame retardant, the total amount of flame retardant component I and flame retardant component VI is 5% o. w. f. Thus, it is difficult to prepare a sample in the same manner as in Example 1 except that the flame retardant processing agent in which the emulsified dispersion is mixed so that the mixing ratio (I / VI) is 1.25 / 1 by mass is used. A flammable polyester fiber was obtained.

(Example 10)
As the flame retardant, the total amount of flame retardant component I and flame retardant component VI is 5% o. w. f. Thus, the flame retardancy used as a sample in the same manner as in Example 1 except that the flame retardant processing agent in which the emulsified dispersion was mixed so that the blending ratio (I / VI) was 2/1 was used. A polyester fiber was obtained.

Example 11
As the flame retardant processing agent, the total amount of the flame retardant processing component I and the flame retardant processing component VII is 5% o. w. f. Thus, it was difficult to prepare a sample in the same manner as in Example 1 except that the flame retardant processing agent in which the emulsified dispersion was mixed so that the mixing ratio (I / VII) was 0.65 / 1 in terms of mass ratio was used. A flammable polyester fiber was obtained.

Example 12
As the flame retardant processing agent, the total amount of the flame retardant processing component I and the flame retardant processing component VIII is 5% o. w. f. Thus, it was difficult to prepare a sample in the same manner as in Example 1 except that the flame retardant processing agent in which the emulsified dispersion was mixed so that the mixing ratio (I / VIII) was 0.65 / 1 in mass ratio was used. A flammable polyester fiber was obtained.

(Example 13)
As flame retardant processing agent, the total amount of flame retardant processing component I and flame retardant processing component IX is 5% o. w. f. Thus, it was difficult to prepare a sample in the same manner as in Example 1 except that the flame retardant processing agent in which the emulsified dispersion was mixed so that the blending ratio (I / IX) was 0.65 / 1 in mass ratio was used. A flammable polyester fiber was obtained.

(Example 14)
As flame retardant processing agent, the total amount of flame retardant processing component II and flame retardant processing component IV is 5% o. w. f. Thus, it was difficult to prepare a sample in the same manner as in Example 1 except that the flame retardant processing agent in which the emulsified dispersion was mixed so that the mixing ratio (II / IV) was 0.65 / 1 in mass ratio was used. A flammable polyester fiber was obtained.

(Example 15)
As the flame retardant processing agent, the total amount of the flame retardant processing component II and the flame retardant processing component V is 5% o. w. f. Thus, it was difficult to prepare a sample in the same manner as in Example 1 except that the flame retardant processing agent in which the emulsified dispersion was mixed so that the mixing ratio (II / V) was 0.65 / 1 in mass ratio was used. A flammable polyester fiber was obtained.

(Example 16)
As the flame retardant processing agent, the total amount of the flame retardant processing component II and the flame retardant processing component VI is 5% o. w. f. Thus, it was difficult to prepare a sample in the same manner as in Example 1 except that the flame retardant processing agent in which the emulsified dispersion was mixed so that the mixing ratio (II / VI) was 0.65 / 1 by mass ratio was used. A flammable polyester fiber was obtained.

(Example 17)
As flame retardant processing agent, the total amount of flame retardant processing component II and flame retardant processing component VII is 5% o. w. f. Thus, it was difficult to prepare a sample in the same manner as in Example 1 except that the flame retardant processing agent in which the emulsified dispersion was mixed so that the mixing ratio (II / VII) was 0.65 / 1 in mass ratio was used. A flammable polyester fiber was obtained.

(Example 18)
As flame retardant processing agent, the total amount of flame retardant processing component II and flame retardant processing component VIII is 5% o. w. f. Thus, it was difficult to prepare a sample in the same manner as in Example 1 except that the flame retardant processing agent in which the emulsified dispersion was mixed so that the mixing ratio (II / VIII) was 0.65 / 1 by mass ratio was used. A flammable polyester fiber was obtained.

