JPWO2008081809A1 - POLYPHOSPHATE-CONTAINING AQUEOUS DISPERSION, FLAME-PROOFING AGENT USING SAME, AND FIBER-PROOFING - Google Patents

Abstract

Aqueous dispersions containing organophosphorus compounds, polyphosphates, surfactants and water are superior in durability to fibers, especially CDP (cation dyeable polyester) fibers or blended fibers containing CDP fibers. It is useful as a flameproofing agent that can impart flameproofing performance and is excellent in dispersion stability.

Description

  The present invention relates to a dispersion-stabilized polyphosphate-containing aqueous dispersion capable of imparting a flameproof performance having excellent durability to a synthetic fiber structure, a flameproofing agent using the same, a flameproofing method for fibers, and a flameproofing Relating to flame processed fibers.

  Conventionally, as a method for imparting flameproofing performance to a fiber by post-processing, a method is known in which a halogen-based compound is dispersed in water to form a flameproofing agent, and the fiber is flameproofed using this. Representative examples of the halogen compounds include brominated cycloalkanes such as 1,2,5,6,9,10-hexabromocyclododecane (Patent Documents 1 and 2). Although it is known that the flameproofing performance of halogenated compounds is generally high, burning halogenated fibers generates harmful halogenated gas, which has harmful effects on the human body and the natural environment. There is. Therefore, in recent years, the use of halogen compounds as flameproofing agents has been regulated.

  Therefore, flame retardants using organophosphorus compounds such as organophosphates as flame retardants instead of halogen compounds and fiber flameproofing methods using the same have been proposed (Patent Documents 3 to 8). . When these are used as a flameproofing agent for fibers, generally a surfactant is often used as an aqueous dispersion. However, among these phosphorus compounds, particularly when phosphites and phosphate esters are used, it is often difficult to disperse or re-aggregate and cannot stably exist as a dispersion. .

Japanese Patent Publication No.53-8840 JP-A-1-213474 Japanese Patent Laid-Open No. 10-298188 Japanese Patent Laid-Open No. 10-212669 JP 2001-254268 A JP 2000-328445 A JP 2004-225176 A JP 2006-70417 A

  An object of the present invention is to provide an aqueous dispersion obtained by stably dispersing an organophosphorus compound capable of imparting excellent durable and flameproofing performance, a flameproofing agent and a flameproofing processing method using the same. There is.

  As a result of intensive studies to solve the above-mentioned problems, the present inventors have found that polyphosphates stabilize the dispersion of organic phosphorus compounds, leading to the present invention.

［式中、Ｒ_１１、Ｒ_１２、Ｒ_１３は、それぞれ独立に水酸基、アミノ基、シアノ基、カルボキシル基、ウレイド基、（Ｃ１−Ｃ４）アルキル基、ジ（Ｃ１−Ｃ４）アルキルアミノ基、ジフェニルアミノ基、アリール基、フェノキシ基若しくは（Ｃ１−Ｃ４）アルコキシ基によって置換されていてもよいアリール基を示す。］で表されるホスファイト、下記一般式（ＩＩ）

［式中、Ｒ_２１、Ｒ_２２、Ｒ_２３は、それぞれ独立に水酸基、アミノ基、シアノ基、カルボキシル基、ウレイド基、（Ｃ１−Ｃ４）アルキル基、ジ（Ｃ１−Ｃ４）アルキルアミノ基、ジフェニルアミノ基、アリール基、フェノキシ基若しくは（Ｃ１−Ｃ４）アルコキシ基によって置換されていてもよいアリール基を示す。］で表されるリン酸エステル、下記一般式（ＩＩＩ）

［式中、Ｒ_３１、Ｒ_３２、Ｒ_３３は、それぞれ独立に水酸基、アミノ基、シアノ基、カルボキシル基、ウレイド基、（Ｃ１−Ｃ４）アルキル基、ジ（Ｃ１−Ｃ４）アルキルアミノ基、ジフェニルアミノ基、アリール基、フェノキシ基若しくは（Ｃ１−Ｃ４）アルコキシ基によって置換されていてもよいアリール基を示す。］で表されるホスフィンオキシド、下記一般式（ＩＶ）

［式中、Ｒ_４１、Ｒ_４２、Ｒ_４３は、それぞれ独立に水酸基、アミノ基、シアノ基、カルボキシル基、ウレイド基、（Ｃ１−Ｃ４）アルキル基、ジ（Ｃ１−Ｃ４）アルキルアミノ基、ジフェニルアミノ基、アリール基、フェノキシ基若しくは（Ｃ１−Ｃ４）アルコキシ基によって置換されていてもよいアリール基を示す。］で表されるホスフィン及び下記一般式（Ｖ）

［式中、Ｒ_５１、Ｒ_５２は、それぞれ独立に水酸基、アミノ基、シアノ基、カルボキシル基、ウレイド基、（Ｃ１−Ｃ４）アルキル基、ジ（Ｃ１−Ｃ４）アルキルアミノ基、ジフェニルアミノ基、アリール基、フェノキシ基若しくは（Ｃ１−Ｃ４）アルコキシ基によって置換されていてもよいアリール基を示し、ｎは０〜２の整数を示す。］で表されるリン酸アミドからなる群から選ばれる少なくとも１つの化合物である上記（１）〜（５）のいずれか一項に記載の水性分散液；
（７） 一般式（Ｉ）のＲ_１１、Ｒ_１２、Ｒ_１３、一般式（ＩＩ）のＲ_２１、Ｒ_２２、Ｒ_２３、一般式（ＩＩＩ）のＲ_３１、Ｒ_３２、Ｒ_３３、一般式（ＩＶ）のＲ_４１、Ｒ_４２、Ｒ_４３、及び一般式（Ｖ）のＲ_５１、Ｒ_５２がそれぞれ独立に、（Ｃ１−Ｃ４）アルキル基若しくはアリール基で置換されたアリール基又は無置換のアリール基である上記（６）記載の水性分散液；
（８） 更に紫外線吸収剤を含有する上記（１）〜（７）のいずれか一項に記載の水性分散液；That is, the present invention relates to the following (1) to (15).
(1) an aqueous dispersion containing an organic phosphorus compound, polyphosphate, surfactant and water;
(2) The aqueous dispersion according to the above (1), which contains 1 to 90% by weight of polyphosphate in the aqueous dispersion;
(3) The aqueous dispersion according to (1) or (2) above, wherein the polyphosphate is a salt of ammonia or amines of polyphosphoric acid, or an alkali metal or alkaline earth metal salt of polyphosphoric acid;
(4) The aqueous dispersion according to any one of (1) to (3) above, wherein the polyphosphate is ammonium polyphosphate or sodium polyphosphate;
(5) The aqueous dispersion according to any one of (1) to (4) above, wherein the total amount of the organophosphorus compound is 1 to 90% by weight in the aqueous dispersion;
(6) The organophosphorus compound is represented by the following general formula (I)

