JPWO2008047897A1 - Non-halogen flameproofing agent and method for flameproofing fiber using the same - Google Patents

Abstract

1 to 3 types of phosphorus selected from the group consisting of phosphine oxide represented by the following general formula (1), phosphine represented by the following general formula (2) and phosphite represented by the following general formula (3) Or an aqueous dispersion containing a phosphoric acid compound, the following general formula (4) phosphate ester, and a surfactant is a fiber, especially a blend containing a CDP (cationic dyeable polyester) fiber or a CDP fiber. Durable and excellent flameproof performance can be imparted to the fiber. (Wherein R11, R12 and R13 each independently represent a phenyl group, etc.) (wherein R21, R22 and R23 each independently represent a phenyl group, etc.) (wherein R31, R32 and R33 each independently represent a phenyl group or the like. (In the formula, R41, R42 and R43 each independently represent a phenyl group or the like.)

Description

  The present invention relates to an aqueous dispersion capable of imparting flameproof performance with excellent durability to a synthetic fiber structure, a non-halogen flameproofing agent using the aqueous dispersion, and a flameproofing method for fibers using the same. And flameproofed 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).

  It is known that the flameproofing performance of halogenated compounds is generally high. However, when fireproofed fibers burn, harmful halogenated gas is generated, which has a harmful effect 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 phosphorus compounds such as organic phosphates as flame retardants in place of halogen compounds and fiber flameproofing methods using the same have been proposed (Patent Documents 3 to 8).

However, when these phosphorus compounds are used, sufficient flameproofing performance cannot be imparted to fibers, particularly blended fibers of CDP (cation dyeable polyester) fibers and polyester fibers.
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

  Provided are a flameproofing agent and a flameproofing processing method capable of imparting durable and excellent flameproofing performance to conventional fibers, particularly blended fibers of CDP fibers and polyester fibers.

  In order to solve the above-mentioned problems, the present inventors have intensively studied. As a result, by using an aqueous dispersion obtained by containing a specific phosphorus compound as a flameproofing agent, the fiber has excellent durability and flameproofing performance. The inventors have found that it can be imparted and have arrived at the present invention.

（式中、Ｒ_１１、Ｒ_１２及びＲ_１３は、それぞれ独立に、（Ｃ１−Ｃ８）アルキル基、又は水酸基、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。）

（式中、Ｒ_２１、Ｒ_２２及び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。）

（式中、Ｒ_３１、Ｒ_３２及び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。）
２)． 一般式（１）で表されるホスフィンオキシド、一般式（２）で表されるホスフィン及び一般式（３）で表されるホスファイトからなる群から選ばれる１種のリン系化合物を含有する上記１）記載の水性分散液。
３）． 更に、リン系化合物として一般式（４）で表されるリン酸エステルを含有する上記１）又は２）記載の水性分散液。

（式中、Ｒ_４１、Ｒ_４２及び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。）
４）． 一般式（１）で表されるホスフィンオキシド、一般式（２）で表されるホスフィン及び一般式（３）で表されるホスファイトからなる群から選ばれる１種のリン系化合物及び一般式（４）で表されるリン酸エステルを含有する上記１）〜３）のいずれか一項の水性分散液。
５）． 更に、紫外線吸収剤を含有する上記１）〜４）のいずれか一項の水性分散液。
６）． 一般式（１）で表されるホスフィンオキシド、一般式（２）で表されるホスフィン、一般式（３）で表されるホスファイト及び一般式（４）で表されるリン酸エステルからなる群から選ばれるリン系化合物を水性分散液中に総量で１〜９０重量％含有する上記１）〜５）のいずれか一項に記載の水性分散液。
７）． 一般式（１）で表されるホスフィンオキシド、一般式（２）で表されるホスフィン及び一般式（３）で表されるホスファイトからなる群から選ばれる１種のリン系化合物を水性分散液中に０．１〜８９．９重量％含有する上記６）記載の水性分散液。
８）． 更に、一般式（４）で表されるリン酸エステルを水性分散液中に０．１〜８９．９重量％含有する上記７）記載の水性分散液。
９）． 界面活性剤が非イオン型界面活性剤及び／又はアニオン型界面活性剤である上記１）〜８）のいずれか一項に記載の水性分散液。
１０） 紫外線吸収剤を水性分散液中に０．１〜１０重量％含有する上記１）〜９）のいずれか一項に記載の水性分散液。
１１）． 界面活性剤を、リン系化合物の量に対して、紫外線吸収剤を含有する場合には、リン系化合物と紫外線吸収剤の総量に対して、５〜２００重量％含有する上記１）〜１０）のいずれか一項に記載の水性分散液。
１２）．上記１）記載の一般式（１）で表されるホスフィンオキシド、一般式（２）で表されるホスフィン及び一般式（３）で表されるホスファイトからなる群から選ばれる１種〜３種のリン系化合物及び界面活性剤を含有する組成物。
１３）．更に、上記２）記載の一般式（４）で表されるリン酸エステルを含有する上記１２）記載の組成物。
１４）．上記１）〜１１）のいずれか一項に記載の水性分散液を用いた防炎剤。
１５）．繊維用である上記１４）の防炎剤。
１６）．繊維がポリエステル繊維である上記１５）記載の防炎剤。
１７）．ポリエステル繊維が、カチオン可染型ポリエステル繊維又はカチオン可染型ポリエステル繊維を含有する混紡繊維である上記１６）記載の防炎剤。
１８）．上記１）〜１１）のいずれか記載の水性分散液でポリエステル繊維を処理することを特徴とする繊維の防炎加工方法。
１９）．上記１８）記載の方法により防炎加工された繊維。That is, the present invention relates to the following 1) to 19).
1). 1 to 3 phosphorus compounds selected from the group consisting of phosphine oxide represented by general formula (1), phosphine represented by general formula (2) and phosphite represented by general formula (3), and An aqueous dispersion containing a surfactant.

(Wherein R ₁₁ , R ₁₂ and R ₁₃ are each independently a (C1-C8) alkyl group, or a hydroxyl group, amino group, cyano group, carboxyl group, ureido group, (C1-C4) alkyl group, di- (C1-C4) represents an aryl group optionally substituted by an alkylamino group, diphenylamino group, aryl group, phenoxy group or (C1-C4) alkoxy group.

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, An aryl group that may be substituted with a diphenylamino group, an aryl group, a phenoxy group, or a (C1-C4) alkoxy group is shown.

(Wherein R ₃₁ , R ₃₂ and R ₃₃ are each independently 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, An aryl group which may be substituted with a diphenylamino group, an aryl group, a phenoxy group or a (C1-C4) alkoxy group is shown.
2). The above containing a phosphorus compound selected from the group consisting of a phosphine oxide represented by the general formula (1), a phosphine represented by the general formula (2) and a phosphite represented by the general formula (3) 1) The aqueous dispersion described.
3). Furthermore, the aqueous dispersion according to 1) or 2) above, which contains a phosphoric ester represented by the general formula (4) as a phosphorus compound.