Example 19
As the flame retardant processing agent, the total amount of the flame retardant processing component II and the flame retardant processing component IX is 5% o. w. f. Thus, it was difficult to prepare a sample in the same manner as in Example 1 except that the flame retardant was mixed with the emulsified dispersion so that the mixing ratio (II / IX) was 0.01 / 1 by mass. A flammable polyester fiber was obtained.

(Example 20)
As the flame retardant processing agent, the total amount of the flame retardant processing component II and the flame retardant processing component IX is 1.25% o. w. f. Thus, it was difficult to prepare a sample in the same manner as in Example 1 except that the flame retardant processing agent in which the emulsified dispersion was mixed so that the blending ratio (II / IX) was 0.65 / 1 was used. A flammable polyester fiber was obtained.

(Example 21)
As the flame retardant processing agent, the total amount of the flame retardant processing component II and the flame retardant processing component IX is 5% o. w. f. Thus, it was difficult to prepare a sample in the same manner as in Example 1 except that the flame retardant processing agent in which the emulsified dispersion was mixed so that the blending ratio (II / IX) was 0.65 / 1 was used. A flammable polyester fiber was obtained.

(Example 22)
As flame retardant processing agent, the total amount of flame retardant processing component II and flame retardant processing component IX is 25% o. w. f. Thus, it was difficult to prepare a sample in the same manner as in Example 1 except that the flame retardant processing agent in which the emulsified dispersion was mixed so that the blending ratio (II / IX) was 0.65 / 1 was used. A flammable polyester fiber was obtained.

(Example 23)
As the flame retardant processing agent, the total amount of the flame retardant processing component II and the flame retardant processing component IX is 50% o. w. f. Thus, it was difficult to prepare a sample in the same manner as in Example 1 except that the flame retardant processing agent in which the emulsified dispersion was mixed so that the blending ratio (II / IX) was 0.65 / 1 was used. A flammable polyester fiber was obtained.

(Example 24)
As the flame retardant processing agent, the total amount of the flame retardant processing component II and the flame retardant processing component IX is 75% o. w. f. Thus, it was difficult to prepare a sample in the same manner as in Example 1 except that the flame retardant processing agent in which the emulsified dispersion was mixed so that the blending ratio (II / IX) was 0.65 / 1 was used. A flammable polyester fiber was obtained.

(Example 25)
As the flame retardant processing agent, the total amount of the flame retardant processing component II and the flame retardant processing component IX is 5% o. w. f. Thus, it was difficult to prepare a sample in the same manner as in Example 1 except that the flame retardant was mixed with the emulsified dispersion so that the blending ratio (II / IX) was 1.25 / 1 by mass. A flammable polyester fiber was obtained.

(Example 26)
As the flame retardant processing agent, the total amount of the flame retardant processing component II and the flame retardant processing component IX is 5% o. w. f. Thus, flame retardant as a sample is obtained in the same manner as in Example 1 except that the flame retardant processing agent in which the emulsified dispersion is mixed so that the mixing ratio (II / IX) is 2/1 is used. A polyester fiber was obtained.

(Comparative Example 1)
A polyester fiber as a sample was obtained in the same manner as in Example 1 except that the flame retardant processing composition was not used.

(Comparative Example 2)
Only flame retardant component IV is used as a flame retardant, and the amount used is 5% o. w. f. A flame retardant polyester fiber was obtained as a sample in the same manner as in Example 1 except that the above was obtained.

(Comparative Example 3)
Only flame retardant component V is used as a flame retardant, and the amount used is 5% o. w. f. A flame retardant polyester fiber was obtained as a sample in the same manner as in Example 1 except that the above was obtained.

(Comparative Example 4)
Only flame retardant component VI is used as the flame retardant, and the amount used is 5% o. w. f. A flame retardant polyester fiber was obtained as a sample in the same manner as in Example 1 except that the above was obtained.

(Comparative Example 5)
Only flame retardant component VII is used as a flame retardant, and the amount used is 5% o. w. f. A flame retardant polyester fiber was obtained as a sample in the same manner as in Example 1 except that the above was obtained.