[Wherein R ₁₁ , R ₁₂ and R ₁₃ are each independently a hydroxyl group, amino group, cyano group, carboxyl group, ureido group, (C1-C4) alkyl group, di (C1-C4) alkylamino group, diphenyl An aryl group which may be substituted with an amino group, an aryl group, a phenoxy group or a (C1-C4) alkoxy group is shown. A phosphite represented by the following general formula (II)

[Wherein R ₂₁ , R ₂₂ and R ₂₃ are each independently a hydroxyl group, amino group, cyano group, carboxyl group, ureido group, (C1-C4) alkyl group, di (C1-C4) alkylamino group, diphenyl An aryl group which may be substituted with an amino group, an aryl group, a phenoxy group or a (C1-C4) alkoxy group is shown. A phosphate ester represented by the following general formula (III)

[Wherein R ₃₁ , R ₃₂ and R ₃₃ are each independently a hydroxyl group, amino group, cyano group, carboxyl group, ureido group, (C1-C4) alkyl group, di (C1-C4) alkylamino group, diphenyl An aryl group which may be substituted with an amino group, an aryl group, a phenoxy group or a (C1-C4) alkoxy group is shown. A phosphine oxide represented by the following general formula (IV)

[Wherein, R ₄₁ , R ₄₂ and R ₄₃ each independently represent a hydroxyl group, an amino group, a cyano group, a carboxyl group, a ureido group, a (C1-C4) alkyl group, a di (C1-C4) alkylamino group, diphenyl. An aryl group which may be substituted with an amino group, an aryl group, a phenoxy group or a (C1-C4) alkoxy group is shown. And the following general formula (V)

[Wherein, R ₅₁ and R ₅₂ each independently represent a hydroxyl group, an amino group, a cyano group, a carboxyl group, a ureido group, a (C1-C4) alkyl group, a di (C1-C4) alkylamino group, a diphenylamino group, The aryl group which may be substituted by the aryl group, the phenoxy group, or the (C1-C4) alkoxy group is shown, n shows the integer of 0-2. The aqueous dispersion according to any one of (1) to (5) above, which is at least one compound selected from the group consisting of phosphoric acid amides represented by the formula:
(7) R ₁₁ , R ₁₂ , R _{13 of} the general formula (I), R ₂₁ , R ₂₂ , R _{23 of} the general formula (II), R ₃₁ , R ₃₂ , R _{33 of} the general formula (III) R ₄₁ , R ₄₂ , R ₄₃ in (IV) and R ₅₁ , R _{52 in} general formula (V) are each independently an aryl group substituted with (C1-C4) alkyl group or aryl group, or unsubstituted The aqueous dispersion according to (6) above, which is an aryl group;
(8) The aqueous dispersion according to any one of (1) to (7), further containing an ultraviolet absorber;

(9) A flameproofing agent using the aqueous dispersion according to any one of (1) to (8) above;
(10) The flameproofing agent according to (9), which is for fibers;
(11) The flameproofing agent according to the above (10), wherein the fiber is a polyester fiber;
(12) The flameproofing agent according to the above (11), wherein the polyester fiber is a cation dyeable polyester fiber or a blended fiber containing a cation dyeable polyester fiber;
(13) The flameproofing agent according to the above (12), wherein the blended fiber is a blended fiber of a cationic dyeable polyester fiber and another polyester fiber;
(14) A flameproofing method for fibers comprising treating polyester fibers with the aqueous dispersion according to any one of (1) to (8) above; and (15) by the method according to (14) above Flame-proof fiber.

  The flameproofing agent using an aqueous dispersion containing an organophosphorus compound, polyphosphate, surfactant and water of the present invention is excellent in dispersion stability and is particularly suitable for fibers, particularly cationic dyeable polyester fibers or cationic dyeable dyes. A durable and high-performance flameproofing treatment can be applied to a blended fiber of a type polyester fiber and another polyester fiber. When the flameproofing agent using the aqueous dispersion of the present invention is used together with a dyeing agent when dyeing a cloth or fiber, it becomes a uniform dyed product without causing spots.

The present invention will be described in detail.
The aqueous dispersion of the present invention contains an organic phosphorus compound, a polyphosphate, a surfactant and water. Examples of the organic phosphorus compound include organic phosphorus compounds containing a trivalent or pentavalent phosphorus atom in the molecule. Preferably, for example, a phosphite represented by the above general formula (I), a phosphate ester represented by the general formula (II), a phosphine oxide represented by the general formula (III), and a general formula (IV) And at least one compound selected from the group consisting of the phosphine represented and the phosphoric acid amide represented by the general formula (V). One of the compounds of the general formula (I), (II), (III), (IV) or (V) may be used, or two or more thereof may be used. Moreover, you may use two or more compounds from the compound contained in one general formula. Usually, it is preferred to use 1 to 5 compounds.

