TW201002729A

TW201002729A - Aqueous dispersions of organic phosphorous compounds and flame retarding modification method using the dispersions

Info

Publication number: TW201002729A
Application number: TW98110153A
Authority: TW
Inventors: Hidehiro Arai; Asako Kondo; Shinya Nagatsuka
Original assignee: Nippon Kayaku Kk
Priority date: 2008-03-28
Filing date: 2009-03-27
Publication date: 2010-01-16
Also published as: WO2009119789A1; CN101981157A; JPWO2009119789A1; CN101981157B

Abstract

Disclosed is an aqueous dispersion that provides excellent and durable flameproof performance to fibers, in particular, to CDP and polyester fibers, and includes a surfactant and at least one of the following organic phosphorus compounds or salts thereof: a phosphinic acid ester compound represented by formula (1), a phosphinic acid ester compound represented by formula (2), a phosphinic acid amide compound represented by formula (3), a phosphinic acid amide compound represented by formula (4), a phosphinic diamide compound represented by formula (5). (In the formulas, R11, R12, R13, R21, R22, R23, R31, R32, R33, R34, R41, R42, R43, R44, R51, R52, R53, R54, and R55 represent phenyl groups and the like.)

Description

201002729 六、發明說明【發明所屬之技術領域】本發明係關於一種有機磷系化合物之用其之阻燃加工方法。更詳細言之，本發合成纖維構造物中利用有機磷系化合物而性之阻燃功能之阻燃加工用之水性分散液 ’以及使用其進行阻燃加工之纖維、以及化合物。【先前技術】傳統上，在纖維藉由後加工處理而賦法’已知有將鹵系化合物分散於水中作成使用其將纖維進行阻燃加工之方法。上述代表例，例如有 1,2,5,6，9，1 0 -六溴環十二烷類。鹵系化合物之阻燃功能，已知一般經阻燃加工之纖維燃燒時，會發生有害之對於人體及自然環境產生有害之影響等問使用鹵系化合物以作爲阻燃劑者，已受到因此’有提案使用有機磷酸酯之類的取代鹵系化合物而作爲阻燃劑，以及提案纖維之阻燃加工方法等（專利文獻1至4 ) 然而，在使用此等磷系化合物時，並其是CDP (陽離子可染型聚酯）纖維及聚維’或被賦予了抗菌加工、消臭加工、表水性分散液及使明係關於一種在賦予具優良耐久及阻燃加工方法新穎之有機磷系予阻燃功能之方阻燃加工劑，而之鹵系化合物之烷之類的溴化環係較高者，惟如鹵化氣體，此會題。從而，近年規制。磷系化合物，以使用該阻燃劑之〇無法在纖維，尤酯纖維之混紡纖面加工等各種功 -5- 201002729 能性之纖維上，再賦予其充分之阻燃功能。此外，專利文獻5中記載了膦酸萘基酯化合物來作爲阻燃用磷系化合物，惟有耐光性低等之問題點。再者，非專利文獻1至2中記載了膦酸化合物，惟其並未記載阻燃功能。專利文獻1 :特開200 1 -254268號公報專利文獻2 :特開2000-328445號公報專利文獻3 :特開2004-225176號公報專利文獻4 :特開2006-704 1 7號公報專利文獻5 :特開2007 -2 3 9 1 0 8號公報非專利文獻 1 : Phosphorus and Sulfur and the Related Elements, 2 9 ( 2-4 )，1 69- 1 7 8 ( 1 9 8 7 ) 非專利文獻 2: J. 〇rg. Chem·，23, 1889-1893 ( 1958 【發明內容】發明之揭不發明所欲解決之課題本發明之課題，提供一種在纖維，尤其是CDP纖維及聚酯纖維之混紡纖維’或賦予功能性之纖維上，可賦予具優良耐久性之阻燃功能的阻燃加工用之水性分散液及阻燃加工方法，以及藉由其進行阻燃加工之纖維、以及新穎之有機磷系化合物。 201002729 解決課題之手段本發明者們，爲解決上述課題而重複進行努力檢討之結果，發現了藉由使用特定之有機磷系化合物’可對纖維賦予具優良耐久性之阻燃功能者，從而完成了本發明。亦即，本發明係關於以下之[1]〜[15]。 [1 ] 一種水性分散液，其特徵係含有：選自下式（1 )所示之次膦酸酯化合物【化1】〇201002729 VI. Description of the Invention [Technical Field] The present invention relates to a flame-retardant processing method for an organophosphorus compound. More specifically, the present invention relates to an aqueous dispersion for flame-retardant processing using an organophosphorus compound-based flame retardant function, and a fiber and a compound which are subjected to flame-retardant processing. [Prior Art] Conventionally, a method in which a fiber is subjected to a post-processing treatment is known to disperse a halogen-based compound in water to perform flame-retardant processing using the fiber. Representative examples of the above are, for example, 1,2,5,6,9,10-hexabromocyclododecane. The flame-retardant function of the halogen-based compound is known to cause harmful effects on the human body and the natural environment when the fiber is generally burned by the flame-retardant processing, and the halogen-based compound is used as a flame retardant. It is proposed to use a halogen-substituted compound such as an organic phosphate as a flame retardant, and a flame-retardant processing method of the proposed fiber (Patent Documents 1 to 4). However, when such a phosphorus-based compound is used, it is a CDP. (Cation-dyeable polyester) fiber and poly-dimensional 'or imparted antibacterial processing, deodorizing processing, surface aqueous dispersion, and an organic phosphorus system which is novel in imparting excellent durability and flame-retardant processing methods. The flame retardant functional party is a flame retardant processing agent, and the brominated ring system such as a halogen compound is higher, such as a halogenated gas, this problem. Thus, regulation in recent years. Phosphorus-based compounds, which are used in the use of the flame retardant, are not able to impart sufficient flame retardancy to fibers of various fibers such as fibers and blended fibers of the polyester fibers. Further, Patent Document 5 discloses a phosphonyl naphthyl ester compound as a phosphorus-based compound for flame retardancy, and has problems such as low light resistance. Further, Non-Patent Documents 1 to 2 disclose a phosphonic acid compound, but the flame retarding function is not described. [Patent Document 1] Japanese Laid-Open Patent Publication No. JP-A-2004-225176 (Patent Document No. JP-A-2006-225176) Patent Document 4: JP-A-2006-704 No. JP-A-2007-2 3 9 1 0 8 Non-Patent Document 1: Phosphorus and Sulfur and the Related Elements, 2 9 ( 2-4 ), 1 69- 1 7 8 (1 9 8 7 ) Non-Patent Document 2 : J. 〇rg. Chem·, 23, 1889-1893 (1958) SUMMARY OF THE INVENTION Problem to be Solved by the Invention The object of the present invention is to provide a blend of fibers, especially CDP fibers and polyester fibers. An aqueous dispersion for flame retardant processing and a flame-retardant processing method, and a fiber for flame-retardant processing, and novel organics, which are imparted to the fiber of the fiber or the functional fiber. In order to solve the above problems, the inventors of the present invention have repeatedly conducted an effort to review the results, and have found that a flame retardant function with excellent durability can be imparted to fibers by using a specific organophosphorus compound. And thus finish The present invention relates to the following [1] to [15]. [1] An aqueous dispersion characterized by comprising: a phosphinate compound selected from the following formula (1) [ 1] 〇

IIII

Rn—P—OR13 ⑴Rn—P—OR13 (1)

Rl2 (式中，Rii、Ri2、及Ris係各自獨立地爲可被取代基群A加以取代之芳基、或（C 1 -C 1 0 )烷基，其中，取代基群A係羥基、硝基、胺基、氰基、甲醯基、羧基、腺、（C1-C10)烷基、（C1-C10)烷基胺基、二（CKCl(] ( )烷基胺基、苯基、苯氧基及（Cl-CIO)烷氧基）；及下式（2 )所示之膦酸酯化合物【化2】 ΟRl2 (wherein Rii, Ri2, and Ris are each independently an aryl group or a (C 1 -C 1 0 ) alkyl group which may be substituted with a substituent group A, wherein the substituent group A is a hydroxyl group or a nitrate Base, amine group, cyano group, formyl group, carboxyl group, gland, (C1-C10) alkyl group, (C1-C10)alkylamino group, bis(CKCl(]()(alkyl) group, phenyl group, benzene An oxy group and a (Cl-CIO) alkoxy group; and a phosphonate compound represented by the following formula (2) [Chemical 2] Ο

II ^21—P—〇尺23 (2) OR22 (式中，Rm係可被取代基群A加以取代之芳基、$ 被取代基群A加以取代之（C7-C15 )芳烷基、或（ C10 )烷基；R22係可被取代基群A加以取代之苯基 11 · 201002729 被取代基群 A加以取代之（C7-C15 )芳烷基、或（Cl-C10 )烷基；R23係可被取代基群A加以取代之苯基、可被取代基群 A加以取代之（C7-C15)芳烷基、或（C1-C10)烷基（該烷基，亦可藉由：可被取代基群A加以取代之芳基氧基、可被取代基群A加以取代之（C7-C15 )芳院基氧基、或（C 1 -C 1 0 )烷氧基，加以取代者）；其中，取代基群A係與上述定義相同者）：及下式（3 )所示之次膦酸醯胺化合物【化3】〇II ^21—P—〇 23 (2) OR22 (wherein Rm is an aryl group which may be substituted with a substituent group A, a (C7-C15) aralkyl group substituted with a substituent group A, or (C10)alkyl; R22 is a phenyl group which may be substituted by a substituent group A. · 201002729 (C7-C15) aralkyl group substituted by a substituent group A, or (Cl-C10) alkyl group; R23 system a phenyl group which may be substituted with a substituent group A, a (C7-C15) aralkyl group which may be substituted with a substituent group A, or a (C1-C10) alkyl group (the alkyl group may also be: a substituted aryloxy group of the group A, a (C7-C15) aryloxy group substituted by the substituent group A, or a (C 1 -C 1 0 ) alkoxy group, substituted); Wherein the substituent group A is the same as defined above: and the phosphinic acid amide compound represented by the following formula (3) [Chemical 3] 〇

II ^31 一P—NR33R34 (3) R32 C式中，R3!、R32、及R33係各自獨立地爲可被取代基群A加以取代之芳基、或（cl_cl〇)烷基，R34係氫原子可被取代基群A加以取代之芳基、或（C1-C10)院基其中’取代基群A係與上述定義相同者）：及下式（4 )所示之膦酸醯胺化合物【化4】 0II ^31 -P-NR33R34 (3) R32 Formula wherein R3!, R32, and R33 are each independently an aryl group which may be substituted with a substituent group A, or a (cl_cl〇) alkyl group, and a hydrogen atom of R34 An aryl group in which an atom may be substituted with a group A, or a (C1-C10) group wherein the 'substituent group A is the same as defined above): and a phosphonium amide compound represented by the following formula (4) [ 4] 0

II R41—P—NR43R44 (4) OR42 (式中 &取代基群 Cl〇)烷基；II R41—P—NR43R44 (4) OR42 (wherein & substituent group Cl〇)alkyl;

Ru係可被取代基群A加以取代之芳基、可 A加以取代之（C7-C15 )芳烷基、或（ci_ R42係可被取代基群A加以取代之芳基、可 -8- 201002729 被取代基群 A加以取代之（C7-C15)芳烷基、或（Cl-C10)烷基（該烷基，亦可藉由：可被取代基群A加以取代之芳基氧基、可被取代基群A加以取代之（C7-C 15 )芳烷基氧基、或（C1-C10 )烷氧基，加以取代者）；R43係可被取代基群A加以取代之芳基、可被取代基群A加以取代之（C7-C15 )芳烷基、或（CM-C10 )烷基；R44係氫原子、可被取代基群A加以取代之芳基、可被取代基群a 加以取代之（C7-C 1 5 )芳烷基 '或可被取代基群A加以取代之（C 1 -C 1 0 )烷基’其中’取代基群A係與上述定義相同者）：以及下式（5 )所示之膦酸二醯胺【化5】 0Ru is an aryl group which may be substituted with a substituent group A, a (C7-C15) aralkyl group which may be substituted with A, or (an aryl group which may be substituted by a substituent group A, -8-802702729) a (C7-C15) aralkyl group or a (Cl-C10) alkyl group substituted with a substituent group A (the alkyl group may also be an aryloxy group which may be substituted by the substituent group A, a (C7-C 15 ) aralkyloxy group substituted with a substituted group A or a (C1-C10 ) alkoxy group substituted with a group); R43 is an aryl group which may be substituted with a substituent group A, a (C7-C15) aralkyl group or a (CM-C10) alkyl group substituted with a substituent group A; an R44-based hydrogen atom, an aryl group which may be substituted by the substituent group A, may be subjected to a substituent group a Substituted (C7-C 1 5 )Aralkyl' or a (C 1 -C 1 0 )alkyl group which may be substituted by a substituent group A wherein 'the substituent group A is the same as defined above): Phosphonic acid diamine of formula (5) [Chemical 5] 0

II R51—P—NR53R54 (5) NR52R55 (式中’ RS1、R52、及R53係各自獨立地爲可被取代基群A加以取代之芳基、或（Cl-cio)烷基，r54及R55 係各自獨立地爲氣原子、可被取代基群A加以取代之芳基、或（C1-C10)烷基，其中，取代基群八係與上述定義相同者）中，至少1種之有機磷系化合物或其等之鹽，以及界面活性劑者。 [2 ]如上述[1 ]之水性分散液’其中可被取代基群A加以取代之芳基係（C1-C10)烷基苯基、聯苯基或（C1-C10 201002729 )院氧基苯基。 [3 ]如上述[1 ]或[2 ]之水性分散液，其中在水性分散液中以總量計，係含有1至90重量％之式（1 )至式（5 )所示之有機磷系化合物者。 [4 ]如上述[1 ]〜[3 ]中任一者之水性分散液，其中界面活性劑係非離子型界面活性劑或陰離子型界面活性劑或其二者。 [5 ]如上述[1 ]〜[4 ]中任一者之水性分散液，其中係進而含有紫外線吸收劑者。 [6 ]如上述[1 ] ~ [ 5 ]中任一者之水性分散液，其中係作爲纖維用之阻燃劑而使用者。 [7] 如上述[6]之水性分散液，其中纖維係聚酯纖維者〇 [8] 如上述[7]之水性分散液，其中聚酯纖維係陽離子可染型聚酯纖維或含有陽離子可染型聚酯纖維之混紡纖維者。 [9] 一種纖維之阻燃加工方法，其特徵係使用上述 [1]〜[8]中任一者之水性分散液者。 [10] —種纖維，其特徵係以上述[9]之方法加以阻燃加工者。 [11] 一種下式（2)所示之膦酸酯化合物或其鹽， -10- 201002729 【化6】 ΟII R51—P—NR53R54 (5) NR52R55 (wherein 'RS1, R52, and R53 are each independently an aryl group which may be substituted with a substituent group A, or a (Cl-cio) alkyl group, r54 and R55 systems At least one of the organophosphorus, each of which is independently a gas atom, an aryl group which may be substituted with a substituent group A, or a (C1-C10) alkyl group, wherein the substituent group is the same as defined above) a compound or a salt thereof, and a surfactant. [2] An aqueous dispersion of the above [1], wherein an aryl group (C1-C10) alkylphenyl group, a biphenyl group or a (C1-C10 201002729) polyoxybenzene which may be substituted with a substituent group A base. [3] The aqueous dispersion of the above [1] or [2], wherein the total amount of the organic phosphorus represented by the formula (1) to the formula (5) is 1 to 90% by weight in the aqueous dispersion. The compound is a compound. [4] The aqueous dispersion according to any one of [1] to [3] wherein the surfactant is a nonionic surfactant or an anionic surfactant or both. [5] The aqueous dispersion according to any one of the above [1] to [4] wherein the ultraviolet absorber is contained. [6] The aqueous dispersion of any one of the above [1] to [5], which is used as a flame retardant for fibers. [7] The aqueous dispersion according to the above [6], wherein the fibrous polyester fiber is [8], the aqueous dispersion of the above [7], wherein the polyester fiber is a cationic dyeable polyester fiber or contains a cation Blended fiber of dyed polyester fiber. [9] A flame-retardant processing method for fibers, which is characterized by using the aqueous dispersion of any one of the above [1] to [8]. [10] A fiber which is characterized in that it is flame-retarded by the method of the above [9]. [11] A phosphonate compound represented by the following formula (2) or a salt thereof, -10- 201002729 [Chemical 6] Ο

D II R21—P—〇R23 (2) OR22 (式中’ RS1係可被取代基群A加以取代之芳基、或可被取代基群A加以取代之（C7-C15)芳烷基；R22係可被取代基群A加以取代之苯基、可被取代基群a加以取代之（C7-C15 )芳烷基、或（cl_ci〇 )烷基；r23係可被取代基群A加以取代之苯基、可被取代基群a加以取代之（C7-C15)芳烷基、或（cl_cl〇)烷基（該烷基’亦可藉由：可被取代基群A加以取代之芳基氧基、可被取代基群A加以取代之（C7_C15 )芳烷基氧基、或（cl_c1〇 ) 院氧基，加以取代者）；其中’取代基群A係與上述定義相同者）：或式（4 )所示之膦酸醯胺化合物【化7】 0D II R21—P—〇 R23 (2) OR22 (wherein RS1 is an aryl group which may be substituted with a substituent group A, or a (C7-C15) aralkyl group which may be substituted with a substituent group A; R22 a phenyl group which may be substituted with a substituent group A, a (C7-C15) aralkyl group which may be substituted with a substituent group a, or a (cl_ci〇) alkyl group; the r23 system may be substituted with a substituent group A a phenyl group, a (C7-C15) aralkyl group or a (cl_cl〇) alkyl group which may be substituted with a substituent group a (the alkyl group ' may also be an aryl oxygen group which may be substituted by the substituent group A a (C7_C15) aralkyloxy group or a (cl_c1〇) alkoxy group which may be substituted by a substituent group A, wherein the 'substituent group A is the same as defined above): or a formula (4) The phosphonium amide compound shown in the formula [Chemical 7] 0