Wherein R ₄₁ , R ₄₂ and R ₄₃ are each independently a hydroxyl group, amino group, cyano group, carboxyl group, ureido group, (C1-C4) alkyl group, di (C1-C4) alkylamino group, An aryl group that may be substituted with a diphenylamino group, an aryl group, a phenoxy group, or a (C1-C4) alkoxy group is shown.
4). One phosphorus compound selected from the group consisting of phosphine oxide represented by general formula (1), phosphine represented by general formula (2) and phosphite represented by general formula (3), and general formula ( The aqueous dispersion according to any one of 1) to 3) above, which contains a phosphate ester represented by 4).
5). The aqueous dispersion according to any one of 1) to 4) above, further comprising an ultraviolet absorber.
6). Group consisting of phosphine oxide represented by general formula (1), phosphine represented by general formula (2), phosphite represented by general formula (3) and phosphate ester represented by general formula (4) The aqueous dispersion according to any one of 1) to 5) above, wherein the phosphorous compound selected from 1 to 90% by weight is contained in the aqueous dispersion in a total amount.
7). An aqueous dispersion containing one type of phosphorus compound selected from the group consisting of a phosphine oxide represented by general formula (1), a phosphine represented by general formula (2), and a phosphite represented by general formula (3) The aqueous dispersion according to 6) above, containing 0.1 to 89.9% by weight.
8). The aqueous dispersion according to 7) above, further comprising 0.1 to 89.9% by weight of the phosphate represented by the general formula (4) in the aqueous dispersion.
9). The aqueous dispersion according to any one of 1) to 8) above, wherein the surfactant is a nonionic surfactant and / or an anionic surfactant.
10) The aqueous dispersion according to any one of 1) to 9) above, wherein the ultraviolet absorbent is contained in an amount of 0.1 to 10% by weight in the aqueous dispersion.
11). In the case where the surfactant is contained in the ultraviolet absorber relative to the amount of the phosphorus compound, the above 1) to 10) containing 5 to 200% by weight based on the total amount of the phosphorus compound and the ultraviolet absorber. The aqueous dispersion according to any one of the above.
12). 1 type-3 types chosen from the group which consists of the phosphine oxide represented by General formula (1) of said 1) description, the phosphine represented by General formula (2), and the phosphite represented by General formula (3). A composition containing a phosphorus compound and a surfactant.
13). Furthermore, the composition of said 12) containing the phosphate ester represented by General formula (4) of said 2) description.
14). The flameproofing agent using the aqueous dispersion as described in any one of 1) to 11) above.
15). The flameproofing agent according to 14), which is used for fibers.
16). The flameproofing agent according to 15) above, wherein the fiber is a polyester fiber.
17). The flameproofing agent according to 16) above, wherein the polyester fiber is a cationic dyeable polyester fiber or a blended fiber containing a cationic dyeable polyester fiber.
18). A fiber flameproofing method comprising treating a polyester fiber with the aqueous dispersion described in any one of 1) to 11) above.
19). Fibers subjected to flameproofing by the method described in 18) above.

  By using a flameproofing agent using an aqueous dispersion containing the specific phosphorus compound of the present invention and a surfactant, fibers, in particular, cationic dyeable polyester fibers or blended fibers of cationic dyeable polyester fibers and other polyester fibers are used. Durable and high performance flameproofing can be applied.

The present invention is described in detail below.
The aqueous dispersion of the present invention is 1 selected from the group consisting of the phosphine oxide represented by the general formula (1), the phosphine represented by the general formula (2), and the phosphite represented by the general formula (3). Contains seed to three phosphorus compounds and a surfactant. A phosphoric acid ester represented by the general formula (4) may be used together with the phosphorus compound. In the present invention, one phosphorus system selected from the group consisting of the phosphine oxide represented by the general formula (1), the phosphine represented by the general formula (2), and the phosphite represented by the general formula (3). From an aqueous dispersion containing a compound and a surfactant, and a phosphine oxide represented by the above general formula (1), a phosphine represented by the general formula (2) and a phosphite represented by the general formula (3) An aqueous dispersion containing a phosphoric ester represented by the general formula (4) and a surfactant as the phosphorus compound, and a phosphorous compound selected from the group is preferred.

R ₁₁ , R ₁₂ , R _{13 of} the general formula (1), R ₂₁ , R ₂₂ , R _{23 of} the general formula (2), R ₃₁ , R ₃₂ , R _{33 of} the general formula (3), the general formula (4) In the definition of R ₄₁ , R ₄₂ and R ₄₃ ), examples of the (C1-C8) alkyl group include (C1-C8) linear or branched alkyl group and (C3-C8) cyclic alkyl group. , Methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-octyl group, cyclopropyl group, cyclopentyl group, Examples include a cyclohexyl group. Examples of the (C1-C4) alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, and a t-butyl group. Examples of the di (C1-4) alkylamino group include N, N-dimethylamino group, N, N-diethylamino group, N, N-di-n-propylamino group, N, N-diisopropylamino group, N , N-di-n-butylamino group, N, N-diisobutylamino group, N, N-di-t-butylamino group, N-methyl, N-ethylamino group, N-methyl, Nn-propyl Amino group, N-ethyl, N-isopropylamino group, N-isopropyl, Nn-butylamino group, N-ethyl, N-isobutylamino group, Nn-propyl, Nt-butylamino group, etc. Can be mentioned. Examples of the aryl group include a phenyl group, a biphenyl group, and a naphthyl group. 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.

  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 Examples of the optionally substituted aryl group include a phenyl group, a methylphenyl group, an ethylphenyl group, an n-propylphenyl group, an i-propylphenyl group, a dimethylphenyl group, a hydroxyphenyl group, a methoxyphenyl group, and an ethoxyphenyl group. 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. Is mentioned. Of these, a phenyl group, a methylphenyl group, a dimethylphenyl group, a biphenyl group, and a naphthyl group are preferable, and a phenyl group, a methylphenyl group, and a naphthyl group are particularly preferable. The substitution position in the aryl group of the substituent is not particularly limited, and may be any position where substitution is possible.

The phosphorus compounds represented by the general formulas (1) to (4) may be commercially available compounds, or may be prepared by ordinary production methods.
Among the phosphorus compounds contained in the aqueous dispersion of the present invention, a plurality of types of compounds may be used for the phosphine oxide represented by the general formula (1).

  Examples of the surfactant contained in the aqueous dispersion of the present invention include cationic, nonionic and / or anionic surfactants. Nonionic, anionic or nonionic and anionic surfactants And are preferably used in combination. The surfactant is used to disperse the aforementioned phosphorus compound.

  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 Is mentioned.