R ₁₁ , R ₁₂ , R _{13 of} the general formula (I), R ₂₁ , R ₂₂ , R _{23 of} the general formula (II), R ₃₁ , R ₃₂ , R _{33 of} the general formula (III), general formula (IV) ) R ₄₁ , R ₄₂ , R ₄₃ , R ₅₁ , R ₅₂ in the general formula (V), a hydroxyl group, an amino group, a cyano group, a carboxyl group, a ureido group, a (C1-C4) alkyl group, a di (C1-C4) In the aryl group optionally substituted by an alkylamino group, diphenylamino group, aryl group, phenoxy group or (C1-C4) alkoxy group, examples of the (C1-C4) alkyl group include a methyl group and an ethyl group. , N-propyl group, isopropyl group, n-butyl group, isobutyl group, t-butyl group and the like. Examples of the (C1-C4) alkoxy group include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, and a t-butoxy group. Examples of the aryl group include a phenyl group, a biphenyl group, and a naphthyl group. Moreover, the substitution position of the substituent in the aryl group is not particularly limited, and may be any position where substitution is possible.
By hydroxyl group, amino group, cyano group, carboxyl group, ureido group, (C1-C4) alkyl group, di (C1-C4) alkylamino group, diphenylamino group, aryl group, phenoxy group or (C1-C4) alkoxy group As the aryl group which may be substituted, for example, phenyl group, methylphenyl group, ethylphenyl group, n-propylphenyl group, isopropylphenyl group, dimethylphenyl group, hydroxyphenyl group, methoxyphenyl group, ethoxyphenyl group, Phenoxyphenyl group, aminophenyl group, N, N-dimethylaminophenyl group, N, N-diethylaminophenyl group, N, N-diphenylaminophenyl group, cyanophenyl group, carboxyphenyl group, biphenyl group, naphthyl group, etc. It is done.

Among them, an aryl group substituted with a (C1-C4) alkyl group or an aryl group or an unsubstituted aryl group is preferable. For example, a phenyl group, a methylphenyl group, a dimethylphenyl group, a biphenyl group, and a naphthyl group are preferable, and a phenyl group , Methylphenyl group and naphthyl group are particularly preferable.
The organophosphorus compounds represented by the general formulas (I) to (V) may be commercially available compounds, or may be prepared and used by applying ordinary production methods.

  As the organic phosphorus compound used in the aqueous dispersion of the present invention, in addition to the compounds represented by the above general formulas (I) to (V), phosphinic acid (for example, phenylphosphinic acid) and phosphonic acid (for example, Or a compound such as diphenylphosphonic acid).

The polyphosphate used in the aqueous dispersion of the present invention is used for the purpose of stabilizing the dispersion. Examples of the polyphosphate include ammonium or amine salts of polyphosphoric acid such as ammonium polyphosphate and triethylamine polyphosphate, or alkali metal or alkaline earth metal salts of polyphosphoric acid such as sodium polyphosphate and magnesium polyphosphate. Can be mentioned. Among these, ammonium polyphosphate and sodium polyphosphate are preferable, and ammonium polyphosphate is particularly preferable.
The average degree of polymerization of phosphoric acid in the polyphosphate is preferably about 3 to 3000, and more preferably about 3 to 2000.

These polyphosphates may be commercially available compounds (Sumitomo Chemical Co., Ltd., Junsei Kagaku Co., Ltd., etc.) or may be prepared by applying ordinary production methods.
Furthermore, what coated polyphosphate with the melanin and what coat | covered with silicon can also be used, and these can also use a commercially available thing.

  Examples of the surfactant used in the aqueous dispersion of the present invention include cationic surfactants, nonionic surfactants and / or anionic surfactants. Nonionic surfactants and anionic surfactants It is preferable to use an agent or a mixture of a nonionic surfactant and an anionic surfactant.

  Examples of anionic surfactants include alkyl sulfate salts such as higher alcohol sulfates, higher alkyl ether sulfates and sulfated fatty acid esters; alkyl sulfonates such as alkylbenzene sulfonates and alkylnaphthalene sulfonates. Alkyl phosphate salts such as higher alcohol phosphate ester salts and alkylene oxide adduct phosphate ester salts of higher alcohols; Also, alkyl aryl sulfonate salt, polyoxyalkylene alkyl ether sulfate salt, polyoxyalkylene alkyl ester phosphate salt, polyoxyalkylene alkyl ether carboxylate salt, polycarboxylate, funnel oil, petroleum sulfonate, alkyl diphenyl ether sulfonate salt Etc.

［式中Ｒは、水素原子、（Ｃ６〜Ｃ１８）アルキル基、スチリル基又はベンジル基を表し、ｎは１〜１５の整数を表す。］で表されるポリオキシエチレンフェニルエーテルの硫酸エステル塩又は高級アルコールのアルキレンオキシド付加物リン酸エステル塩（例えば、第一工業製薬株式会社製：プライサーフ）である。なお、一般式（１０７）では便宜上、遊離酸として記載しているが、塩としての対カチオンとしては、アルカリ金属（例えば、リチウム、ナトリウム、カリウム等）、アンモニウム等が挙げられ、ナトリウム又はアンモニウムが好ましい。Among these, a preferred anionic surfactant is represented by the following general formula (107)

[Wherein R represents a hydrogen atom, a (C6 to C18) alkyl group, a styryl group or a benzyl group, and n represents an integer of 1 to 15. ] The polyoxyethylene phenyl ether sulfate ester salt or higher alcohol alkylene oxide adduct phosphate ester salt represented by the formula (for example, Daiichi Kogyo Seiyaku Co., Ltd .: Prisurf). In general formula (107), it is described as a free acid for convenience, but examples of the counter cation as a salt include alkali metals (for example, lithium, sodium, potassium, etc.), ammonium and the like. preferable.

  Among the surfactants represented by the general formula (107), a compound in which R is a linear alkyl group having (C6 to C12) and n is 4 to 12, and R is a nonyl group and n is 7 is preferable. More preferred are compounds.

で示される化合物又はその混合物が好ましい。一般式（１０８）において、ｍ’は１〜３、ｎ’は８〜３０である。Examples of the nonionic surfactant include polyoxyethylene styrenated phenyl ether, such as polyoxyethylene distyrenated phenyl ether or polyoxyethylene tristyrenated phenyl ether, and the following general formula (108)

Or a mixture thereof is preferred. In general formula (108), m 'is 1-3 and n' is 8-30.

  Examples of the mixture of the compound represented by the general formula (108) include Neugen EA-87 (manufactured by Daiichi Kogyo Seiyaku Co., Ltd.). In the formulas in this specification, Me represents a methyl group.

The above surfactants may be used alone or in combination, and even if a plurality of types of anionic or nonionic surfactants are mixed, one to a plurality of types of anionic and nonionic types, respectively. A surfactant may be mixed and used.
The above surfactant may be a commercially available compound, or may be prepared by applying a normal production method.