II ^41 P—NR43R44 (4) OR42 (式中’ Ru係可被取代基群A加以取代之芳基、可被取代基群A加以取代之（C7-C15 )芳烷基；R42係可被取代基群A加以取代之芳基、可被取代基群A加以取代之（C7-C15)芳烷基、或（C1-C10)烷基（該烷基，亦可 _由：可被取代基群A加以取代之芳基氧基、可被取代基 -11 - 201002729 群A加以取院氧基’加以之芳基、可被或（C1-C10 ) 取代之（C7-( (C1-C10)院 )° [12]如上可被羥基、硝 )烷氧基加以烷基、苯基或羥基、硝基、氧基加以取代 C1-C6 )烷基基、苯基或（基、氰基、甲、苯氧基或（基：R 2 3係可 C1-C6 )烷氧 3 (C1-C6 )烷. 基或脲基加以、甲醯基、竣或（C 1 - C 6 ) % [1 3 ]如上代之（C7-C15)芳烷基氧基、或（C1-C10) 取代者）；R43係可被取代基群A加以取代取代基群A加以取代之（c 7 - C 1 5 )芳烷基、烷基；R44係氫原子、可被取代基群A加以〕1 5 )芳烷基、或可被取代基群a加以取代之 :基’其中’取代基群A係與上述定義相同者述Π1]之膦酸酯化合物或其鹽，其中r21係基、氰基、（C1-C6)院基、苯基或（C1-C6 取代之苯基；可被羥基、氰基、（C1-C6 ) (C1-C6 )烷氧基加以取代之萘基；或可被氰基、（C1-C6)烷基、苯基或（C1_C6)烷之（C 7 - c 1 2 )芳烷基；R 2 2係可被硝基、（、（C 1 - C 6 )烷基胺基、二（c丨-C 6 )烷基胺 C1_C6 )烷氧基加以取代之苯基；或可被羥醯基、羧基、脲基、（C1-C6)烷基、苯基 ci-co烷氧基加以取代之（C7_C12)芳烷被經基、氰基、（C1_C6)烷基、苯基或（ S加以取代之（C7-Cl2)芳烷基氧基；可被 I基、羥基、胺基、（C1_C6)烷基胺基、羧取代之（C1-C6 )烷基；或可被羥基、氰基基、脲基、（C1-C6)烷基、苯基、苯氧基宅氧基加以取代之（C7_C12)芳院基。述[11]或[12]之膦酸酯化合物或其鹽，其中 -12- 201002729 R2,係苯基、甲苯基、硝基苯基、硝基苄基、或聯苯基；尺22係可被（C1_C6)烷基、硝基、或苯基加以取代之苯基 ;R23係可被苯氧基加以取代之（Cl-C6)烷基、节基或苯乙基。 [14]如上述[11]之膦酸醯胺化合物或其鹽，其中R41 係可被羥基、氰基、（C1_C6)烷基、苯基或（C1_C6)烷氧基加以取代之苯基；可被羥基'氰基、（C1-C6)院基、本基或（C1_c6)烷氧基加以取代之萘基；或可被經基、硝基、氰基、（CM-C6)烷基、苯基或（C1_C6 )烷氧基加以取代之（c 7 - C 1 2 )芳烷基；R 4 2係可被羥基、胺基、氰基、（C1-C6)烷基、（C1-C6)烷基胺基、二（C1_C6 )烷基胺基、苯基、苯氧基、（C7-C12)芳烷基或（C1· C6)院氧基加以取代之苯基、可被羥基、胺基、氰基、（ C1-C6)烷基、（C1-C6)烷基胺基、二（Ci_C6)烷基胺基、苯基、苯氧基、（C7-C12)芳烷基或（C1-C6)烷氧基加以取代之萘基、可被羥基、氰基、甲醯基、羧基、脲基、（CH-C0)院基、苯基、苯氧基或（C1-C6)烷氧基加以取代之（C7-C12)芳烷基、或可被苯氧基加以取代之（ C1-C6)烷基；R43係可被羥基、胺基、氰基、（C1-C6) 烷基、（C1-C0)烷基胺基、二（C1-C6)烷基胺基、苯基、苯氧基或（C1-C6 )烷氧基加以取代之苯基、可被羥基、胺基、氰基、（C1-C6)烷基、（CM-C6)烷基胺基、二 (C1-C6)烷基胺基、苯基、苯氧基或（C1-C6)烷氧基加以取代之萘基、或可被羥基、氰基、甲醯基、羧基、脲基 -13- 201002729 、（C1-C6)烷基、苯基、苯氧基或（C1-C6)烷氧基力口以取代之（C7-C12)芳烷基；係（CM-C6)烷基或氫原子。 [15]如上述[11]或[14]之鱗酸酿胺化合物或其鹽，其中R41係苯基、p-甲氧基苯基、或苄基；R42係可被（Cl_ C6)院基、苯基、节基、苯乙基或苯基丙基加以取代之苯基、萘基；可被羥基、氰基、甲醯基、羧基、脲基、（ C1-C6)垸基、苯基、苯氧基或（C1-C6)烷氧基加以取代之（C7-C12)芳烷基或2-苯氧基乙基；R43係苯基、苄基或苯乙基；R44係甲基、乙基或氫原子。本發明所提供之含有前述式（1)至（5)所示之有機磷系化合物與界面活性劑之水性分散液，由於其作爲阻燃劑優良，且使用其在纖維上施以阻燃加工之故，而能賦予具有耐光性、耐久性之優良阻燃功能。此外’前述式（2 )及（4)所示之有機磷系化合物中之大部分之膦酸酯化合物及膦酸酯醯胺化合物，係新穎之化合物。【實施方式】實施發明之最佳型態以下，茲詳細地說明本發明。本發明中，（Cl-C10)烷基，係碳數1至1〇之直鏈、分枝鏈、環狀之院基，例如有甲基、乙基、η -丙基、異丙基、η-丁基、s-丁基、異丁基、t_ 丁基、η_戊基、η_己基、η-辛基、η-癸基、環丙基、環戊基、環己基等。（ci- -14- 201002729 C6)烷基，係碳數丨至6之直鏈、分枝鏈、環狀之烷基，例如有甲基、乙基、n-丙基、異丙基、η-丁基、s-丁基、異丁基、t-丁基、η-戊基、環丙基、環戊基、環己基等。本發明中’ （C1-C10)烷氧基，係上述之（ci-CIO) 烷基結合於氧原子之基’例如有甲氧基、乙氧基、η-丙氧基、異丙氧基、η· 丁氧基、s-丁氧基、t-丁氧基、η-戊基氧基、η-己基氧基、η-辛基氧基、心癸基氧基、環戊基氧基、環己基氧基等。（CM-C6)烷氧基，係上述之（C1-C6 )烷基結合於氧原子之基’例如有甲氧基、乙氧基、η-丙氧基、異丙氧基、η -丁氧基、s -丁氧基、t_ 丁氧基、η -戊基氧基、η -己基氧基、環戊基氧基、環己基氧基等。本發明中，（C1-C10)烷基胺基，係上述之（C1-C10 )烷基1個結合於氮原子之基，例如有甲基胺基、乙基胺基、η -丙基胺基、異丙基胺基、η_ 丁基胺基、卜丁基胺基、η-戊基胺基、η-己基胺基、η_辛基胺基、η_癸基胺基、環丙基胺基、環戊基胺基、環己基胺基等。（C1-C6)烷基胺基’係上述之（C1-C6)烷基1個結合於氮原子之基，例如有甲基胺基、乙基胺基、η -丙基胺基、異丙基胺基、η -丁基胺基、t -丁基胺基、η戊基胺基、η·己基胺基、環戊基胺基、環己基胺基等。本發明中’二（C1-C10)烷基胺基，係上述之（C1-C10)烷基2個結合於氮原子之基，例如有二甲基胺基、二乙基胺基、二（η-丙基）胺基、二異丙基胺基、二（η_ 丁基）胺基、二（t -丁基）胺基、二（η_戊基）胺基、二 -15- 201002729 (η -己基）胺基、二（n_辛基）胺基、二（n -癸基）胺基、二環丙基胺基、二環戊基胺基、二環己基胺基等。二（ C1-C6 )烷基胺基，係上述之（Ci_C6 )烷基2個結合於氮原子之基’例如有二甲基胺基、二乙基胺基、二（η -丙基 )胺基、二異丙基胺基、二（η-丁基）胺基、二（t-丁基 )胺基、二（η-戊基）胺基、二（n_己基）胺基、二環戊基胺基、二環己基胺基等。本發明中之芳基，例如有苯基、萘基等。本發明中，（C7-C15)芳烷基，係在苯基、萘基等上結合了烷基之基，例如有苄基、苯乙基、苯基丙基、苯基丁基、苯基戊基、苯基己基、苯基辛基、萘基甲基、萘基乙基、萘基丙基等。（C7-C12 )芳烷基，例如有苄基、苯乙基、苯基丙基、苯基丁基、苯基戊基、萘基甲基、萘基乙基等。本發明中，芳基氧基，例如有苯基氧基或萘基氧基等〇本發明中’ （C7-C15)芳烷基氧基，係在上述（C7- C15)芳烷基上結合了氧原子之基，例如有苄基氧基、苯乙基氧基、苯基丙基氧基、苯基丁基氧基、苯基戊基氧基 '苯基己基氧基、苯基辛基氧基、萘基甲氧基、萘基乙氧基、萘基丙基氧基等。（C7-C12)芳院基氧基，係在上述 (C7-C12)芳烷基上結合了氧原子之基，例如有节基氧基、苯乙基氧基、苯基丙基氧基、苯基丁基氧基、苯基戊基氧基、萘基甲氧基、萘基乙氧基等。 -16- 201002729 本發明中，所謂之取代基群A，係指羥基、硝基、胺基、氰基、甲醯基、殘基、脲基、（C1-C10)院基、（ C1-C10)烷基胺基、二（C1-C10)烷基胺基、苯基、苯氣基及（C1-C10)烷氧基。由此等之取代基群A選擇之取代基，一般可於各官能基上取代1個至3個。其中，在本發明中可以取代基群A加以取代之芳基，係以（Cl-C10)烷基苯基、聯苯基或（Cl-C10)烷氧基苯基、苯氧基苯基、硝基苯基等爲最佳。本發明之阻燃加工上使用之水性分散液中所含之前述式（1)至（5)所示之有機磷系化合物中，至R13、 R31至R33、r41至r43、r51至r53之較佳之基，例如有苯基、甲基苯基、聯苯基、甲氧基苯基、苯氧基苯基、苄基，其中又以苯基、聯苯基、甲氧基苯基爲最佳。R34、R44 、R54、R55 ’係以氫原子爲較佳。r21至r23，例如以苯基、甲基苯基、甲氧基苯基、硝基苯基、苯氧基苯基、苄基、聯苯基、硝基苄基爲較佳，並以苯基、聯苯基、甲氧基苯基爲最佳。以下’在本發明所含之前述式（2 )所示之化合物中 ’茲就新穎之磷系化合物加以說明。亦即’在式（2 )之中，r2 1係可被取代基群A加以取代之芳基、或可被取代基群A加以取代之（C7-C15 )芳烷基；R22係可被取代基群A加以取代之苯基、可被取代基群A加以取代之（c7_ci5 )芳烷基、或（C1-C10)烷基 ;R23係可被取代基群A加以取代之苯基、可被取代基群 -17- 201002729 A加以取代之（C7-C15)芳烷基、或（C卜CIO)烷基（該烷基，亦可藉由：可被取代基群A加以取代之芳基氧基、可被取代基群A加以取代之（C7-C1 5 )芳烷基氧基、或（ C 1 -C 1 0 )烷氧基，加以取代者），所成之膦酸酯化合物，係新穎化合物者。其中’ Rii係可被經基、氰基、硝基、（C1-C6)院基、苯基或（C 1 - C 6 )烷氧基加以取代之苯基；可被羥基、氰基、（C1-C6)烷基、苯基或（C1-C6)烷氧基加以取代之萘基；或可被羥基、硝基、氰基、（C1-C6 )烷基、苯基或（C1-C6 )烷氧基加以取代之（C7-C12 )芳烷基；r22 係可被硝基、（C1-C6)烷基、（C1-C6)烷基胺基、二（ C1-C6)烷基胺基、苯基或（C1_C6)烷氧基加以取代之苯基；或可被羥基、氰基、甲醯基、羧基、脲基、（ci-C6 )院基、苯基、苯氧基或（C1-C6)烷氧基加以取代之（ C7_C12)芳院基；r23係可被經基、氰基、（ci_C6)院基、苯基或（C1-C6 )烷氧基加以取代之（C7-C12 )芳院基氧基；可被（C1-C6)烷氧基、羥基、胺基、（C1_C6) 院基胺基、羧基或脲基加以取代之（C ! _C6 )院基；或可被羥基、氰基、甲醯基、羧基、脲基、（C1_C6)烷基、本基、本氧基或（C1-C6)院氧基加以取代之（C7-C12) 芳院基；所成之膦酸酯化合物爲較佳。再者，R21係苯基、甲苯基、硝基苯基、硝基苄基、或聯苯基；R22係可被硝基、（C1-C6)烷基、或苯基加以取代之苯基；R23係可被苯基、苯氧基加以取代之（C1_C6 )烷基、节基或苯乙 -18- 201002729 基；所成之膦酸酯化合物爲最佳。其中’又以式（2 )中之係苯基、甲基苯基、聯苯基、甲氧基苯基、硝基苯基、苄基、硝基苄基、苯乙基爲較佳；並以苯基、甲基苯基、苄基爲更佳；再以苯基爲最佳。R22係苯基、甲基苯基、聯苯基、甲氧基苯基、节基、本乙基爲較佳；並以苯基、甲氧基苯基、苄基爲最佳。R23係苯基、苄基、苯乙基、苯氧基乙基爲最佳。在本發明所含之前式（4 )所示之化合物中，茲就新穎之磷系化合物加以說明。亦即，在式（4 )中，R4,係可被取代基群A加以取代之方基、可被取代基群A加以取代之（C7_C15)芳烷基； R·42係可被取代基群A加以取代之芳基、可被取代基群a 加以取代之（C7-C15)芳烷基、或（C1_C10)烷基（該院基，亦可藉由：可被取代基群A加以取代之芳基氧基、可被取代基群A加以取代之（C7-CI5)芳烷基氧基、或（ C 1 _C 1 0 )烷氧基，加以取代者）；R43係可被取代基群a 加以取代之芳基、可被取代基群A加以取代之（C7_C丨5 ) 方烷基、或（C1-C10 )烷基；R44係氫原子、可被取代基群A加以取代之（C7_C15 )芳烷基、或可被取代基群a 加以取代之（C 1 -C 1 0 )烷基，所成之膦酸醯胺化合物，係新穎化合物者。在此’ Rq係可被羥基、氰基、（ci-c6 )烷基、苯基或（C1-C6 )焼氧基加以取代之苯基；可被羥基、氰基、 (C1-C6)烷基、苯基或（Cl_c6)烷氧基加以取代之萘基 -19- 201002729 :或可被羥基、硝基、氰基、（C1-C6)烷基、苯基或（ C1-C6 )烷氧基加以取件（C7-C12)芳烷基；R42係可被羥基、胺基、氰基、f ^ ^廿& (Cl-C6 )烷基、（C1-C6 )烷基胺基、二（C1-C6 )烷基胳货、进妝基、苯基、苯氧基、（C7-C12) 芳烷基或（C1-C6 )烷氣 π _基加以取代之苯基、可被羥基、胺基、氰基、（C 1 - c 6 ) h # 基、（C1-C6)烷基胺基、二（ C1-C6)烷基胺基、苯其 _ 本基、苯氧基、（C7-C12 )芳烷基或 (C1-C6 )烷氧基加以取代之萘基、可被羥基、氰基、甲醯基、羧基 '脲基、（C1-C6)烷基、苯基、苯氧基或（ C1-C6)院氧基加以取代之（c：7_ci2)芳烷基、或可被苯氧基加以取代之（C 1 _C6 )烷基；R43係可被羥基、胺基、氰基、（C1-C6)烷基、（C1-C6)烷基胺基、二（C1-C6 )烷基胺基、苯基、苯氧基或（C1-C6)烷氧基加以取代之苯基、可被羥基、胺基、氰基、（C1-C6)烷基、（C1-C6)烷基胺基、二（C1-C6)烷基胺基、苯基、苯氧基或 (C 1-C6 )烷氧基加以取代之萘基、或可被羥基、氰基、甲醯基、羧基、脲基、（C1-C6)烷基、苯基、苯氧基或 (C1-C6 )烷氧基加以取代之（C7-C12 )芳烷基；R44係 (C1-C6)烷基或氫原子，所成之膦酸醯胺化合物，係較佳者。其中，尤以尺^係苯基、p-甲氧基苯基、或苄基；R42 係可被（C1-C6)烷基、苯基、苄基 '苯乙基或苯基丙基加以取代之苯基、萘基；可被羥基、氰基、甲醯基、羧基、脲基、（C1-C6)烷基、苯基、苯氧基或（C1-C6)烷氧 • 20- 201002729 基加以取代之（C7-C12)芳烷基或2_苯氧基乙基；r43係苯基、苄基或苯乙基；係甲基、乙基或氫原子，所成之膦酸醯胺化合物，係最佳者。其中’又以式（4)中之R41係苯基、甲基苯基、聯苯基、甲氧基苯基、苄基、苯乙基爲較佳；並以苯基、甲氧基苯基、苄基爲更佳；再以苯基爲最佳。r42係苯基、苄基、苯乙基、苯氧基乙基等爲較佳。r43係以苯基、甲基苯基、聯苯基、甲氧基苯基、苄基、苯乙基爲較佳，並以苯基、甲氧基苯基、苄基、苯乙基爲更佳，再以苯基、苄基或苯乙基爲最佳。R44係甲基、乙基、氫原子爲最佳 0 式（1)〜式（5)之有機磷系化合物，亦可爲其等之鹽。鹽’例如有鋰、鈉、鉀、銨等之鹽，並以鈉鹽及銨鹽爲較佳。式（1)、式（3)及式（5)之有機磷系化合物，可以習知之方法或應用習知之方法而製造。此外，式（2 ) 及式（4)之有機磷系化合物之一部分習知化合物，亦可以習知之方法而製造。式（2)及式（4)之有機磷系化合物中，其上述之新穎化合物，亦可應用習知之方法而製造。具體而言，例如可參考非專利文獻2等之文獻所記載之類緣化合物之製造法而製造。舉例而言，可將配合目的化合物之鹵化磷系化合物與醇類、苯酚類或胺類，在無溶劑或有機溶劑中，如有必要再於鹼存在下使其發生反應之方法，而加以製造。關於實施例所使用之化合物，其製造法 -21 - 201002729 係如後述，惟本發明之式（2 )之新穎膦酸酯化合物及式 (4 )之新穎膦酸醯胺化合物’其製造法則不限於此等之範圍。本發明之水性分散液，其特徵係使用：選自式（1 ) 至式（5 )之有機磷系化合物之至少一種化合物或其等之鹽，以及界面活性劑。此外，其亦可基於更進一步提升耐光堅固度之目的，而含有紫外線吸收劑。界面活性劑，已知有陽離子型、非離子型及陰離子型，而本發明之水性分散液中所含之界面活性劑，則可使用任何一種類。在調製本發明之水性分散液時，亦可將非離子型或陰離子型、或非離子型與陰離子型，加以混合使用〇該陰離子型界面活性劑，例如有高級醇硫酸酯鹽、高級烷醚硫酸酯鹽、硫酸化脂肪酸酯等之烷基硫酸鹽或烷基苯磺酸鹽、烷基萘磺酸鹽等之烷基磺酸鹽，甚至還有高級醇磷酸酯鹽、高級醇之環氧化物加成物、磷酸酯鹽等之烷基磷酸鹽。此外，還例如有烷基芳基磺酸鹽、聚氧基伸烷基烷基醚硫酸鹽、聚氧基伸烷基烷基酯磷酸鹽、聚氧基伸烷基烷基醚羧酸鹽、聚羧酸鹽、土耳其紅油、石油磺酸鹽、烷基二苯基醚磺酸鹽。較佳者例如有聚氧基伸乙基二苯乙烯化苯基醚硫酸酯鹽、或聚氧基伸乙基三苯乙烯化苯基醚硫酸酯鹽。上述中，最佳之陰離子界面活性劑，例如有下式（ 107)所示之聚氧基伸乙基苯基醚之硫酸酯， -22- 201002729 【化8】II ^41 P-NR43R44 (4) OR42 (wherein Ru is an aryl group which may be substituted by a substituent group A, a (C7-C15) aralkyl group which may be substituted by a substituent group A; the R42 system may be An aryl group substituted with a substituent group A, a (C7-C15) aralkyl group which may be substituted with a substituent group A, or a (C1-C10) alkyl group (the alkyl group may also be: a substituent which may be substituted The aryloxy group substituted by the group A, the aryl group which can be substituted by the substituent -11 - 201002729 group A, can be substituted by (C1-C10) (C7-((C1-C10)) (12) The above may be substituted by a hydroxy, nitro) alkoxy group with an alkyl group, a phenyl group or a hydroxy group, a nitro group, an oxy group, a C1-C6 alkyl group, a phenyl group or a phenyl group or a phenyl group. , phenoxy or (yl: R 2 3 can be C1-C6 ) alkoxy 3 (C1-C6 ) alkane. Group or urea group, formazan, hydrazine or (C 1 - C 6 ) % [1 3 Wherein (C7-C15) aralkyloxy, or (C1-C10) substituted); R43 may be substituted by substituted group A with substituted substituent A (c 7 - C 1 5 ) Aralkyl, alkyl; R44 is a hydrogen atom, which can be substituted by a group A] 1 5 ) aralkyl Or a group which may be substituted by a substituent group a: a phosphonate compound wherein the substituent group A is the same as defined above, or a salt thereof, wherein the r21 group, the cyano group, (C1-C6) a phenyl group or a (C1-C6 substituted phenyl group; a naphthyl group which may be substituted by a hydroxy group, a cyano group, or a (C1-C6) (C1-C6) alkoxy group; or may be a cyano group, (C1) -C6) (C 7 - c 1 2 ) aralkyl group of alkyl, phenyl or (C1_C6) alkane; R 2 2 may be nitro, (, (C 1 - C 6 ) alkylamino group, (c丨-C 6 )alkylamine C1_C6 ) alkoxy substituted phenyl; or may be hydroxymethyl, carboxy, ureido, (C1-C6) alkyl, phenyl ci-co alkoxy Substituted (C7_C12) aralkyl by a thiol group, a cyano group, a (C1_C6) alkyl group, a phenyl group or a (C7-Cl2) aralkyloxy group substituted by S; may be an I group, a hydroxyl group, an amine group, C1_C6) alkylamino group, carboxy-substituted (C1-C6) alkyl group; or may be substituted by hydroxy group, cyano group, ureido group, (C1-C6) alkyl group, phenyl group, phenoxy oxy group (C7_C12) A compound of the compound [11] or [12] or a salt thereof, wherein -12-201002729 R2 is a phenyl group, a tolyl group, a nitrophenyl group, a nitrobenzyl group or a biphenyl group; the ruthenium 22 is a phenyl group which may be substituted by a (C1_C6)alkyl group, a nitro group or a phenyl group; (Cl-C6)alkyl, a benzyl or a phenethyl group substituted by a phenoxy group. [14] The phosphonium amide compound or a salt thereof according to [11] above, wherein R41 is a phenyl group which may be substituted by a hydroxyl group, a cyano group, a (C1_C6) alkyl group, a phenyl group or a (C1_C6) alkoxy group; a naphthyl group substituted with a hydroxy 'cyano group, a (C1-C6) group, a base or a (C1_c6) alkoxy group; or a phenyl group, a nitro group, a cyano group, a (CM-C6) alkyl group, or a benzene group a (c 7 -C 1 2 )aralkyl group substituted with a (C1_C6 ) alkoxy group; the R 4 2 group may be a hydroxyl group, an amine group, a cyano group, a (C1-C6) alkyl group, (C1-C6) An alkylamino group, a di(C1_C6)alkylamino group, a phenyl group, a phenoxy group, a (C7-C12) aralkyl group or a (C1·C6)-substituted phenyl group, which may be substituted with a hydroxyl group or an amine group. , cyano, (C1-C6)alkyl, (C1-C6)alkylamino, bis(Ci_C6)alkylamino, phenyl, phenoxy, (C7-C12) aralkyl or (C1- C6) alkoxy-substituted naphthyl, which may be hydroxy, cyano, decyl, carboxy, ureido, (CH-C0), phenyl, phenoxy or (C1-C6) alkoxy a substituted (C7-C12) aralkyl group or a (C1-C6) alkyl group which may be substituted by a phenoxy group; the R43 group may be a hydroxyl group, an amine group, Substituted by cyano, (C1-C6)alkyl, (C1-C0)alkylamino, bis(C1-C6)alkylamino, phenyl, phenoxy or (C1-C6)alkoxy Phenyl, may be hydroxy, amine, cyano, (C1-C6)alkyl, (CM-C6)alkylamino, di(C1-C6)alkylamino, phenyl, phenoxy or a C1-C6) alkoxy group substituted with a naphthyl group, or may be hydroxy, cyano, methionyl, carboxy, ureido-13-201002729, (C1-C6)alkyl, phenyl, phenoxy or a C1-C6) alkoxy group substituted with a (C7-C12) aralkyl group; a (CM-C6) alkyl group or a hydrogen atom. [15] The squamous amine compound of the above [11] or [14], wherein R41 is a phenyl group, a p-methoxyphenyl group, or a benzyl group; and the R42 system is a (Cl_C6) hospital base. a phenyl group, a naphthyl group substituted with a phenyl group, a phenyl group, a phenethyl group or a phenylpropyl group; a hydroxy group, a cyano group, a decyl group, a carboxyl group, a ureido group, a (C1-C6) fluorenyl group, a phenyl group a (C7-C12) aralkyl group or a 2-phenoxyethyl group substituted with a phenoxy group or a (C1-C6) alkoxy group; R43 is a phenyl group, a benzyl group or a phenethyl group; Ethyl or hydrogen atom. The aqueous dispersion containing the organophosphorus compound and the surfactant represented by the above formulas (1) to (5) provided by the present invention is excellent as a flame retardant, and is used for flame retardant processing on the fiber. Therefore, it is possible to impart excellent flame retardancy to light resistance and durability. Further, most of the phosphonate compounds and phosphonate oxime compounds of the organophosphorus compounds represented by the above formulas (2) and (4) are novel compounds. [Embodiment] BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail. In the present invention, the (Cl-C10) alkyl group is a linear, branched, or cyclic group having a carbon number of 1 to 1 Å, and is, for example, a methyl group, an ethyl group, an η-propyl group, an isopropyl group, or the like. Η-butyl, s-butyl, isobutyl, t-butyl, η-pentyl, η-hexyl, η-octyl, η-fluorenyl, cyclopropyl, cyclopentyl, cyclohexyl and the like. (ci- -14-201002729 C6) alkyl group, a straight chain, a branched chain, a cyclic alkyl group having a carbon number of 丨6, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, or a η - butyl, s-butyl, isobutyl, t-butyl, η-pentyl, cyclopropyl, cyclopentyl, cyclohexyl and the like. In the present invention, the '(C1-C10) alkoxy group is a group in which the above (ci-CIO) alkyl group is bonded to an oxygen atom, for example, a methoxy group, an ethoxy group, a η-propoxy group, an isopropoxy group. , η·butoxy, s-butoxy, t-butoxy, η-pentyloxy, η-hexyloxy, η-octyloxy, fluorenyloxy, cyclopentyloxy , cyclohexyloxy and the like. (CM-C6) alkoxy group, wherein the above (C1-C6) alkyl group is bonded to a group of an oxygen atom, for example, a methoxy group, an ethoxy group, a η-propoxy group, an isopropoxy group, and an η-butyl group. Oxy, s-butoxy, t-butoxy, η-pentyloxy, η-hexyloxy, cyclopentyloxy, cyclohexyloxy and the like. In the present invention, the (C1-C10)alkylamino group is a group in which the above (C1-C10) alkyl group is bonded to a nitrogen atom, and examples thereof include a methylamino group, an ethylamino group, and an η-propylamine. , isopropylamino, η-butylamino, butylamino, η-pentylamino, η-hexylamino, η-octylamino, η-decylamino, cyclopropylamino , cyclopentylamino group, cyclohexylamine group and the like. The (C1-C6)alkylamino group is a group in which the above (C1-C6)alkyl group is bonded to a nitrogen atom, and examples thereof include a methylamino group, an ethylamino group, an η-propylamino group, and an isopropyl group. Amino group, η-butylamino group, t-butylamino group, η-pentylamino group, η·hexylamino group, cyclopentylamino group, cyclohexylamino group and the like. In the present invention, the 'di(C1-C10)alkylamino group is a group in which the above (C1-C10) alkyl group is bonded to a nitrogen atom, and examples thereof include a dimethylamino group, a diethylamino group, and a second group. Η-propyl)amino, diisopropylamino, bis(η-butyl)amine, bis(t-butyl)amine, bis(η-pentyl)amine, 2-4-201002729 ( Η-hexyl)amino group, di(n-octyl)amino group, bis(n-fluorenyl)amino group, dicyclopropylamino group, dicyclopentylamino group, dicyclohexylamino group and the like. a di(C1-C6)alkylamino group which is a group of the above (Ci_C6)alkyl group bonded to a nitrogen atom, such as a dimethylamino group, a diethylamino group, a di(n-propyl)amine , diisopropylamino, bis(η-butyl)amine, bis(t-butyl)amine, bis(η-pentyl)amine, bis(n-hexyl)amine, bicyclic A pentylamino group, a dicyclohexylamino group, and the like. The aryl group in the invention may, for example, be a phenyl group, a naphthyl group or the like. In the present invention, the (C7-C15) aralkyl group is a group in which an alkyl group is bonded to a phenyl group, a naphthyl group or the like, and examples thereof include a benzyl group, a phenethyl group, a phenylpropyl group, a phenylbutyl group, and a phenyl group. Butyl, phenylhexyl, phenyloctyl, naphthylmethyl, naphthylethyl, naphthylpropyl and the like. The (C7-C12)aralkyl group may, for example, be a benzyl group, a phenethyl group, a phenylpropyl group, a phenylbutyl group, a phenylpentyl group, a naphthylmethyl group or a naphthylethyl group. In the present invention, an aryloxy group, for example, a phenyloxy group or a naphthyloxy group, etc., is a '(C7-C15) aralkyloxy group in the present invention, which is bonded to the above (C7-C15) aralkyl group. A group of an oxygen atom, for example, a benzyloxy group, a phenethyloxy group, a phenylpropyloxy group, a phenylbutyloxy group, a phenylpentyloxy 'phenylhexyloxy group, a phenyloctyl group An oxy group, a naphthylmethoxy group, a naphthylethoxy group, a naphthylpropyloxy group or the like. (C7-C12) a aryloxy group which is bonded to an oxygen atom group on the above (C7-C12) aralkyl group, for example, a benzyloxy group, a phenethyloxy group, a phenylpropyloxy group, Phenylbutyloxy, phenylpentyloxy, naphthylmethoxy, naphthylethoxy, and the like. -16- 201002729 In the present invention, the substituent group A means a hydroxyl group, a nitro group, an amine group, a cyano group, a decyl group, a residue, a ureido group, a (C1-C10) yard group, (C1-C10). An alkylamino group, a di(C1-C10)alkylamino group, a phenyl group, a benzene group and a (C1-C10) alkoxy group. Thus, the substituent selected by the substituent group A can be generally substituted with one to three on each functional group. Wherein, in the present invention, the aryl group which may be substituted with the group A is a (Cl-C10) alkylphenyl group, a biphenyl group or a (Cl-C10) alkoxyphenyl group, a phenoxyphenyl group, Nitrophenyl groups and the like are preferred. In the organophosphorus compound represented by the above formulas (1) to (5) contained in the aqueous dispersion used in the flame-retardant processing of the present invention, the ratios to R13, R31 to R33, r41 to r43, and r51 to r53 are compared. Preferred examples include phenyl, methylphenyl, biphenyl, methoxyphenyl, phenoxyphenyl and benzyl, of which phenyl, biphenyl and methoxyphenyl are preferred. . R34, R44, R54 and R55' are preferably a hydrogen atom. R21 to r23, for example, phenyl, methylphenyl, methoxyphenyl, nitrophenyl, phenoxyphenyl, benzyl, biphenyl, nitrobenzyl are preferred, and phenyl Biphenyl or methoxyphenyl is the most preferred. Hereinafter, the novel phosphorus-based compound will be described as a compound represented by the above formula (2) contained in the present invention. That is, in the formula (2), r2 1 is an aryl group which may be substituted with a substituent group A, or a (C7-C15) aralkyl group which may be substituted with a substituent group A; the R22 system may be substituted a phenyl group substituted with a group A, a (c7_ci5) aralkyl group which may be substituted with a substituent group A, or a (C1-C10) alkyl group; and a phenyl group which may be substituted by the substituent group A, may be Substituent group -17- 201002729 A substituted (C7-C15) aralkyl, or (C-CIO) alkyl (this alkyl group may also be substituted by aryl oxygen which may be substituted by substituent group A) a (C7-C1 5 ) aralkyloxy group or a (C 1 -C 1 0 ) alkoxy group which may be substituted by a substituent group A, which is substituted, and a phosphonate compound Novel compounds. Wherein ' Rii is a phenyl group which may be substituted by a phenyl group, a cyano group, a nitro group, a (C1-C6) group, a phenyl group or a (C 1 -C 6 ) alkoxy group; may be a hydroxy group, a cyano group, a C1-C6 alkyl, phenyl or (C1-C6) alkoxy substituted naphthyl group; or may be hydroxy, nitro, cyano, (C1-C6)alkyl, phenyl or (C1-C6 Alkoxy group substituted (C7-C12) aralkyl; r22 is nitro, (C1-C6)alkyl, (C1-C6)alkylamino, di(C1-C6)alkylamine a phenyl group substituted with a phenyl group or a (C1_C6) alkoxy group; or a hydroxy group, a cyano group, a decyl group, a carboxyl group, a ureido group, a (ci-C6) group, a phenyl group, a phenoxy group or C1-C6) alkoxy substituted (C7_C12) aryl group; r23 can be substituted by a thiol, cyano, (ci_C6), phenyl or (C1-C6) alkoxy group (C7- C12) a aryloxy group; a C-C6 alkoxy group, a hydroxyl group, an amine group, a (C1_C6)-based amine group, a carboxyl group or a ureido group (C! _C6); or Hydroxy, cyano, formyl, carboxyl, ureido, (C1_C6)alkyl, benzyl, oxy or (C1-C6) oxy The substituted (C7-C12) aromatic compound is preferred; the phosphonate compound is preferred. Further, R21 is a phenyl group, a tolyl group, a nitrophenyl group, a nitrobenzyl group or a biphenyl group; and R22 is a phenyl group which may be substituted by a nitro group, a (C1-C6)alkyl group or a phenyl group; R23 is a (C1_C6) alkyl group which may be substituted by a phenyl group or a phenoxy group, a nodal group or a phenylethyl group of 18-201002729; the resulting phosphonate compound is preferred. Wherein 'further in the formula (2) is a phenyl group, a methylphenyl group, a biphenyl group, a methoxyphenyl group, a nitrophenyl group, a benzyl group, a nitrobenzyl group, a phenethyl group; Phenyl, methylphenyl and benzyl are more preferred; and phenyl is most preferred. R22 is a phenyl group, a methylphenyl group, a biphenyl group, a methoxyphenyl group, a benzyl group or a hexyl group; and a phenyl group, a methoxyphenyl group or a benzyl group is preferred. R23 is preferably a phenyl group, a benzyl group, a phenethyl group or a phenoxyethyl group. In the compound represented by the above formula (4) contained in the present invention, a novel phosphorus-based compound will be described. That is, in the formula (4), R4 is a group which may be substituted with a substituent group A, a (C7_C15) aralkyl group which may be substituted with a substituent group A; and a R.42 group may be substituted group A substituted aryl group, a (C7-C15) aralkyl group or a (C1_C10) alkyl group which may be substituted by a substituent group a (this group may also be substituted by a substituent group A) An aryloxy group, a (C7-CI5) aralkyloxy group substituted by a substituent group A, or a (C 1 -C 1 0 ) alkoxy group, substituted;) R43 may be substituted by a group a a substituted aryl group, a (C7_C丨5) squaryl group or a (C1-C10) alkyl group which may be substituted with a substituent group A; and a R44 hydrogen atom which may be substituted by a substituent group A (C7_C15) An aralkyl group or a (C 1 -C 1 0 )alkyl group which may be substituted by a substituent group a, which is a phosphonium amide compound, is a novel compound. Here, 'Rq is a phenyl group which may be substituted by a hydroxyl group, a cyano group, a (ci-c6) alkyl group, a phenyl group or a (C1-C6) alkoxy group; may be a hydroxyl group, a cyano group, or a (C1-C6) alkane. Naphthyl substituted with a phenyl or (Cl-c6) alkoxy group - 19,027,029: or may be hydroxy, nitro, cyano, (C1-C6)alkyl, phenyl or (C1-C6) alkoxy The base is taken (C7-C12) aralkyl; R42 can be hydroxy, amine, cyano, f ^ ^ 廿 & (Cl-C6) alkyl, (C1-C6) alkyl amine, two (C1-C6) alkyl, phenyl, phenoxy, (C7-C12) aralkyl or (C1-C6) alkene π _ group substituted phenyl, can be hydroxyl, Amino, cyano, (C 1 - c 6 ) h # group, (C1-C6)alkylamino, bis(C1-C6)alkylamino, benzoquinone, phenoxy, (C7 -C12) an alkylene group substituted with an aralkyl group or a (C1-C6) alkoxy group, which may be substituted by a hydroxyl group, a cyano group, a decyl group, a carboxy 'ureido group, a (C1-C6) alkyl group, a phenyl group, a phenoxy group. a (c:7-ci2)aralkyl group substituted with (C1-C6) alkoxy, or a (C 1 -C6 )alkyl group which may be substituted by a phenoxy group; R43 may be substituted by a hydroxy group Amino, cyano, (C1-C6)alkyl, (C1-C6)alkylamino, di(C1-C6)alkylamino, phenyl, phenoxy or (C1-C6) alkoxy Substituted phenyl, which may be substituted by hydroxy, amine, cyano, (C1-C6)alkyl, (C1-C6)alkylamino, di(C1-C6)alkylamino, phenyl, phenoxy A naphthyl group substituted with a (C 1-C6 ) alkoxy group, or may be hydroxy, cyano, decyl, carboxy, ureido, (C1-C6)alkyl, phenyl, phenoxy or The C1-C6) alkoxy group-substituted (C7-C12) aralkyl group; the R44-based (C1-C6) alkyl group or a hydrogen atom, and the phosphonium amide compound are preferred. Wherein, especially phenyl, p-methoxyphenyl or benzyl; R42 can be substituted by (C1-C6)alkyl, phenyl, benzyl 'phenethyl or phenylpropyl Phenyl, naphthyl; may be hydroxy, cyano, decyl, carboxy, ureido, (C1-C6)alkyl, phenyl, phenoxy or (C1-C6) alkoxy • 20- 201002729 Substituted (C7-C12) aralkyl or 2-phenoxyethyl; r43 is phenyl, benzyl or phenethyl; methyl, ethyl or hydrogen atom, a phosphonium amide compound , the best. Wherein 'furrowing R41 in the formula (4), methylphenyl, biphenyl, methoxyphenyl, benzyl, phenethyl is preferred; and phenyl, methoxyphenyl The benzyl group is more preferred; the phenyl group is most preferred. R42 is preferably a phenyl group, a benzyl group, a phenethyl group or a phenoxyethyl group. R43 is preferably a phenyl group, a methylphenyl group, a biphenyl group, a methoxyphenyl group, a benzyl group or a phenethyl group, and is more preferably a phenyl group, a methoxyphenyl group, a benzyl group or a phenethyl group. Preferably, phenyl, benzyl or phenethyl is preferred. The methyl group, the ethyl group and the hydrogen atom of R44 are preferably the organophosphorus compound of the formula (1) to the formula (5), and may be a salt thereof. The salt 'is, for example, a salt of lithium, sodium, potassium, ammonium or the like, and preferably a sodium salt or an ammonium salt. The organophosphorus compound of the formula (1), the formula (3) and the formula (5) can be produced by a conventional method or a conventional method. Further, a part of the conventional compound of the organophosphorus compound of the formula (2) and the formula (4) can be produced by a conventional method. Among the organophosphorus compounds of the formulae (2) and (4), the above novel compounds can also be produced by a known method. Specifically, for example, it can be produced by referring to the production method of the rim compound described in the literature of Non-Patent Document 2 or the like. For example, a phosphorus-halogen compound compounded with a target compound may be produced by reacting an alcohol, a phenol or an amine in a solvent-free or organic solvent, if necessary, in the presence of a base. . Regarding the compound used in the examples, the production method of the invention - 21,027,027 is as follows, but the novel phosphonate compound of the formula (2) of the present invention and the novel phosphonium amide compound of the formula (4) are not produced. Limited to these areas. The aqueous dispersion of the present invention is characterized by using at least one compound selected from the group consisting of the organophosphorus compounds of the formula (1) to the formula (5) or a salt thereof, and a surfactant. In addition, it can also contain an ultraviolet absorber based on the purpose of further improving the light fastness. As the surfactant, a cationic type, a nonionic type, and an anionic type are known, and any of the surfactants contained in the aqueous dispersion of the present invention can be used. In the preparation of the aqueous dispersion of the present invention, a nonionic or anionic type, or a nonionic type and an anionic type may be used in combination, and the anionic surfactant may be used, for example, a higher alcohol sulfate salt or a higher alkyl ether. An alkyl sulfonate such as a sulfate salt, a sulfated fatty acid ester or the like, an alkyl sulfonate such as an alkylbenzene sulfonate or an alkylnaphthalene sulfonate, or even a higher alcohol phosphate salt or a higher alcohol ring An alkyl phosphate such as an oxide adduct or a phosphate salt. Further, for example, there are an alkyl aryl sulfonate, a polyoxyalkylene alkyl ether sulfate, a polyoxyalkylene alkyl phosphate, a polyoxyalkylene alkyl carboxylate, a polycarboxylic acid. Salt, Turkish red oil, petroleum sulfonate, alkyl diphenyl ether sulfonate. Preferred examples are polyoxyalkylene diphenylvinylated phenyl ether sulfate or polyoxyethylidene trisylated phenyl ether sulfate. Among the above, the most preferred anionic surfactant is, for example, a sulfate of polyoxyethylidene ether represented by the following formula (107), -22-201002729.