（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。）で示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、あるいは下記一般式（３０１）
Ｒ_５Ｏ（ＣＨ_２ＣＨ_２Ｏ）_ｎＰＯ（ＯＨ）（ＯＲ_６） （３０１）
（式中Ｒ_５はアルキル基又はアルキルアリール基、Ｒ_６は水素原子又はＲ_７Ｏ（ＣＨ_２ＣＨ_２Ｏ）_ｎ基を表し、Ｒ_７はアルキル基又はアルキルアリール基を表し、ｎは正の整数を表す。）で示されるポリオキシエチレンアルキルアリールエーテルのリン酸エステルが挙げられる。なお、一般式（１０７）、一般式（３０１）では便宜上、遊離酸として記載したが、塩における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。
一般式（１０７）で表される界面活性剤は、Ｒが（Ｃ１〜Ｃ１２）の直鎖のアルキル基、ｎが４〜１２である化合物が特に好ましく、Ｒがノニル基、ｎが７の化合物が更に好ましい。
一般式（３０１）で表される界面活性剤は、例えば、プライサーフ ＡＬ（商品名：第一工業製薬株式会社製）等が挙げられる。Among these, preferred anionic surfactants include the following general formula (107)

(Wherein R represents a hydrogen atom, a (C6-C18) alkyl group, a styryl group or a benzyl group, and n represents an integer of 1 to 15), or a sulfate ester salt of polyoxyethylene phenyl ether represented by The following general formula (301)
_{R 5 O (CH 2 CH 2} O) n PO (OH) (OR 6) (301)
(Wherein R ₅ represents an alkyl group or an alkylaryl group, R ₆ represents a hydrogen atom or R ₇ O (CH ₂ CH ₂ O) _n group, R ₇ represents an alkyl group or an alkylaryl group, and n is a positive number) A phosphoric acid ester of polyoxyethylene alkylaryl ether represented by the following formula: In general formula (107) and general formula (301), although described as a free acid for convenience, examples of the counter cation in the salt include alkali metals (for example, lithium, sodium, potassium, etc.), ammonium, etc. Or ammonium is preferable.
The surfactant represented by the general formula (107) is particularly preferably a compound in which R is a linear alkyl group of (C1 to C12), n is 4 to 12, and R is a nonyl group and n is 7. Is more preferable.
Examples of the surfactant represented by the general formula (301) include Prisurf AL (trade name: manufactured by Daiichi Kogyo Seiyaku Co., Ltd.).

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。一般式（１０８）で表される化合物の混合物として、例えば、ノイゲンＥＡ−８７（商品名；第一工業製薬株式会社製）等が挙げられる。As the nonionic surfactant as the surfactant contained in the aqueous dispersion of the present invention, polyoxyethylene styrenated phenyl ether, for example, polyoxyethylene distyrenated phenyl ether or polyoxyethylene tristyrenated phenyl Ethers and the like, 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 compounds represented by the general formula (108) include Neugen EA-87 (trade name; manufactured by Daiichi Kogyo Seiyaku Co., Ltd.).

The above surfactants may be used alone or in combination, and even if a plurality of types of anionic or nonionic surfactants are mixed, a plurality of types of anionic and nonionic surfactants are used. May be used in combination.
The surfactant described above may be a commercially available compound or may be prepared by 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). Alkyl groups are preferred. More preferred is a linear or branched alkyl group of (C3 to C6), and further preferred is a branched alkyl group of (C3 to C5), for example, isopropyl group, isobutyl group, s-butyl group, t -Butyl group, 1-methylbutyl group, 2-methylbutyl group, 3-methylbutyl group, 1-ethylpropyl group are mentioned.
R ₁₆ represents a hydroxy group, a linear or branched alkyl group of (C1 to C12), a linear or branched alkyl group of (C1 to C12), or a benzyloxy group, and a linear or branched group of (C1 to C12). A straight chain or branched chain alkyl group of (C1 to C6), more preferably a straight chain or branched chain alkyl group of (C1 to C3), such as a methyl group. , Ethyl group, n-propyl group, and 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); 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, R ₁₃ represents a hydrogen atom, a hydroxyl group, 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 a normal production method.

  The aqueous dispersion of the present invention is used as a flameproofing agent, and the composition containing the specific phosphorus compound and the surfactant is also included in the present invention. The flameproofing agent is also included in the present invention. Here, the composition includes an aqueous dispersion, or a mixture of the specific phosphorus compound and the surfactant before being prepared into the aqueous dispersion.

  As a preferable aspect in the aqueous dispersion for flameproofing of the present invention, a phosphorus compound selected from the group consisting of compounds of general formula (1), general formula (2), general formula (3) and general formula (4) Is generally contained in the aqueous dispersion in an amount of 1 to 90% by weight, preferably 5 to 70% by weight, particularly preferably 10 to 50% by weight.

As described above, the aqueous dispersion of the present invention contains one phosphorus-based compound selected from the group consisting of the compounds of general formula (1), general formula (2) and general formula (3), and A compound containing one type of phosphorus compound selected from the group consisting of compounds of general formula (1), general formula (2) and general formula (3) and a compound of general formula (4) is preferable.
What contains 0.1-89.9 weight% of 1 type of phosphorus compounds chosen from the group which consists of a compound of General formula (1), General formula (2), and General formula (3) in the aqueous dispersion liquid. preferable. Furthermore, what contains 0.1-89.9 weight% of compounds of General formula (4) in the aqueous dispersion liquid is preferable.
In addition, the phosphorus compound represented by the general formula (1) may be selected from a plurality of compounds represented by the same general formula.

When the aqueous dispersion of the present invention contains an ultraviolet absorber, its content is usually 0.1 to 10% by weight, preferably 0.1 to 8% by weight, particularly preferably 0.1 to 5% by weight. It is.
The content of the surfactant contained in the aqueous dispersion of the present invention is usually 5 to 200% by weight, preferably 10%, based on the total amount of the phosphorus compound and the ultraviolet absorber. It is in the range of -100% by weight, particularly preferably 10-50% by weight.

  In the aqueous dispersion of the present invention, a protective colloid agent such as polyvinyl alcohol, methylcellulose, carboxymethylcellulose, starch paste and the like for enhancing storage stability within a range not impairing the effect; flameproofing for enhancing the flameproofing effect An auxiliary agent; may contain an antioxidant or the like 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 and use a foam agent, an antifungal agent, a pigment | dye, or a pigment.

The aqueous dispersion of the present invention is prepared by adding a phosphorus compound and a surfactant, and if necessary, an ultraviolet absorber to water and mixing the resulting mixture with a wet grinder using, for example, a sand grinder. It can be prepared by preparing an aqueous dispersion containing particles having an average particle diameter.
Generally, when the fiber is post-processed with a flameproofing agent, the particle size of the flameproofing agent used is a very important factor for the flameproofing performance, and the smaller the flameproofing agent particle size, the higher the flameproofing performance of the fiber. Can be granted. For example, it is known that when the dispersibility is poor, the flame retardant reaggregates and the particle size increases. In particular, when durability is required for the flameproofing performance of the flameproofing agent, it is preferable that the flameproofing agent has a small particle size so that the flameproofing agent can sufficiently diffuse inside the fiber. Fine particles having an average particle diameter of 2 μm or less are preferable. In the present invention, by using a surfactant as a dispersant, it is possible to stably disperse a phosphorus compound and further an ultraviolet absorber as fine particles having an average particle size of 2 μm or less in water in a stable and high concentration state. it can.

The aqueous dispersion of the present invention is preferably used for fibers as a flameproofing agent, and the fibers to be flameproofed are preferably polyester fibers, particularly CDP fibers, or blended fibers of CDP fibers and other polyester fibers.
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.
The structure of these fibers may be any form such as yarn, woven fabric, knitted fabric, and non-woven fabric.