  The aqueous dispersion of the present invention may contain an ultraviolet absorber for the purpose of improving light fastness. The ultraviolet absorber is not particularly limited as long as it is a compound that absorbs ultraviolet rays. Examples thereof include compounds that emit ultraviolet light by absorbing ultraviolet rays typified by system compounds, so-called fluorescent whitening agents.

The structural formulas of preferred ultraviolet absorbers are shown below as formulas (101) to (106).

In the general formula (106), which is a benzotriazole-based ultraviolet absorber, R ₁₅ represents a linear or branched alkyl group or cumyl group of (C1 to C12), and a linear or branched chain of (C1 to C12). An alkyl group is preferred, more preferably a (C3 to C6) linear or branched alkyl group, still more preferably a (C3 to C5) branched alkyl group, such as an isopropyl group, an isobutyl group, Examples thereof include s-butyl group, t-butyl group, 1-methylbutyl group, 2-methylbutyl group, 3-methylbutyl group and 1-ethylpropyl group.

R ₁₆ represents a hydroxyl group, a linear or branched alkyl group of (C1 to C12), a linear or branched alkoxy group of (C1 to C12), or a benzyloxy group, and a linear or branched chain of (C1 to C12). An alkyl group is preferable, more preferably a (C1-C6) linear or branched alkyl group, and still more preferably a (C1-C3) linear or branched alkyl group, such as a methyl group, Examples include an ethyl group, an n-propyl group, and an isopropyl group.
R ₁₇ represents a hydrogen atom, a hydroxyl group, a linear or branched alkyl group of (C1 to C12) or a linear or branched alkoxy group of (C1 to C12), and a hydrogen atom or a linear or branched chain of (C1 to C3) A branched alkyl group is preferable, and examples thereof include the same groups as the linear or branched alkyl group represented by (C1 to C3) in the above R ₁₆ . More preferably, it is a hydrogen atom.
R ₁₈ represents a hydrogen atom or a hydroxyl group, preferably a hydroxyl group.
X represents a hydrogen atom or a chlorine atom, and a chlorine atom is more preferable.

In a particularly preferred combination of R _{15 to} R ₁₈ and X, R ₁₅ is a t-butyl group, R ₁₆ is a methyl group, R ₁₇ is a hydrogen atom, R ₁₈ is a hydroxyl group, and X is a chlorine atom.

Examples of the ultraviolet absorber other than the benzotriazole compound represented by the general formula (106) include a benzophenone compound represented by the formula (101), the formula (102), or the formula (103), and the general formula (104). A triazine compound represented by the formula (wherein R ₉ and R ₁₀ each independently represents a hydrogen atom, a hydroxyl group or an alkyl group of (C1 to C5)), a benzotriazole compound represented by the general formula (105) And a benzophenone-based compound (wherein R ₁₁ represents a methyl group, an ethyl group or a cumyl group, R ₁₂ represents a hydroxyl group, a methoxy group, an ethoxy group or a benzyloxy group, and R ₁₃ represents a hydrogen atom, a hydroxyl group or a methoxy group) Or an ethoxy group, R ₁₄ represents a hydrogen atom or a hydroxyl group, and X represents a hydrogen atom or a chlorine atom.

Of the above ultraviolet absorbers, those particularly preferred are those of the benzotriazole type represented by the general formula (106).
The ultraviolet absorber may be a commercially available compound, or may be prepared by applying a normal production method.

The aqueous dispersion of the present invention is used as a flameproofing agent, and the flameproofing agent is also included in the present invention.
As a preferred embodiment of the aqueous dispersion for flameproofing of the present invention, the total amount of the organophosphorus compound in the aqueous dispersion is 1 to 90% by weight, preferably 5 to 70% by weight, particularly preferably 10 to 50% by weight. In the range of 0.1 to 90% by weight, preferably 0.5 to 50% by weight, particularly preferably 1 to 30% by weight.

The content of the surfactant contained in the aqueous dispersion of the present invention is usually 5 to 200% by weight with respect to the total amount of the organophosphorus compound and the ultraviolet absorber when it contains an ultraviolet absorber, preferably Is in the range of 10 to 100% by weight, particularly preferably 10 to 50% by weight. When no ultraviolet absorber is contained, it is usually in the range of 5 to 200% by weight, preferably 10 to 100% by weight, particularly preferably 10 to 50% by weight, based on the amount of the organophosphorus compound.
When the aqueous dispersion of the present invention contains an ultraviolet absorber, the content thereof is usually 0.1 to 10% by weight, preferably 0.1 to 8% by weight, particularly preferably 0.1% by weight in the aqueous dispersion. It is in the range of 1 to 5% by weight.

The method for preparing the aqueous dispersion of the present invention is not particularly limited, and examples thereof include a method of stirring the dispersoid pulverized in a dispersion medium containing water.
The average particle size of the dispersoid fine particles dispersed in the aqueous dispersion of the present invention is preferably 20 μm or less as measured by a Shimadzu laser diffraction particle size distribution analyzer SALD-2000.

  The aqueous dispersion of the present invention includes a protective colloid agent such as polyvinyl alcohol, methyl cellulose, carboxymethyl cellulose, starch paste and the like for enhancing storage stability within the range not impairing the effect; Flame auxiliaries; antioxidants and the like may be included as necessary. Furthermore, if necessary, alkaline agents, acids, fats and oils, higher alcohols, higher fatty acids, lower alcohols, organic solvents, penetration enhancers, polyhydric alcohols, preservatives, chelating agents, pH adjusters, wetting agents, You may add a foaming agent, a fungicide, a pigment | dye, or a pigment.

The flameproofing agent using the aqueous dispersion of the present invention is preferably used for fibers, and the fibers to be flameproofed are polyester fibers, particularly CDP (cation dyeable polyester) fibers, or CDP fibers and other fibers, particularly Polyester fiber blend fibers are preferred.
Examples of CDP fibers and polyester fibers include polyethylene fibers such as polyethylene terephthalate, polybutylene terephthalate, polyoxyethoxybenzoate, polyethylene naphthalate, and cyclohexanedimethylene terephthalate; and isophthalic acid, adipic acid, and sulfoisophthalic acid Examples thereof include fibers obtained by additionally copolymerizing diol components such as dicarboxylic acid components such as propylene glycol, butylene glycol, cyclohexane dimethanol, and diethylene glycol, but are not limited thereto.
In the present invention, these fibers include any form such as yarn, woven fabric, knitted fabric, and non-woven fabric.

