JP2002322189A - Phosphazene composition, flame retardant containing the same and production method therefor - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a phosphazene composition which has an excellent flame- retardant effect even when used with a small amount, a production method for the same, a flame retardant containing the same as an effective ingredient, a resin composition containing the same and a molded product consisting of the resin composition. SOLUTION: Characteristically, the phosphazene composition comprises the mixture of cyclic phosphazene compounds represented by general formula (1) (wherein, m is an integer of 3 to 10; Q is a group independently selected from the group consisting of a halogen, aryloxy group, alkoxy group, amino group, aryloxy group having a halogen, alkoxy group having a halogen or amino group having a halogen; and at least one of the Q is a halogen), and in addition the content of halogen is 1 weight % or greater to the whole amount of the cyclic phosphazene compounds. The flame retardant containing such phosphazene composition and its production method.

Description

DETAILED DESCRIPTION OF THE INVENTION

The present invention relates to a phosphazene composition, a flame retardant containing the same, a method for producing the same, a resin composition containing the flame retardant, and a molded product thereof.

[0002]

2. Description of the Related Art Conventionally, resins have been known for their workability, chemical resistance,
Utilizing advantages such as weather resistance, electrical characteristics, and mechanical strength, it is widely used in fields such as industrial and household electrical products, and the amount of resin used is increasing. However, resins are also strongly required to have flame retardancy, and the degree of the demand has been gradually increasing in recent years.

[0003] Metal hydrates such as aluminum hydroxide and magnesium hydroxide have a flame-retardant effect because the endothermic reaction of dehydration pyrolysis occurs in the temperature range overlapping with the thermal decomposition and combustion start temperatures of the resin at the combustion temperature of the resin. Used as can grow. However, since metal hydrate alone does not have a strong flame-retardant effect, it has to be blended in a large amount, which has a drawback such as adversely affecting the mechanical strength of a molded product obtained. .

[0004] Conventional phosphorus-based flame retardants have not only a flame-retardant effect but also excellent properties such as functioning as a plasticizer or an antioxidant when added to a resin. However, triaryl phosphates such as triphenyl phosphate, tricresyl phosphate, and cresyl diphenyl phosphate have low boiling points, and thus have disadvantages such as volatilization during molding, contaminating the mold, and bleeding out to the resin surface. The condensation type phosphate ester solves the above-mentioned drawbacks, but if the catalyst used during production remains in this phosphate ester, not only the phosphate ester but also the resin will decompose at the time of molding, causing a decrease in performance. It is known that the productivity is sometimes reduced to gel, and the productivity is remarkably reduced. Ammonium polyphosphate has drawbacks in that processing conditions are limited due to poor thermal stability, and that a large amount of phosphorus must be added due to its low phosphorus content.

[0005] Various studies have been made on phosphazene compounds having phosphorus and nitrogen as a skeleton because they are expected to be effective as flame retardants. For example, JP-A-4-154851 discloses a flame-retardant electrical insulating composition comprising a polyolefin, a metal hydroxide and phosphazene. JP-A-6-263908 discloses a composition comprising an ethylene-vinyl acetate copolymer, an inorganic flame retardant, a phosphazene and a urea derivative. JP-A-7-292233 discloses a flame-retardant resin composition comprising a polycarbonate-based resin, phosphazene and a fluorine-based resin. JP-A-9-53009 discloses an aromatic polycarbonate and a graft copolymer. Japanese Patent Application Laid-Open No. Hei 9-71708 proposes a flame-retardant resin composition comprising coalesced and phosphazene. A flame-retardant resin composition comprising rubber-reinforced styrene, polyphenylene ether and phosphazene is proposed. However, these flame retardant resin compositions have not obtained sufficient flame retardancy.

[0006]

Accordingly, an object of the present invention is to provide a phosphazene composition having excellent flame retardancy with a small amount of addition, a method for producing the same, a flame retardant containing the phosphazene composition as an active ingredient, and a phosphazene composition. Another object of the present invention is to provide a resin composition containing an article and a molded article made thereof.

[0007]

Means for Solving the Problems The present inventors have conducted intensive studies on various flame retardants and additives or their addition amounts in order to improve the flame retardancy of the resin composition. It has been found that by doing so, the flame retardancy of the resin composition is improved, and the present invention has been completed.

A first aspect of the present invention is the following general formula (1)

Embedded image (In the formula, m is an integer of 3 to 10, and Q is a halogen, an aryloxy group, an alkoxy group, an amino group, an aryloxy group having a halogen, an alkoxy group having a halogen, and an amino group having a halogen. Each independently selected group, at least one of Q
Phosphazene compounds having a halogen content of at least 1% by weight based on the total amount of all the cyclic phosphazene compounds. In the second aspect of the present invention, the following general formula (1)

Embedded image (In the formula, m is an integer of 3 to 10, and Q is a halogen, an aryloxy group, an alkoxy group, an amino group, an aryloxy group having a halogen, an alkoxy group having a halogen, and an amino group having a halogen. Each independently selected group, at least one of Q
And a mixture of cyclic phosphazene compounds represented by the following general formula (2):

Embedded image (In the formula, n is an integer of 1 to 20, and Q is independently selected from the group consisting of halogen, an aryloxy group, an alkoxy group, an amino group, an alkoxy group having a halogen, and an amino group having a halogen. And at least one of Q is an alkoxy group), and a mixture of linear phosphazene compounds of formula (I), wherein all cyclic phosphazene compounds and all linear phosphazene compounds have a halogen content of The present invention relates to a phosphazene composition, which is 1% by weight or more based on the total amount of the compound. The third aspect of the present invention is
(A) The following general formula (3)