(Comparative Example 6)
Only flame retardant component VIII is used as a flame retardant, and the amount used is 5% o. w. f. A flame retardant polyester fiber was obtained as a sample in the same manner as in Example 1 except that the above was obtained.

(Comparative Example 7)
Only flame retardant component IX is used as a flame retardant, and the amount used is 5% o. w. f. A flame retardant polyester fiber was obtained as a sample in the same manner as in Example 1 except that the above was obtained.

(Comparative Example 8)
Only flame retardant component I is used as a flame retardant, and the amount used is 5% o. w. f. A polyester fiber as a sample was obtained in the same manner as in Example 1 except that the following was obtained.

(Comparative Example 9)
Only flame retardant component II is used as a flame retardant, and the amount used is 5% o. w. f. A polyester fiber as a sample was obtained in the same manner as in Example 1 except that the following was obtained.

(Comparative Example 10)
Only flame retardant component III is used as a flame retardant, and the amount used is 5% o. w. f. A polyester fiber as a sample was obtained in the same manner as in Example 1 except that the following was obtained.

(Comparative Example 11)
As flame retardant processing agent, the total amount of flame retardant processing component III and flame retardant processing component IV is 5% o. w. f. The polyester used as a sample in the same manner as in Example 1 except that the flame retardant was mixed with the emulsified dispersion so that the mixing ratio (III / IV) was 0.65 / 1 by mass. A system fiber was obtained.

(Comparative Example 12)
As the flame retardant processing agent, the total amount of the flame retardant processing component III and the flame retardant processing component V is 5% o. w. f. The polyester used as a sample in the same manner as in Example 1 except that the flame retardant was mixed with the emulsified dispersion so that the blending ratio (III / V) was 0.65 / 1 by mass. A system fiber was obtained.

(Comparative Example 13)
As flame retardant processing agent, the total amount of flame retardant processing component III and flame retardant processing component VI is 5% o. w. f. The polyester used as a sample in the same manner as in Example 1 except that the flame retardant was mixed with the emulsified dispersion so that the blending ratio (III / VI) was 0.65 / 1 by mass. A system fiber was obtained.

(Comparative Example 14)
As the flame retardant processing agent, the total amount of flame retardant processing component III and flame retardant processing component VII is 5% o. w. f. The polyester used as a sample in the same manner as in Example 1 except that the flame retardant was mixed with the emulsified dispersion so that the mixing ratio (III / VII) was 0.65 / 1 by mass. A system fiber was obtained.

(Comparative Example 15)
As flame retardant processing agent, the total amount of flame retardant processing component III and flame retardant processing component VIII is 5% o. w. f. The polyester used as a sample in the same manner as in Example 1 except that the flame retardant was mixed with the emulsified dispersion so that the blending ratio (III / VIII) was 0.65 / 1 by mass. A system fiber was obtained.

(Comparative Example 16)
As the flame retardant processing agent, the total amount of the flame retardant processing component III and the flame retardant processing component IX is 5% o. w. f. The polyester used as a sample in the same manner as in Example 1 except that the flame retardant was mixed with the emulsified dispersion so that the blending ratio (III / IX) was 0.65 / 1 by mass. A system fiber was obtained.

  About each (flame retardant) polyester fiber obtained in Examples 1-26 and Comparative Examples 1-16, the flame retardance was evaluated by the above-mentioned method. The obtained results are shown in Tables 1 and 2.

  As is apparent from the results shown in Tables 1 and 2, the polyester fibers (Examples 1 to 26) obtained using the flame retardant processing agent for polyester fibers of the present invention are organophosphorus flame retardant. What was obtained using only a compound as a flame retardant processing agent (Comparative Examples 2-7), and what was obtained using only a diphenyl sulfone type compound or a diphenyl propane type compound as a flame retardant processing agent (Comparative Examples 8 to 10) and having higher flame retardancy than those obtained by using a combination of a diphenylpropane-based compound and an organic phosphorus-based flame retardant compound as a flame retardant processing agent (Comparative Examples 11 to 16). Moreover, it was confirmed that the flame retardancy was sufficiently maintained even after washing and dry cleaning.