  Also included in the present invention is a fiber flameproofing method characterized by using the aqueous dispersion of the present invention. In order to flameproof the fibers, methods such as dip dyeing and padding can be used. For example, when the dip dyeing method is used, fibers, a disperse dye such as a dispersion-type cationic dye, and the aqueous dispersion of the present invention are used in combination at a temperature of 110 to 150 ° C., preferably 120 to 140 ° C. for 10 to 60 minutes. Do some processing. Further, the dyeing and flameproofing may be performed in multiple stages. Furthermore, if necessary, a dye such as a fluorescent dye can be further added.

  When the padding method is used, the fiber structure is padded and then subjected to heat treatment such as dry heat treatment or steam heat treatment (saturated atmospheric steam treatment, superheated steam treatment, high pressure steam treatment, etc.). In both the dry heat treatment and the steam heat treatment, the heat treatment temperature is usually 110 to 210 ° C, preferably 170 to 210 ° C. If the heat treatment temperature exceeds 210 ° C, the polyester synthetic fiber may be yellowed or embrittled.

  If necessary, the dip dyeing bath method and the padding method may be used in combination. In this case, the fiber may be subjected to a flameproofing process by the dip dyeing bath method and then reprocessed by the padding method. Higher flameproof performance can be imparted by using two kinds of methods together.

The present invention will be described more specifically with reference to the following examples, but the present invention is not limited to these examples. In the examples, “parts” and “%” indicate “parts by weight” and “% by weight”, respectively, unless otherwise specified.
The particle size distribution of particles such as phosphorus compounds dispersed in the aqueous dispersion was measured with a Shimadzu laser diffraction particle size distribution analyzer SALD-2000, and the median diameter was described as the average particle size.
The structural formulas of the compounds used in the following Examples and Comparative Examples are collectively described below.

The compound of following formula (201) is a compound of the said general formula (I) whose R < ₁₁ >, R < ₁₂ >, R < ₁₃ > is a phenyl group. This compound is commercially available from Wako Pure Chemical Industries, Ltd.
The compound of following formula (202) is a compound of the said general formula (II) whose R <_21> , R <_22> , R < ₂₃ > is a phenyl group. This compound is marketed as TPP (made by Daihachi Chemical Co., Ltd.).
The compound of the following formula (203) is a compound of the above general formula (III) in which R ₃₁ , R ₃₂ and R ₃₃ are phenyl groups. This compound can be synthesized, for example, by the method described in JP-A-62-145095. In addition, this compound is commercially available as TPPO (trade name; manufactured by Hokuko Chemical Co., Ltd.).
Compounds of formula (204) _is a compound of the general formula R _41, R _{42, R 43} is a phenyl group (IV). This compound can be synthesized by the method described in JP-A-2004-43405. Moreover, this compound is marketed as TPP (trade name; manufactured by Hokuko Chemical Co., Ltd.).
A compound of the following formula (205) is a compound of the above general formula (II) in which R ₂₁ , R ₂₂ and R ₂₃ are a 4-methylphenyl group. This compound can be synthesized by the method described in JP-A-2004-43405. Moreover, this compound is marketed as p-TCP (brand name; Daihachi Chemical Co., Ltd. product).
The compound of the following formula (206) is a compound of the above general formula (II) in which R ₂₁ , R ₂₂ and R ₂₃ are methylphenyl groups. This compound can be synthesized by the method described in JP-A-2004-43405. This compound is commercially available as TCP (trade name; manufactured by Daihachi Chemical Co., Ltd.).
The compound of the following formula (207) is a compound of the above general formula (II) in which R ₂₁ is a naphthyl group, and R ₂₂ and R ₂₃ are phenyl groups. This compound can be synthesized by the method described in JP-A-2006-70417. This compound is commercially available as NDPP (trade name; manufactured by Daihachi Chemical Co., Ltd.).
The following formula (208) is a compound of the above general formula (V) in which R ₅₁ and R ₅₂ are phenyl groups and n = 2. This compound can be obtained by reacting diphenyl phosphorochloridate with aniline in an organic solvent in the presence of an amine catalyst, as described in JP-A No. 2000-154277. Is a compound of the above general formula (V), wherein R ₅₁ and R ₅₂ are phenyl groups and n = 0. This compound can be obtained by reacting aniline with phosphorus oxychloride in an organic solvent, as described in JP-A-49-53241.
The compound of the following formula (212) is an anionic surfactant represented by the above general formula (107) in which R is an n-nonyl group and n is 7. A 30% aqueous solution containing the compound is commercially available as Haitenol NE-05 (trade name; manufactured by Daiichi Kogyo Seiyaku Co., Ltd.). In this example, a commercially available 30% aqueous solution was used as it was.
The compound of the following formula (213) is represented by the above general formula (106) in which R ₁₅ is a t-butyl group, R ₁₆ is a methyl group, R ₁₇ is a hydrogen atom, R ₁₈ is a hydroxyl group, and X is a chlorine atom. UV absorber. This compound is commercially available as EVERSORB73 (trade name; manufactured by Everlight Chemical Industrial Corporation).

Neugen EA-87 (trade name; manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) was used as the nonionic surfactant. As described above, this nonionic surfactant is commercially available as a mixture of compounds having the general formula (108) wherein m ′ is 1 to 3 and n ′ is 8 to 30.

  In the examples, ammonium polyphosphate manufactured by Sumitomo Chemical Co., Ltd. was used.

Example 1
Preparation of aqueous dispersion having an average particle diameter of 0.893 μm A mixture having the composition described in Table 1 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle diameter of 0.893 μm.

Example 2
Preparation of aqueous dispersion having an average particle diameter of 0.899 μm A mixture having the composition described in Table 2 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle diameter of 0.899 μm.

Example 3
Preparation of aqueous dispersion having an average particle size of 0.919 μm A mixture having the composition described in Table 3 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.919 μm.