Embedded image (Wherein X is a halogen, m is an integer of 3 to 10) and (B) phenols, alcohols, amines, phenols having a halogen, alcohols having a halogen, 2. The phosphazene composition according to claim 1, wherein at least one compound selected from the group consisting of amines and halogen-containing amines is reacted with (C) an alcohol in the presence of an alkali. It relates to a manufacturing method. A fourth aspect of the present invention is that (A ′) the following general formula (3)

Embedded image (Wherein X is a halogen, m is an integer of 3 to 10) and a cyclic halogenated phosphazene represented by the following general formula (4)

Embedded image (Wherein, X is a halogen, and n is an integer of 1 to 20).
(B) at least one compound selected from the group consisting of phenols, alcohols, amines, phenols having a halogen, alcohols having a halogen and amines having a halogen, and (C) alcohols;
And reacting in the presence of an alkali. The method for producing a phosphazene composition according to claim 2, wherein
A fifth aspect of the present invention relates to a flame retardant comprising the phosphazene composition according to claim 1 or 2 as an active ingredient. A sixth aspect of the present invention relates to a resin composition containing the phosphazene composition according to claim 1 or 2. A seventh aspect of the present invention relates to a molded article comprising the resin composition according to claim 6.

The halogenated phosphazenes used in the present invention are not particularly limited, and the cyclic halogenated phosphazenes of the general formula (3) may be a single product such as trimer, a mixture of trimer and tetramer, or a mixture of trimer and tetramer. Oligomers containing a large amount of trimers and tetramers are listed. Examples of the chain halogenated phosphazene of the general formula (4) include single products or mixtures in which n is 1 or more, and oligomers containing many n = 2. Among them, oligomers containing a large amount of trimers and tetramers are particularly preferable. In the present invention, a crude halogenated phosphazene containing impurities can also be used.

A method for synthesizing halogenated phosphazenes is described, for example, in Yokoyama [Nippon Kagaku Magazine Vol. 80, No. 10, p 118
(1959)], a cyclic and linear chlorophosphazene mixture was obtained by reacting phosphorus pentachloride and ammonium chloride in monochlorobenzene, and this chlorophosphazene mixture was recrystallized from petroleum ether to give m
p. It is publicly known that it is reported that hexachlorocyclotriphosphazene [general formula (3) m = 3] of white rhombic crystals at 112 to 113 ° C. is obtained.

Since chlorophosphazene is synthesized by reacting phosphorus pentachloride and ammonium chloride, it has a structure in which P and N are bonded alternately, and the chain phosphazene represented by the general formula (4) has N-terminals at both ends. With N and P ends
And both ends are P. Naturally, the terminal of the phosphazene represented by the general formula (2) obtained by using this chain phosphazene is derived from the terminal of the raw material.

As a reaction, for example, tetrahydrofuran (THF) is added to (B) at least one member selected from the group consisting of phenols, amines, phenols having a halogen, alcohols having a halogen, and amines having a halogen. A compound, (C) an alcohol and an alkali are added, and the halogenated phosphazene TH is added thereto.
A method of dropping and reacting an F solution; a THF solution of a halogenated phosphazene is added to a THF solution of a phenol, an amine, a phenol having a halogen, a phenol having a halogen, an alcohol having a halogen and an amine having a halogen. A method in which at least one selected compound, (C) an alcohol and an alkali are added dropwise and reacted, halogenated phosphazenes in THF,
Reacting at least one compound selected from the group consisting of (B) phenols, amines, phenols having a halogen, alcohols having a halogen and amines having a halogen with (C) an alcohol and an alkali And the like.

The phenols (phenol, naphthol, 4-phenylphenol and the like) include monovalent phenols (substituents having 0 to 5 substituents and C1 to C1 as substituents).
8 linear or branched alkyl groups, C1 to C8 linear or branched alkoxy groups, etc.), divalent phenol (0 to 5 substituents, C1 to C8 linear or branched alkyl groups as substituents, C1 to C8) A C8 linear or branched alkoxy group).