  As described above, according to the present invention, it is possible to impart flame retardancy excellent in washing durability to polyester fibers, and in particular, regular polyester fibers and cationic dyeable polyesters that are difficult to flame retardant. A flame-retardant processing agent for polyester fibers that can impart flame retardancy excellent in washing durability even to composite fibers with fibers, a polyester fiber having flame resistance excellent in washing durability, and a method for producing the same It becomes possible to provide.

  Therefore, the polyester fiber of the present invention obtained by using the flame retardant processing agent of the present invention has excellent flame retardancy, and the flame retardancy is improved in washing durability, particularly dry cleaning durability. Because it is excellent, it can be used suitably for various applications such as clothing, bedding, curtains, roll curtains, sheets, seat covers, notebooks, wall cloths, ceiling cloths, carpets, tents, curing sheets, etc. Ideal for washing and dry cleaning.

  In addition, in the flame retardant processing agent for polyester fiber of the present invention, halogen compounds are not used as a flame retardant processing component. Generation of the organic residue can be sufficiently prevented. Furthermore, according to the present invention, the present invention can also contribute to the reduction of the amount of phosphorus-based flame retardant compound that is one of the causative substances of river eutrophication, so the present invention is also extremely effective from the viewpoint of environmental conservation. This is a useful technique.

Claims (5)

A flame retardant processing agent for polyester fibers, comprising a diphenyl sulfone compound (A) represented by the following general formula [1] and an organophosphorus flame retardant compound (B) as flame retardant processing components: .

(In the formula [1], R ¹ , R ² , R ³ and R ⁴ may be the same or different, and are each —H, —OH, —NH ₂ , —COOH, —O (CH ₂ CH ₂ O). _n H [n is an integer of 1 to 5], —CH ₂ CH═CH ₂ , —O—CH ₂ CH═CH ₂ , —OCH (CH ₃ ) CH ₃ and —OCH ₂ C ₆ H ₅ Represents one to be selected.) The organophosphorus flame retardant compound (B) is represented by a phosphoric acid ester represented by the following general formula [2], an aromatic phosphate represented by the following general formula [3], and the following general formula [4]. First aromatic phosphorus compound, second aromatic phosphorus compound represented by the following general formula [6], alkali metal salt, alkaline earth metal salt, aluminum salt, zinc of the second aromatic phosphorus compound Salt, amine salt, phosphazene compound represented by the following general formula [8], first phosphoric acid amide compound represented by the following general formula [9], second phosphorus represented by the following general formula [10] An acid amide compound, a third phosphoric acid amide compound represented by the following general formula [11], and at least one phosphorus compound selected from the group consisting of triphenylphosphine oxide represented by the following formula [12] Claims Polyester fiber for flame retarding agent according to.

(In the formula [2], R ⁵ , R ⁶ and R ⁷ may be the same or different, and are each an alkyl group having 1 to 24 carbon atoms, an alkenyl group having 2 to 22 carbon atoms, or an oil having 5 to 6 carbon atoms. It represents one selected from the group consisting of a cyclic alkyl group and an aryl group which may have a substituent.)

(In the formula [3], R ⁸ , R ⁹ , R ¹⁰ and R ¹¹ may be the same or different and each represents an aryl group which may have a substituent, and R ¹² has 1 to 10 carbon atoms. And any one selected from the group consisting of an alkylene group and an arylene group which may have a substituent, and m represents an integer of 1 to 20.)