Example 4
Preparation of aqueous dispersion having an average particle diameter of 0.877 μm A mixture having the composition described in Table 4 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle diameter of 0.877 μm.

Example 5
Preparation of aqueous dispersion having an average particle size of 7.453 μm A mixture having the composition described in Table 5 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 7.453 μm.

Example 6
Preparation of aqueous dispersion having an average particle size of 7.883 μm A mixture having the composition described in Table 6 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 7.883 μm.

Example 7
Preparation of aqueous dispersion having an average particle size of 7.232 μm A mixture having the composition described in Table 7 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 7.232 μm.

Example 8
Preparation of aqueous dispersion having an average particle size of 6.866 μm A mixture having the composition described in Table 8 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 6.866 μm.

Example 9
Preparation of aqueous dispersion having an average particle size of 0.924 μm A mixture having the composition described in Table 9 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.924 μm.

Example 10
Preparation of aqueous dispersion having an average particle size of 0.959 μm A mixture having the composition described in Table 10 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.959 μm.

Example 11
Preparation of aqueous dispersion having an average particle size of 0.889 μm A mixture having the composition described in Table 11 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.889 μm.

Example 12
Preparation of aqueous dispersion having an average particle size of 0.921 μm A mixture having the composition shown in Table 12 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.921 μm.

Example 13
Preparation of aqueous dispersion having an average particle size of 0.931 μm A mixture having the composition described in Table 13 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.931 μm.

Example 14
Preparation of aqueous dispersion having an average particle diameter of 4.676 μm A mixture having the composition described in Table 14 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle diameter of 4.676 μm.

Example 15
Preparation of aqueous dispersion having an average particle size of 0.901 μm A mixture having the composition described in Table 15 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.901 μm.

Example 16
Preparation of aqueous dispersion having an average particle size of 0.922 μm A mixture having the composition described in Table 16 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.922 μm.

Example 17
Preparation of aqueous dispersion having an average particle size of 0.925 μm A mixture having the composition described in Table 17 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.925 μm.

Example 18
Preparation of aqueous dispersion having an average particle size of 0.915 μm A mixture having the composition described in Table 18 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.915 μm.

Example 19
Preparation of aqueous dispersion having an average particle diameter of 0.818 μm A mixture having the composition described in Table 19 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle diameter of 0.818 μm.

Example 20
Preparation of aqueous dispersion having an average particle size of 0.918 μm A mixture having the composition described in Table 20 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.918 μm.

Comparative Example 1
Preparation of an aqueous dispersion having an average particle size of 0.894 μm A comparative mixture having an average particle size of 0.918 μm by wet-grinding a mixture of the composition described in Table 21 without using polyphosphate using a sand grinder An aqueous dispersion of was prepared.

Comparative Example 2
Preparation of an aqueous dispersion having an average particle size of 0.900 μm A comparative mixture having an average particle size of 0.900 μm by wet-grinding a mixture having the composition described in Table 22 without using polyphosphate using a sand grinder An aqueous dispersion of was prepared.

Comparative Example 3
Preparation of aqueous dispersion having an average particle size of 0.928 μm Without using polyphosphate, a mixture having the composition shown in Table 23 was wet-ground using a sand grinder and had an average particle size of 0.928 μm. An aqueous dispersion of was prepared.

Comparative Example 4
Preparation of aqueous dispersion having an average particle size of 0.918 μm Without using polyphosphate, a mixture having the composition described in Table 24 was wet-ground using a sand grinder and had an average particle size of 0.918 μm. An aqueous dispersion of was prepared.

Comparative Example 5
Preparation of aqueous dispersion having an average particle size of 4.949 μm A mixture having the composition shown in Table 25 was wet-ground using a sand grinder without using a polyphosphate, and used for comparison having an average particle size of 4.949 μm. An aqueous dispersion of was prepared.

Comparative Example 6
Preparation of an aqueous dispersion having an average particle size of 4.894 μm A mixture having the composition shown in Table 26 was wet-ground using a sand grinder without using a polyphosphate, and for comparison having an average particle size of 4.894 μm An aqueous dispersion of was prepared.

Comparative Example 7
Preparation of an aqueous dispersion having an average particle size of 3.959 μm A comparative mixture having an average particle size of 3.959 μm obtained by wet-grinding a mixture having the composition described in Table 27 without using polyphosphate and using a sand grinder An aqueous dispersion of was prepared.

Comparative Example 8
Preparation of an aqueous dispersion having an average particle size of 4.455 μm A comparative mixture having a mean particle size of 4.455 μm obtained by wet-grinding a mixture of the composition described in Table 28 without using polyphosphate using a sand grinder An aqueous dispersion of was prepared.

Comparative Example 9
Preparation of an aqueous dispersion having an average particle size of 0.928 μm For the purpose of comparison, a mixture having the composition shown in Table 29 was wet-ground using a sand grinder without using a polyphosphate, and had an average particle size of 0.928 μm. An aqueous dispersion of was prepared.

Comparative Example 10
Preparation of aqueous dispersion having an average particle size of 0.989 μm A comparative mixture having an average particle size of 0.989 μm by wet-grinding a mixture having the composition described in Table 30 without using polyphosphate using a sand grinder An aqueous dispersion of was prepared.

Comparative Example 11
Preparation of an aqueous dispersion having an average particle size of 0.893 μm A comparative mixture having an average particle size of 0.893 μm by wet-grinding a mixture having the composition shown in Table 31 without using polyphosphate using a sand grinder An aqueous dispersion of was prepared.

Comparative Example 12
Preparation of aqueous dispersion having an average particle size of 0.927 μm A comparative mixture having an average particle size of 0.927 μm by wet-grinding a mixture having the composition described in Table 32 without using polyphosphate using a sand grinder An aqueous dispersion of was prepared.

Comparative Example 13
Preparation of aqueous dispersion having an average particle size of 0.901 μm A comparative mixture having an average particle size of 0.901 μm by wet-grinding a mixture having the composition described in Table 33 without using polyphosphate using a sand grinder An aqueous dispersion of was prepared.