Specific examples of the monovalent phenol include phenols such as phenol, 1-naphthol, 2-naphthol and 4-phenylphenol; o-cresol, m-phenol.
-Cresol, p-cresol, o-ethylphenol, m-ethylphenol, p-ethylphenol, o
-Propylphenol, m-propylphenol, p-
Propylphenol, o-iso-propylphenol, m-iso-propylphenol, p-iso-propylphenol, o-butylphenol, m-butylphenol, p-butylphenol, o- (2-methylpropyl) phenol, m- (2 -Methylpropyl) phenol, p- (2-methylpropyl) phenol, o
-Tert-butylphenol, m-tert-butylphenol, p-tert-butylphenol, o-pentylphenol, m-pentylphenol, p-pentylphenol, o- (2-methylbutyl) phenol, m- (2-methylbutyl) phenol, p- (2-
Methylbutyl) phenol, o- (3-methylbutyl)
Phenol, m- (3-methylbutyl) phenol, p
-(3-methylbutyl) phenol, o-tert-amylphenol, m-tert-amylphenol, p
1-hydroxy-, such as -tert-amylphenol
2-methylnaphthalene, 1-hydroxy-3-methylnaphthalene, 1-hydroxy-4-methylnaphthalene, 1
-Hydroxy-5-methylnaphthalene, 1-hydroxy-6-methylnaphthalene, 1-hydroxy-7-methylnaphthalene, 1-hydroxy-8-methylnaphthalene,
2-ethyl-1-hydroxynaphthalene, 3-ethyl-
1-hydroxynaphthalene, 4-ethyl-1-hydroxynaphthalene, 5-ethyl-1-hydroxynaphthalene, 6-ethyl-1-hydroxynaphthalene, 7-ethyl-1-hydroxynaphthalene, 8-ethyl-1-hydroxynaphthalene, 2-hydroxy-1-methylnaphthalene, 2-hydroxy-3-methylnaphthalene, 2-hydroxy-4-methylnaphthalene, 2-hydroxy-5
-Methylnaphthalene, 2-hydroxy-6-methylnaphthalene, 2-hydroxy-7-methylnaphthalene, 2-
Hydroxy-8-methylnaphthalene, 1-ethyl-2-
Hydroxynaphthalene, 3-ethyl-2-hydroxynaphthalene, 4-ethyl-2-hydroxynaphthalene, 5
-Ethyl-2-hydroxynaphthalene, 6-ethyl-2
Monoalkylphenols such as 2-methyl-4-phenylphenol and 2-ethyl-4-phenylphenol, such as -hydroxynaphthalene, 7-ethyl-2-hydroxynaphthalene and 8-ethyl-2-hydroxynaphthalene; 2,3-xylenol , 2,4-xylenol,
2,5-xylenol, 2,6-xylenol, 3,4
-Xylenol, 3,5-xylenol, 2-ethyl-
6-methylphenol, 3-ethyl-6-methylphenol, 4-ethyl-6-methylphenol, 5-ethyl-6-methylphenol, 2-ethyl-3-methylphenol, 2-ethyl-4-methylphenol, 2-ethyl-5-methylphenol, 3-ethyl-4-methylphenol, 3-ethyl-5-methylphenol, 2-methyl-3-propylphenol, 2-methyl-4-propylphenol, 2-methyl-5 -Propylphenol, 2-methyl-6-propylphenol, 3-methyl-2-propylphenol, 4-methyl-2-propylphenol, 5-methyl-2-propylphenol, 3
-Methyl-4-propylphenol, 3-methyl-5
Propylphenol, 2-methyl-3-iso-propylphenol, 2-methyl-4-iso-propylphenol, 2-methyl-5-iso-propylphenol, 2-methyl-6-iso-propylphenol,
-Methyl-2-iso-propylphenol, 4-methyl-2-iso-propylphenol, 5-methyl-2
-Iso-propylphenol, 3-methyl-4-is
o-propylphenol, 3-methyl-5-iso-propylphenol, 2-butyl-6-methylphenol, 3-butyl-6-methylphenol, 4-butyl-
6-methylphenol, 5-butyl-6-methylphenol, 2-butyl-3-methylphenol, 2-butyl-4-methylphenol, 2-butyl-5-methylphenol, 3-butyl-4-methylphenol, 3-butyl-5-methylphenol, 2- (2-methylpropyl) -6-methylphenol, 3- (2-methylpropyl) -6-methylphenol, 4- (2-methylpropyl) -6-methylphenol , 5- (2-methylpropyl) -6-methylphenol, 2- (2-methylpropyl) -3-methylphenol, 2- (2-methylpropyl) -4-methylphenol, 2- (2-methylpropyl) ) -5-Methylphenol, 3- (2-methylpropyl) -4-methylphenol, 3- (2-methylpropyl) -5-methylphenol , 2- (3-methylpropyl) -6-methylphenol, 3- (3-methylpropyl) -6-methylphenol, 4- (3-methylpropyl) -6-methylphenol, 5- (3-methyl Propyl) -6-methylphenol, 2- (3-methylpropyl) -3-methylphenol, 2- (3-methylpropyl) -4-methylphenol, 2- (3-methylpropyl) -5-methylphenol, 3- (3-methylpropyl) -4-methylphenol, 3- (3-methylpropyl) -5-methylphenol, 2-tert-butyl-
6-methylphenol, 3-tert-butyl-6-methylphenol, 4-tert-butyl-6-methylphenol, 5-tert-butyl-6-methylphenol, 2-tert-butyl-3-methylphenol, 2
-Tert-butyl-4-methylphenol, 2-te
rt-butyl-5-methylphenol, 3-tert-
Butyl-4-methylphenol, 3-tert-butyl-5-methylphenol, 2,3-diethylphenol, 2,4-diethylphenol, 2,5-diethylphenol, 2,6-diethylphenol, 3,4- Diethylphenol, 3,5-diethylphenol, 2,3
-Dipropylphenol, 2,4-dipropylphenol, 2,5-dipropylphenol, 2,6-dipropylphenol, 3,4-dipropylphenol, 3,5
-Dipropylphenol, 2,3-di-iso-propylphenol, 2,4-di-iso-propylphenol, 2,5-di-iso-propylphenol, 2,6
-Di-iso-propylphenol, 3,4-di-is
o-propylphenol, 3,5-di-iso-propylphenol, 2,3-di-tert-butylphenol, 2,4-di-tert-butylphenol, 2,5
-Di-tert-butylphenol, 2,6-di-te
rt-butylphenol, 3,4-di-tert-butylphenol, 3,5-di-tert-butylphenol, 2,3-di-tert-amylphenol, 2,4
-Di-tert-amylphenol, 2,5-di-te
rt-amylphenol, 2,6-di-tert-amylphenol, 3,4-di-tert-amylphenol, 3,5-di-tert-amylphenol, 1-hydroxy-2,3-dimethylnaphthalene, 1 -Hydroxy-2,5-dimethylnaphthalene, 1-hydroxy-
2,6-dimethylnaphthalene, 1-hydroxy-2,7
-Dimethylnaphthalene, 2-hydroxy-1,3-dimethylnaphthalene, 2-hydroxy-1,5-dimethylnaphthalene, 2-hydroxy-1,7-dimethylnaphthalene, 2-hydroxy-1,8-dimethylnaphthalene,
2,3-diethyl-1-hydroxynaphthalene, 2,5
-Diethyl-1-hydroxynaphthalene, 2,6-diethyl-1-hydroxynaphthalene, 2,7-diethyl-
1-hydroxynaphthalene, 1,3-diethyl-2-hydroxynaphthalene, 1,5-diethyl-2-hydroxynaphthalene, 1,7-diethyl-2-hydroxynaphthalene, 1,8-diethyl-2-hydroxynaphthalene and the like, 2,6-dimethyl-4-phenylphenol,
2-methoxyphenol, such as dialkylphenols such as 2,6-diethyl-4-phenylphenol, 3
-Methoxyphenol, 4-methoxyphenol, 2-
Ethoxyphenol, 3-ethoxyphenol, 4-ethoxyphenol, 2-propoxyphenol, 3-propoxyphenol, 4-propoxyphenol, 2-
Phenol substituted with an alkoxy group such as iso-propoxyphenol, 3-iso-propoxyphenol, and 4-iso-propoxyphenol is exemplified.