  A method for flameproofing a fiber using the aqueous dispersion of the present invention as a flameproofing agent is also included in the present invention. In order to flame-proof the fibers, methods such as a dip dyeing bath method and a padding method can be used. For example, when the dip dyeing bath method is used, a dispersion dye such as a fiber, 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. Processing is performed for about 60 minutes. If necessary, a dye such as a fluorescent dye can be further added.

When using the padding method, the fiber structure is padded and then subjected to heat treatment such as dry heat treatment or steam heat treatment (using 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.

In the above formula, Me represents a methyl group, Ph represents a phenyl group, and Et represents an ethyl group.
The compound of the said Formula (201) is a compound of the said General formula (2) whose R <_21> , R <_22> and R < ₂₃ > are phenyl groups. This compound can be synthesized by the method described in JP-A-2004-43405. This compound is commercially available as TPP (trade name; manufactured by Hokuko Chemical Co., Ltd.).
The compound of the said Formula (202) is a compound of the said General formula (1) whose R <_11> , R < ₁₂ > and R < ₁₃ > are phenyl groups. This compound can be synthesized, for example, by the method described in JP-A-62-145095. This compound is commercially available as TPPO (trade name; manufactured by Hokuko Chemical Co., Ltd.).
The compound of the said Formula (203) is a compound of the said General formula (2) whose R <_21> , R <_22> and R < ₂₃ > are 3-methylphenyl groups. This compound is commercially available from Wako Pure Chemical Industries, Ltd.
The compound of the said Formula (204) is a compound of the said General formula (3) whose R _{< 31>} , R _<32> and R _<33> are phenyl groups. This compound is commercially available from Wako Pure Chemical Industries, Ltd.
The compound of the said Formula (205) is a compound of the said General formula (3) whose R _{< 31>} , R _<32> and R _<33> are 4-methylphenyl groups. This compound is commercially available from Wako Pure Chemical Industries, Ltd.
Compounds of formula _{(207), R 41} is _{naphthyl, R 42} and _{R 43} is a compound of the general formula is a phenyl group (4). 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.).
Compounds of formula (208) _is a compound of the general formula R _{41, R 42} and _{R 43} is a 4-methylphenyl group (4). 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 above formula (209) is a compound of the above general formula (4) in which R ₄₁ is a diphenyl group, and R ₄₂ and R ₄₃ are a phenyl group, and # 5 (trade name; manufactured by Daihachi Chemical Co., Ltd.) It is commercially available.
Compounds of formula _{(211), R 41,} R ₄₂ and _{R 43} is a compound of the general formula is a phenyl group (4). This compound is marketed as TPP (trade name; manufactured by Daihachi Chemical Co., Ltd.).
The compound of the above formula (220) is a compound of the above general formula (1) in which R ₁₁ and R ₁₂ are phenyl groups and R ₁₃ is a methyl group, and is commercially available from Sigma-Aldrich Corporation. The compound of the above formula (221) is a compound of the above general formula (1) in which R ₁₁ and R ₁₂ are phenyl groups and R ₁₃ is an ethyl group, and is commercially available from Sigma-Aldrich Corporation. The compound of the above formula (222) is the compound of the above general formula (1) in which R ₁₁ and R ₁₂ are a phenyl group and R ₁₃ is a cyclohexyl group. This compound can be prepared, for example, by subjecting a compound marketed as DPCP (trade name: manufactured by Hokuko Chemical Co., Ltd.) to air oxidation or oxidation using hydrogen peroxide.
The compound of the said Formula (223) is a compound of the said General formula (1) whose R < ₁₁ >, R < ₁₂ > and R < ₁₃ > are 4-methylphenyl groups. This compound can be prepared, for example, by subjecting a compound marketed as TPTP (trade name: manufactured by Hokuko Chemical Co., Ltd.) to air oxidation or oxidation using hydrogen peroxide.
The compound of the said Formula (224) is a compound of the said General formula (1) whose R < ₁₁ >, R < ₁₂ > and R < ₁₃ > are n-octyl groups. This compound is marketed as TOPO (trade name: manufactured by Hokuko Chemical Co., Ltd.).
The compound of the above formula (210) is resorcinol bis (diphenyl phosphate) and is commercially available as RDP.

The compound of the above formula (213) is represented by the general formula (106) wherein 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).
The compound of the above 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.
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, commercially available products may be used as appropriate for the wetting agent, antifoaming agent, and antifungal agent.

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.
Table 1
Composition amount
Water 56.9%
Formula (201) (Compound of general formula (2)) 15.0%
Formula (207) (Compound of general formula (4)) 15.0%
Formula (213) (Ultraviolet absorber) 4.0%
Neugen EA-87 2.6%
Hightenol NE-05 5.8%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

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.
Table 2
Composition amount
Water 56.9%
Formula (202) (Compound of general formula (1)) 15.0%
Formula (207) (Compound of general formula (4)) 15.0%
Formula (213) (Ultraviolet absorber) 4.0%
Neugen EA-87 2.6%
Hightenol NE-05 5.8%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

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.
Table 3
Composition amount
Water 56.9%
Formula (203) (Compound of general formula (2)) 15.0%
Formula (207) (Compound of general formula (4)) 15.0%
Formula (213) (Ultraviolet absorber) 4.0%
Neugen EA-87 2.6%
Hightenol NE-05 5.8%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

Example 4
Preparation of aqueous dispersion having an average particle size of 0.959 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 size of 0.959 μm.
Table 4
Composition amount
Water 56.9%
Formula (204) (Compound of General Formula (3)) 15.0%
Formula (207) (Compound of general formula (4)) 15.0%
Formula (213) (Ultraviolet absorber) 4.0%
Neugen EA-87 2.6%
Hightenol NE-05 5.8%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

Example 5
The mixture of the composition described in Preparation Table 5 of an aqueous dispersion having an average particle diameter of 0.883Myuemu, wet grinding with a sand grinder, to prepare an aqueous dispersion of the present invention having an average particle size of 0.883μm.
Table 5
Composition amount
Water 56.9%
Formula (205) (Compound of general formula (3)) 15.0%
Formula (207) (Compound of general formula (4)) 15.0%
Formula (213) (Ultraviolet absorber) 4.0%
Neugen EA-87 2.6%
Hightenol NE-05 5.8%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

Example 6
Preparation of aqueous dispersion having an average particle diameter of 0.866 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 diameter of 0.866 μm.
Table 6
Composition amount
Water 59.9%
Formula (201) (Compound of general formula (2)) 15.0%
Formula (211) (Compound of general formula (4)) 15.0%
Formula (213) (Ultraviolet absorber) 1.0%
Neugen EA-87 2.6%
Hightenol NE-05 5.8%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

Example 7
Preparation of aqueous dispersion having an average particle size of 0.924 μm A mixture having the composition shown 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 0.924 μm.
Table 7
Composition amount
Water 59.9%
Formula (202) (Compound of general formula (1)) 15.0%
Formula (211) (Compound of general formula (4)) 15.0%
Formula (213) (Ultraviolet absorber) 1.0%
Neugen EA-87 2.6%
Hightenol NE-05 5.8%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