Comparative Example 14
Preparation of an aqueous dispersion having an average particle size of 0.861 μm Without using polyphosphate, a mixture having the composition described in Table 34 was wet-ground using a sand grinder and had an average particle size of 0.861 μm. An aqueous dispersion of was prepared.

Comparative Example 15
Preparation of aqueous dispersion having an average particle size of 0.951 μm A comparative mixture having an average particle size of 0.951 μm by wet-grinding a mixture having the composition shown in Table 35 without using polyphosphate using a sand grinder An aqueous dispersion of was prepared.

Comparative Example 16
Preparation of an aqueous dispersion having an average particle size of 0.944 μm A comparative mixture having an average particle size of 0.944 μm by wet-grinding a mixture having the composition described in Table 36 without using polyphosphate using a sand grinder An aqueous dispersion of was prepared.

Comparative Example 17
Preparation of aqueous dispersion having an average particle size of 0.943 μm Without using polyphosphate, a mixture having the composition shown in Table 37 was wet-ground using a sand grinder and had an average particle size of 0.943 μm. An aqueous dispersion of was prepared.

Comparative Example 18
Preparation of an aqueous dispersion having an average particle size of 0.920 μm A comparative mixture having an average particle size of 0.920 μm by wet-grinding a mixture having the composition shown in Table 38 without using polyphosphate using a sand grinder An aqueous dispersion of was prepared.

Comparative Example 19
Preparation of an aqueous dispersion having an average particle size of 0.899 μm Without using polyphosphate, a mixture having the composition shown in Table 39 was wet-ground using a sand grinder and had an average particle size of 0.899 μm. An aqueous dispersion of was prepared.

Comparative Example 20
Preparation of an aqueous dispersion having an average particle size of 0.928 μm A comparative mixture having an average particle size of 0.928 μm by wet-grinding a mixture of the composition described in Table 40 without using polyphosphate using a sand grinder An aqueous dispersion of was prepared.

Example 21 and Comparative Example 21
Flameproofing of Polyester / CDP Blended Fiber Fabric with Aqueous Dispersion Using the aqueous dispersions prepared in Examples 1-20 and Comparative Examples 1-20, 50% of CDP and other polyesters were subjected to the dip dyeing bath treatment method. Each of 40 cm squares of the blended fiber fabrics containing each was dyed and fireproofed at the same time.

That is, 0.72% o. w. f. (On weight of fiber) and cationic dye 0.92% o. w. f. The dye solution and each aqueous dispersion prepared in Examples 1-20 or Comparative Examples 1-20 were each treated at 130 ° C. for 40 minutes at a bath ratio (amount of liquid with respect to the dough used) of 1:20.
The dyes used were Kyalon Microester Yellow AQ-LE 0.24% as a disperse dye, Kayalon Microester Red AQ-LE 0.24%, Kayaron Microester Blue AQ-LE 0.24%; Kayakrill Yellow 3RL-ED 0.46%, Kayakrill Red GL-ED 0.24%, Kayakrill Blue GSL-ED 0.22%.

Thereafter, each fabric was subjected to reduction cleaning, and then heat-treated at 180 ° C. for 30 seconds. Further, according to JIS K 3371, a weak alkaline first-class detergent was used at a rate of 1 g / L, and the bath ratio was 1:40. Rinsing at 5 ° C. for 5 minutes was performed 3 times, and centrifugal dehydration was performed for 2 minutes. Thereafter, hot air drying at 60 ° C. ± 5 ° C. was taken as one cycle, and this was performed for 5 cycles.
Forty kinds of blended fiber fabrics obtained by the above operation were used as test pieces, and these were subjected to a combustion test.
The above-described reduction cleaning means preparing an aqueous solution of hydrosulfite 2 g / L, caustic soda 2 g / L, and surfactant 1 g / L, heating to 80 ° C., adding a flame-proofed fabric, and adding 20 It is an operation to process for a minute.

Test example 1
Re-aggregation test Re-agglomeration test by test method A 1) Aqueous dispersions prepared in method examples 1 to 20 and comparative examples 1 to 20 are allowed to stand at room temperature for 14 days and tested for the presence of re-agglomerated bottom mass (precipitate). The following evaluation was performed. The results are shown in Table 41-1 and Table 41-2 below as Evaluation A.
2) Evaluation ○: There is no lump at the bottom, and redispersion can be easily performed when shaken. X: Lump is at the bottom, and redispersion is not easily possible when shaken: Separation into two layers

2. Re-aggregation test by test method B 1) 3 ml of the aqueous dispersion prepared in method examples 1 to 20 and comparative examples 1 to 20 was placed in a centrifuge (rotation speed: 5000 rpm) for 20 minutes, and then the hardness of the bottom was tested. Then, the following reaggregation was evaluated. The results are shown in Table 41-1 and Table 41-2 below as Evaluation B.
2) A glass rod is stabbed into the mass at the bottom of the evaluation , and a length from the interface between the precipitate and water to the bottom is a, and a length through which the glass rod passes from the interface between the precipitate and water is x.
: X = a (a glass rod passed easily to the bottom)
○: x ≧ a / 2
Δ: a / 2>x> 0
X: x = 0

Test example 2
Dispersibility test Test Methods 10 ml of the aqueous dispersion prepared in Examples 1 to 20 and Comparative Examples 1 to 20 were left in a thermostatic chamber at 60 ° C. for 7 days, and the dispersibility was evaluated as follows. The results are shown in Tables 41-1 and 41-2 below.
2. Evaluation ○: Re-dispersed when stirring the left dispersion liquid ×: Separated into two layers and does not re-disperse even after stirring

Test example 3
Flameproof test 1. Test method Using the aqueous dispersions prepared in Examples 1 to 20 and Comparative Examples 1 to 20, in Example 21 and Comparative Example 21, a blended fiber fabric subjected to flameproofing by the dip dyeing bath treatment method was used as a test piece. A fire test was conducted by the Fire Service Act JIS L 1091 A-1 method (45 degree micro burner method), and the following evaluation was performed. The results are shown in Tables 41-1 and 41-2 below.
2. Evaluation ○: Measurement was performed 5 times, all after flame time was 3 seconds or less ×: Other than that