Examples of the dihydric phenol include catechol, 1,2-dihydroxynaphthalene, 1,8-dihydroxynaphthalene, 2,3-dihydroxynaphthalene, 3,4-dihydroxynaphthalene, o, o'-biphenol and the like. Is mentioned.

Examples of the amines include ammonia, methylamine, ethylamine, propylamine, n
Monoalkylamines such as -butylamine, iso-butylamine, tert-butylamine, pentylamine and hexylamine; dialkylamines such as dimethylamine and diethylamine; diamines such as ethylenediamine and phenylenediamine; aniline, benzylamine;
And aromatic amines such as dibenzylamine.

Examples of the phenols having a halogen as a substituent include 2-chlorophenol, 3-chlorophenol, 4-chlorophenol, 2,3-dichlorophenol, 2,4-dichlorophenol, and 2,5-dichlorophenol. , 2,6-dichlorophenol, 3,4
-Dichlorophenol, 3,5-dichlorophenol,
2-bromo-4-chlorophenol, 4-bromo-2-
Chlorophenol, 2-chloro-4-fluorophenol, 3-chloro-4-fluorophenol, 4-chloro-2-fluorophenol, 4-chloro-3-fluorophenol, 2-chloro-3,5-difluorophenol, 2,6-dichloro-4-fluorophenol, 2,
3,4-trichlorophenol, 2,3,6-trichlorophenol, 2,4,5-trichlorophenol,
2,4,6-trichlorophenol, pentachlorophenol, 2-chloro-4-methylphenol, 2-chloro-5-methylphenol, 2-chloro-6-methylphenol, 4-chloro-2-methylphenol, -Chloro-3-methylphenol, 2-chloro-4-methoxyphenol, 4-chloro-2-methoxyphenol,
2-chloro-4,5-dimethylphenol, 4-chloro-3,5-dimethylphenol, 4-chloro-3-ethylphenol, 4-chloro-1-naphthol, 2,4-
Dichloro-1-naphthol, 5-chloro-2- (2,4
-Dichlorophenoxy) phenol, 2-bromophenol, 3-bromophenol, 4-bromophenol,
2,4-dibromophenol, 2,6-dibromophenol, 2-bromo-4-fluorophenol, 2-bromo-5-fluorophenol, 4-bromo-2-fluorophenol, 2-bromo-4,5-difluoro Phenol, 2,6-dibromo-4-fluorophenol,
2,4,6-tribromophenol, pentabromophenol, 2-bromo-4-methylphenol, 4-bromo-3-methylphenol, 2,6-dibromo-4-methylphenol, 4-bromo-2,6 -Dimethylphenol, 4-bromo-3,5-dimethylphenol, 1-
Bromo-2-naphthol, 6-bromo-2-naphthol, 1,6-dibromo-2-naphthol, 4'-bromo- [1,1'-biphenyl] -4-ol, 2-fluorophenol, 3-fluoro Phenol, 4-fluorophenol, 2,3-difluorophenol, 2,4-difluorophenol, 2,5-difluorophenol,
2,6-difluorophenol, 3,4-difluorophenol, 3,5-difluorophenol, 2,3,4
-Trifluorophenol, 2,3,5-trifluorophenol, 2,3,6-trifluorophenol,
2,4,6-trifluorophenol, 2,3,5,6
-Tetrafluorophenol, pentafluorophenol, 2-fluoro-5-methylphenol, 4-fluoro-2-methylphenol, 4-fluoro-3-methylphenol, 2-iodophenol, 3-iodophenol, 4-iodo Phenol and the like.