RR

—0(CH2CH2〇)n-S〇3H (107) (式中，R係氫原子、（Cl-C18)烷基、苯乙烯基或节基，η爲1〜15之整數）或下式（31)所示之聚氧基伸乙基烷基烯丙基醚之磷酸酯，【化9】 RO(CH2CH20>n—0(CH2CH2〇)nS〇3H (107) (wherein R is a hydrogen atom, a (Cl-C18) alkyl group, a styryl group or a benzyl group, and η is an integer of 1 to 15) or the following formula (31) The phosphate of the polyoxyethylidene alkyl allyl ether shown, [Chemical 9] RO (CH2CH20>n

OR" (31) (式中，R’係（C8-C30)烷基或（C8-C30)烷基芳基，η爲1〜30之整數，R’'係氫原子或R’〇 ( CH2CH20 ) η基 ° ) 式（31)所示之化合物，例如有Plysurf AL(商品名稱，第一工業製藥（股）製）等。式（107)、式（31)爲方便起見，係記載爲游離酸，惟對陽離子亦可作成鹼金屬、銨鹽等鹽類而使用，該對陽離子，例如有鋰、鈉、鉀、銨鹽等，並以鈉鹽及銨鹽爲較佳。較佳之式（107)之化合物，例如有R爲（C6-C12) 直鏈院基，且η爲4至12之化合物，其中並以R爲壬基且η爲7之化合物爲最佳。 -23- 201002729 非離子型界面活性劑’例如有聚氧基伸乙基苯乙苯基醚、聚氧基伸乙基二苯乙烯化苯基醚或聚氧基伸三苯乙烯化苯基醚等爲較佳。聚氧基伸乙基苯乙燦化苯基醚，例如有下式（1 所示之化合物，【化1 0】烯化乙基 08 )OR" (31) (wherein R' is a (C8-C30) alkyl or (C8-C30) alkylaryl group, η is an integer from 1 to 30, R'' is a hydrogen atom or R'〇 (CH2CH20 η base °) The compound represented by the formula (31) is, for example, Plysurf AL (trade name, manufactured by Daiichi Kogyo Co., Ltd.). For the sake of convenience, the formula (107) and the formula (31) are described as a free acid, and the cation may be used as a salt such as an alkali metal or an ammonium salt, for example, lithium, sodium, potassium or ammonium. Salt and the like, and sodium salt and ammonium salt are preferred. Preferred are compounds of the formula (107), for example, a compound wherein R is a (C6-C12) linear chain and η is a compound of 4 to 12, and a compound wherein R is a fluorenyl group and η is 7 is preferred. -23- 201002729 Non-ionic surfactants are, for example, polyoxyethylidene phenylethyl ether, polyoxyethylidene styrenated phenyl ether or polyoxylated trisylated phenyl ether. good. Polyoxyethylidene phenylethyl phenyl ether, for example, has the following formula (1 compound, [10] alkylated ethyl 08)

或式（108)所示之化合物之混合物。在式（108 ，係以m1爲1至3’且η爲8至30之化合物爲較佳。式（1 0 8 )所示之化合物之混合物，例如有第一製藥（股）製之商品名稱NeugeneEA-87等。界面活性劑可以單獨亦可混合使用。亦即，可將子型或非離子型各自多種類地加以混合，亦可將各自類之陰離子型或非離子型加以混合。可在本發明之水性分散液中含有之紫外線吸收劑要是可吸收紫外線之化合物者即可，並無特別之限制外’該紫外線吸收劑，亦可基於更進一步地提升耐光度之目的而使用。紫外線吸收劑，例如可使用水楊酸系化合物、二酮系化合物 '苯並***系化合物、受阻胺系化合物、系化合物、肉桂酸系化合物、芪系化合物；或以苯並 ¥ fk合物爲代表之吸收紫外線並發出螢光之化合物（ )中工業陰離多種，只。此堅固苯甲三嗪噁唑所謂 -24- 201002729 螢光增白劑）。較佳之紫外線吸收劑之構造式，例如有下述所示者。【化1 1】Or a mixture of compounds of formula (108). In the formula (108, a compound in which m1 is 1 to 3' and η is 8 to 30 is preferable. A mixture of compounds represented by the formula (108) is, for example, a trade name of the first pharmaceutical product. Neugene EA-87, etc. The surfactants may be used singly or in combination, that is, subtypes or nonionics may be mixed in various types, or anionic or nonionic types of the respective types may be mixed. The ultraviolet absorber contained in the aqueous dispersion of the present invention may be a compound that absorbs ultraviolet rays, and is not particularly limited to the ultraviolet absorber, and may be used for the purpose of further improving the light resistance. For the agent, for example, a salicylic acid-based compound, a diketone-based compound, a benzotriazole-based compound, a hindered amine-based compound, a compound, a cinnamic acid-based compound, an anthraquinone-based compound, or a benzohexacene compound can be used. The compound that absorbs ultraviolet light and emits fluorescent light ( ) is industrially inhabited by a variety of only. This strong benzotriazine oxazole is called -24-201002729 fluorescent whitening agent). The structural formula of the preferred ultraviolet absorber is, for example, as described below. [1 1]

(103)(103)

(1〇5)(1〇5)