Example 8
Preparation of aqueous dispersion having an average particle size of 0.959 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 0.959 μm.
Table 8
Composition amount
Water 59.9%
Formula (204) (Compound of General Formula (3)) 15.0%
Formula (211) (Compound of general formula (4)) 15.0%
Formula (213) (Ultraviolet absorber) 1.0%
Neugen EA-87 2.6%
Hightenol NE-05 5.8%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

Example 9
Preparation of aqueous dispersion having an average particle diameter of 0.889 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 diameter of 0.889 μm.
Table 9
Composition amount
Water 59.9%
Formula (201) (Compound of general formula (2)) 15.0%
Formula (208) (Compound of General Formula (4)) 15.0%
Formula (213) (Ultraviolet absorber) 1.0%
Neugen EA-87 2.6%
Hightenol NE-05 5.8%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

Example 10
The mixture of the composition according to the preparation table 10 of an aqueous dispersion having an average particle diameter of 0.901Myuemu, wet grinding with a sand grinder, to prepare an aqueous dispersion of the present invention having an average particle size of 0.901μm.
Table 10
Composition amount
Water 59.9%
Formula (202) (Compound of general formula (1)) 15.0%
Formula (208) (Compound of General Formula (4)) 15.0%
Formula (213) (Ultraviolet absorber) 1.0%
Neugen EA-87 2.6%
Hightenol NE-05 5.8%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

Example 11
Preparation of aqueous dispersion having an average particle size of 0.892 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 0.892 μm.
Table 11
Composition amount
Water 59.9%
Formula (204) (Compound of General Formula (3)) 15.0%
Formula (208) (Compound of General Formula (4)) 15.0%
Formula (213) (Ultraviolet absorber) 1.0%
Neugen EA-87 2.6%
Hightenol NE-05 5.8%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

Example 12
Preparation of aqueous dispersion having an average particle diameter of 0.894 μm A mixture having the composition described in Table 12 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle diameter of 0.894 μm.
Table 12
Composition amount
Water 59.9%
Formula (202) (Compound of general formula (1)) 15.0%
Formula (204) (Compound of General Formula (3)) 15.0%
Formula (213) (Ultraviolet absorber) 1.0%
Neugen EA-87 2.6%
Hightenol NE-05 5.8%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

Example 13
Preparation of aqueous dispersion having an average particle size of 0.921 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 0.921 μm.
Table 13
Composition amount
Water 59.9%
Formula (202) (Compound of general formula (1)) 10.0%
Formula (204) (Compound of General Formula (3)) 10.0%
Formula (211) (Compound of general formula (4)) 10.0%
Formula (213) (Ultraviolet absorber) 1.0%
Neugen EA-87 2.6%
Hightenol NE-05 5.8%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

Comparative Example 1
Preparation of aqueous dispersion having an average particle size of 0.963 μm A mixture having the composition described in Table 14 was wet-ground using a sand grinder to prepare a comparative aqueous dispersion having an average particle size of 0.963 μm.
Table 14
Composition amount
Water 56.9%
Formula (207) (Compound of general formula (4)) 30.0%
Formula (213) (Ultraviolet absorber) 4.0%
Neugen EA-87 2.6%
Hightenol NE-05 5.8%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

Comparative Example 2
Preparation of aqueous dispersion having an average particle size of 0.966 μm A mixture having the composition described in Table 15 was wet-ground using a sand grinder to prepare a comparative aqueous dispersion having an average particle size of 0.966 μm.
Table 15
Composition amount
Water 59.9%
Formula (208) (Compound of general formula (4)) 30.0%
Formula (213) (Ultraviolet absorber) 1.0%
Neugen EA-87 2.6%
Hightenol NE-05 5.8%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

Comparative Example 3
Preparation of aqueous dispersion having an average particle size of 0.935 μm A mixture having the composition described in Table 16 was wet-ground using a sand grinder to prepare a comparative aqueous dispersion having an average particle size of 0.935 μm.
Table 16
Composition amount
Water 56.9%
Formula (209) (Compound of general formula (4)) 30.0%
Formula (213) (Ultraviolet absorber) 4.0%
Neugen EA-87 2.6%
Hightenol NE-05 5.8%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Composition 100.0%

Comparative Example 4
Preparation of aqueous dispersion having an average particle size of 0.998 μm A mixture having the composition described in Table 17 was wet-ground using a sand grinder to prepare a comparative aqueous dispersion having an average particle size of 0.998 μm.
Table 17
Composition amount
Water 56.9%
Formula (210) 30.0%
Formula (213) (Ultraviolet absorber) 4.0%
Neugen EA-87 2.6%
Hightenol NE-05 5.8%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

Comparative Example 5
Preparation of Aqueous Dispersion with Average Particle Size of 0.945 μm A mixture having the composition described in Table 18 was wet-ground using a sand grinder to prepare a comparative aqueous dispersion having an average particle size of 0.945 μm.
Table 18
Composition amount
Water 59.9%
Formula (211) (Compound of general formula (4)) 30.0%
Formula (213) (Ultraviolet absorber) 1.0%
Neugen EA-87 2.6%
Hightenol NE-05 5.8%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

Example 14 and Comparative Example 6
Flameproofing of polyester / CDP blended fiber fabrics with aqueous dispersions Using the aqueous dispersions prepared in Examples 1-13 and Comparative Examples 1-5, CDP and other Each of 40 cm squares of a blended fiber fabric (CDP / PET blend A) containing 50% of polyester 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 aqueous dye dispersions prepared in Examples 1 to 13 and Comparative Examples 1 to 5 were each treated at 130 ° C. for 60 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.
Eight kinds of blended fiber fabrics obtained by the above operation were used as test pieces, and a flammability test was performed on these.
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
Flame Retardancy Test Using the aqueous dispersion prepared in Examples 1 to 13 or Comparative Examples 1 to 5, the polyester / CDP blend fiber fabric subjected to flameproofing in Example 14 or Comparative Example 6 was subjected to a flame retardance test. It was. The results are shown in Table 19.

(1) Test method Tests were conducted by the fire fighting method JIS L 1091 A-1 method (45 degree micro burner method), and the following evaluation was performed.
1) Evaluation A: Acceptance rate The case where the afterflame time was 3 seconds or less was regarded as acceptable, and a numerical value obtained by dividing the number of acceptable times during the measurement by the number of measurements was described as the acceptance rate. The fractional part is rounded off and the unit is%. The higher the acceptance rate, the higher the flameproof performance. The parentheses after the pass rate shown in Table 19 are the number of passes and the number of measurements used to calculate the pass rate, and are expressed as “(pass times / measurement times)”.
2) Evaluation B: Average afterflame time The average afterflame time was calculated by dividing the total sum of afterflame times measured in Test A by the number of measurements. The unit is seconds. The shorter the average afterflame time, the higher the flameproof performance.
3) Evaluation C: Average combustion area The combustion area of the test piece was measured, and the total combustion area was calculated by dividing the sum by the number of measurements. The unit is cm ² . The smaller the average combustion area, the higher the flameproof performance.

(2) Test results A flame retardancy test was conducted and the results of evaluations A, B and C are shown in Table 19.