Examples of the alcohol having a halogen as a substituent include 2-chloroethanol, 2,2-dichloroethanol, 1,3-dichloro-2-propanol, 1-chloro-2-propanol, and 3-chloro-1. −
Propanol, 4-chloro-1-butanol, 1-chloro-2-methyl-2-propanol, 3-chloro-2,
2-dimethyl-1-propanol, 2-bromoethanol, 3-bromo-1,1,1-trifluoro-2-propanol, 1,3-dibromo-2-propanol, 2,
3-dibromopropanol, 1-bromo-2-propanol, 3-bromo-1-propanol, 3-bromo-2
-Methyl-1-propanol, 3-bromo-2,2-dimethyl-1-propanol, 2-fluoroethanol,
2,2,2-trifluoroethanol, 1,1,1,
3,3,3-hexafluoro-2-propanol, 2,
2,3,3,3-pentafluoro-1-propanol,
2,2,3,3-tetrafluoro-1-propanol,
1,3-difluoro-2-propanol, perfluoro-tert-butyl alcohol, 1,1,1,3,3
4,4,4-octafluoro-2-butanol, 2,
2,3,3,4,4,4-heptafluoro-1-butanol, 2,2,3,4,4,4-hexafluoro-1-
Butanol, 1,1,1,3,3,3-hexafluoro-2-methyl-2-propanol, 2,2,3,3
4,4,5,5-octafluoro-1-pentanol,
2,3,4,5,6-pentafluorobenzyl alcohol, 2,3-difluorobenzyl alcohol, 2,4-
Difluorobenzyl alcohol, 2,5-difluorobenzyl alcohol, 2,6-difluorobenzyl alcohol, 3,4-difluorobenzyl alcohol, 3,5
-Difluorobenzyl alcohol, 2-fluorobenzyl alcohol, 3-fluorobenzyl alcohol, 4-
Fluorobenzyl alcohol, 2,2,3,3,4
4,5,5,6,6,7,7,8,8,8-pentadecafluoro-1-octanol and the like.

Examples of the amines having a halogen as a substituent include halides of the amines such as trifluoromethylamine and 2,2,2-trifluoroethylamine.

The alcohols include, for example, methanol, ethanol, n-propanol, iso-propanol, n-butanol, 2-butanol, tert-
Butanol, n-pentanol, 2-methylbutanol, 3-methylbutanol, 4-methylbutanol,
2,2-dimethylpropanol, 3,3-dimethylpropanol, 3-ethylpropanol, n-hexanol, 2-methylpentanol, 3-methylpentanol, 4-methylpentanol, 5-methylpentanol, 2,2 -Dimethylbutanol, 2,3-dimethylbutanol, 2,4-dimethylbutanol, 3,3-dimethylbutanol, 3,4-dimethylbutanol, 3-ethylbutanol, 4-ethylbutanol, 2,2,3-
Trimethylpropanol, 2,3,3-trimethylpropanol, 3-ethyl-2-methylpropanol, 3-
iso-propylpropanol, n-heptanol, n
-Octanol and the like.

As the phosphazene compound represented by the general formula (1) containing halogen, for example, when m = 3

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[0022]

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[0023]

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[0024]

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[0025]

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[0026]

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[0027]

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[0028]

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[0029]

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[0030]

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As the chain phosphazene, those corresponding to the above-mentioned examples of the cyclic phosphazenes exist, and both terminals are N-terminal.
, Those having ends N and P, and those having both ends P.

Examples of the alkali include sodium metal, sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, triethylamine, pyridine and the like. Any solvent may be used as long as it does not react with the reaction substrate. For example, tetrahydrofuran, 1,4
-Dioxane, toluene, benzene, xylene, monochlorobenzene, o-dichlorobenzene, hexane, heptane, cyclohexane and the like are preferred. The reaction temperature is between 5 and
150 ° C. is preferred.

In the production of the phosphazene of the present invention, organic nitrogen compounds, conventional dispersants and ion exchange resins may be added.

The organic nitrogen compounds include, for example, amines and amides. Examples of the amines include triethylamine, tri-n-butylamine, pyridine, 2-methylpyridine, 3-methylpyridine, 4-methylpyridine, 2,3-lutidine, 2,4-
Lutidine, 2,5-lutidine, 2,6-lutidine, 3,
4-lutidine, 3,5-lutidine, morpholine, piperidine, pyrrolidine, 1-methylpiperidine, 2-methylpiperidine, 3-methylpiperidine, 4-methylpiperidine, 2,6-lupetidine, 3,5-lupetidine, hexamethylene Tetramine and the like.

Examples of amides include N, N-dimethylformamide, N, N-diethylformamide, N
-Methyl-N-phenylformamide, N, N-dimethylacetamide, N, N-diethylacetamide, 2-
Pyrrolidone, 3-pyrrolidone, 4-pyrrolidone, N-methyl-2-pyrrolidone, 1,3-dimethyl-2-imidazolidinone, and the like. Further, organic nitrogen compounds alone can be used as the solvent. In this case, for example, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, 1,3
-Dimethyl-2-imidazolidinone and the like.

As dispersants, tetramethylammonium chloride, tetraethylammonium chloride,
Tetrabutylammonium bromide, tetrabutylammonium hydroxide, tetrabutylammonium hydrogensulfate, trilaurylmethylammonium chloride, di-hardened tallow alkyldimethylammonium acetate trimethylphenylammonium chloride, benzyltrimethylammonium chloride, cetyltrimethylammonium chloride, stearyltrimethylammonium chloride , Distearyl dimethyl ammonium chloride and the like.

As ion exchange resins, for example, Amberlite IR-116, IR-118 (H), IR-120
B, IR-122, IR-124 (trade name, manufactured by Organo) and Amberlist 15, A-26, A-27,
A-21, 252, 200C, 200CT, IRC-5
0, IRC-84, IRC-718, IRA-401,
IRA-402, IRA-400 (trade name, manufactured by Organo Corporation) and the like.