苯並***系之紫外線吸收劑之式（1 06 )中，R15例如有（C1-C12)直鏈或分枝鏈烷基或枯烯基，更佳者有（ C3-C6)直鏈或分枝鏈烷基，最佳者有（C3_C5)分枝鏈烷 -25- 201002729 基’例如異丙基、異丁基、s -丁基、t-丁基、1-甲基丁基、2-甲基丁基、3-甲基丁基、1-乙基丙基等。上述式（106)中，R16例如有羥基、（C1-C12)直鏈或分枝鏈烷基、（C1-C12)直鏈或分枝鏈烷氧基或苄基氧基，並以（C1-C12)直鏈或分枝鏈烷基爲較佳。更佳者有 (C1-C6)直鏈或分枝鏈烷基，最佳者有（C1-C3)直鏈或分枝鏈烷基，例如甲基、乙基、η-丙基、異丙基。式（106)中，R丨7例如有氫原子、羥基、（C1-C12) 直鏈或分枝鏈烷基、或（C卜C12)直鏈或分枝鏈烷氧基，並以氫原子、甲基、乙基、η -丙基、或異丙基爲較佳，且以氫原子爲最佳。式（106)中，R18例如有氫原子或羥基，並以羥基爲較佳，而X則例如有氫原子或氯原子，並以氯原子爲較佳〇最佳之Rl5至Rl8及X之組合，係R15爲t-丁基、R16 爲甲基、R17爲氫原子、Ri8爲羥基、X爲氯原子者。此外，式（1 〇 6 )所示之苯並***系化合物以外之紫外線吸收劑，其較佳之化合物’有式（1 0 1 )、式（1 02 ) 及式（103)所不之二苯甲酮系化合物、式（104)所示之三嗪系化合物（式中，R·9及Ri〇係各自獨立地爲氫原子、羥基或（C1-C5)烷基）、式（105)所示之苯並***系及二苯甲酮系之複合系化合物（式中’ 係（C1_C2)院基或枯烯基，r2係羥基、（ci-c2)烷氧基或苄基氧基，R3 係氫原子、經基或（C1-C2)院氧基’ R4係氫原子或羥基 -26- 201002729 ，χ爲氫原子或氯原子）。上述之紫外線吸收劑之內，最佳之化合物係式（106 )所示之苯並***系化合物。本發明之阻燃劑之水性分散劑中，其較佳之態樣係如以下所示者。亦即，式（1)、式（2)、式（3)、式（4)或式（ 5 )之化合物’在水性分散液中，一般而言，其等化合物之總量係1-90重量％，較佳係5-50重量％，最佳係5-30 重量％之範圍所含有者。如含有紫外線吸收劑時，其含有量在水性分散劑中，一般係0.1-10重量％ ’較佳係0.5-10重量％，最佳係1-5 重量％之範圍而含有者。界面活性劑’相對於有機磷系化合物及任意成分之紫外線吸收劑之總重’ 一'般係5 - 8 0重量％，較佳係10-50重量％，最佳係15-35重量％之範圍而含有者。在不損及本發明之效果的範圍內，如有必要，在本發明之水性分散液中亦可含有上述以外之界面活性劑或分散劑等之添加劑。亦可再根據需要，爲提高貯藏安定性，而含有聚乙烯醇、甲基纖維素、羧基甲基纖維素、澱粉糊等之保護膠體劑、磷酸酯或磷酸醯胺等之用以提高阻燃效果之阻燃助劑、抗氧化劑。進一步，如有需要，亦可添加鹼劑、酸類、油脂、闻級醇類、高級脂肪酸、低級醇類、有機溶劑、滲透促進劑、多價醇類、防腐劑、鉗合劑、pH 調整劑、色素、及顏料等。 -27- 201002729 藉由將上述之各成分添加於水中，即可調製本發明之水性分散液。可以本發明之分散液而進行阻燃加工之纖維，並無特別之限制，惟例如有聚酯纖維，尤其是CDP纖維以及 CDP纖維與聚酯纖維之混紡纖維。 CDP纖維或聚酯纖維，例如有在聚對苯二甲酸乙二醇酯、聚對苯二甲酸丁二醇酯、聚氧基乙氧基苯甲酸酯、聚伸乙基萘二甲酸酯、環己烷二伸甲基對苯二甲酸酯等之聚酯纖維及上述之聚酯，再將附加成分之異苯二甲酸、己二酸、磺基異苯二甲酸等之二羧酸成分、或丙二醇、丁二醇、環己烷二甲醇、二乙二醇等之二醇成分，進行共聚合所成之材質之纖維等，惟不限於此等之範圍。此外’纖維構造物’可爲紗線、織物、編物、不織物等任一型態。以本發明之水性分散液來將纖維進行阻燃加工時，可使用浸染同浴法或塡塞法等習知之方法。如使用浸染同浴法時，係倂用纖維用之分散染料、或分散型陽離子染料等及水性分散液，一般於11〇_15〇。(3，較佳爲120-l4〇°C範圍之溫度下，而進行1〇_6〇分鐘左右之加工處理。如有必要’亦可進一步加入螢光染料等之染料。如使用塡塞（Padding )法時，可將纖維構造物進行塡塞之後’以乾熱處理或飽和常壓蒸汽處理、過熱蒸汽處理或高壓蒸汽處理等之蒸熱處理，而進行熱處理。不論是 -28- 201002729 乾熱處理、蒸熱處理之任一者，該熱處理溫度，一般係 1 1 0 - 2 1 0 °c之範圍，較佳係1 7 0 - 2 1 0 °c之範圍。熱處理溫度如超過210°C時，聚酯系合成纖維將有黃變或脆化之虞。如有必要，亦可倂用浸染同浴法及塡塞法。此時，可以浸染同浴法在纖維上進行阻燃加工後，進一步以塡塞法進行再加工即可。藉由此方法，可賦予其更高之阻燃功能實施例以下兹依據實施例具體地說明本發明，惟本發明並不限於此等實施例之範圍。實施例中如記載爲「份」及「％」時，如有特別說明外’係各自表示「重量份」及「重量 %」之意。以下之實施例1 - 1 2及比較例1 _3所使用之有機磷系化合物，其構造式係整理如以下所示者。Me係甲基，Ph則係表示苯基之意。各化合物可根據文獻習知之製造方法，或應用該製造方法而加以製造。 -29- 201002729 【化12】In the formula (106) of the benzotriazole-based ultraviolet absorber, R15 is, for example, a (C1-C12) linear or branched alkyl group or a cumenyl group, and more preferably a (C3-C6) straight chain or Branched chain alkyl, the most preferred being (C3_C5) branched alkane-25- 201002729 base 'eg isopropyl, isobutyl, s-butyl, t-butyl, 1-methylbutyl, 2 -methylbutyl, 3-methylbutyl, 1-ethylpropyl, and the like. In the above formula (106), R16 has, for example, a hydroxyl group, a (C1-C12) linear or branched alkyl group, a (C1-C12) linear or branched alkoxy group or a benzyloxy group, and (C1) -C12) A straight or branched alkyl group is preferred. More preferably, there are (C1-C6) straight or branched alkyl groups, and the most preferred ones are (C1-C3) straight or branched alkyl groups such as methyl, ethyl, η-propyl, isopropyl. base. In the formula (106), R丨7 has, for example, a hydrogen atom, a hydroxyl group, a (C1-C12) linear or branched alkyl group, or a (C-C12) linear or branched alkoxy group, and has a hydrogen atom. A methyl group, an ethyl group, an η-propyl group or an isopropyl group is preferred, and a hydrogen atom is preferred. In the formula (106), R18 has, for example, a hydrogen atom or a hydroxyl group, and preferably a hydroxyl group, and X has, for example, a hydrogen atom or a chlorine atom, and preferably a chlorine atom, preferably a combination of Rl5 to Rl8 and X. Further, R15 is a t-butyl group, R16 is a methyl group, R17 is a hydrogen atom, Ri8 is a hydroxyl group, and X is a chlorine atom. Further, in the ultraviolet absorber other than the benzotriazole compound represented by the formula (1 〇6), the preferred compound 'is of the formula (1 0 1 ), the formula (102) and the formula (103). An benzophenone-based compound or a triazine-based compound represented by the formula (104) (wherein R·9 and Ri〇 are each independently a hydrogen atom, a hydroxyl group or a (C1-C5)alkyl group), and the formula (105) a benzotriazole-based and benzophenone-based complex compound (wherein 'C1_C2) or cumene, r2 hydroxy, (ci-c2) alkoxy or benzyloxy R3 is a hydrogen atom, a thiol group or a (C1-C2) alkoxy group 'R4 hydrogen atom or a hydroxy group-26-201002729, and a hydrazine is a hydrogen atom or a chlorine atom). Among the above ultraviolet absorbers, the most preferred compound is a benzotriazole compound represented by the formula (106). Among the aqueous dispersants of the flame retardant of the present invention, preferred embodiments are as shown below. That is, the compound of the formula (1), the formula (2), the formula (3), the formula (4) or the formula (5) is in the aqueous dispersion, and generally, the total amount of the compounds is 1-90. The weight %, preferably 5 to 50% by weight, is preferably in the range of 5 to 30% by weight. When the ultraviolet absorber is contained, the content thereof is usually from 0.1 to 10% by weight, preferably from 0.5 to 10% by weight, based on the aqueous dispersion, and preferably from 1 to 5% by weight. The total amount of the surfactant 'relative to the organophosphorus compound and the ultraviolet absorber of the optional component is -5 to 80% by weight, preferably 10 to 50% by weight, and most preferably 15 to 35% by weight. The scope is included. The aqueous dispersion of the present invention may contain an additive such as a surfactant or a dispersant other than the above, if necessary, within the range which does not impair the effects of the present invention. In addition, as needed, in order to improve storage stability, a protective colloidal agent such as polyvinyl alcohol, methyl cellulose, carboxymethyl cellulose, starch paste, etc., phosphate or guanamine phosphate may be used to improve flame retardancy. The effect of flame retardant additives, antioxidants. Further, if necessary, an alkali agent, an acid, a fat, an alcohol, a higher fatty acid, a lower alcohol, an organic solvent, a penetration enhancer, a polyvalent alcohol, a preservative, a chelating agent, a pH adjuster, or the like may be added. Pigments, pigments, etc. -27- 201002729 The aqueous dispersion of the present invention can be prepared by adding the above components to water. The fiber which can be subjected to flame-retardant processing by the dispersion of the present invention is not particularly limited, and is, for example, a polyester fiber, particularly a CDP fiber, and a blended fiber of a CDP fiber and a polyester fiber. CDP fibers or polyester fibers, for example, in polyethylene terephthalate, polybutylene terephthalate, polyoxyethoxybenzoate, polyethylene naphthalate a polyester fiber such as cyclohexane dimethyl terephthalate or the above polyester, and an additional component of a dicarboxylic acid such as isophthalic acid, adipic acid or sulfoisophthalic acid. The component or a diol component such as propylene glycol, butanediol, cyclohexanedimethanol or diethylene glycol is a fiber of a material obtained by copolymerization, but is not limited thereto. Further, the 'fiber structure' may be of any type such as a yarn, a woven fabric, a knitted fabric, or a non-woven fabric. When the fiber is subjected to flame-retardant processing using the aqueous dispersion of the present invention, a conventional method such as a bathing method or a immersion method can be used. When using the dip dyeing and bathing method, it is a disperse dye for fibers, a disperse cationic dye, etc., and an aqueous dispersion, generally 11 〇 15 〇. (3, preferably in the range of 120-l4 〇 ° C, and processing is performed for about 1 〇 6 〇 minutes. If necessary, a dye such as a fluorescent dye may be further added. In the Padding method, the fiber structure may be subjected to a heat treatment by dry heat treatment or saturated atmospheric steam treatment, superheated steam treatment or high pressure steam treatment, etc., whether it is -28-201002729 dry heat treatment, In any of the steaming heat treatments, the heat treatment temperature is generally in the range of 1 10 - 2 1 0 °c, preferably in the range of 1 70 - 2 1 0 ° C. When the heat treatment temperature exceeds 210 ° C, the polymerization is performed. The ester-based synthetic fiber will have yellowing or embrittlement. If necessary, the same bathing method and tamping method can be used. In this case, the same bath method can be used for flame-retardant processing on the fiber, and further The tamping method can be further processed. By this method, a higher flame retardant function can be imparted. Hereinafter, the present invention will be specifically described based on the examples, but the present invention is not limited to the scope of the embodiments. In the example, it is recorded as "parts" and "%" In the meantime, unless otherwise stated, the meanings of "parts by weight" and "% by weight" are used. The organic phosphorus compounds used in the following Examples 1 - 2 and Comparative Examples 1 - 3 are structured. As shown below, Me is a methyl group, and Ph is a phenyl group. Each compound can be produced according to a known production method of the literature or by using the production method. -29- 201002729

OMe OMe (210) (211) (212) ca 〇一 p-o i 〇OMe OMe (210) (211) (212) ca 〇 a p-o i 〇

(302)(302)

Or 七Or seven

(301) (303) 式（201 )之化合物，係至R13之全部係苯基之前式（1 )之化合物。此化合物係將二苯基膦酸氯化物及苯 -30- 201002729 酚以及三乙基胺’在四氫呋喃中以1小時使其進行加熱反應而合成。式（202)之化合物’係R21、R22及R23之全部係苯基之前式（2)之化合物。此化合物係將苯基次膦酸二氯化物及苯酣以及三乙基胺，在四氫呋喃中以1小時使其進行加熱反應而合成。式（203 )之化合物’係R31、r32、R33係苯基，且 R·34係氫原子之前式（3)之化合物。此化合物係將二苯基膦酸氯化物及苯胺以及三乙基胺，在四氫呋喃中以1小時使其進行加熱反應而合成。式（204 )之化合物，係R41、r42及r43係苯基，且 R·44係氫原子之前式（4)之化合物。此化合物係將苯基次膦酸二氯化物及苯酚以及三乙基胺，在四氫呋喃中以1小時使其進行加熱反應後’再與苯胺加熱反應1小時而合成〇式（205)之化合物，係R51、R52及R53係苯基，且 R 5 4、R 5 5係氫原子之前式（5 )之化合物。此化合物係將苯基次膦酸二氯化物及苯胺以及三乙基胺，在四氫呋喃中以1小時使其進行加熱反應而合成。式（206)之化合物，係Rn、R12係苯基，且R13係 3 -甲基苯基之前式（1)之化合物。此化合物係將二苯基膦酸氯化物及m-甲酚以及三乙基胺，在四氫呋喃中以1 小時使其進行加熱反應而合成。式（207 )之化合物，係R21係苯基，且R22、R23係 -31 - 201002729 3 -甲基苯基之前式（2 )之化合物。此化合物係將苯基次膦酸二氯化物及m-甲酚以及三乙基胺，在四氫呋喃中以1 小時使其進行加熱反應而合成。式（2 0 8 )之化合物，係R !!、R i 2係苯基，且R i 3係 4 -甲基苯基之前式（1)之化合物。此化合物係將二苯基膦酸氯化物及P-甲酚以及三乙基胺，在四氫呋喃中以1小時使其進行加熱反應而合成。式（2 09 )之化合物，係R21係苯基，且R22、r23係 4 -甲基苯基之前式（2 )之化合物。此化合物係將苯基次膦酸二氯化物及P -甲酚以及三乙基胺，在四氫呋喃中以1 小時使其進行加熱反應而合成。式（2 1 0 )之化合物，係R】,、R12係苯基，且R】3係 4 -甲基苯基之前式（1)之化合物。此化合物係將二苯基膦酸氯化物及P -甲氧基苯酚以及三乙基胺，在四氫呋喃中以1小時使其進行加熱反應而合成。式（21 1 )之化合物，係R21係苯基，且r22、r23係 4-甲基苯基之前式（2 )之化合物。此化合物係將苯基次膦酸二氯化物及p-甲氧基苯酚以及三乙基胺，在四氫呋喃中以1小時使其進行加熱反應而合成。式（212 )之化合物，係R41、R43係苯基，r42係p_ 甲氧基苯基’且R44係氫原子之前式（4 )之化合物。此化合物係將苯基次膦酸二氯化物及P -甲氧基苯酣以及三乙基胺，在四氫呋喃中以1小時使其進行加熱反應後，再與苯胺加熱反應1小時而合成。 -32- 201002729 式（3 01 )之化合物，有大八化學（股）製之商品名稱NDPP市售中。式（3 02 )之化合物，有北興化學（股）製之商品名稱TPPO市售中。式（3 03 )之化合物，有大八化學（股）製之商品名稱TPP市售中。在以下之實施例1-12及比較例1-3中，將表1-15所示之各有機磷系化合物，如有必要並以砂磨機磨碎，再將各成分加入水中，而製得水性分散液。實施例1 〔表1〕水 6 3.0% 式（2 0 1 )之化合物（前式（1)之化合物） 30.0% PLYSURF ALNa 鹽 6.3% 增黏劑 0.5% 消泡劑 0.1% 防黴菌劑 0.1% 實施例2 10 0.0% 〔表2〕水 6 3.0% 式（202)之化合物 (前式（2)之化合物） 3 0.0% PLYSURF ALNa 鹽 6.3% 增黏劑 0.5% 消泡劑 0.1% 防黴菌劑 0.1% 10 0.0% -33- 201002729 實施例3 〔表3〕水式（203 )之化合物 PLYSURF ALNa 鹽增黏劑消泡劑防黴菌劑 (前式（3 )之化合物） 6 3.0% 3 0.0% 6.3% 0.5% 0.1% 0.1% 實施例4 10 0.0% 〔表4〕水 6 3.0% 式（2 0 4 )之化合物 (前式（4)之化合物） 3 0.0% PLYSURF ALNa 鹽 6.3% 增黏齊ί 0.5% 消泡齊!1 0.1% 防黴菌劑 0.1% 10 0.0% 實施例5 〔表5〕水 6 3.0% 式（2 0 5 )之化合物 (前式（5)之化合物） 3 0.0% PLYSURF ALNa 鹽 6.3% 增黏劑 0.5% 消泡劑 0.1% 防黴菌劑 0.1% 10 0.0% -34- 201002729 實施例6 〔表6〕水式（206)之化合物 PLYSURF ALNa 鹽增黏劑消泡劑防黴菌劑 (前式（1)之化合物） 6 3.0% 3 0.0% 6.3% 0.5% 0.1% 0.1% 實施例7 10 0.0% 〔表7〕水 6 3.0% 式（2 0 7 )之化合物 (前式（2 )之化合物） 3 0.0% PLYSURF ALNa 鹽 6.3% 增黏劑 0.5% 消泡劑 0.1% 防黴菌劑 0.1% 10 0.0% 實施例8 〔表8〕水 6 3.0% 式（208)之化合物（前式（1)之化合物） 3 0.0% PLYSURF ALNa 鹽 6.3% 增黏劑 0.5% 消泡劑 0.1% 防黴菌劑 0.1% 10 0.0% -35- 201002729 實施例9 〔表9〕水 6 3.0% 式（2 0 9 )之化合物 (前式（2)之化合物） 3 0.0% PLYSURF ALNa 鹽 6.3% 增黏齊U 0.5% 消泡齊Ί 0.1% 防黴菌劑 0.1% 10 0.0% 實施例1 〇〔表 1 〇〕水式（2 1 0 )之化合物 PLYSURF ALNa 鹽增黏劑消泡劑防黴菌劑 (前式（1)之化合物） 6 3.0% 3 0.0% 6.3% 0.5% 0.1% 0.1% 實施例1 1 10 0.0% 〔表 1 1〕水 6 3.0% 式（211)之化合物 (前式（2)之化合物） 3 0.0% PLYSURF ALNa 鹽 6.3% 增黏劑 0.5% 消泡劑 0.1% 防黴菌劑 0.1% 10 0.0% -36- 201002729 實施例1 2 〔表 12〕水 6 3.0% 式（212)之化合物 (前式（4)之化合物） 3 0.0% PLYSURF ALNa 鹽 6.3% 增黏劑 0.5% 消泡劑 0.1% 防黴菌劑 0.1% 10 0.0% 比較例1 〔表 13〕水式（3 0 1 )之化合物 PLYSURF ALNa 鹽增黏劑消泡劑防黴菌劑 6 3.0% 3 0.0% 6.3% 0.5% 0.1% 0.1% 比較例2 10 0.0% 〔表 14〕水 6 3.0% 式（3 02)之化合物 3 0.0% PLYSURF ALNa 鹽 6.3% 增黏劑 0.5% 消泡劑 0.1% 防黴菌劑 0.1% 10 0.0% -37- 201002729 比較例3 〔表 15〕水 6 3.0% 式（303)之化合物 3 0.0% PLYSURF ALNa 鹽 6.3% 增黏齊U 0.5% 消泡劑 0.1% 防黴菌劑 0.1% 1 ο ο. ο % 試驗例1 使用以上述實施例1 -1 2或比較例1 - 3所調製之阻燃劑之水性分散液’再以浸染同浴處理法，將含有3 0 %聚酯及 70% CDP之混紡纖維布帛之4 0公分四方分別進行染色，同時並施以阻燃加工。亦即，染浴係將分散染料0.72% o.w.f. ( on weight of fiber)及陽離子染料0.92% o.w.f.及在實施例1-12或比較例1 - 3所調製之阻燃加工劑，分別以浴比1 : 2 0、1 3 0 °C X60分鐘進行處理。所使用之染料’係作爲分散染料之卡雅隆微酯黃AQ-LE 0.24%、卡雅隆微酯紅AQ-LE 0.24%、卡雅隆微酯藍 AQ-LE 0.24%、作爲陽離子染料之卡雅庫立爾黃3RL-ED 0.46% (皆爲日本化藥（股）製）、卡雅庫立爾紅GL-ED 0.24%、卡雅庫立爾藍GSL-ED 0.22% (皆爲日本化藥（股）製）。其後，對於各布帛進行還原洗淨，再以1 70 °C實施60 -38- 201002729 秒之熱處理。接著，根據JIS K3 37 1，以1 g/L之比例使用弱鹼性第1種洗劑，並以浴比1 : 40，60 °C ±2 °C處理1 5 分鐘’然後將各布帛以水濯後，再以4CTC ±2 t處理5分鐘之方式水洗三次，離心脫水2分鐘，再於60 X： ±5 t下進行熱風乾燥爲1循環，共進行5循環。將以上述之操作所得到之1 5種之混紡纖維布帛作成試驗片，再關於其等進行燃燒性試驗。又上述所謂之還原洗淨，係指以下之操作。亦即，調製亞硫酸氫鹽2 g/L、苛性鈉2 g/L、界面活性劑1 g/L之水溶液，將其加溫至8 0 °C後，加入經過阻燃加工之上述布帛，進行20分鐘之操作處理。燃燒性試驗之試驗方法以消防法J I S L 1 0 9 1 A -1法（4 5度微焰燈法）進行試驗’再進行以下之評價。其結果示於下述表16中。評價A :合格率以殘焰時間在3秒以下者爲合格，並以測定次數與該測定中之合格次數相除，所得之數値作爲合格率而記載。將小數點以下四捨五入，單位則爲％。如合格率高者則其阻燃功能越高。合格率後方之括弧，係以合格率計算之合格次數與測定次數，並以「（合格次數/測定次數）」表示。 -39- 201002729 評價B :平均殘焰時間將以試驗A測定之殘焰時間之總計’除以測定次數’ 而計算其平均殘焰時間。單位爲秒。平均殘焰時間越短者，其阻燃功能越高。評價C :平均燃燒面積量測試驗片之燃燒面積，將其總和除以測定次數’而計算平均燃燒面積。單位爲cm2。平均燃燒面積越小者’ 其阻燃功能越高。〔表 16〕阻燃劑對纖維評價 __ (重量％) A B C 未處理布 0 0(0/11) 3 7.8 70.5 實施例1 2 0% 100(20/20) 0.9 3.9 實施例2 2 0% 100(19/19) 0.5 3.6 實施例3 2 0% 100(19/19) 0.7 3.7 實施例4 20% 100(21/21) 0.8 3.7 實施例5 2 0% 95(20/21) 0.9 4.1 實施例6 2 0% 95(20/21) 0.9 3.9 實施例7 2 0% 95(20/21) 0.8 4.0 實施例8 2 0% 100(21/21) 0.7 3.7 實施例9 2 0% 100(20/20) 0.9 3.9 實施例1 0 2 0% 100(19/19) 0.6 3.6 實施例1 1 2 0% 100(21/21) 0.7 3.7 實施例1 2 2 0% 100(21/21) 0.8 3.7 比較例1 2 0% 57(12/21) 3.8 7.1 比較例2 20% 65(13/20) 2.5 6.7 比較例3 2 0% 64(14/22) 2.7 5.6 -40- 201002729 由表16之結果明顯可知者’評價A之合格率’相對於本發明之實施例1 · 1 2爲9 5至1 〇〇 %，各比較例係5 7至 6 5 %，故本發明之實施例爲合格率較高者。此外’關於評價B之平均殘焰時間，相對於實施例1 -1 2爲0 _ 5至0 _ 9，各比較例係2.5至3.8，故後者爲3至7倍’其平均殘焰時間爲更長者。進一步，關於評價C之平均燃燒面積’相對於實施例1 -1 2爲3.6至4 · 1，各比較例係5.6至7.1 ’故後者爲1.4至2.0倍，其平均燃燒面積爲更大者。如上所述，使用本發明之水性分散液之試驗片，明顯可知具有優良之阻燃功能。此外，再將使用本發明之水性分散液之試驗片重複進行5次循環，惟仍能保持上述之功能，明顯可知其即使在耐久性上亦爲極優良者。實施例1 3 由本發明所提供之前式（2)及前式（4)所示之新穎化合物，係以下式（2 1 3 )至（2 3 8 )所示之化合物製造。此外，比較化合物，係使用下式（3 0 4 )及（3 0 5 )之化合物。 -41 - 201002729(301) (303) A compound of the formula (201), wherein all of R13 are a compound of the formula (1) before the phenyl group. This compound was synthesized by heating a diphenylphosphonic acid chloride and benzene-30-201002729 phenol and triethylamine in tetrahydrofuran for 1 hour. The compound of the formula (202) is a compound of the formula (2) before all of R21, R22 and R23. This compound was synthesized by subjecting phenylphosphinic acid dichloride, phenylhydrazine and triethylamine to heating in tetrahydrofuran for 1 hour. The compound of the formula (203) is a compound of the formula (3) wherein R31, R32 and R33 are a phenyl group, and R.34 is a hydrogen atom. This compound was synthesized by subjecting diphenylphosphonic acid chloride, aniline and triethylamine to heating in tetrahydrofuran for 1 hour. The compound of the formula (204) is a compound of the formula (4) wherein R41 is a hydrogen atom of R41, r42 and r43. This compound is obtained by synthesizing phenylphosphinic acid dichloride, phenol and triethylamine in tetrahydrofuran for 1 hour, and then reacting with aniline for 1 hour to synthesize a compound of formula (205). A compound of the formula (5) wherein R51, R52 and R53 are a phenyl group, and R 5 4 and R 5 5 are a hydrogen atom. This compound was synthesized by subjecting phenylphosphinic acid dichloride, aniline and triethylamine to heating in tetrahydrofuran for 1 hour. The compound of the formula (206) is a phenyl group of Rn or R12, and R13 is a compound of the formula (1) before the 3-methylphenyl group. This compound was synthesized by subjecting diphenylphosphonic acid chloride, m-cresol and triethylamine to heating reaction in tetrahydrofuran for 1 hour. A compound of the formula (207) which is a phenyl group of R21 and a compound of the formula (2) wherein R22 and R23 are -31 - 201002729 3-methylphenyl. This compound was synthesized by heating a phenylphosphinic acid dichloride, m-cresol and triethylamine in tetrahydrofuran over 1 hour. The compound of the formula (208) is a compound of the formula (1) wherein R?!, R i 2 is a phenyl group, and R i 3 is a 4-methylphenyl group. This compound was synthesized by subjecting diphenylphosphonic acid chloride, P-cresol and triethylamine to heating reaction in tetrahydrofuran at 1 hour. The compound of the formula (2:09) is a compound of the formula (2) wherein R22 is a phenyl group, and R22 and r23 are a 4-methylphenyl group. This compound was synthesized by subjecting phenylphosphinic acid dichloride, P-cresol and triethylamine to heating in tetrahydrofuran for 1 hour. The compound of the formula (2 10 0) is a compound of the formula (1), R, R12 is a phenyl group, and R is a 3-methylphenyl group. This compound was synthesized by subjecting diphenylphosphonic acid chloride, P-methoxyphenol and triethylamine to heating reaction in tetrahydrofuran for 1 hour. The compound of the formula (21 1 ) is a compound of the formula (21), and R22 is a compound of the formula (2). This compound was synthesized by subjecting phenylphosphinic acid dichloride, p-methoxyphenol and triethylamine to heating in tetrahydrofuran for 1 hour. The compound of the formula (212) is a compound of the formula (4) wherein R41 is a phenyl group of R43 and R42 is a p-methoxyphenyl group, and R44 is a hydrogen atom. This compound was synthesized by subjecting phenylphosphinic acid dichloride, P-methoxybenzoquinone, and triethylamine to heating in tetrahydrofuran for 1 hour, followed by heating reaction with aniline for 1 hour. -32- 201002729 The compound of formula (3 01 ) is commercially available as NDPP under the trade name of Da Ba Chemical Co., Ltd. The compound of the formula (3 02 ) is commercially available under the trade name TPPO manufactured by Beixing Chemical Co., Ltd. The compound of the formula (3 03 ) is commercially available as TBP, which is manufactured by Daisaku Chemical Co., Ltd. In the following Examples 1-12 and Comparative Examples 1-3, the respective organophosphorus compounds shown in Tables 1-15 were ground in a sand mill if necessary, and then the components were added to water. An aqueous dispersion is obtained. Example 1 [Table 1] Water 6 3.0% Compound of the formula (2 0 1 ) (compound of the former formula (1)) 30.0% PLYSURF ALNa salt 6.3% tackifier 0.5% defoamer 0.1% antifungal agent 0.1% Example 2 10 0.0% [Table 2] Water 6 3.0% Compound of the formula (202) (compound of the former formula (2)) 3 0.0% PLYSURF ALNa salt 6.3% tackifier 0.5% antifoaming agent 0.1% antifungal agent 0.1% 10 0.0% -33- 201002729 Example 3 [Table 3] Compound of the formula (203) PLYSURF ALNa Salt tackifier Antifoaming agent Antifungal agent (Compound of the former formula (3)) 6 3.0% 3 0.0% 6.3% 0.5% 0.1% 0.1% Example 4 10 0.0% [Table 4] Water 6 3.0% Compound of the formula (2 0 4 ) (Compound of the former formula (4)) 3 0.0% PLYSURF ALNa Salt 6.3% Addition ί 0.5% defoaming! 1 0.1% antifungal agent 0.1% 10 0.0% Example 5 [Table 5] Water 6 3.0% Compound of formula (2 0 5 ) (compound of formula (5)) 3 0.0% PLYSURF ALNa salt 6.3% tackifier 0.5% defoamer 0.1% antifungal agent 0.1% 10 0.0% -34- 201002729 Example 6 [Table 6] Compound of formula (206) PLYSURF ALNa salt Tackifier antifoaming agent antifungal agent (compound of formula (1)) 6 3.0% 3 0.0% 6.3% 0.5% 0.1% 0.1% Example 7 10 0.0% [Table 7] Water 6 3.0% Formula (2 0 7) Compound (compound of formula (2)) 3 0.0% PLYSURF ALNa salt 6.3% tackifier 0.5% defoamer 0.1% antifungal agent 0.1% 10 0.0% Example 8 [Table 8] Water 6 3.0% Compound of formula (208) (compound of formula (1)) 3 0.0% PLYSURF ALNa salt 6.3% tackifier 0.5% antifoaming agent 0.1% antifungal agent 0.1% 10 0.0% -35- 201002729 Example 9 [Table 9] Water 6 3.0% Compound of formula (2 0 9 ) (compound of formula (2)) 3 0.0% PLYSURF ALNa salt 6.3% viscosity increase U 0.5% defoaming 0.1% antifungal agent 0.1% 10 0.0 % Example 1 〇 [Table 1 〇] Water (2 1 0 ) Compound PLYSURF ALNa Salt Tackifier Antifoaming Agent Antifungal Agent (Compound of Formula (1)) 6 3.0% 3 0.0% 6.3% 0.5% 0.1% 0.1% Example 1 1 10 0.0% [Table 1 1] Water 6 3.0% Compound of the formula (211) (compound of the former formula (2)) 3 0.0% PLYSURF ALNa salt 6.3% tackifier 0.5% Foaming agent 0.1% Antifungal agent 0.1% 10 0.0% -36- 201002729 Example 1 2 [Table 12] Water 6 3.0% Compound of the formula (212) (compound of the former formula (4)) 3 0.0% PLYSURF ALNa salt 6.3 % tackifier 0.5% defoamer 0.1% antifungal agent 0.1% 10 0.0% Comparative Example 1 [Table 13] Water (3 0 1 ) compound PLYSURF ALNa salt tackifier antifoaming agent antifungal agent 6 3.0% 3 0.0% 6.3% 0.5% 0.1% 0.1% Comparative Example 2 10 0.0% [Table 14] Water 6 3.0% Compound 3 of formula (3 02) 0.0% PLYSURF ALNa salt 6.3% tackifier 0.5% defoamer 0.1% Antifungal agent 0.1% 10 0.0% -37- 201002729 Comparative Example 3 [Table 15] Water 6 3.0% Compound 3 of formula (303) 0.0% PLYSURF ALNa Salt 6.3% Viscosity U 0.5% Defoamer 0.1% Antifungal Agent 0.1% 1 ο ο. ο % Test Example 1 The aqueous dispersion of the flame retardant prepared by using the above Example 1-1 or Comparative Example 1-3 was further subjected to the same bath treatment method, and it contained 3 0. The polyester of 70% and 70% of CDP blended fiber cloth was dyed by 40 square meters, and flame retardant processing was applied. That is, the dyeing bath system disperse the dye 0.72% owf (on weight of fiber) and the cationic dye 0.92% owf and the flame retardant processing agent prepared in Examples 1-12 or Comparative Example 1-3, respectively, in bath ratio 1 : 2 0, 1 3 0 °C X60 minutes for processing. The dye used was Kayalon microester yellow AQ-LE 0.24% as disperse dye, Kayalon microester red AQ-LE 0.24%, Kayalon microester blue AQ-LE 0.24%, and Kayaku as a cationic dye. Lierhuang 3RL-ED 0.46% (all made by Nippon Chemical Co., Ltd.), Kayakuli Red GL-ED 0.24%, Kayakuli Blue GSL-ED 0.22% (all are Japanese chemical products ( Stock system)). Thereafter, each fabric was subjected to reduction washing, and then heat treatment was carried out at 70 °C for 60 - 38 - 201002729 seconds. Next, use a weakly alkaline first lotion in a ratio of 1 g/L according to JIS K3 37 1, and treat it at a bath ratio of 1:40, 60 °C ± 2 °C for 15 minutes. After the leeches, the mixture was washed three times with 4 CTC ± 2 t for 5 minutes, centrifuged for 2 minutes, and then dried at 60 X: ± 5 t for 1 cycle for 5 cycles. The blended fiber fabric of 15 kinds obtained by the above operation was used as a test piece, and the flammability test was performed thereon. The above-mentioned so-called reduction washing means the following operations. That is, an aqueous solution of 2 g/L of bisulfite, 2 g/L of caustic soda, and 1 g/L of a surfactant is prepared, and after heating to 80 ° C, the above-mentioned fabric subjected to flame retardant processing is added. Perform a 20-minute operation. Test method for flammability test The test was carried out by the fire method J I S L 1 0 9 1 A -1 method (45-degree micro-flame lamp method), and the following evaluation was performed. The results are shown in Table 16 below. Evaluation A: Pass rate The pass after the residual flame time is 3 seconds or less, and the number of times of measurement is divided by the number of passes in the measurement, and the obtained number is described as the pass rate. Round off the decimal point and the unit is %. If the pass rate is high, the flame retardant function is higher. The brackets after the pass rate are the number of passes and the number of passes calculated by the pass rate, and are expressed as "(number of passes/number of measurements)". -39- 201002729 Evaluation B: Average afterflame time The average afterflame time was calculated by dividing the total of the afterflame times measured in Test A by the number of measurements. The unit is seconds. The shorter the average afterflame time, the higher the flame retardant function. Evaluation C: Average burning area The burning area of the test piece was measured, and the average burning area was calculated by dividing the total of the test pieces by the number of measurements. The unit is cm2. The smaller the average burning area, the higher the flame retardant function. [Table 16] Evaluation of fiber by flame retardant __ (% by weight) ABC Untreated cloth 0 0 (0/11) 3 7.8 70.5 Example 1 2 0% 100 (20/20) 0.9 3.9 Example 2 2 0% 100(19/19) 0.5 3.6 Example 3 2 0% 100(19/19) 0.7 3.7 Example 4 20% 100(21/21) 0.8 3.7 Example 5 2 0% 95(20/21) 0.9 4.1 Implementation Example 6 2 0% 95 (20/21) 0.9 3.9 Example 7 2 0% 95 (20/21) 0.8 4.0 Example 8 2 0% 100 (21/21) 0.7 3.7 Example 9 2 0% 100 (20 /20) 0.9 3.9 Example 1 0 2 0% 100 (19/19) 0.6 3.6 Example 1 1 2 0% 100 (21/21) 0.7 3.7 Example 1 2 2 0% 100 (21/21) 0.8 3.7 Comparative Example 1 2 0% 57(12/21) 3.8 7.1 Comparative Example 2 20% 65(13/20) 2.5 6.7 Comparative Example 3 2 0% 64(14/22) 2.7 5.6 -40- 201002729 Results from Table 16 It is apparent that the 'eligibility rate of evaluation A' is 9.5 to 10,000% with respect to the embodiment 1 · 1 2 of the present invention, and each comparative example is 57 to 65 %, so the embodiment of the present invention is a pass rate. Higher. In addition, the average residual flame time for evaluation B is 0 _ 5 to 0 _ 9 with respect to Example 1-1, and each comparative example is 2.5 to 3.8, so the latter is 3 to 7 times 'the average afterflame time is The longer. Further, the average combustion area with respect to the evaluation C was 3.6 to 4·1 with respect to Example 1-1, and each of the comparative examples was 5.6 to 7.1', and the latter was 1.4 to 2.0 times, and the average burning area was larger. As described above, the test piece using the aqueous dispersion of the present invention is clearly known to have an excellent flame retardant function. Further, the test piece using the aqueous dispersion of the present invention was repeated for 5 cycles, but the above functions were maintained, and it was apparent that it was excellent even in durability. [Example 1] The novel compounds of the above formula (2) and the above formula (4) which are provided by the present invention are produced by the compounds represented by the following formulas (2 1 3 ) to (2 3 8 ). Further, as a comparative compound, a compound of the following formula (304) and (305) was used. -41 - 201002729