  As is clear from the results in Table 19, the pass rate of evaluation A is 75-100% of the fabric flameproofed with the aqueous dispersion prepared in Examples 1 to 13 of the present invention. The fabric flameproofed with the aqueous dispersions prepared in Comparative Examples 1 to 5 is 0 to 69%, and the fabric flameproofed with the aqueous dispersion of the present invention has a higher pass rate. For the average afterflame time of Evaluation B, the fabric fire-treated with the aqueous dispersion prepared in Examples 1 to 13 was 0.5 to 2.9, whereas the aqueous prepared in Comparative Examples 1 to 5 was used. Fabrics subjected to flameproofing with the dispersion are 4.1 to 18.3 and have a long average afterflame time. Further, for the average burning area of Evaluation C, the fabric fire-treated with the aqueous dispersion prepared in Examples 1 to 13 was 3.6 to 4.7, whereas the aqueous prepared in Comparative Examples 1 to 5 was used. The fabric fireproofed with the dispersion is 7.1 to 33.6, and the average burning area is large.

  As is clear from Table 19, as in the aqueous dispersions prepared in Examples 1 to 11 and 13, the phosphorus compound of general formula (4), the compound of general formula (1), and general formula (2) When one compound selected from the group consisting of the compound of formula (3) and the compound of general formula (3) is combined, a high flameproofing effect is obtained.

Example 15
Preparation of aqueous dispersion having an average particle diameter of 0.899 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 diameter of 0.899 μm.
Table 20
Composition amount
Water 56.9%
Formula (201) (Compound of general formula (2)) 30.0%
Formula (213) (Ultraviolet absorber) 4.0%
Neugen EA-87 2.6%
Hightenol NE-05 5.8%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

Example 16
The mixture of the composition according to the average particle diameter of the preparation table 21 of an aqueous dispersion of 0.912Myuemu, wet ground using a sand grinder, to prepare an aqueous dispersion for comparison having an average particle size of 0.912μm.
Table 21
Composition amount
Water 56.9%
Formula (202) (Compound of general formula (1)) 30.0%
Formula (213) (Ultraviolet absorber) 4.0%
Neugen EA-87 2.6%
Hightenol NE-05 5.8%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

Example 17
Preparation of a dispersion having an average particle size of 0.894 μm A mixture having the composition described in Table 22 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.894 μm.
Table 22
Composition amount
Water 56.9%
Formula (203) (Compound of general formula (2)) 30.0%
Formula (213) (Ultraviolet absorber) 4.0%
Neugen EA-87 2.6%
Hightenol NE-05 5.8%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

Example 18
Preparation of aqueous dispersion having an average particle size of 0.909 μm A mixture having the composition shown in Table 23 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.909 μm.
Table 23
Composition amount
Water 56.9%
Formula (204) (Compound of general formula (3)) 30.0%
Formula (213) (Ultraviolet absorber) 4.0%
Neugen EA-87 2.6%
Hightenol NE-05 5.8%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

Example 19
Preparation of aqueous dispersion having an average particle diameter of 0.898 μm A mixture having the composition described in Table 24 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle diameter of 0.898 μm.
Table 24
Composition amount
Water 56.9%
Formula (205) (Compound of general formula (3)) 30.0%
Formula (213) (Ultraviolet absorber) 4.0%
Neugen EA-87 2.6%
Hightenol NE-05 5.8%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

Comparative Example 7
Preparation of aqueous dispersion having an average particle size of 0.957 μm A mixture having the composition described in Table 25 was wet-ground using a sand grinder to prepare a comparative aqueous dispersion having an average particle size of 0.957 μm.
Table 25
Composition amount
Water 56.9%
Formula (207) (Compound of general formula (4)) 30.0%
Formula (213) (Ultraviolet absorber) 4.0%
Neugen EA-87 2.6%
Hightenol NE-05 5.8%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

Comparative Example 8
Preparation of aqueous dispersion having an average particle size of 0.954 μm A mixture having the composition described in Table 26 was wet-ground using a sand grinder to prepare a comparative aqueous dispersion having an average particle size of 0.954 μm.
Table 26
Composition amount
Water 56.9%
Formula (208) (Compound of general formula (4)) 30.0%
Formula (213) (Ultraviolet absorber) 4.0%
Neugen EA-87 2.6%
Hightenol NE-05 5.8%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

Comparative Example 9
Preparation of aqueous dispersion having an average particle size of 0.978 μm A mixture having the composition described in Table 27 was wet-ground using a sand grinder to prepare a comparative aqueous dispersion having an average particle size of 0.978 μm.
Table 27
Composition amount
Water 56.9%
Formula (209) (Compound of general formula (4)) 30.0%
Formula (213) (Ultraviolet absorber) 4.0%
Neugen EA-87 2.6%
Hightenol NE-05 5.8%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

Comparative Example 10
Preparation of aqueous dispersion having an average particle size of 0.998 μm A mixture having the composition described in Table 28 was wet-ground using a sand grinder to prepare a comparative aqueous dispersion having an average particle size of 0.998 μm.
Table 28
Composition amount
Water 56.9%
Formula (210) 30.0%
Formula (213) (Ultraviolet absorber) 4.0%
Neugen EA-87 2.6%
Hightenol NE-05 5.8%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

Comparative Example 11
Preparation of aqueous dispersion having an average particle size of 0.945 μm A mixture having the composition described in Table 29 was wet-ground using a sand grinder to prepare a comparative aqueous dispersion having an average particle size of 0.945 μm.
Table 29
Composition amount
Water 56.9%
Formula (211) (Compound of general formula (4)) 30.0%
Formula (213) (Ultraviolet absorber) 4.0%
Neugen EA-87 2.6%
Hightenol NE-05 5.8%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

Example 20 and Comparative Example 12
Flameproofing of Polyester / CDP Blended Fiber Fabric with Aqueous Dispersion Using the aqueous dispersions prepared in Examples 15 to 19 and Comparative Examples 7 to 11, the same dyeing bath treatment as in Example 14 and Comparative Example 6 According to the method, 40 cm squares of a blended fiber fabric (CDP / PET blend fabric B) each containing 50% of CDP and other polyesters were dyed simultaneously and flameproofed.

Test example 2
Flame retardant test Polyester / CDP blended fiber fabric subjected to flameproofing in Example 20 or Comparative Example 12 using the aqueous dispersions prepared in Examples 15 to 19 and Comparative Examples 7 to 11 were the same as in Test Example 1. Thus, a flame retardancy test was conducted. The results are shown in Table 30.

  As is clear from the results of Table 30, the pass rate of evaluation A is 100% for all fabrics flameproofed with the aqueous dispersions prepared in Examples 15 to 19 of the present invention. Fabrics flameproofed with the aqueous dispersions prepared in Comparative Examples 7 to 11 containing a phosphate ester type compound such as the compound (4) alone are 0 to 82%, and flameproofing with the aqueous dispersions of the present invention The processed fabric has a higher acceptance rate. Regarding the average afterflame time of Evaluation B, the fabrics flame-proofed with the aqueous dispersions prepared in Examples 15 to 19 were 0.5 to 0.9, whereas the aqueouss prepared in Comparative Examples 7 to 11 were used. The fabric fireproofed with the dispersion is 2.5 to 18.3, the latter being about 3 to 37 times longer in average afterflame time. Further, for the average burning area of Evaluation C, the fabric fire-treated with the aqueous dispersion prepared in Examples 15 to 19 was 3.6 to 3.9, whereas the aqueous prepared in Comparative Examples 7 to 11 was used. The fabric fireproofed with the dispersion is 4.7-33.6, and the latter has an average burning area as large as 1.2-9.3 times.