The phosphazene composition of the present invention can be solid, waxy or liquid by changing the substituent. There is an advantage in handling by making use of each property, and phosphazenes having appropriate properties can be appropriately selected and used according to the properties of the counterpart to be added.
The flame retardant according to the present invention can be expected to have a further effect when used by mixing the phosphazenes or when using another flame retardant in combination.

Flame retardants which may be added to the flame retardant according to the present invention include metal hydroxide compounds, silicates, organosilicon compounds, fluororesins, inorganic flame retardants, phosphorus flame retardants, halogen flame retardants and nitrogen flame retardants. A fuel may be used, and these may be used in combination.

The metals of the metal hydroxide compound which may be added to the flame retardant of the present invention include Group 2 and Group 13 of the Periodic Table of the Elements (Group 2 of the new IUPAC formats 1 to 18;
Metals of the 13th group and corresponding to conventional groups IIa and IIIb of the periodic table) and zinc, and preferably magnesium and aluminum. These metal hydroxide compounds may be used alone, but they may be used as organic compounds such as higher aliphatic carboxylic acids, hydrogenated oils or higher aliphatic carboxylic acids in the first periodic table of the element.
Group, group 2, group 12 or group 13 (group 1, group 12, group 12 or group 13 from the new IUPAC format 1 to group 18 and the conventional periodic table Ia, IIa, IIb or IIIb) (Corresponding to group 3). The metal hydroxide compound, especially magnesium hydroxide,
Kismer 5A, 5B, 5E, 5J (trade name, manufactured by Kyowa Chemical), Magseeds N-3, N-1, water mug 200, 1
0, 10A, Starmag UM, M, L, S, C, CY
(Trade name, manufactured by Kamishima Chemical Co., Ltd.), FR-200 (trade name, manufactured by Bromochem Far East), etc., and these may be used as they are.

Examples of the silicate that may be added to the flame retardant of the present invention include sodium silicate, sodium metasilicate, sodium orthosilicate, water glass, magnesium silicate, potassium silicate, potassium magnesium silicate, calcium silicate, aluminum silicate, Layered silicates such as zirconium silicate, silicate molybdic acid, formic olivine, olivine, etc. Three-dimensional silicates such as mica and clay minerals include silicon dioxide, feldspar and zeolite.

The organic silicon compound which may be added to the flame retardant of the present invention includes, for example, tetramethoxysilane, tetraethoxysilane, tetrapropoxysilane, trimethoxysilane, triethoxysilane, tripropoxysilane, methyltrimethoxysilane , Methyltriethoxysilane, methyltripropoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, dimethoxymethylphenylsilane, dimethoxy-3-mercaptopropylmethylsilane, 3-mercaptopropyltrimethoxysilane, 3-aminopropyldiethoxymethyl Silane, 3- (2-aminoethylaminopropyl) trimethoxysilane, 3- (2-aminoethylaminopropyl) dimethoxymethylsilane, 3-glycidopropyltrimethoxysilane, -Alkoxysilane compounds such as methacryloxypropyltrimethoxysilane and diethoxy-3-glycidoxypropylmethylsilane, polysiloxane compounds such as dimethylpolysiloxane, methylhydrogenpolysiloxane and methylphenylpolysiloxane, and alkyl-modified silicone and amino-modified Examples include silicone, epoxy-modified silicone, carboxyl-modified silicone, mercapto-modified silicone, alcohol-modified silicone, alkyl higher alcohol ester-modified silicone, polyether-modified silicone, and alkyl aralkyl / polyether-modified silicone.

Examples of the fluorine resin which may be added to the flame retardant of the present invention include polytetrafluoroethylene resin (PTEF), tetrafluoroethylene-hexafluoropropylene copolymer resin (FEP), and tetrafluoroethylene-perfluoroalkyl. Vinyl ether copolymer resin (PFA), tetrafluoroethylene-ethylene copolymer resin (ETFE), polytrifluoroethylene chloride resin (CTFE), polyvinylidene fluoride resin (PVD)
F) and the like.

Examples of the inorganic flame retardant which may be added to the flame retardant of the present invention include antimony trioxide, antimony tetroxide, antimony pentoxide, sodium antimonate, zinc borate, magnesium oxide, calcium oxide and the like. Can be

Examples of the phosphorus-based flame retardant that may be added to the flame retardant of the present invention include red phosphorus, ammonium polyphosphate, triphenyl phosphate, triethyl phosphate, trimethyl phosphate, tricresyl phosphate, tricylenyl phosphate, and the like. Cresylphenyl phosphate, tris (3-hydroxypropyl) phosphine oxide, glycidyl-α-methyl-β-dibutoxyphosphenylpropionate, dibutylhydroxymethylphosphonate, dibutoxyphosphphenylpropylamide, dimethylhydroxymethylphospho Phonate, dibutoxyphosphenylpropylamide, dimethylmethylphosphonate, di (polyoxyethylene)-
Examples include hydroxymethylphosphonate and condensed aromatic phosphate.

Red phosphorus may be used alone, coated with an appropriate inorganic or organic compound, or diluted with a non-halogen organic polymer composition. As commercial products of the red phosphorus, Nova Red 120, 120 UF, 120 UFA, Nova Excel ST, W, MG, RX series, various Nova pallets (trade name, manufactured by Rin Kagaku), Hishigard CP, CP-15,
UR-15, TP-10, Safe TP-10 (manufactured by Nippon Chemical), RP-120 (manufactured by Suzuhiro Chemical) and the like can be used as they are.