-42- 201002729 【化1 3 — 2】-42- 201002729 【化1 3 — 2】

(224) (225) (226)(224) (225) (226)

(228) (227) ό(228) (227) ό

(231)(231)

(232) (230) ^r°-〇 ο Ο-γ-Ο ? 〇 α° σ° ) (233) (234) (235) -43 201002729(232) (230) ^r°-〇 ο Ο-γ-Ο ? 〇 α° σ° ) (233) (234) (235) -43 201002729

1. 式（213)之化合物，係R~21、R22爲苯基、R23爲节基之前式（2)之化合物。在四氫呋喃200份中，以二苯基膦酸氯化物50份、苯酚2 4份及三乙基胺5 7份，在1 〇 °C下使其反應1小時後，再與苄基醇在室溫下反應1小時。添加水1 〇〇份，再以稀鹽酸作成pH値7以下靜置。將上層進行分液，再以飽和食鹽水洗淨後，另將下層進行分液、廢棄，由上層部以氣化器將四氫呋喃等加以餾去，而得到膦酸化合物。所得到之化合物，係淡黃色之液體，且由L C - M S (高速液體色層分析法-質量分析計）之測定鑑定爲式（2丨3 )之化合物〇 MS ： 3 24.09 (理論値 324.09) 2. 式（214 )之化合物，係、爲苯基、R43爲节 -44- 201002729 基、R44爲氫原子之前式（4 )之化合物。與式（2 1 3 )之化合物之製造法爲相同地，在四氫呋喃中，使二苯基膦酸氯化物、苯酚及三乙基胺進行反應1 小時後，再與苄基胺進行反應1小時而合成。 MS ： 3 23.1 1 (理論値 3 23.1 1 ) 3. 式（215 )之化合物，係R21爲苯基、R22爲4-甲基苯基、R23爲苄基之前式（2 )之化合物。與式（2 1 3 )之化合物之製造法爲相同地，在四氫呋喃中，使二苯基膦酸氯化物、p-甲酚及三乙基胺進行反應 1小時後，再與苄基醇進行反應1小時而合成。 MS ： 3 3 8.1 1 (理論値 3 3 8.1 1 ) 4. 式（216 )之化合物，係R41爲苯基、R42爲3_甲基苯基、R43爲苄基、R44爲氫原子之前式（4 )之化合物。與式（2 1 3 )之化合物之製造法爲相同地，在四氫呋喃中，使二苯基膦酸氯化物、m-甲酚及三乙基胺進行反應 1小時後，再與苄基胺進行反應1小時而合成。 MS: 337.12 (理論値 337.12) 5. 式（217 )之化合物，係R41、R43爲苯基、R42爲3-甲基苯基、r44爲氫原子之前式（4)之化合物。與式（2 1 3 )之化合物之製造法爲相同地，在四氫呋喃中，使二苯基膦酸氯化物、m-甲酚及三乙基胺進行反應 1小時後，再與苯胺進行反應1小時而合成。 MS ： 3 23.1 1 (理論値 3 23.1 1 ) 6. 式（21 8 )之化合物，係R21爲苯基、R22爲4-苯基 -45- 201002729 苯基、R_23爲节基之前式（2)之化合物。與式（213)之化合物之製造法爲相同地’在四氫呋喃中，使二苯基膦酸氯化物、P-甲酚及三乙基胺進行反應 1小時後，再與苄基醇進行反應1小時而合成。 MS ： 400.1 2 (理論値 400.12) 7.式（219)之化合物，係R41爲苯基、R4 2爲4·甲基苯基、R43爲苄基、R44爲氫原子之前式（4 )之化合物。與式（2 1 3 )之化合物之製造法爲相同地’在四氫呋喃中，使二苯基膦酸氯化物、p-甲酚及三乙基胺進行反應 1小時後，再與苄基胺進行反應1小時而合成。 MS ： 3 3 7.1 2 (理論値 337.12) 8 ·式（220 )之化合物，係R4i、R43爲苯基、R42爲4-甲基苯基、R44爲氫原子之前式（4)之化合物。與式（2 1 3 )之化合物之製造法爲相同地，在四氫呋喃中，使二苯基膦酸氯化物、p-甲酚及三乙基胺進行反應 1小時後，再與苯胺進行反應1小時而合成。 MS ： 3 23.1 1 (理論値 323_11) 9. 式（22 1 )之化合物，係R21爲苯基、R22爲4-t-丁基苯基、R23爲苄基之前式（2)之化合物。與式（213)之化合物之製造法爲相同地，在四氫呋喃中，使二苯基膦酸氯化物、4_t-丁基苯酚及三乙基胺進行反應1小時後，再與苄基醇進行反應1小時而合成。 MS ： 3 80.1 5 (理論値 380.15) 10. 式（ 222)之化合物，係R41爲苯基、R42爲4-t -丁 -46 - 201002729 基本基、R4 3爲卞基、R4 4爲氣原子之前式（4 )之化合物〇與式（213)之化合物之製造法爲相同地，在四氫咲喃中，使二苯基膦酸氯化物、4-t-丁基苯酣及三乙基胺進行反應1小時後’再與节基胺進彳了反應1小時而合成。 MS : 3 79.1 7 (理論値 3 79.1 7 ) 11. 式（223)之化合物，係尺^爲苯基、r42爲苯基苯基、R43爲节基、R44爲氫原子之前式（4)之化合物。與式（2 1 3 )之化合物之製造法爲相同地，在四氫呋喃中’使二苯基膦酸氯化物、p -苯基苯酚及三乙基胺進行反應1小時後，再與苄基胺進行反應1小時而合成。 MS ： 3 99.1 4 (理論値 399.1 4 ) 12. 式（224)之化合物，係R41爲苯基、r42爲p-枯烯基苯基、R_43爲予基、R44爲氫原子之前式（4)之化合物。與式（213)之化合物之製造法爲相同地，在四氫呋喃中，使二苯基膦酸氯化物、P -枯烯基苯酚及三乙基胺進行反應1小時後，再與节基胺進行反應1小時而合成。 MS ： 441.19 (理論値 441.19) 13. 式（225 )之化合物，係R4i爲苯基、R42爲2-萘基、R43爲苄基、R44爲氫原子之前式（4 )之化合物。與式（2 1 3 )之化合物之製造法爲相同地，在四氫呋喃中，使二苯基膦酸氯化物、2 -萘酚及三乙基胺進行反應 1小時後，再與苄基胺進行反應1小時而合成。 -47- 201002729 MS ： 3 73.1 2 (理論値 373_12) 14_式（226 )之化合物，係R41、R43爲本基、R42爲 2-萘基、R44爲氫原子之前式（4 )之化合物。與式（213)之化合物之製造法爲相同地’在四氫咲喃中，使二苯基膦酸氯化物、2_萘酌及三乙基胺進行反應 1小時後，再與苯胺進行反應1小時而合成。 MS: 359.11 (理論値 359.11) 15. 式（227)之化合物，係R41、R42爲苯基、R43爲 2 -甲基苄基、R44爲氫原子之前式（4)之化合物。與式（2 1 3 )之化合物之製造法爲相同地’在四氫呋喃中，使二苯基膦酸氯化物、苯酚及三乙基胺進行反應1 小時後，再與2 -甲基苄基胺進行反應1小時而合成。 MS ： 3 3 7.1 2 (理論値 337.12) 16. 式（ 228)之化合物，係Κ·4ΐ、R42爲苯基、R43爲苄基、R44爲甲基之前式（4 )之化合物。與式（213)之化合物之製造法爲相同地，在四氫呋喃中，使二苯基膦酸氯化物 '苯酚及三乙基胺進行反應1 小時後，再與N-甲基苄基胺進行反應1小時而合成。 MS ： 3 3 7.1 2 (理論値 3 3 7.1 2 ) 17. 式（229)之化合物，係R41爲苯基、爲4-t-丁基苯基、R43爲苯基、R44爲氫原子之前式（4 )之化合物〇與式（2 1 3 )之化合物之製造法爲相同地’在四氫呋喃中，使二苯基膦酸氯化物、4-t-丁基苯酚及三乙基胺進 -48 - 201002729 行反應1小時後，再與苯胺進行反應1小時而合成。 MS： 3 65.1 5 (理論値 365.1 5 ) 1 8_式（23 0 )之化合物，係R41、R42、r43爲苯基、 R4 4爲N-甲基苯基之前式（4)之化合物。與式（2 1 3 )之化合物之製造法爲相同地，在四氫呋喃中，使二苯基膦酸氯化物、苯酚及三乙基胺進行反應！小時後，再與N-甲基苯胺進行反應1小時而合成。 MS ： 3 2 3.1 1 (理論値 3 23.1 1 ) 1 9.式（23 1 )之化合物，係R4i爲苯基、R42爲2-苯基苯基、R43爲节基、R44爲氫原子之前式（4)之化合物〇與式（2 1 3 )之化合物之製造法爲相同地，在四氫呋喃中，使二苯基膦酸氯化物、2 -苯基苯酚及三乙基胺進行反應1小時後，再與苄基胺進行反應1小時而合成。 MS: 3 99.1 4 (理論値 399.14) 20.式（232)之化合物，係R_4i爲苯基、R4 2爲2-苯基苯基、R4 3爲苯基、R44爲氫原子之前式（4)之化合物〇與式（2 1 3 )之化合物之製造法爲相同地，在四氫呋喃中，使二苯基膦酸氯化物、2-苯基苯酚及三乙基胺進行反應1小時後，再與苯胺進行反應1小時而合成。 MS: 385.12 (理論値 385.12) 2 1 .式（23 3 )之化合物，係R2i、R23爲苯基、R22爲 2 -苯氧基乙基之前式（2)之化合物。 -49- 201002729 與式（213)之化合物之製造法爲相同地，在四氫呋喃中，使二苯基膦酸氯化物、苯酚及三乙基胺進行反應1 小時後，再與2 -苯氧基乙醇進行反應1小時而合成。 MS ： 3 54.1 0 (理論値 3 5 4.1 0 ) 22. 式（234)之化合物，係r41、R43爲苯基、R42爲 2 -苯氧基乙基、R44爲氫原子之前式（4)之化合物。與式（2 1 3 )之化合物之製造法爲相同地，在四氫呋喃中，使二苯基膦酸氯化物、2·苯氧基乙醇及三乙基胺進行反應1小時後，再與苯胺進行反應1小時而合成。 MS ： 3 5 3.1 2 (理論値 353.12) 23. 式（23 5 )之化合物，係R41、R43爲苯基、R42爲 p -枯嫌基苯基、R44爲氫原子之前式（4)之化合物。與式（2 1 3 )之化合物之製造法爲相同地，在四氫呋喃中，使二苯基膦酸氯化物、p_枯烯基苯酚及三乙基胺進行反應1小時後，再與苯胺進行反應1小時而合成。 MS ： 427.1 7 (理論値 427.17) 24. 式（ 236)之化合物’係R41爲苯基、R42、R43爲苄基、R44爲氫原子之前式（4 )之化合物。與式（213)之化合物之製造法爲相同地，在四氫呋喃中，使二苯基膦酸氯化物、苄基醇及三乙基胺進行反應 1小時後，再與苄基胺進行反應1小時而合成。 MS ： 3 3 7.1 2 (理論値 337.12) 2 5.式（23 7 )之化合物’係1141、1143爲苯基、1142爲苄基、R4 4爲氫原子之前式（4)之化合物。 -50- 201002729 與式（2 1 3 )之化合物之製造法爲相同地’在四氫咲喃中，使二苯基膦酸氯化物、苄基醇及三乙基胺進行反應 1小時後，再與苯胺進行反應1小時而合成。 MS ： 3 23.1 1 (理論値 323.11) 26.式（23 8 )之化合物，係R41、尺42爲苯基、R43爲環己基、R44爲氫原子之前式（4)之化合物。與式（213)之化合物之製造法爲相同地，在四氫呋喃中，使二苯基膦酸氯化物、苯酚及三乙基胺進行反應1 小時後，再與環己胺進行反應1小時而合成。 MS ： 3 15.14 (理論値 315.14) 式（3 04 )之化合物，係在四氫呋喃中，使二苯基次膦酸氯化物、苯酚及三乙基胺進行反應1小時後，再與苯胺進行反應1小時而合成。式（3 0 5 )之化合物，係R21、R23爲苯基、R22爲2- 萘基之專利文獻5所記載之膦酸酯化合物。在四氫呋喃中，使二苯基膦酸氯化物、苯酚及三乙基胺進行反應1小時後’再與2 -萘酚進行反應1小時而合成〇在以下之實施例14-39及比較例4-5中，將表17-44 所示之各有機磷系化合物，如有必要再以砂磨機進行磨碎，將各成分加入水中而製得水性分散液。 -51 - 201002729 實施例1 4 〔表 17〕水 6 3.0% 式（2 13)之化合物 (前式（2 )之化合物） 3 0.0% PLYSURF ALNa 鹽 6.3% 增黏劑 0.5% 消泡劑 0.1% 防黴菌劑 0.1% 10 0.0% 實施例1 5 〔表 18〕水 6 3.0% 式（214)之化合物 (前式（4)之化合物） 3 0.0% PLYSURF ALNa 鹽 6.3% 增黏劑 0.5% 消泡劑 0.1% 防黴菌劑 0.1% 10 0.0% 實施例1 6 〔表 19〕水 6 3.0% 式（2 15)之化合物 (前式（2 )之化合物） 3 0.0% PLYSURF ALNa 鹽 6.3% 增黏齊U 0.5% 消泡劑 0.1% 防黴菌劑 0.1% 10 0.0% -52 - 201002729 實施例1 7 〔表 20〕水式（2 1 6 )之化合物 PLYSURF ALNa 鹽增黏劑消泡劑防黴菌劑 (前式（4)之化合物） 6 3.0% 3 0.0% 6.3% 0.5% 0.1% 0.1% 實施例1 8 10 0.0% 〔表 21〕水 6 3.0% 式（217)之化合物 (前式（4)之化合物） 3 0.0% PLYSURF ALNa 鹽 6.3% 增黏劑 0.5% 消泡劑 0.1% 防黴菌劑 0.1% 10 0.0% 實施例1 9 〔表 22〕水 6 3.0% 式（2 1 8)之化合物 (前式（2)之化合物） 3 0.0% PLYSURF ALNa 鹽 6.3% 增黏劑 0.5% 消泡劑 0.1% 防黴菌劑 0.1% 10 0.0% -53- 201002729 實施例2 0 〔表 23〕水 6 3.0% 式（2 1 9 )之化合物 (前式（4 )之化合物） 3 0.0% PLYSURF ALNa 鹽 6.3% 增黏劑 0.5% 消泡劑 0.1% 防黴菌劑 0.1% 10 0.0% 實施例2 1 〔表 24〕水式（2 2 0 )之化合物 PLYSURF ALNa 鹽增黏劑消泡劑防黴菌劑 (前式（4 )之化合物） 6 3.0% 3 0.0% 6.3% 0.5% 0.1% 0.1% 實施例2 2 10 0.0% 〔表 25〕水 6 3.0% 式（2 2 1 )之化合物 (前式（2 )之化合物） 3 0.0% PLYSURF ALNa 鹽 6.3% 增黏齊ί 0.5% 消泡齊U 0.1% 防黴菌劑 0.1% 10 0.0% -54- 201002729 實施例2 3 〔表 26〕水式（222)之化合物 PLYSURF ALNa 鹽增黏劑消泡劑防黴菌劑 (前式（4)之化合物） 6 3.0% 3 0.0% 6.3% 0.5% 0.1% 0.1% 實施例24 10 0.0% 〔表 27〕水 6 3.0% 式（223 )之化合物 (前式（4)之化合物） 3 0.0% PLYSURF ALNa 鹽 6.3% 增黏劑 0.5% 消泡劑 0.1% 防黴菌劑 0.1% 10 0.0% 實施例2 5 〔表 28〕水 6 3.0% 式（224)之化合物 (前式（4)之化合物） 3 0.0% PLYSURF ALNa 鹽 6.3% 增黏劑 0.5% 消泡劑 0.1% 防黴菌劑 0.1% 10 0.0% -55- 201002729 實施例2 6 〔表 29〕水 6 3.0% 式（225 )之化合物 (前式（4)之化合物） 3 0.0% PLYSURF ALNa 鹽 6.3% 增黏劑 0.5% 消泡劑 0.1% 防黴菌劑 0.1% 10 0.0% 實施例2 7 〔表 30〕水式（2 2 6 )之化合物 PLYSURF ALNa 鹽增黏劑消泡劑防黴菌劑 (前式（4 )之化合物） 6 3.0% 3 0.0% 6.3% 0.5% 0.1% 0.1% 實施例2 8 10 0.0% 〔表 3 1〕水 6 3.0% 式（227)之化合物 (前式（4)之化合物） 3 0.0% PLYSURF ALNa 鹽 6.3% 增黏劑 0.5% 消泡劑 0.1% 防黴菌劑 0.1% 10 0.0% -56- 201002729 實施例2 9 〔表 32〕水式（228)之化合物 PLYSURF ALNa 鹽增黏劑消泡劑防黴菌劑 (前式（4)之化合物） 6 3.0% 3 0.0% 6.3% 0.5% 0.1% 0.1% 實施例3 0 10 0.0% 〔表 33〕水 6 3.0% 式（2 2 9 )之化合物 (前式（4)之化合物） 3 0.0% PLYSURF ALNa 鹽 6.3% 增黏劑 0.5% 消泡劑 0.1% 防黴菌劑 0.1% 10 0.0% 實施例3 1 〔表 34〕水 6 3.0% 式（2 3 0)之化合物 (前式（2)之化合物） 3 0.0% PLYSURF ALNa 鹽 6.3% 增黏劑 0.5% 消泡劑 0.1% 防黴菌劑 0.1% 10 0.0% -57- 201002729 實施例3 2 〔表 35〕水 6 3.0% 式（231)之化合物 (前式（4 )之化合物） 3 0.0% PLYSURF ALNa 鹽 6.3% 增黏劑 0.5% 消泡劑 0.1% 防黴菌劑 0.1% 10 0.0% 實施例3 3 〔表 36〕水式（2 3 2 )之化合物 PLYSURF ALNa 鹽增黏劑消泡劑防黴菌劑 (前式（4 )之化合物） 6 3.0% 3 0.0% 6.3% 0.5% 0.1% 0.1% 實施例3 4 10 0.0% 〔表 37〕水 6 3.0% 式（23 3 )之化合物 (前式（2 )之化合物） 3 0.0% PLYSURF ALNa 鹽 6.3% 增黏劑 0.5% 消泡劑 0.1% 防黴菌劑 0.1% 10 0.0% -58- 201002729 實施例3 5 〔表 38〕水 6 3.0% 式（23 4)之化合物 (前式（4)之化合物） 3 0.0% PLYSURF ALNa 鹽 6.3% 增黏劑 0.5% 消泡劑 0.1% 防黴菌劑 0.1% 10 0.0% 實施例3 6 〔表 39〕水式（23 5 )之化合物 PLYSURF ALNa 鹽增黏劑消泡劑防黴菌劑 (前式（4)之化合物） 6 3.0% 3 0.0% 6.3% 0.5% 0.1% 0.1% 實施例3 7 〔表 40〕水 10 0.0% 6 3.0% 式（2 3 6)之化合物 PLYSURF ALNa 鹽 (前式（4)之化合物） 3 0.0% 6.3% 0.5% 0.1% 0.1% 增黏劑消泡劑防黴菌劑 10 0.0% -59- 201002729 實施例3 8 〔表 41〕水 6 3.0% 式（23 7)之化合物 (前式（4 )之化合物） 3 0.0% PLYSURF ALNa 鹽 6.3% 增黏劑 0.5% 消泡劑 0.1% 防黴菌劑 0.1% 10 0.0% 實施例3 9 〔表 42〕水式（23 8)之化合物 PLYSURF ALNa 鹽增黏劑消泡劑防黴菌劑 (前式（4 )之化合物） 6 3.0% 3 0.0% 6.3% 0.5% 0.1% 0.1% 比較例4 10 0.0% 〔表 4 3〕水 6 3.0% 式（3 04)之化合物 3 0.0% PLYSURF ALNa 鹽 6.3% 增黏劑 0.5% 消泡劑 0.1% 防黴菌劑 0.1% 1 ο ο. ο % -60 - 201002729 比較例5 〔表 44〕水 6 3.0% 式（3 0 5 )之化合物 3 0.0% PLYSURF ALNa 鹽 6.3% 增黏劑 0.5% 消泡劑 0.1% 防黴菌劑 0.1% 10 0.0% 試驗例2 使用以上述實施例14_39或比較例4-5所調製之阻燃劑之水性分散液，再與試驗例1同樣地進行操作’以浸染同浴處理法，將含有30%聚酯及70% CDP之混紡纖維布帛之20公分四方分別進行染色，同時並施以阻燃加工。其後，與實施例1同樣地，實施燃燒試驗（評價A、評價B )。進而，用以下之評價D (耐光堅固度）之試驗來取代試驗例1之評價C (平均燃燒面積）。結果示於下述表4 5中。評價D:耐光堅固度將耐光堅固度以1〜5級加以列表。 201002729 〔表 45〕阻燃劑對纖維 (重量％) 評價 A B C 未處理布 0 0(0/23) 39.8 5 實施例1 4 2 0% 100(20/20) 0.5 4 實施例1 5 2 0% 100(22/22) 0.5 4 實施例1 6 2 0% 95(20/21) 1.1 4 實施例1 7 2 0% 95(20/21) 1 .2 4 實施例1 8 2 0% 95(20/21) 1.3 4 實施例1 9 2 0% 86(18/21) 3.4 3 實施例2 0 2 0% 95(20/21) 1 .0 4 實施例2 1 2 0% 95(20/21) 1 .4 4 實施例2 2 2 0% 95(20/21) 1 .6 4 實施例23 2 0% 95(20/21) 1 . 8 4 實施例24 2 0% 86(18/21) 4.4 3 實施例2 5 2 0% 86(18/21) 4.5 4 實施例2 6 2 0% 95(20/21) 1 .3 3 實施例2 7 2 0% 95(20/21) 1.6 3 實施例2 8 2 0% 95(20/21) 1.1 4 實施例2 9 20% 95(20/21) 1.3 4 實施例3 0 2 0% 95(20/21) 1.6 4 實施例3 1 2 0% 95(20/21) 1 .3 4 實施例3 2 2 0% 86(18/21) 3.3 3 實施例3 3 2 0% 86(18/21) 3.4 3 實施例3 4 2 0% 95(20/21) 1.0 4 實施例3 5 2 0% 95(20/21) 1.1 4 實施例3 6 2 0% 86(18/21) 3.5 4 實施例3 7 2 0% 100(22/22) 0.6 4 實施例3 8 2 0% 95(22/22) 0.7 4 實施例3 9 2 0% 95(20/21) 1.4 4 比較例4 2 0% 57(12/21) 7.8 3-4 比較例5 2 0% 86(18/21) 4.9 3 -62- 201002729 由表45之結果明顯可知者，評價A之合格率，相對於本發明之實施例14-39爲86至1〇〇% ’比較例4係57 %，故本發明之實施例爲合格率較高者。而比較例5’其評價A之合格率係86%爲高，但其耐光堅固度低而耐光性差。此外，關於評價B之平均殘焰時間，相對於實施例 14-39爲0.5至4.5，比較例4-5係4.9至7.8，故後者之平均殘焰時間爲更長者。亦即，本發明之阻燃劑，其在評價A及評價B及評價 D顯示出優異之平衡性質，明顯可作爲阻燃劑而使用者。實施例4 0 由本發明所提供之前式（2)及式（4)所示之新穎化合物’係下式（23 9 )至（246 )所示之化合物製造者。 -63- 201002729 【化1 4】A compound of the formula (213), which is a compound of the formula (2) wherein R~21 and R22 are a phenyl group and R23 is a benzyl group. In 200 parts of tetrahydrofuran, 50 parts of diphenylphosphonic acid chloride, 24 parts of phenol and 57 parts of triethylamine were reacted at 1 ° C for 1 hour, and then with benzyl alcohol in the room. The reaction was carried out for 1 hour under temperature. 1 part of water was added, and the mixture was allowed to stand at pH 値7 or less with dilute hydrochloric acid. The upper layer was separated and washed with saturated brine, and the lower layer was separated and discarded, and tetrahydrofuran or the like was distilled off from the upper portion by a gasifier to obtain a phosphonic acid compound. The obtained compound is a pale yellow liquid, and is identified as a compound of the formula (2丨3) by LC-MS (High Speed Liquid Chromatography-Mass Analyzer) 〇MS : 3 24.09 (theoretical 値324.09) 2. A compound of the formula (214), which is a phenyl group, a compound of the formula (4) wherein R.sup.43 is a group of -44-201002729, and R44 is a hydrogen atom. In the same manner as in the production of the compound of the formula (2 1 3 ), diphenylphosphonic acid chloride, phenol and triethylamine were reacted in tetrahydrofuran for 1 hour, and then reacted with benzylamine for 1 hour. And synthesis. MS: 3 23.1 1 (theory 値 3 23.1 1 ) 3. A compound of the formula (215) wherein R21 is phenyl, R22 is 4-methylphenyl, and R23 is benzyl before compound of formula (2). In the same manner as in the production of the compound of the formula (2 1 3 ), diphenylphosphonic acid chloride, p-cresol and triethylamine were reacted in tetrahydrofuran for 1 hour, and then with benzyl alcohol. The reaction was carried out for 1 hour. MS : 3 3 8.1 1 (theory 値 3 3 8.1 1 ) 4. The compound of the formula (216), wherein R41 is a phenyl group, R42 is a 3-methylphenyl group, R43 is a benzyl group, and R44 is a hydrogen atom. 4) Compounds. In the same manner as in the production of the compound of the formula (2 1 3 ), diphenylphosphonic acid chloride, m-cresol and triethylamine were reacted in tetrahydrofuran for 1 hour, and then with benzylamine. The reaction was carried out for 1 hour. MS: 337.12 (theoretical 337 337.12) 5. The compound of the formula (217) is a compound of the formula (4) before R41 and R43 are a phenyl group, R42 is a 3-methylphenyl group, and r44 is a hydrogen atom. In the same manner as in the production of the compound of the formula (2 1 3 ), diphenylphosphonic acid chloride, m-cresol and triethylamine are reacted in tetrahydrofuran for 1 hour, and then reacted with aniline. Synthesized in hours. MS : 3 23.1 1 (theory 値 3 23.1 1 ) 6. The compound of the formula (21 8 ), wherein R21 is a phenyl group, R22 is a 4-phenyl-45-201002729 phenyl group, and R_23 is a nodal group before the formula (2) Compound. In the same manner as in the production method of the compound of the formula (213), in the tetrahydrofuran, diphenylphosphonic acid chloride, P-cresol and triethylamine are reacted for 1 hour, and then reacted with benzyl alcohol. Synthesized in hours. MS: 400.1 2 (theory 値400.12) 7. A compound of the formula (219), wherein R41 is phenyl, R4 2 is 4 methylphenyl, R43 is benzyl, and R44 is a hydrogen atom before the compound of formula (4) . In the same manner as in the production of the compound of the formula (2 1 3 ), the diphenylphosphonic acid chloride, p-cresol and triethylamine are reacted in tetrahydrofuran for 1 hour, and then with benzylamine. The reaction was carried out for 1 hour. MS: 3 3 7.1 2 (theoretical 337 337.12) 8 · The compound of the formula (220) is a compound of the formula (4) before R4i and R43 are a phenyl group, R42 is a 4-methylphenyl group, and R44 is a hydrogen atom. In the same manner as in the production of the compound of the formula (2 1 3 ), diphenylphosphonic acid chloride, p-cresol and triethylamine are reacted in tetrahydrofuran for 1 hour, and then reacted with aniline. Synthesized in hours. MS: 3 23.1 1 (theoretical 323 323_11) 9. A compound of the formula (22 1 ) wherein R21 is phenyl, R22 is 4-t-butylphenyl, and R23 is benzyl before compound of formula (2). In the same manner as in the production of the compound of the formula (213), diphenylphosphonic acid chloride, 4_t-butylphenol and triethylamine are reacted in tetrahydrofuran for 1 hour, and then reacted with benzyl alcohol. Synthesized in 1 hour. MS : 3 80.1 5 (theoretical 値380.15) 10. The compound of formula (222), R41 is phenyl, R42 is 4-t-butyl-46 - 201002729 basic group, R4 3 is fluorenyl group, and R4 4 is a gas atom. The compound of the formula (4) is prepared in the same manner as the compound of the formula (213). In the tetrahydrofuran, diphenylphosphonic acid chloride, 4-t-butylphenylhydrazine and triethyl are used. After the amine was reacted for 1 hour, it was further synthesized by reacting with the sulfhydrylamine for 1 hour. MS : 3 79.1 7 (theory 値 3 79.1 7 ) 11. The compound of the formula (223), wherein the formula is phenyl, r42 is phenylphenyl, R43 is a benzyl group, and R44 is a hydrogen atom before the formula (4) Compound. In the same manner as in the production of the compound of the formula (2 1 3 ), the reaction of diphenylphosphonic acid chloride, p-phenylphenol and triethylamine in tetrahydrofuran is carried out for 1 hour, followed by benzylamine. The reaction was carried out for 1 hour to synthesize. MS : 3 99.1 4 (theory 値399.1 4 ) 12. The compound of the formula (224), wherein R41 is phenyl, r42 is p-cumenylphenyl, R_43 is a substituent, and R44 is a hydrogen atom before formula (4) Compound. In the same manner as in the production of the compound of the formula (213), diphenylphosphonic acid chloride, P-cumenylphenol and triethylamine are reacted in tetrahydrofuran for 1 hour, and then with a benzylamine. The reaction was carried out for 1 hour. MS: 441.19 (theoretical 441 441.19) 13. The compound of the formula (225), wherein R4i is phenyl, R42 is 2-naphthyl, R43 is benzyl, and R44 is a hydrogen atom before the compound of formula (4). In the same manner as in the production of the compound of the formula (2 1 3 ), diphenylphosphonic acid chloride, 2-naphthol and triethylamine were reacted in tetrahydrofuran for 1 hour, and then with benzylamine. The reaction was carried out for 1 hour. -47- 201002729 MS : 3 73.1 2 (theoretical 373 373_12) 14_ The compound of the formula (226) is a compound of the formula (4) before R41 and R43 are a group, R42 is a 2-naphthyl group, and R44 is a hydrogen atom. In the same manner as in the production method of the compound of the formula (213), in the tetrahydrofuran, the diphenylphosphonic acid chloride, the 2-phenylene group and the triethylamine are reacted for 1 hour, and then reacted with aniline. Synthesized in 1 hour. MS: 359.11 (theoretical 359 359.11) 15. The compound of the formula (227) is a compound of the formula (4) before R41 and R42 are a phenyl group, R43 is a 2-methylbenzyl group, and R44 is a hydrogen atom. In the same manner as in the production of the compound of the formula (2 1 3 ), in the tetrahydrofuran, diphenylphosphonic acid chloride, phenol and triethylamine are reacted for 1 hour, followed by 2-methylbenzylamine. The reaction was carried out for 1 hour to synthesize. MS: 3 3 7.1 2 (theory 337 337.12) 16. A compound of the formula (228), which is a compound of the formula (4), wherein R42 is a phenyl group, R43 is a benzyl group, and R44 is a methyl group. In the same manner as in the production of the compound of the formula (213), the diphenylphosphonic acid chloride 'phenol and triethylamine are reacted in tetrahydrofuran for 1 hour, and then reacted with N-methylbenzylamine. Synthesized in 1 hour. MS : 3 3 7.1 2 (theoretical 値 3 3 7.1 2 ) 17. A compound of the formula (229) wherein R41 is phenyl, 4-t-butylphenyl, R43 is phenyl, and R44 is a hydrogen atom. (4) The compound 〇 is produced in the same manner as the compound of the formula (2 1 3 ) in the tetrahydrofuran, and the diphenylphosphonic acid chloride, 4-t-butylphenol and triethylamine are fed into the -48 - 201002729 After reacting for 1 hour, it was further reacted with aniline for 1 hour to synthesize. MS: 3 65.1 5 (theory 値 365.1 5 ) 1 8_ The compound of the formula (23 0 ) is a compound of the formula (4) wherein R41, R42 and r43 are a phenyl group and R4 4 is an N-methylphenyl group. In the same manner as in the production of the compound of the formula (2 1 3 ), diphenylphosphonic acid chloride, phenol and triethylamine are reacted in tetrahydrofuran! After an hour, it was further reacted with N-methylaniline for 1 hour to synthesize. MS : 3 2 3.1 1 (theory 値 3 23.1 1 ) 1 9. A compound of the formula (23 1 ) wherein R 4i is a phenyl group, R 42 is a 2-phenylphenyl group, R 43 is a benzyl group, and R 44 is a hydrogen atom. (4) The compound 〇 is produced in the same manner as the compound of the formula (2 13 ), and the diphenylphosphonic acid chloride, 2-phenylphenol and triethylamine are reacted in tetrahydrofuran for 1 hour. And reacted with benzylamine for 1 hour to synthesize. MS: 3 99.1 4 (theory 値399.14) 20. The compound of the formula (232), wherein R_4i is a phenyl group, R4 2 is a 2-phenylphenyl group, R4 3 is a phenyl group, and R44 is a hydrogen atom before the formula (4) The compound 〇 is prepared in the same manner as the compound of the formula (2 1 3 ), and diphenylphosphonic acid chloride, 2-phenylphenol and triethylamine are reacted in tetrahydrofuran for 1 hour, and then The aniline was reacted for 1 hour to synthesize. MS: 385.12 (theoretical 値 385.12) 2 1. A compound of the formula (23 3 ) wherein R 2i and R 23 are a phenyl group, and R 22 is a 2-phenoxyethyl group before the compound of the formula (2). -49- 201002729 In the same manner as in the production of the compound of the formula (213), diphenylphosphonic acid chloride, phenol and triethylamine are reacted in tetrahydrofuran for 1 hour, followed by 2-phenoxy Ethanol was reacted for 1 hour to synthesize. MS : 3 54.1 0 (theoretical 値 3 5 4.1 0 ) 22. The compound of the formula (234), wherein R41 and R43 are phenyl, R42 is 2-phenoxyethyl, and R44 is a hydrogen atom before the formula (4) Compound. In the same manner as in the production of the compound of the formula (2 1 3 ), diphenylphosphonic acid chloride, 2-phenoxyethanol and triethylamine are reacted in tetrahydrofuran for 1 hour, and then with aniline. The reaction was carried out for 1 hour. MS : 3 5 3.1 2 (theory 値353.12) 23. A compound of the formula (23 5 ), wherein R41 and R43 are phenyl, R42 is p-isophenyl, and R44 is a hydrogen atom before the compound of formula (4) . In the same manner as in the production of the compound of the formula (2 1 3 ), diphenylphosphonic acid chloride, p-cumenylphenol and triethylamine are reacted in tetrahydrofuran for 1 hour, and then with aniline. The reaction was carried out for 1 hour. MS: 427.1 7 (theory 値 427.17) 24. The compound of the formula (236) is a compound of the formula (4) wherein R41 is a phenyl group, R42 and R43 are a benzyl group, and R44 is a hydrogen atom. In the same manner as in the production of the compound of the formula (213), diphenylphosphonic acid chloride, benzyl alcohol and triethylamine were reacted in tetrahydrofuran for 1 hour, and then reacted with benzylamine for 1 hour. And synthesis. MS: 3 3 7.1 2 (theoretical 337 337.12) 2 5. The compound of the formula (23 7 ) is a compound of the formula (4) before the compound 1141 and 1143 are a phenyl group, 1142 is a benzyl group, and R4 4 is a hydrogen atom. -50- 201002729 In the same manner as in the production of the compound of the formula (2 1 3 ), after reacting diphenylphosphonic acid chloride, benzyl alcohol and triethylamine in tetrahydrofuran for 1 hour, It was further reacted with aniline for 1 hour to synthesize. MS: 3 23.1 1 (theoretical 323 323.11) 26. The compound of the formula (23 8 ) is a compound of the formula (4) before R41, the ruthenium 42 is a phenyl group, the R42 is a cyclohexyl group, and the R44 is a hydrogen atom. In the same manner as in the production method of the compound of the formula (213), diphenylphosphonic acid chloride, phenol and triethylamine were reacted in tetrahydrofuran for 1 hour, and then reacted with cyclohexylamine for 1 hour to synthesize. . MS : 3 15.14 (theoretical 値 315.14) The compound of the formula (3 04 ) is reacted with aniline after reacting diphenylphosphinic acid chloride, phenol and triethylamine in tetrahydrofuran for 1 hour. Synthesized in hours. The compound of the formula (3 0 5 ) is a phosphonate compound described in Patent Document 5 in which R21 and R23 are a phenyl group and R22 is a 2-naphthyl group. In a tetrahydrofuran, diphenylphosphonic acid chloride, phenol and triethylamine were reacted for 1 hour, and then reacted with 2-naphthol for 1 hour to synthesize hydrazine in the following Examples 14-39 and Comparative Example 4 In -5, each of the organophosphorus compounds shown in Tables 17-44 is ground in a sand mill if necessary, and each component is added to water to prepare an aqueous dispersion. -51 - 201002729 Example 1 4 [Table 17] Water 6 3.0% Compound of formula (2 13) (compound of formula (2)) 3 0.0% PLYSURF ALNa salt 6.3% tackifier 0.5% defoamer 0.1% Antifungal agent 0.1% 10 0.0% Example 1 5 [Table 18] Water 6 3.0% Compound of formula (214) (compound of formula (4)) 3 0.0% PLYSURF ALNa salt 6.3% tackifier 0.5% defoaming Agent 0.1% Antifungal agent 0.1% 10 0.0% Example 1 6 [Table 19] Water 6 3.0% Compound of formula (2 15) (compound of formula (2)) 3 0.0% PLYSURF ALNa salt 6.3% adhesion U 0.5% antifoaming agent 0.1% antifungal agent 0.1% 10 0.0% -52 - 201002729 Example 1 7 [Table 20] Water (2 1 6 ) compound PLYSURF ALNa salt tackifier antifoaming agent antifungal agent ( Compound of the above formula (4)) 6 3.0% 3 0.0% 6.3% 0.5% 0.1% 0.1% Example 1 8 10 0.0% [Table 21] Water 6 3.0% Compound of the formula (217) (formula (4) Compound) 3 0.0% PLYSURF ALNa salt 6.3% tackifier 0.5% defoamer 0.1% antifungal agent 0.1% 10 0.0% Example 1 9 [Table 22] Water 6 3 .0% Compound of formula (2 18) (compound of formula (2)) 3 0.0% PLYSURF ALNa salt 6.3% tackifier 0.5% defoamer 0.1% antifungal agent 0.1% 10 0.0% -53- 201002729 Example 2 0 [Table 23] Water 6 3.0% Compound of the formula (2 1 9 ) (compound of the former formula (4)) 3 0.0% PLYSURF ALNa salt 6.3% tackifier 0.5% antifoaming agent 0.1% antifungal agent 0.1% 10 0.0% Example 2 1 [Table 24] Compound of formula (2 2 0 ) PLYSURF ALNa salt tackifier antifoaming agent antifungal agent (formula of formula (4)) 6 3.0% 3 0.0% 6.3 % 0.5% 0.1% 0.1% Example 2 2 10 0.0% [Table 25] Water 6 3.0% Compound of the formula (2 2 1 ) (Compound of the former formula (2)) 3 0.0% PLYSURF ALNa Salt 6.3% Addition 0.5 0.5% defoaming U 0.1% antifungal agent 0.1% 10 0.0% -54- 201002729 Example 2 3 [Table 26] Water (222) compound PLYSURF ALNa salt tackifier antifoaming agent anti-fungal agent Compound of formula (4)) 6 3.0% 3 0.0% 6.3% 0.5% 0.1% 0.1% Example 24 10 0.0% [Table 27] Water 6 3.0% Compound of formula (223) (formation of the former formula (4) 3 0.0% PLYSURF ALNa salt 6.3% tackifier 0.5% defoamer 0.1% antifungal agent 0.1% 10 0.0% Example 2 5 [Table 28] Water 6 3.0% Compound of formula (224) (former formula (4) Compound) 3 0.0% PLYSURF ALNa salt 6.3% tackifier 0.5% defoamer 0.1% antifungal agent 0.1% 10 0.0% -55- 201002729 Example 2 6 [Table 29] Water 6 3.0% Formula (225) Compound (compound of formula (4)) 3 0.0% PLYSURF ALNa salt 6.3% tackifier 0.5% defoamer 0.1% antifungal agent 0.1% 10 0.0% Example 2 7 [Table 30] Water type (2 2 6) Compound PLYSURF ALNa Salt Tackifier Defoamer Antifungal Agent (Compound of Formula (4)) 6 3.0% 3 0.0% 6.3% 0.5% 0.1% 0.1% Example 2 8 10 0.0% [Table 3 1 〕 Water 6 3.0% Compound of formula (227) (compound of formula (4)) 3 0.0% PLYSURF ALNa salt 6.3% tackifier 0.5% defoamer 0.1% antifungal agent 0.1% 10 0.0% -56- 201002729 Example 2 9 [Table 32] Compound of formula (228) PLYSURF ALNa salt tackifier antifoaming agent antifungal agent (compound of formula (4)) 6 3.0% 3 0.0% 6.3% 0.5% 0.1% 0.1% Example 3 0 10 0.0% [Table 33] Water 6 3.0% Compound of the formula (2 2 9 ) (compound of the former formula (4)) 3 0.0% PLYSURF ALNa Salt 6.3% tackifier 0.5% defoamer 0.1% antifungal agent 0.1% 10 0.0% Example 3 1 [Table 34] Water 6 3.0% Compound of formula (2 3 0) (compound of formula (2)) 3 0.0% PLYSURF ALNa salt 6.3% tackifier 0.5% defoamer 0.1% antifungal agent 0.1% 10 0.0% -57- 201002729 Example 3 2 [Table 35] Water 6 3.0% Compound of formula (231) (previous Compound of formula (4)) 3 0.0% PLYSURF ALNa salt 6.3% tackifier 0.5% antifoaming agent 0.1% antifungal agent 0.1% 10 0.0% Example 3 3 [Table 36] Compound of water type (2 3 2 ) PLYSURF ALNa salt tackifier antifoaming agent antifungal agent (formula of formula (4)) 6 3.0% 3 0.0% 6.3% 0.5% 0.1% 0.1% Example 3 4 10 0.0% [Table 37] Water 6 3.0% Compound of formula (23 3 ) (compound of formula (2)) 3 0.0% PLYSURF ALNa salt 6.3% tackifier 0.5% defoamer 0.1% antifungal agent 0.1% 10 0.0% -58- 2010027 29 Example 3 5 [Table 38] Water 6 3.0% Compound of formula (23 4) (compound of formula (4)) 3 0.0% PLYSURF ALNa salt 6.3% tackifier 0.5% antifoaming agent 0.1% antifungal agent 0.1% 10 0.0% Example 3 6 [Table 39] Compound of water type (23 5 ) PLYSURF ALNa Salt tackifier Antifoaming agent Antifungal agent (Compound of formula (4)) 6 3.0% 3 0.0% 6.3% 0.5% 0.1% 0.1% Example 3 7 [Table 40] Water 10 0.0% 6 3.0% Compound of formula (2 3 6) PLYSURF ALNa salt (compound of formula (4)) 3 0.0% 6.3% 0.5% 0.1% 0.1% tackifier antifoaming agent antifungal agent 10 0.0% -59- 201002729 Example 3 8 [Table 41] Water 6 3.0% Compound of formula (23 7) (compound of formula (4)) 3 0.0% PLYSURF ALNa salt 6.3% tackifier 0.5% defoamer 0.1% antifungal agent 0.1% 10 0.0% Example 3 9 [Table 42] Water (23 8) compound PLYSURF ALNa salt tackifier antifoaming agent antifungal agent (Compound of formula (4)) 6 3.0% 3 0.0% 6.3% 0.5% 0.1% 0.1% Comparative Example 4 10 0.0% [Table 4 3] Water 6 3.0% Formula (3 04) 3 0.0% PLYSURF ALNa salt 6.3% tackifier 0.5% defoamer 0.1% antifungal agent 0.1% 1 ο ο. ο % -60 - 201002729 Comparative Example 5 [Table 44] Water 6 3.0% Formula (3 0 5 ) Compound 3 0.0% PLYSURF ALNa salt 6.3% tackifier 0.5% antifoaming agent 0.1% antifungal agent 0.1% 10 0.0% Test Example 2 The flame retardant prepared in the above Example 14-39 or Comparative Example 4-5 was used. The aqueous dispersion was further processed in the same manner as in Test Example 1 by the same bath treatment method, and 20 parts of the blended fiber cloth containing 30% polyester and 70% CDP was dyed separately, and flame-retardant processing was applied. . Thereafter, in the same manner as in Example 1, a combustion test (evaluation A, evaluation B) was carried out. Further, the evaluation C (average burning area) of Test Example 1 was replaced by the following evaluation of D (light fastness). The results are shown in Table 45 below. Evaluation D: Light fastness The light fastness is listed in the order of 1 to 5. 201002729 [Table 45] Flame Retardant vs. Fiber (% by weight) Evaluation ABC Untreated cloth 0 0 (0/23) 39.8 5 Example 1 4 2 0% 100 (20/20) 0.5 4 Example 1 5 2 0% 100(22/22) 0.5 4 Example 1 6 2 0% 95(20/21) 1.1 4 Example 1 7 2 0% 95(20/21) 1 .2 4 Example 1 8 2 0% 95 (20 /21) 1.3 4 Example 1 9 2 0% 86(18/21) 3.4 3 Example 2 0 2 0% 95(20/21) 1 .0 4 Example 2 1 2 0% 95(20/21) 1 .4 4 Example 2 2 2 0% 95(20/21) 1 .6 4 Example 23 2 0% 95(20/21) 1 . 8 4 Example 24 2 0% 86(18/21) 4.4 3 Example 2 5 2 0% 86 (18/21) 4.5 4 Example 2 6 2 0% 95 (20/21) 1 .3 3 Example 2 7 2 0% 95 (20/21) 1.6 3 Example 2 8 2 0% 95(20/21) 1.1 4 Example 2 9 20% 95(20/21) 1.3 4 Example 3 0 2 0% 95(20/21) 1.6 4 Example 3 1 2 0% 95 (20/21) 1 .3 4 Example 3 2 2 0% 86(18/21) 3.3 3 Example 3 3 2 0% 86(18/21) 3.4 3 Example 3 4 2 0% 95(20/ 21) 1.0 4 Example 3 5 2 0% 95 (20/21) 1.1 4 Example 3 6 2 0% 86 (18/21) 3.5 4 Example 3 7 2 0% 100 (22/22) 0.6 4 Implementation Example 3 8 2 0% 95 (22/22) 0.7 4 Example 3 9 2 0 % 95(20/21) 1.4 4 Comparative Example 4 2 0% 57(12/21) 7.8 3-4 Comparative Example 5 2 0% 86(18/21) 4.9 3 -62- 201002729 It is apparent from the results of Table 45 The yield of the evaluation A was 86 to 1% by weight with respect to Examples 14 to 39 of the present invention, and Comparative Example 4 was 57%. Therefore, the examples of the present invention are those having a higher yield. On the other hand, in Comparative Example 5', the yield of the evaluation A was 86%, but the light resistance was low and the light resistance was poor. Further, regarding the average afterflame time of the evaluation B, it was 0.5 to 4.5 with respect to Examples 14 to 39, and the comparative example 4-5 was 4.9 to 7.8, so that the average afterflame time of the latter was longer. That is, the flame retardant of the present invention exhibits excellent balance properties in Evaluation A and Evaluation B and Evaluation D, and is apparently useful as a flame retardant. Example 4 The novel compound represented by the above formulas (2) and (4) provided by the present invention is a compound of the compounds represented by the following formulas (23 9 ) to (246). -63- 201002729 【化1 4】