Example 21
Preparation of aqueous dispersion having an average particle size of 0.502 μm A mixture having the composition described in Table 31 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.502 μm.
Table 31
Composition amount
Water 56.9%
Formula (220) (Compound of general formula (1)) 30.0%
Formula (213) (Ultraviolet absorber) 4.0%
Neugen EA-87 2.6%
Hightenol NE-05 5.8%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

Example 22
Preparation of aqueous dispersion having an average particle diameter of 0.602 μm A mixture having the composition described in Table 32 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle diameter of 0.602 μm.
Table 32
Composition amount
Water 56.9%
Formula (221) (Compound of general formula (1)) 30.0%
Formula (213) (Ultraviolet absorber) 4.0%
Neugen EA-87 2.6%
Hightenol NE-05 5.8%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

Example 23
Preparation of aqueous dispersion having an average particle size of 0.867 μm A mixture having the composition described in Table 33 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.867 μm.
Table 33
Composition amount
Water 56.9%
Formula (220) (Compound of general formula (1)) 15.0%
Formula (207) (Compound of general formula (4)) 15.0%
Formula (213) (Ultraviolet absorber) 4.0%
Neugen EA-87 2.6%
Hightenol NE-05 5.8%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Composition 100.0%

Example 24
Preparation of aqueous dispersion having an average particle size of 0.766 μm A mixture having the composition described in Table 34 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.766 μm.
Table 34
Composition amount
Water 56.9%
Formula (221) (Compound of general formula (1)) 15.0%
Formula (207) (Compound of general formula (4)) 15.0%
Formula (213) (Ultraviolet absorber) 4.0%
Neugen EA-87 2.6%
Hightenol NE-05 5.8%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

Example 25
Preparation of aqueous dispersion having an average particle diameter of 0.872 μm A mixture having the composition described in Table 35 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle diameter of 0.872 μm.
Table 35
Composition amount
Water 56.3%
Formula (221) (Compound of general formula (1)) 15.0%
Formula (207) (Compound of general formula (4)) 15.0%
Formula (213) (Ultraviolet absorber) 4.0%
Price Surf AL 9.0%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

Example 26
Preparation of aqueous dispersion having an average particle diameter of 0.888 μm A mixture having the composition described in Table 36 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle diameter of 0.888 μm.
Table 36
Composition amount
Water 56.3%
Formula (202) (Compound of general formula (1)) 15.0%
Formula (204) (Compound of General Formula (3)) 15.0%
Formula (213) (Ultraviolet absorber) 4.0%
Price Surf AL 9.0%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

Example 27
Preparation of aqueous dispersion having an average particle size of 0.997 μm A mixture having the composition described in Table 37 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.997 μm.
Table 37
Composition amount
Water 56.3%
Formula (202) (Compound of general formula (1)) 15.0%
Formula (207) (Compound of general formula (4)) 15.0%
Formula (213) (Ultraviolet absorber) 4.0%
Price Surf AL 9.0%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

Example 28
Flameproofing of polyester / CDP blended fiber fabric with aqueous dispersion Using the aqueous dispersion prepared in Examples 21 to 27, CDP and other polyesters were treated in the same manner as in Example 14 by the dip dyeing bath treatment method. Each 40 cm square of a blended fiber fabric (CDP / PET mixed fabric B) containing 50% each was dyed and fireproofed at the same time.

Test example 3
Flame Retardancy Test Using the aqueous dispersions prepared in Examples 21 to 27, a flame retardancy test was conducted in the same manner as in Test Example 1 on the polyester / CDP blended fiber fabric subjected to flameproofing in Example 28. . The results are shown in Table 38.

Example 29
Preparation of aqueous dispersion having an average particle size of 0.688 μm A mixture having the composition described in Table 39 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.688 μm.
Table 39
Composition amount
Water 56.9%
Formula (222) (Compound of general formula (1)) 30.0%
Formula (213) (Ultraviolet absorber) 4.0%
Prisurf AL Na salt 8.4%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

Example 30
Preparation of aqueous dispersion having an average particle diameter of 0.622 μm A mixture having the composition described in Table 40 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle diameter of 0.622 μm.
Table 40
Composition amount
Water 56.9%
Formula (223) (Compound of general formula (1)) 30.0%
Formula (213) (Ultraviolet absorber) 4.0%
Prisurf AL Na salt 8.4%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

Example 31
Preparation of aqueous dispersion having an average particle size of 0.660 μm A mixture having the composition described in Table 41 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.660 μm.
Table 41
Composition amount
Water 56.9%
Formula (224) (Compound of general formula (1)) 30.0%
Formula (213) (Ultraviolet absorber) 4.0%
Prisurf AL Na salt 8.4%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

Example 32
Flameproofing of polyester / CDP blended fiber fabric with aqueous dispersion Using the aqueous dispersion prepared in Examples 29-31, CDP and other polyesters were treated in the same manner as in Example 14 in the same dyeing bath treatment method. Each 40 cm square of a blended fiber fabric (CDP / PET mixed fabric A) containing 50% each was dyed and fireproofed at the same time.

Test example 4
Flame Retardancy Test Using the aqueous dispersions prepared in Examples 29-31, flame retardancy tests were conducted in the same manner as in Test Example 1 on the polyester / CDP blended fiber fabric subjected to flameproofing in Example 32. . The results are shown in Table 42.

Example 33
Preparation of aqueous dispersion having an average particle size of 0.901 μm A mixture having the composition shown in Table 43 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.
Table 43
Composition amount
Water 56.9%
Formula (222) (Compound of general formula (1)) 15.0%
Formula (211) (Compound of general formula (4)) 15.0%
Formula (213) (Ultraviolet absorber) 4.0%
Prisurf AL Na salt 8.4%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

Example 34
Preparation of aqueous dispersion having an average particle size of 0.769 μm A mixture having the composition described in Table 44 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.769 μm.
Table 44
Composition amount
Water 56.9%
Formula (223) (Compound of general formula (1)) 15.0%
Formula (211) (Compound of general formula (4)) 15.0%
Formula (213) (Ultraviolet absorber) 4.0%
Prisurf AL Na salt 8.4%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

Example 35
Preparation of aqueous dispersion having an average particle diameter of 0.862 μm A mixture having the composition described in Table 45 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle diameter of 0.862 μm.
Table 45
Composition amount
Water 56.9%
Formula (224) (Compound of general formula (1)) 15.0%
Formula (211) (Compound of general formula (4)) 15.0%
Formula (213) (Ultraviolet absorber) 4.0%
Prisurf AL Na salt 8.4%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