Examples of the halogen-based flame retardant which may be added to the flame retardant of the present invention include, for example, tris (chloroethyl) phosphate, tris (dichloropropyl) phosphate and bis (2,3-dibromopropyl) -2,3-dichloro. Propyl phosphate, tris (2,3-dibromopropyl) phosphate, bis (chloropropyl) monooctyl phosphate, hexabromobenzene, hexabromobiphenyl ether, tribromophenol, tetrabromobisphenol A, tetrabromophthalic anhydride, hexabromocyclododecane , Bis (bromoethyl ether) tetrabromobisphenol A, ethylenebistetrabromophthalimide, brominated epoxy oligomer, brominated polystyrene, decabromodiphenylethane,
Brominated aromatic triazine, tetrabromoethane, octabromotrimethylphenylindane, polydibromophenylene oxide, pentabromobenzyl acrylate, pentabromobenzyl polyacrylate, bis (tribromophenoxine) ethane, dibromocresyl glycidyl ether, dibromophenyl glycidyl Ether and tetrabromophthalate diol tetradibromophthalate ester.

Examples of the nitrogen-based flame retardant which may be added to the flame retardant of the present invention include guanidine sulfamate, guanidine phosphate, guanine urea phosphate, melamine phosphate, dimelamine phosphate, melamine borate and melamine cyanurate. No.

The flame retardant according to the present invention may further contain, for example, conventional additives, for example, a filler, a plastic reinforcing agent, a lubricant and the like.

The fillers which may be added to the flame retardant according to the present invention include, for example, calcium carbonate, titanium oxide,
Clay, calcined clay, silane modified clay, talc, mica, silica, wollastonite, bentonite, diatomaceous earth, silica sand, pumice powder, slate powder, alumina white, aluminum sulfate, barium sulfate, lithopone, calcium sulfate,
Molybdenum disulfide, surface-treated filler, recycled rubber, rubber powder, ebonite powder, shellac and the like can be mentioned.

Examples of the plastic reinforcing agent that may be added to the flame retardant according to the present invention include mica powder, graphite, glass fiber, glass sphere, volcanic glass hollow body, carbon fiber, carbon hollow body, anthracite powder, artificial ice crystal Examples include stone, silicon resin powder, silica spherical fine particles, polyvinyl alcohol fiber, aramid fiber, alumina fiber, and high-strength polyacrylate fiber.

As the lubricant which may be added to the flame retardant of the present invention, for example, paraffin wax, liquid paraffin,
Paraffin synthetic wax, polyethylene wax, composite wax, montan wax, silicone oil, stearic acid, lithium stearate, sodium stearate, magnesium stearate, potassium stearate, aluminum stearate, calcium stearate, zinc stearate, hydroxystearic acid , 1
Magnesium 2-hydroxystearate, calcium 12-hydroxystearate, barium 12-hydroxystearate, zinc 12-hydroxystearate, calcium laurate, barium laurate, zinc laurate, etc., coconut oil, palm kernel oil, herring oil And cod liver oil, whale oil, palm oil, cottonseed oil, olive oil, peanut oil, soybean oil, linseed oil, castor oil, and hydrogenated hydrogenated oils thereof.

The resin composition according to the present invention may further contain, for example, a conventional additive, for example, an antioxidant, a light stabilizer and a metal deactivator. May contain various fillers, conductive powders, and the like.

The antioxidants which may be added to the resin composition according to the present invention include, for example, 2,6-di-tert.
-Butyl-4-methylphenol, 2-tert-butyl-4,6-dimethylphenol, 2,6-di-ter
t-butyl-4-ethylphenol, 2,6-di-te
rt-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-iso-butylphenol,
2,6-dicyclopentyl-4-methylphenol, 2
-(Α-methylcyclohexyl) -4,6-dimethylphenol, 2,6-dioctadecyl-4-methylphenol, 2,4,6-tricyclohexylphenol,
2,6-dinonyl-4-methylphenol, 2,6-di-tert-butyl-4-methoxymethylphenol,
2,4-dimethyl-6- (1'-methyl-undeca-
1'-yl) -phenol, 2,4-dimethyl-6
(1'-methyl-trideca-1'-yl) -phenol and mixtures thereof, 2,4-di-octylthiomethyl-6-tert-butylphenol, 2,4-dioctylthiomethyl-6-methylphenol, , 4-Dioctylthiomethyl-6-ethylphenol, 2,6-di-dodecylthiomethyl-4-nonylphenol and mixtures thereof, 2,6-di-tert-butyl-4-methoxyphenol, 2,5-diphenol -Tert-butylhydroquinone, 2,5-di-tert-amylhydroquinone, 2,6-diphenyl-4-octadecyloxyphenol, 2,6-di-tert-butylhydroquinone, 2,5-di-tert-butyl- 4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyanisole, , 5-di -tert- butyl-4
Hydroxyphenyl stearate, bis (3,5-di-
tert-butyl-4-hydroxyphenyl) adipate and mixtures thereof, 2,4-bis-octylmercapto-6- (3,5-di-tert-butyl-4-hydroxyanilino) -1,3,5- Triazine, 2-octylmercapto-4,6-bis (3,5-di-ter
t-butyl-4-hydroxyanilino) -1,3,5-
Triazine, 2-octylmercapto-4,6-bis (3,5-di-tert-butyl-4-hydroxyphenoxy) -1,3,5-triazine, 2,4,6-tris (3,5-di -Tert-butyl-4-hydroxyphenoxy) -1,2,3-triazine, 1,3,5-tris (3,5-di-tert-butyl-4-hydroxybenzyl) -isocyanurate, 1,3,3 5-tris (4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) -isocyanurate, 2,4,6-tris (3,5-di-tert-butyl-4-hydroxyphenylethyl)- 1,3,5-triazine, 1,3
5-tris (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) -hexahydro-1,
3,5-triazine, 1,3,5-tris (3,5-dicyclohexyl-4-hydroxybenzyl) -isocyanurate and the like, and 2,2'-methylenebis (6-ter
t-butyl-4-methylphenol), 2,2'-methylenebis (6-tert-butyl-4-ethylphenol), 2,2'-ethylidenebis (4,6-di-ter
t-butylphenol), 2,2'-ethylidenebis (6-tert-butyl-4-iso-butylphenol), 4,4'-methylenebis (2,6-di-tert)
-Butylphenol), 4,4'-methylenebis (6-
tert-butyl-2-methylphenol), 1,1-
Bis (5-tert-butyl-4-hydroxy-2-methylphenyl) butane, ethylene glycol bis [3
3'-bis (3'-tert-butyl-4'-hydroxyphenyl) butyrate] and 1,3,5-tris (3,5-di-tert-butyl-4-hydroxybenzyl) -2,4 , 6-trimethylbenzene, 1,4
-Bis (3,5-di-tert-butyl-4-hydroxybenzyl) -2,3,5,6-tetramethylbenzene, 2,4,6-tris (3,5-di-tert-butyl-4) -Hydroxybenzyl) -phenol and the like.