(241)(241)

(246) 1 .式（23 9 )之化合物，係R21爲苄基、R22、R23爲苯基之前式（2 )之化合物。該化合物係在四氫呋喃中，使苄基次膦酸二氯化物、苯酚進行加熱反應1小時後而合成〇 MS ： 3 24.0 9 (理論値 324.09) 2.式（240)之化合物，係R21爲苯基、R22爲P -硝基苯基、R23爲苯基之前式（2)之化合物。該化合物係在四氫呋喃中，使苯基次膦酸二氯化物、P-硝基苯酚、三乙基胺進行加熱反應1小時後，再與苯酚加熱反應1小時而合 -64- 201002729 成。 MS: 355.06 (理論値 355.06) 3. 式（241 )之化合物，係R21爲p-甲酚基、R22、R23 爲苯基之前式（2 )之化合物。該化合物係在四氫呋喃中，使甲酚基次膦酸二氯化物、苯酚、三乙基胺進行加熱反應1小時後而合成。 MS ： 324.09 (理論値 324.09) 4. 式（242 )之化合物，係R21爲m-硝基苯基、R22、 R23爲苯基之前式（2)之化合物。該化合物係在四氫呋喃中，使m-硝基苯基次鱗酸二氯化物、苯酚、三乙基胺進行加熱反應1小時後而合成。 MS ： 3 5 5.06 (理論値 3 5 5.06 ) 5. 式（ 243)之化合物，係R21爲p -硝基卞基、R22、 R23爲苯基之前式（2 )之化合物。該化合物係在四氫呋喃中，使P-硝基苄基次膦酸二氯化物、苯酚、三乙基胺進行加熱反應1小時而合成。 MS: 369.08 (理論値 369.08) 6. 式（244)之化合物，係R21爲4-苯基苯基、R22、 R23爲苯基之前式（2 )之化合物。該化合物係在四氫呋喃中，使4-苯基苯基次膦酸二氯化物、苯酚、三乙基胺進行加熱反應1小時而合成。 MS： 3 86.1 1 (理論値 3 86.1 1 ) 7. 式（245 )之化合物，係R4i爲苄基、R42、R43爲苯基、R44爲氫原子之前式（4)之化合物。該化合物係在四 -65- 201002729 氫呋喃中，使苄基次膦酸二氯化物、苯酚、三乙基胺進行加熱反應1小時後，再與苯胺加熱反應I小時而合成。 MS ： 3 23.1 1 (理論値 323.11) 8·式（246 )之化合物，係R41爲甲氧基苯基、R42、 R43爲苯基、R44爲氫原子之前式（4 )之化合物。該化合物係在四氫呋喃中，使甲氧基苯基次膦酸二氯化物、苯酚、三乙基胺進行加熱反應1小時後，再與苯胺加熱反應1 小時而合成。 MS ： 3 23.1 1 (理論値 339.10) 在以下之實施例4 1 - 4 8中，將表4 6 - 5 3所示之各有機磷系化合物，如有必要再以砂磨機進行磨碎’將各成分加入水中而製得水性分散液。實施例4 1 〔表 46〕水 6 3.0% 式（23 9) (―般式（2)之化合物） 30.0% PLYSURFALNa 鹽 6.3% 增黏劑 0.5% 消泡劑 0.1% 防黴菌齊!J___ 0.1% 10 0.0% -66 - 201002729 實施例42 〔表 47〕水 6 3.0% 式（240) (—般式（2)之化合物） 30.0% PLYSURFALNa 鹽 6.3% 增黏劑 0.5% 消泡劑 0.1% 防黴菌齊ί_0.1% 10 0.0% 實施例4 3 〔表 48〕水 6 3.0% 式（241) (—般式（2)之化合物） 30.0% PLYSURF ALNa 鹽 6.3% 增黏劑 0.5% 消泡劑 0.1% 防黴菌劑_0.1% 10 0.0% 實施例4 4 〔表 49〕水 6 3.0% 式（242) (—般式（2)之化合物） 30.0% PLYSURF ALNa 鹽 6.3% 增黏劑 0.5% 消泡劑 0.1% 防黴菌劑_0.1% 10 0.0% -67- 201002729 實施例4 5 〔表 50〕水 6 3.0% 式（243) (—般式（2)之化合物） 30.0% PLYSURFALNa 鹽 6.3% 增黏劑 0.5% 消泡劑 0.1% 防黴菌劑 0.1% 10 0.0% 實施例46 〔表 51〕水 6 3.0% 式（244) ‘（一般式（2)之化合物） 3 0.0% PLYSURF ALNa 鹽 6.3% 增黏劑 0.5% 消泡劑 0.1% 防黴菌劑 0.1% 10 0.0% 實施例47 〔表 52〕水 6 3.0% 式（23 9) (一般式（4 )之化合物） 3 0.0% PLYSURF ALNa 鹽 6.3% 增黏劑 0.5% 消泡劑 0.1% 防黴菌劑 0.1% 10 0.0% -68- 201002729 實施例4 8 〔表 53〕 6 3.0% 3 0.0% 6.3% 0.5% 0.1% 0.1% 水式（246) (—般式（4)之化合物） PLYSURF ALNa 鹽增黏劑消泡劑防黴菌劑_ 10 0.0% 試驗例3 使用以上述實施例4 1 - 4 8所調製之阻燃劑之水性分散液，再與試驗例1同樣地進行操作，以浸染同浴處理法，將含有30%聚酯及70%CDP之混紡纖維布帛之20公分四方分別進行染色，同時並施以阻燃加工。其後，與實施例1同樣地’實施燃燒試驗（評價A、評價B)及平均燃燒面積（評價c)。結果示於下述表54 [表 54] 阻燃齊!1 對纖維 (重量％) 評價 A B C 實施例4 1 20% 100(22/22) 0.7 3.3 實施例4 2 20% 100(22/22) 0.6 3.6 實施例4 3 20% 100(23/23) 0.7 3.7 實施例4 4 20% 100(21/21) 0.8 3.7 實施例4 5 20% 100(21/21) 0.7 3.9 實施例4 6 20% 100(23/23) 0.7 3.1 實施例47 20% 100(21/21) 0.5 3.2 實施例48 20% 100(21/21) 0.8 3.1 -69- 201002729 由表54之結果明顯可知者’評價A之合格率’本發明之實施例4 1 - 4 8皆爲1 0 0 %，評價B之平均殘焰時間爲 0.5-0.8，而評價C之平均燃燒面積則爲3.1-3.9，明確可知使用本發明之水性分散液之試驗片，其具有優異之阻燃功能。如上所述，使用本發明之水性分散液之試驗片，明顯可知具有優良之阻燃功能。此外，再將使用本發明之水性分散液之試驗片重複進行5次循環，惟仍能保持上述之功能，明顯可知其即使在耐久性上亦爲極優良者。產業上可利用性根據本發明，可提供一種能在纖維上、特別是C D P 與聚酯之混紡纖維上賦予其具耐久性之優良阻燃功能之有機磷系化合物之水性分散液。 -70-(246) A compound of the formula (23 9 ), which is a compound of the formula (2) wherein R21 is a benzyl group, and R22 and R23 are a phenyl group. The compound is synthesized in tetrahydrofuran, and the benzylphosphinic acid dichloride and phenol are heated and reacted for 1 hour to synthesize 〇MS: 3 24.0 9 (theoretical 値324.09) 2. The compound of the formula (240), the R21 is benzene A compound of the formula (2) wherein R22 is a P-nitrophenyl group and R23 is a phenyl group. This compound was subjected to a heating reaction for 1 hour in phenylphosphinic acid dichloride, P-nitrophenol or triethylamine in tetrahydrofuran, and then heated and reacted with phenol for 1 hour to form -64 to 201002729. MS: 355.06 (theory 値 355.06) 3. A compound of the formula (241), wherein R21 is a p-cresol group, and R22 and R23 are a compound of the formula (2) before the phenyl group. This compound was synthesized in tetrahydrofuran by heating a reaction of cresylphosphinic acid dichloride, phenol and triethylamine for 1 hour. MS: 324.09 (theoretical 324 324.09) 4. The compound of the formula (242) is a compound of the formula (2) wherein R21 is m-nitrophenyl, R22 and R23 are phenyl. This compound was synthesized in tetrahydrofuran by subjecting m-nitrophenylphosphinic acid dichloride, phenol and triethylamine to a heating reaction for 1 hour. MS: 3 5 5.06 (theoretical 値 3 5 5.06 ) 5. A compound of the formula (243), wherein R21 is p-nitroindenyl, and R22 and R23 are a compound of the formula (2) before the phenyl group. This compound was synthesized in tetrahydrofuran by subjecting P-nitrobenzylphosphinic acid dichloride, phenol and triethylamine to a heating reaction for 1 hour. MS: 369.08 (theoretical 369 369.08) 6. A compound of the formula (244), wherein R21 is 4-phenylphenyl, R22, and R23 are a compound of formula (2) before phenyl. This compound was synthesized in tetrahydrofuran by subjecting 4-phenylphenylphosphinic acid dichloride, phenol and triethylamine to a heating reaction for 1 hour. MS: 3 86.1 1 (theory 値 3 86.1 1 ) 7. A compound of the formula (245), which is a compound of the formula (4) before R4i is a benzyl group, R42 and R43 are a phenyl group, and R44 is a hydrogen atom. This compound was synthesized by reacting benzylphosphinic acid dichloride, phenol, and triethylamine in tetrahydrogen fluoride at 0.45-201002729 for 1 hour, followed by heating with aniline for 1 hour. MS: 3 23.1 1 (theory 値 323.11) 8. A compound of the formula (246) wherein R41 is a methoxyphenyl group, R42 and R43 are a phenyl group, and R44 is a hydrogen atom before the compound of the formula (4). This compound was synthesized in tetrahydrofuran by heating a reaction of methoxyphenylphosphinic acid dichloride, phenol and triethylamine for 1 hour, followed by heating with aniline for 1 hour. MS : 3 23.1 1 (theoretical 値 339.10) In the following Examples 4 1 - 4 8 , the respective organophosphorus compounds shown in Tables 4 6 - 5 3 were ground by a sand mill if necessary. The components were added to water to prepare an aqueous dispersion. Example 4 1 [Table 46] Water 6 3.0% Formula (23 9) ("Compound of formula (2)) 30.0% PLYSURFALNa Salt 6.3% Viscosity agent 0.5% Defoamer 0.1% Antifungal compound! J___ 0.1% 10 0.0% -66 - 201002729 Example 42 [Table 47] Water 6 3.0% Formula (240) (Compound of formula (2)) 30.0% PLYSURFALNa Salt 6.3% Viscosity 0.5% Defoamer 0.1% Antifungal Qiί_0.1% 10 0.0% Example 4 3 [Table 48] Water 6 3.0% Formula (241) (Compound of formula (2)) 30.0% PLYSURF ALNa Salt 6.3% Viscosity agent 0.5% Defoamer 0.1 %Antifungal agent_0.1% 10 0.0% Example 4 4 [Table 49] Water 6 3.0% Formula (242) (Compound of formula (2)) 30.0% PLYSURF ALNa Salt 6.3% Viscosity agent 0.5% Defoaming Agent 0.1% Antifungal agent _0.1% 10 0.0% -67- 201002729 Example 4 5 [Table 50] Water 6 3.0% Formula (243) (Compound of formula (2)) 30.0% PLYSURFALNa Salt 6.3% Viscosity Agent 0.5% Antifoaming agent 0.1% Antifungal agent 0.1% 10 0.0% Example 46 [Table 51] Water 6 3.0% Formula (244) '(General formula (2) compound) 3 0.0% PLYSURF ALNa salt 6.3% Increase Adhesive 0.5% defoamer 0.1% Antifungal agent 0.1% 10 0.0% Example 47 [Table 52] Water 6 3.0% Formula (23 9) (Compound of general formula (4)) 3 0.0% PLYSURF ALNa Salt 6.3% Viscosity agent 0.5% Defoamer 0.1 % Antifungal agent 0.1% 10 0.0% -68- 201002729 Example 4 8 [Table 53] 6 3.0% 3 0.0% 6.3% 0.5% 0.1% 0.1% Water (246) (Compound of formula (4)) PLYSURF ALNa salt tackifier antifoaming agent antifungal agent _ 10 0.0% Test Example 3 An aqueous dispersion of the flame retardant prepared in the above Examples 4 1 - 4 8 was used, and the same operation as in Test Example 1 was carried out. In the same bath treatment method, 20 parts of the blended fiber cloth containing 30% polyester and 70% CDP was dyed separately, and flame-retardant processing was applied. Thereafter, the combustion test (evaluation A, evaluation B) and the average burning area (evaluation c) were carried out in the same manner as in the first embodiment. The results are shown in the following Table 54 [Table 54] Flame retardant align! 1 Pair of fibers (% by weight) Evaluation of ABC Example 4 1 20% 100 (22/22) 0.7 3.3 Example 4 2 20% 100 (22/22) 0.6 3.6 Example 4 3 20% 100 (23/23) 0.7 3.7 Example 4 4 20% 100 (21/21) 0.8 3.7 Example 4 5 20% 100 (21/21) 0.7 3.9 Example 4 6 20% 100(23/23) 0.7 3.1 Example 47 20% 100(21/21) 0.5 3.2 Example 48 20% 100(21/21) 0.8 3.1 -69- 201002729 The results from Table 54 are clearly known as 'evaluation A' Qualification rate 'Embodiment 4 1 - 4 8 of the present invention is 100%, the average afterflame time of evaluation B is 0.5-0.8, and the average burning area of evaluation C is 3.1-3.9, and it is clear that the present invention is used. A test piece of an aqueous dispersion which has an excellent flame retardant function. As described above, the test piece using the aqueous dispersion of the present invention is clearly known to have an excellent flame retardant function. Further, the test piece using the aqueous dispersion of the present invention was repeated for 5 cycles, but the above functions were maintained, and it was apparent that it was excellent even in durability. Industrial Applicability According to the present invention, it is possible to provide an aqueous dispersion of an organic phosphorus compound which can impart excellent flame retardancy to fibers, particularly a blended fiber of C D P and polyester. -70-