As is clear from the results of Table 41-1 and Table 41-2, a blended fiber fabric and a polyphosphate that were flameproofed with the aqueous dispersions of Examples 1 to 20 prepared using a polyphosphate were used. All of the blended fiber fabrics flameproofed with the aqueous dispersions of Comparative Examples 1 to 16 and 18 to 20 that were prepared have all passed the flameproofness, and the flameproofing performance of the aqueous dispersion by the presence or absence of polyphosphate There is almost no impact. However, the flame resistance of the blended fiber fabric subjected to flameproofing with the aqueous dispersion of Comparative Example 17 was x.
In the evaluation A of the re-aggregation test, all of the aqueous dispersions of Examples 1 to 20 of the present invention containing a polyphosphate were ○, whereas the aqueous dispersions of Comparative Examples 1 to 20 not containing a polyphosphate were used. In the liquid, all except Comparative Example 17 were x or separated, and reaggregation occurred. Moreover, in evaluation B, all the aqueous dispersions of Examples 1 to 20 of the present invention are ◯ or ◎.
In the evaluation of the dispersibility test, all of the aqueous dispersions of Examples 1 to 20 of the present invention are ◯, while the general formula (I) is similar to the aqueous dispersions of Comparative Examples 1 to 4, 12, 13, and 16. ), The aqueous dispersion of the present invention using a polyphosphate was shown to be highly effective in terms of dispersion stability, particularly when the compound of general formula (I) and the like were included.

  As described above, the test results using the aqueous dispersion of the present invention as a flameproofing agent indicate that the aqueous dispersion of the present invention has high dispersibility while maintaining excellent flameproofing performance. In addition, when the aqueous dispersion of the present invention is used as a flameproofing agent, it retains the above performance despite repeated water washing and the like for 5 cycles, and is extremely excellent in durability. It is clear that there is.

As is apparent from the above, according to the present invention, an aqueous dispersion of a non-halogen flameproofing agent capable of imparting durable and excellent flameproofing performance to fibers, particularly blended fibers of CDP and other polyesters. Can be provided.

Claims (15)

  An aqueous dispersion containing an organic phosphorus compound, a polyphosphate, a surfactant and water.   The aqueous dispersion according to claim 1, comprising 1 to 90% by weight of polyphosphate in the aqueous dispersion.   The aqueous dispersion according to claim 1 or 2, wherein the polyphosphate is an ammonia or amine salt of polyphosphoric acid or an alkali metal or alkaline earth metal salt of polyphosphoric acid.   The aqueous dispersion according to any one of claims 1 to 3, wherein the polyphosphate is ammonium polyphosphate or sodium polyphosphate.   The aqueous dispersion according to any one of 1 to 4, wherein the organic phosphorus compound is contained in the aqueous dispersion in an amount of 1 to 90% by weight in total. The organophosphorus compound is represented by the following general formula (I)

[Wherein R ₁₁ , R ₁₂ and R ₁₃ are each independently a hydroxyl group, amino group, cyano group, carboxyl group, ureido group, (C1-C4) alkyl group, di (C1-C4) alkylamino group, diphenyl An aryl group which may be substituted with an amino group, an aryl group, a phenoxy group or a (C1-C4) alkoxy group is shown. A phosphite represented by the following general formula (II)

[Wherein R ₂₁ , R ₂₂ and R ₂₃ are each independently a hydroxyl group, amino group, cyano group, carboxyl group, ureido group, (C1-C4) alkyl group, di (C1-C4) alkylamino group, diphenyl An aryl group which may be substituted with an amino group, an aryl group, a phenoxy group or a (C1-C4) alkoxy group is shown. A phosphate ester represented by the following general formula (III)

[Wherein R ₃₁ , R ₃₂ and R ₃₃ are each independently a hydroxyl group, amino group, cyano group, carboxyl group, ureido group, (C1-C4) alkyl group, di (C1-C4) alkylamino group, diphenyl An aryl group which may be substituted with an amino group, an aryl group, a phenoxy group or a (C1-C4) alkoxy group is shown. A phosphine oxide represented by the following general formula (IV)

[Wherein, R ₄₁ , R ₄₂ and R ₄₃ each independently represent a hydroxyl group, an amino group, a cyano group, a carboxyl group, a ureido group, a (C1-C4) alkyl group, a di (C1-C4) alkylamino group, diphenyl. An aryl group which may be substituted with an amino group, an aryl group, a phenoxy group or a (C1-C4) alkoxy group is shown. And the following general formula (V)

[Wherein, R ₅₁ and R ₅₂ each independently represent a hydroxyl group, an amino group, a cyano group, a carboxyl group, a ureido group, a (C1-C4) alkyl group, a di (C1-C4) alkylamino group, a diphenylamino group, The aryl group which may be substituted by the aryl group, the phenoxy group, or the (C1-C4) alkoxy group is shown, n shows the integer of 0-2. The aqueous dispersion according to any one of claims 1 to 5, which is at least one compound selected from the group consisting of phosphoric acid amides represented by the formula: R ₁₁ , R ₁₂ , R ₁₃ in general formula (I), R ₂₁ , R ₂₂ , R ₂₃ in general formula (II), R ₃₁ , R ₃₂ , R ₃₃ in general formula (III), general formula (IV) R ₄₁ , R ₄₂ , R ₄₃ , and R ₅₁ , R _{52 in} general formula (V) are each independently an aryl group substituted with a (C1-C4) alkyl group or aryl group, or an unsubstituted aryl group. The aqueous dispersion according to claim 6.   Furthermore, the aqueous dispersion liquid as described in any one of Claims 1-7 containing a ultraviolet absorber.   The flameproofing agent using the aqueous dispersion as described in any one of Claims 1-8.   The flameproofing agent according to claim 9, which is used for fibers.   The flameproofing agent according to claim 10, wherein the fiber is a polyester fiber.   The flameproofing agent according to claim 11, wherein the polyester fiber is a cationic dyeable polyester fiber or a blended fiber containing a cationic dyeable polyester fiber.   The flameproofing agent according to claim 12, wherein the blended fiber is a blended fiber of a cationic dyeable polyester fiber and another polyester fiber.   A fiber flameproofing method comprising treating a polyester fiber with the aqueous dispersion according to any one of claims 1 to 8. A fiber that has been flameproofed by the method of claim 14.