[In the formula [4], R ¹³ is an alkyl group having 1 to 24 carbon atoms, an alkenyl group having 2 to 22 carbon atoms, a hydroxyalkyl group having 1 to 10 carbon atoms, an aralkyl group which may have a substituent, -OH group, an alkoxy group having 1 to 10 carbon atoms, an aralkyloxy group which may have a substituent, and the following general formula [5]:

(In the formula [5], R ¹⁴ represents one selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 24 carbon atoms, and an alicyclic alkyl group having 5 to 6 carbon atoms.)
Any one selected from the group consisting of groups represented by: ]

[In the formula [6], R ¹⁵ is an alkyl group having 1 to 24 carbon atoms, an alkenyl group having 2 to 22 carbon atoms, a hydroxyalkyl group having 1 to 10 carbon atoms, an aralkyl group which may have a substituent, -OH group, an alkoxy group having 1 to 10 carbon atoms, an aralkyloxy group which may have a substituent, and the following general formula [7]:

(In the formula [7], R ¹⁶ represents any one selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 24 carbon atoms, and an alicyclic alkyl group having 5 to 6 carbon atoms.)
Any one selected from the group consisting of groups represented by: ]

(In the formula [8], R ¹⁷ and R ¹⁸ may be the same or different, and each may have an alkyl group having 1 to 24 carbon atoms, an alkenyl group having 2 to 22 carbon atoms and an aryl group which may have a substituent. Represents any one selected from the group consisting of groups, and k represents an integer of 3 to 10.)

(In the formula [9], R ²¹ and R ²² may be the same or different and each represents an aryl group which may have a substituent, and R ¹⁹ and R ²⁰ may be the same or different, Each has a hydrogen atom, an alkyl group having 1 to 24 carbon atoms, an alkenyl group having 2 to 22 carbon atoms, an alicyclic alkyl group having 5 to 6 carbon atoms, an aryl group which may have a substituent, and a substituent. Represents any one selected from the group consisting of aralkyl groups which may optionally be present, and R ¹⁹ and R ²⁰ may be bonded to each other to form a ring together with the nitrogen atom bonded to the phosphorus atom.

(In the formula [10], R ²⁷ represents an aryl group which may have a substituent, and R ²³ , R ²⁴ , R ²⁵ and R ²⁶ may be the same or different, and each represents a hydrogen atom or a carbon number. An alkyl group having 1 to 24 carbon atoms, an alkenyl group having 2 to 22 carbon atoms, an alicyclic alkyl group having 5 to 6 carbon atoms, an aryl group which may have a substituent, and an aralkyl group which may have a substituent R ²³ and R ²⁴ or R ²⁵ and R ²⁶ may be bonded to each other to form a ring together with the nitrogen atom bonded to the phosphorus atom.

(In the formula [11], R ²⁸ , R ²⁹ , R ³⁰ , R ³¹ , R ³² and R ³³ may be the same or different, and each is a hydrogen atom, an alkyl group having 1 to 24 carbon atoms, or 2 to 2 carbon atoms. Represents any one selected from the group consisting of 22 alkenyl groups, C5-C6 alicyclic alkyl groups, optionally substituted aryl groups, and optionally substituted aralkyl groups. , R ²⁸ and R ²⁹ , R ³⁰ and R ³¹ , or R ³² and R ³³ may be bonded to each other to form a ring together with the nitrogen atom bonded to the phosphorus atom.)

  The compounding ratio (A: B) of the diphenylsulfone compound (A) and the organophosphorus flame retardant compound (B) is 0.01: 1 to 1.25: 1 by mass ratio. The flame retardant processing agent for polyester fibers according to claim 1 or 2.   The process which makes the polyester fiber the flame retardant processing agent for polyester fibers as described in any one of Claims 1-3 contact, and the said diphenyl sulfone type compound (A) and the said organophosphorus flame retardant by heating And a step of fixing the property compound (B) to the polyester fiber. Polyester fiber,
It comprises a diphenylsulfone compound (A) represented by the following general formula [1] and an organic phosphorus flame retardant compound (B), which are fixed to the polyester fiber as a flame retardant component. Flame retardant polyester fiber.

(In the formula [1], R ¹ , R ² , R ³ and R ⁴ may be the same or different, and are each —H, —OH, —NH ₂ , —COOH, —O (CH ₂ CH ₂ O). _n H [n is an integer of 1 to 5], —CH ₂ CH═CH ₂ , —O—CH ₂ CH═CH ₂ , —OCH (CH ₃ ) CH ₃ and —OCH ₂ C ₆ H ₅ Represents one to be selected.)