Claims

201002729 七、申請專利範圍 1 _ —種水性分散液，其特徵係含有：選自下式（1 )所示之次膦酸酯化合物【化1】 Ο (1) B II 0 Rn—P—OR13 I Rl2 (式中，Rh、R12、及Ri3係各自獨立地爲可被取代基群A加以取代之芳基、或（C1-C10)院基，其中，取代基群A係羥基、硝基、胺基、氰基、甲醯基、羧基、脲基、（C1-C10)院基、（C 卜 C10)烷基胺基、二（C1-C10 )院基胺基、苯基、苯氧基及（C1-C10)院氧基）：及下式（2 )所示之膦酸酯化合物【化2】 Ο R2「f —OR23 (2) OR22 (式中，R2!係可被取代基群A加以取代之芳基、可被取代基群A加以取代之（C7-C15 )芳烷基、或（C1-Cl0)烷基；R22係可被取代基群A加以取代之苯基、可被取代基群A加以取代之（C7-C15 )芳烷基、或（C1-C 1 0 )烷基；R23係可被取代基群A加以取代之苯基、可被取代基群A加以取代之（C7-C15 )芳烷基、或（C1-Cl〇)烷基（該烷基，亦可藉由：可被取代基群A加以取 -71 - 201002729 代之芳基氧基、可被取代基群A加以取代之（C7_C15) $ 烷基氧基、或（C1-C10)烷氧基，加以取代者），·其中，取代基群A係與上述定義相同者）：及下式（3 )所示之次膦酸醯胺化合物【化3】 0 II R31——P——NR33R34 (3) R32 (式中，Rm、R32、及R·33係各自獨立地爲可被取代基群A加以取代之芳基、或（C 1 - C 1 0 )烷基，R34係氫原子、可被取代基群A加以取代之芳基、或（C 1 -C 1 0 )烷基 ’其中，取代基群A係與上述定義相同者）：及下式（4 )所示之膦酸醯胺化合物【化4】 Ο II (4) R41—P—NR43R44 OR42 (式中，R4,係可被取代基群A加以取代之芳基、可被取代基群A加以取代之（C7-C15)芳烷基、或（C1-C10)烷基；R4 2係可被取代基群A加以取代之芳基、可被取代基群A加以取代之（C7-C15 )芳烷基、或（C1-C10)烷基（該烷基，亦可藉由：可被取代基群A加以取代之芳基氧基、可被取代基群A加以取代之（C7-C15 )芳烷基氧基、或（C卜C10 )烷氧基，加以取代者）；R43係 -72- 201002729 可被取代基群A加以取代之芳基、可被取代基群a加以取代之（C7-C15)芳烷基、或（cl_cl〇)烷基；r44係氫原子、可被取代基群A加以取代之芳基、可被取代基群a 加以取代之（C 7 - C 1 5 )芳院基、或可被取代基群a加以取代之（C1-C10)烷基，其中，取代基群A係與上述定義相同者）；以及下式（5 )所示之鱗酸二醯胺【化5】 0 II R51—P—NR53R54 (5) NR52R55 (式中，Rm、R52、及Rss係各自獨立地爲可被取代基群A加以取代之芳基、或（C1-C10)烷基，1154及r55 係各自獨立地爲氫原子、可被取代基群A加以取代之芳基、或（C1-C10)烷基，其中，取代基群A係與上述定義相同者）中’至少1種之有機磷系化合物或其等之鹽，以及界面活性劑者。 2 ·如申請專利範圍第1項之水性分散液，其中可被取代基群A加以取代之芳基係（c 1 - c 1 0 )院基苯基、聯苯基或（C1-C10)烷氧基苯基。 3如申請專利範圍第1或2項之水性分散液，其中在水性分散液中以總量計，係含有丨至9 0重量％之式（丄 )至式（5)所示之有機磷系化合物者。 -73- 201002729 4.如申請專利範圍第1〜3項中任一項之水性分散液，其中界面活性劑係非離子型界面活性劑或陰離子型界面活性劑或其二者。 5-如申請專利範圍第1〜4項中任一項之水性分散液，其中係進而含有紫外線吸收劑者。 6 ·如申請專利範圍第1〜5項中任一項之水性分散液，其中係作爲纖維用之阻燃劑而使用者。 7 ·如申請專利範圍第6項之水性分散液，其中纖維係聚酯纖維者。 8 ·如申請專利範圍第7項之水性分散液，其中聚酯纖維係陽離子可染型聚酯纖維或含有陽離子可染型聚酯纖維之混紡纖維者。 9. 一種纖維之阻燃加工方法，其特徵係使用申請專利範圍第1至8項中任一項之水性分散液者。 1 〇 . —種纖維，其特徵係以申請專利範圍第9項之方法加以阻燃加工者。 11. 一種下式（2)所示之膦酸酯化合物或其鹽’ 【化6】 Ο II R21—P—OR23 (2) OR22 (式中，R21係可被取代基群A加以取代之芳基、或可被取代基群A加以取代之（C7-C15 )芳烷基；R22係可被取代基群A加以取代之苯基、可被取代基群A加以取 -74- 201002729 代之（C7-Cl5)芳烷基、或（C1_Cl〇)烷基；R23係可被取代基群A加以取代之苯基、可被取代基群a加以取代之（C7-C15)芳烷基、或（C1-C10)烷基（該烷基，亦可藉由•可被取代基群A加以取代之芳基氧基、可被取代基群A加以取代之（C7-C15)方院基氧基、或（ci_cl〇) 烷氧基，加以取代者）：其中，取代基群A係與上述定義相同者）：或式（4)所示之膦酸醯胺化合物【化7】 0 II R41—P—NR43R44 (4) OR42 (式中’ 係可被取代基群A加以取代之芳基、可被取代基群A加以取代之（C7_C15)芳烷基；r42係可被取代基群A加以取代之芳基、可被取代基群a加以取代之（C7-C15)芳烷基、或（C1-C10)烷基（該烷基，亦可藉由：可被取代基群A加以取代之芳基氧基、可被取代基群A加以取代之（C7_C15 )芳烷基氧基、或（C1_C10) 燒氧基’加以取代者）；Re係可被取代基群A加以取代之芳基、可被取代基群A加以取代之（C7-C15)芳烷基、或（C 1 -C 1 0 )烷基；R44係氫原子、可被取代基群a加以取代之（C7-C 1 5 )芳烷基、或可被取代基群a加以取代之 (C1-C10)烷基’其中’取代基群a係與上述定義相同者 -75- 201002729 1 2 .如申請專利範圍第u項之膦酸酯化合物或其鹽，其中係可被羥基、硝基、氰基、（C1_C6)烷基、苯基或（C 1 -C6 )烷氧基加以取代之苯基；可被羥基、氰基、（C1-C6)烷基、苯基或（C1_C6)烷氧基加以取代之萘基；或可被羥基、硝基、氰基、（c卜C6)烷基、苯基或（C1-C6 )烷氧基加以取代之（C7_C12 )芳烷基；係可被硝基、（C1-C6)烷基、（C1_C6)烷基胺基、二（ C1-C6)烷基胺基、苯基或（C1_C6)烷氧基加以取代之苯基·，或可被羥基、氰基、甲醯基、羧基、脲基、（ei_C6 )烷基、苯基、苯氧基或（C丨_C6)烷氧基加以取代之（ C7-C12 )芳烷基；R23係可被羥基、氰基、（C1_C6 )烷基、苯基或（ci-c6)烷氧基加以取代之（C7_C12)芳烷基氧基；可被（C1-CO院氧基、羥基、胺基、（C1_C6) 烷基胺基、羧基或脲基加以取代之（C1_C6)烷基；或可被羥基、氰基、甲醯基、羧基、脲基、（C1_C6)烷基、本基、苯氧基或（CM-C6)烷氧基加以取代之（C厂Cl2) 方院基。 1 3 .如申請專利範圍第丨丨或丨2項之膦酸酯化合物或其鹽’其中Rzl係苯基、甲苯基、硝基苯基、硝基苄基、或聯苯基；R22係可被（Cl-C6)烷基、硝基、或苯基加以取代之苯基；R2 3係可被本氧基加以取代之（C 1 - c 6 )院基、苄基或苯乙基。 14.如申請專利範圍第1 1項之滕酸醯胺化合物或其鹽，其中係可被淫基、氰基、（C1-C6)烷基、苯基 -76- 201002729 或（C1-C6 )烷氧基加以 (C1-C6 )院基•、苯基或取代之苯基；可被羥基、氰 (Cl-C6 )烷氧基力□以取代之 ;或可被羥基、硝基、氰基 C 1 - C 6 )烷基、苯基 C1-C6)烷氧基加以取被羥基、胺基、氰基、代之（C7-C 1 2 )芳烷基；R42 (Cl-C6 )烷基、（C1-C6 )烷基、—（C1-C6)烷基胺基、苯基、苯氧基、（c7_c 方k基或（C 1 - C 6 )烷氧基加以取代之苯基、可被羥201002729 VII. Patent application scope 1 _ an aqueous dispersion characterized by containing: a phosphinate compound selected from the following formula (1) [1] Ο (1) B II 0 Rn-P-OR13 I Rl2 (wherein, Rh, R12, and Ri3 are each independently an aryl group which may be substituted with a substituent group A or a (C1-C10) group, wherein the substituent group A is a hydroxyl group, a nitro group, Amine, cyano, methionyl, carboxyl, ureido, (C1-C10), (C, C10) alkylamino, bis(C1-C10), phenyl, phenoxy And (C1-C10) alkoxylate: and a phosphonate compound represented by the following formula (2) [Chemical 2] Ο R2 "f - OR23 (2) OR22 (wherein, R2! can be substituted group a substituted aryl group, a (C7-C15) aralkyl group or a (C1-Cl0) alkyl group which may be substituted with a substituent group A; and a phenyl group which may be substituted by the substituent group A, may be a substituted (C7-C15) aralkyl group or a (C1-C10O)alkyl group substituted with a group A; a phenyl group which may be substituted by the substituent group A, may be substituted by the substituent group A (C7-C15) aralkyl, or (C1-Cl An alkyl group (which may also be obtained by substituting a group A to -71 - 201002729 aryloxy group, which may be substituted by a substituent group A (C7_C15) $ alkyloxy group, Or (C1-C10) alkoxy group, substituted), wherein the substituent group A is the same as defined above: and the phosphinic acid amide compound represented by the following formula (3) [Chemical 3] 0 II R31——P——NR33R34 (3) R32 (wherein Rm, R32, and R·33 are each independently an aryl group which may be substituted by the substituent group A, or (C 1 - C 1 0 ) An alkyl group, an R34 hydrogen atom, an aryl group which may be substituted with a substituent group A, or a (C 1 -C 1 O )alkyl group wherein the substituent group A is the same as defined above: 4) The phosphonium amide compound shown is 化 ( II (4) R41—P—NR43R44 OR42 (wherein R 4 is an aryl group which may be substituted by the substituent group A, and may be substituted group A a substituted (C7-C15) aralkyl group or a (C1-C10) alkyl group; R4 2 is an aryl group which may be substituted with a substituent group A, which may be substituted by a substituent group A (C7-C15) Aralkyl, or (C 1-C10)alkyl group (the alkyl group may also be an aryloxy group which may be substituted by the substituent group A, a (C7-C15) aralkyloxy group which may be substituted by the substituent group A, Or (C a C10 ) alkoxy group, substituted); R43 is -72- 201002729 aryl group which may be substituted by substituent group A, (C7-C15) aralkyl group which may be substituted by substituent group a Or (cl_cl〇)alkyl; r44 is a hydrogen atom, an aryl group which may be substituted by a substituent group A, a (C 7 - C 1 5 ) aromatic group which may be substituted by a substituent group a, or may be a (C1-C10)alkyl group in which a substituent group a is substituted, wherein the substituent group A is the same as defined above; and a bismuthamine bisamine as shown in the following formula (5) [Chem. 5] 0 II R51 —P—NR53R54 (5) NR52R55 (wherein Rm, R52, and Rss are each independently an aryl group or a (C1-C10) alkyl group which may be substituted with a substituent group A, and 1154 and r55 are each independently The ground is a hydrogen atom, an aryl group which may be substituted with a substituent group A, or a (C1-C10) alkyl group, wherein the substituent group A is the same as defined above, and at least one of the organic phosphorus systems Or a salt thereof, etc., and those boundary surfactant. 2. An aqueous dispersion according to claim 1, wherein the aryl group (c 1 - c 1 0 ) is substituted with a substituent group A, a phenyl group, a biphenyl group or a (C1-C10) alkane. Oxyphenyl. [3] The aqueous dispersion according to claim 1 or 2, wherein the total amount of the organic phosphorus system represented by the formula (5) is from 丨 to 90% by weight in the aqueous dispersion. Compound. The aqueous dispersion according to any one of claims 1 to 3, wherein the surfactant is a nonionic surfactant or an anionic surfactant or both. The aqueous dispersion according to any one of claims 1 to 4, which further contains an ultraviolet absorber. The aqueous dispersion according to any one of claims 1 to 5, which is used as a flame retardant for fibers. 7 · An aqueous dispersion according to item 6 of the patent application, wherein the fiber is a polyester fiber. 8. The aqueous dispersion according to claim 7, wherein the polyester fiber is a cationic dyeable polyester fiber or a blended fiber containing a cationic dyeable polyester fiber. A method of flame-retardant processing of a fiber, which is characterized by using the aqueous dispersion of any one of claims 1 to 8. 1 〇 . — A type of fiber characterized by a flame retardant process in accordance with the method of claim 9 of the patent application. A phosphonate compound represented by the following formula (2) or a salt thereof [Chemical Formula 6] Ο II R21-P-OR23 (2) OR22 (wherein R21 is substituted by a substituent group A) a (C7-C15) aralkyl group which may be substituted with a substituent group A; a phenyl group which may be substituted by the substituent group A, which may be substituted by the substituent group A, -74-201002729 ( C7-Cl5) aralkyl, or (C1_Cl〇)alkyl; R23 is a phenyl group which may be substituted by a substituent group A, a (C7-C15) aralkyl group which may be substituted with a substituent group a, or C1-C10)alkyl (the alkyl group may also be an aryloxy group which may be substituted by the substituent group A, a (C7-C15) aryl group oxy group which may be substituted by the substituent group A, Or (ci_cl〇) alkoxy group, substituted by: wherein, the substituent group A is the same as defined above): or the phosphonium amide compound represented by formula (4) [Chemical 7] 0 II R41-P —NR43R44 (4) OR42 (wherein ' an aryl group which may be substituted with a substituent group A, a (C7_C15) aralkyl group which may be substituted with a substituent group A; the r42 system may be substituted with a substituent group A An aryl group, a (C7-C15) aralkyl group or a (C1-C10) alkyl group which may be substituted with a substituent group a (the alkyl group may also be an aryl group which may be substituted by the substituent group A) An oxy group, a (C7_C15) aralkyloxy group substituted with a substituent group A, or a (C1_C10) alkoxy group substituted; a Re group which may be substituted with a substituent group A, may be a substituted (C7-C15) aralkyl group or a (C 1 -C 1 0 ) alkyl group substituted with a group A; a hydrogen atom of R44, which may be substituted by a group a (C7-C 1 5 ) An alkyl group, or a (C1-C10)alkyl group which may be substituted by a substituent group a, wherein the 'substituent group a is the same as defined above-75-201002729 1 2 . The phosphonic acid according to the scope of claim U An ester compound or a salt thereof, which is a phenyl group which may be substituted by a hydroxyl group, a nitro group, a cyano group, a (C1_C6) alkyl group, a phenyl group or a (C 1 -C6 ) alkoxy group; may be a hydroxyl group, a cyano group, a C1-C6 alkyl, phenyl or (C1_C6) alkoxy substituted naphthyl group; or may be hydroxy, nitro, cyano, (c-C6)alkyl, phenyl or (C1-C6) alkane The oxy group is substituted (C7_C12) An alkyl group; a phenyl group which may be substituted by a nitro group, a (C1-C6)alkyl group, a (C1_C6)alkylamino group, a di(C1-C6)alkylamino group, a phenyl group or a (C1_C6) alkoxy group. · (C7-C12) aryl substituted by hydroxy, cyano, decyl, carboxy, ureido, (ei_C6)alkyl, phenyl, phenoxy or (C丨_C6) alkoxy An alkyl group; R23 is a (C7_C12) aralkyloxy group which may be substituted by a hydroxy group, a cyano group, a (C1_C6) alkyl group, a phenyl group or a (ci-c6) alkoxy group; a (C1_C6)alkyl group substituted with a hydroxyl group, an amine group, a (C1_C6) alkylamino group, a carboxyl group or a ureido group; or a hydroxy group, a cyano group, a decyl group, a carboxyl group, a ureido group, a (C1_C6) alkyl group, The base, phenoxy or (CM-C6) alkoxy group substituted (C plant Cl2) square yard base. 13. A phosphonate compound or a salt thereof according to the scope of claim 2 or 2 wherein Rzl is a phenyl group, a tolyl group, a nitrophenyl group, a nitrobenzyl group or a biphenyl group; a phenyl group substituted with a (Cl-C6)alkyl group, a nitro group, or a phenyl group; and R2 3 is a (C 1 - c 6 ) group, a benzyl group or a phenethyl group which may be substituted by the present oxy group. 14. The guanidinium amide compound or a salt thereof according to the scope of claim 1, wherein the guanidinium group, the cyano group, the (C1-C6) alkyl group, the phenyl group - 76-201002729 or (C1-C6) Alkoxy group (C1-C6), phenyl or substituted phenyl; may be substituted by hydroxy, cyan (Cl-C6) alkoxy; or may be hydroxy, nitro, cyano C 1 -C 6 )alkyl, phenyl C1-C6)alkoxy is taken as hydroxy, amine, cyano, (C7-C 1 2 ) aralkyl; R42 (Cl-C6 ) alkyl a (C1-C6)alkyl group, a (C1-C6)alkylamino group, a phenyl group, a phenoxy group, a (c7-c-square-k group or a (C 1 -C 6 ) alkoxy group substituted with a phenyl group, Hydroxyl

胺基、氰基、 (C1-C6)烷基、（C1-C6)烷基胺基、 C1-C6 )烷基胺基、苯基、苯氧基、 (C1-C6)院氧基力□以取代之季基、 (C7-C12 )芳烷可被羥基、氰基醯基、羧基、脲基、（Cl-C6)烷基、苯基、苯氧基 C1-C6)院氧基加以取代之（C7-C12)芳烷基、或可氧基加以取代之（C 1 -C 6 )烷基；r43係可被羥基 '胺氰基、（C1-C6)烷基、（c卜C6)烷基胺基、二（c )院基胺基、苯基 '苯氧基或（C1-C6 )烷氧基加以之苯基、可被羥基、胺基 '氰基、（C1_C6 )烷基、j C6)烷基胺基、二（Cl-C6)烷基胺基、苯基、苯氧 (C1-C6)烷氧基加以取代之萘基、或可被羥基、氰甲醯基、羧基、脲基、（C1-C6)烷基、苯基、苯氧 (C1-C6)烷氧基加以取代之（C7-C12)芳烷基；R, (C1-C6 )烷基或氫原子。 1 5 _如申請專利範圍第〗i或〗4項之膦酸醯胺化或其鹽，其中係苯基、p_甲氧基苯基、或苄基係可被（C1-C6)院基、苯基、苄基、苯乙基或苯基基、萘基或（係可基胺 12 ) 基、二（基或、甲或（被苯墓、 KC6 取代〔Ci_ 基、基或 “係合物;r42 柯基 -77- 201002729 加以取代之苯基、萘基；可被羥基、氰基、、脲基、（CM-C6)烷基、苯基、苯氧基或λ ( 基加以取代之（C7-C12)芳烷基或2-苯氧基苯基、苄基或苯乙基；R44係甲基、乙基或氫甲醯基、羧基 CM-C6 )烷氧乙基；R43係原子。 -78- 201002729 四指定代表圖： (一）本案指定代表圖為：無 (二）本代表圖之元件符號簡單說明：無五、本案若有化學式時，請揭示最能顯示發明特徵的化學式：無Amino, cyano, (C1-C6)alkyl, (C1-C6)alkylamino, C1-C6)alkylamino, phenyl, phenoxy, (C1-C6) The substituted quaternary group, (C7-C12) aralkyl can be substituted by hydroxy, cyanoguanidino, carboxy, ureido, (Cl-C6) alkyl, phenyl, phenoxy C1-C6) alkoxy a (C7-C12) aralkyl group or a (C 1 -C 6 ) alkyl group which may be substituted with an oxy group; the r43 group may be a hydroxy 'amine cyano group, a (C1-C6) alkyl group, or a (c-C6) alkyl group. a phenyl group of an alkylamino group, a di(c)-based amine group, a phenyl 'phenoxy group or a (C1-C6) alkoxy group, which may be a hydroxyl group, an amino group 'cyano group, a (C1_C6) alkyl group, j C6) an alkylamino group, a di(Cl-C6)alkylamino group, a phenyl group, a phenoxy (C1-C6) alkoxy group substituted with a naphthyl group, or a hydroxy group, a cyanocyanyl group, a carboxyl group, (C7-C12) aralkyl substituted with ureido, (C1-C6)alkyl, phenyl, phenoxy (C1-C6) alkoxy; R, (C1-C6)alkyl or a hydrogen atom. 1 5 _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ , phenyl, benzyl, phenethyl or phenyl, naphthyl or (systemylamine 12), di(yl or yl) or substituted by benzene tomb, KC6 [Ci_yl, yl or ". R42 keki-77- 201002729 substituted phenyl, naphthyl; may be substituted by hydroxy, cyano, ureido, (CM-C6) alkyl, phenyl, phenoxy or λ (group) (C7-C12) aralkyl or 2-phenoxyphenyl, benzyl or phenethyl; R44 methyl, ethyl or hydrocarbyl, carboxyl CM-C6) alkoxyethyl; R43 atom -78- 201002729 Four designated representatives: (1) The representative representative of the case is: None (2) The symbol of the representative figure is a simple description: No. 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention. :no