Example 36
Preparation of aqueous dispersion having an average particle diameter of 0.878 μm A mixture having the composition described in Table 46 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle diameter of 0.878 μm.
Table 46
Composition amount
Water 56.9%
Formula (202) (Compound of general formula (1)) 15.0%
Formula (222) (Compound of general formula (1)) 15.0%
Formula (213) (Ultraviolet absorber) 4.0%
Prisurf AL Na salt 8.4%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

Example 37
Preparation of aqueous dispersion having an average particle diameter of 1.004 μm A mixture having the composition described in Table 47 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle diameter of 1.004 μm.
Table 47
Composition amount
Water 56.9%
Formula (202) (Compound of general formula (1)) 15.0%
Formula (223) (Compound of general formula (1)) 15.0%
Formula (213) (Ultraviolet absorber) 4.0%
Prisurf AL Na salt 8.4%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

Example 38
Preparation of aqueous dispersion having an average particle size of 0.988 μm A mixture having the composition shown in Table 48 was wet-ground using a sand grinder to prepare an aqueous dispersion of the present invention having an average particle size of 0.988 μm.
Table 48
Composition amount
Water 56.9%
Formula (202) (Compound of general formula (1)) 15.0%
Formula (224) (Compound of general formula (1)) 15.0%
Formula (213) (Ultraviolet absorber) 4.0%
Prisurf AL Na salt 8.4%
Wetting agent 0.5%
Antifoam 0.1%
Antifungal agent 0.1%
Total 100.0%

Example 39
Flameproofing of Polyester / CDP Blended Fiber Fabric with Aqueous Dispersion Using the aqueous dispersion prepared in Examples 33 to 38, CDP and other polyesters were treated in the same manner as in Example 14 by the dip dyeing bath treatment method. Each 40 cm square of a blended fiber fabric (CDP / PET mixed fabric B) containing 50% each was dyed and fireproofed at the same time.

Test Example 5
Flame retardancy test Using the aqueous dispersions prepared in Examples 33 to 38, the flame retardancy test was conducted in the same manner as in Test Example 1 for the flameproofed polyester / CDP blended fiber fabric in Example 39. . The results are shown in Table 49.

  As is clear from Tables 47 to 49 showing the results of Test Examples 3 to 5, the pass rate of evaluation A was 100% for all fabrics flameproofed with the aqueous dispersion of the present invention, and the average residual of evaluation B was Regarding the flame time, the fabric flame-proofed with the aqueous dispersion of the present invention is 0.7 to 0.9, and the average burning area of Evaluation C is 3.6 to 4.6. Compared with the result of the treated cloth, the superior performance of the flameproofing agent of the present invention is shown.

  As described above, all the test results using the aqueous dispersion of the present invention show the excellent flameproof performance of the present invention. Further, it is apparent that the flameproofing agent of the present invention maintains the above-mentioned performance and is extremely excellent in durability despite repeated washing with water for 5 cycles.

  According to the present invention, it is possible to provide an aqueous dispersion of a non-halogen flameproofing agent capable of imparting durable and excellent flameproofing performance to fibers, particularly CDP and other polyester blended fibers.

Claims (19)

1 to 3 phosphorus compounds selected from the group consisting of phosphine oxide represented by general formula (1), phosphine represented by general formula (2) and phosphite represented by general formula (3), and An aqueous dispersion containing a surfactant.

(Wherein R ₁₁ , R ₁₂ and R ₁₃ are each independently a (C1-C8) alkyl group, or a hydroxyl group, amino group, cyano group, carboxyl group, ureido group, (C1-C4) alkyl group, di- (C1-C4) represents an aryl group optionally substituted by an alkylamino group, diphenylamino group, aryl group, phenoxy group or (C1-C4) alkoxy group.

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, An aryl group that may be substituted with a diphenylamino group, an aryl group, a phenoxy group, or a (C1-C4) alkoxy group is shown.

(Wherein R ₃₁ , R ₃₂ and R ₃₃ are each independently 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, An aryl group that may be substituted with a diphenylamino group, an aryl group, a phenoxy group, or a (C1-C4) alkoxy group is shown.   Claim which contains 1 type of phosphorus compound chosen from the group which consists of the phosphine oxide represented by General formula (1), the phosphine represented by General formula (2), and the phosphite represented by General formula (3). Item 4. An aqueous dispersion according to Item 1. Furthermore, the aqueous dispersion liquid of Claim 1 or 2 containing the phosphoric acid ester represented by General formula (4) as a phosphorus compound.

Wherein R ₄₁ , R ₄₂ and R ₄₃ are each independently a hydroxyl group, amino group, cyano group, carboxyl group, ureido group, (C1-C4) alkyl group, di (C1-C4) alkylamino group, An aryl group that may be substituted with a diphenylamino group, an aryl group, a phenoxy group, or a (C1-C4) alkoxy group is shown.   One phosphorus compound selected from the group consisting of phosphine oxide represented by general formula (1), phosphine represented by general formula (2) and phosphite represented by general formula (3), and general formula ( The aqueous dispersion according to any one of claims 1 to 3, comprising a phosphate ester represented by 4).   Furthermore, the aqueous dispersion liquid as described in any one of Claims 1-4 containing a ultraviolet absorber.   Group consisting of phosphine oxide represented by general formula (1), phosphine represented by general formula (2), phosphite represented by general formula (3) and phosphate ester represented by general formula (4) The aqueous dispersion according to claim 1, wherein the phosphorous compound selected from 1 to 90% by weight is contained in the aqueous dispersion in a total amount.   An aqueous dispersion containing one phosphorus compound selected from the group consisting of a phosphine oxide represented by general formula (1), a phosphine represented by general formula (2), and a phosphite represented by general formula (3) The aqueous dispersion according to claim 6, containing 0.1 to 89.9% by weight.   Furthermore, the aqueous dispersion of Claim 7 which contains 0.1-89.9 weight% of phosphate ester represented by General formula (4) in an aqueous dispersion.   The aqueous dispersion according to any one of claims 1 to 8, wherein the surfactant is a nonionic surfactant and / or an anionic surfactant.   The aqueous dispersion as described in any one of Claims 1-9 which contains 0.1-10 weight% of ultraviolet absorbers in an aqueous dispersion.   The surfactant is contained in an amount of 5 to 200% by weight based on the total amount of the phosphorus compound and the ultraviolet absorber when the ultraviolet absorber is contained relative to the amount of the phosphorus compound. The aqueous dispersion as described in any one of Claims.   A phosphine oxide represented by the general formula (1) according to claim 1, a phosphine represented by the general formula (2) and a phosphite represented by the general formula (3). A composition containing a phosphorus compound and a surfactant.   Furthermore, the composition of Claim 12 containing the phosphate ester represented by General formula (4) of Claim 2.   A flameproofing agent using the aqueous dispersion according to any one of claims 1 to 11.   The flameproofing agent according to claim 14, which is used for fibers.   The flameproofing agent according to claim 15, wherein the fiber is a polyester fiber.   The flameproofing agent according to claim 16, wherein the polyester fiber is a cationic dyeable polyester fiber or a blended fiber containing a cationic dyeable polyester fiber.   A flameproofing method for fibers, comprising treating polyester fibers with the aqueous dispersion according to any one of claims 1 to 11. A fiber which has been flameproofed by the method according to claim 18.