Light stabilizers that may be added to the resin composition according to the present invention include, for example, 2- (2′-hydroxy-5′-methylphenyl) benzotriazole,
(3 ', 5'-di-tert-butyl-2-hydroxyphenyl) benzotriazole, 2- (5'-tert
-Butyl-2'-hydroxyphenyl) benzotriazole, 2- [2'-hydroxy-5 '-(1,1,3,
3-tetramethylbutyl) phenyl] benzotriazole, 2- (3 ', 5'-di-tert-butyl-2'-
(Hydroxyphenyl) -5-chlorobenzotriazole, 2- (3'-tert-butyl-2'-hydroxy-5'-methylphenyl) -5-chlorobenzotriazole, 2- (2'-hydroxy-4'-oct) (Xyphenyl) benzotriazole, 2- (3 ', 5'-di-t
tert-amyl-2'-hydroxyphenyl) benzotriazole, 2- [3'-tert-butyl-2'-hydroxy-5 '-(2'-octyloxycarbonylethylphenyl)]-5-chlorobenzotriazole and the like;
4-hydroxy-, 4-methoxy-, 4-octoxy-, 4-decyloxy-, 4-dodecyloxy-, 4-
Benzyloxy, 4,2 ', 4'-trihydroxy, 2'-hydroxy-4,4'-dimethoxy- or 4- (2-ethylhexyloxy) -2-hydroxybenzophenone derivative; 4-tert -Butylphenyl salicylate, phenyl salicylate, octylphenyl salicylate, dibenzoylresorcinol, bis (4-tert-butylbenzoylresorcinol), 2,4-di-tert-butylphenylresorcinol, 3,5-di-tert-butyl-4 -Hydroxybenzoate, hexadecyl-3,5-di-ter
t-butyl-4-hydroxybenzoate and the like; ethyl
α-cyano-β, β-diphenyl acrylate, iso
-Octyl α-cyano-β, β-diphenylacrylate, methyl α-carbomethoxycinnamate, methyl α-cyano-β-methyl-p-methoxycinnamate, etc .; bis (2,2,6,6-tetramethyl- 4-piperidyl) sebacate, bis (2,2,6,6-tetramethyl-4-piperidyl) succinate, bis (1,2,2
2,6,6-pentamethyl-4-piperidyl) sebacate, bis (1-octyloxy-2,2,6,6-tetramethyl-4-piperidyl) sebacate, bis (1,
2,2,6,6-pentamethyl-4-piperidyl) adipate and the like; 4,4′-dioctyloxyoxanilide,
2,2'-diethoxyoxyoxanilide, 2,2'-
Dioctyloxy-5,5'-di-tert-butyloxanilide, 2,2'-didodecyloxy-5,5'-
Di-tert-butyl oxanilide, 2-ethoxy-
2'-ethyloxanilide, N, N'-bis (3-dimethylaminopropyl) oxanilide, 2-ethoxy-5
-Tert-butyl-2'-ethoxyoxanilide and the like;
2,4,6-tris (2-hydroxy-4-octyloxyphenyl) -1,3,5-triazine, 2- (2-
(Hydroxy-4-octyloxyphenyl) -4,6-
Bis (2,4-dimethylphenyl) -1,3,5-triazine, 2- (2,4-dihydroxyphenyl) -4,
6-bis (2,4-dimethylphenyl) -1,3,5-
Triazine, 2,4-bis (2-hydroxy-4-propyloxyphenyl) -6- (2,4-dimethylphenyl) -1,3,5-triazine, 2- (2-hydroxy-4-dodecyloxyphenyl ) -4,6-bis (2,
4-dimethylphenyl) -1,3,5-triazine and the like. Examples of the metal deactivator which may be added to the resin composition in the present invention include, for example, N, N'-di-
Phenyl oxalic acid diamide, N-sartilal-N'-salicyloylhydrazine, N, N'-bis (salicyloyl) hydrazine, N, N'-bis (3,5-di-ter
t-butyl-4-hydroxyphenylpropionyl) hydrazine, 3-salicyloylamino-1,2,3-triazole, bis (benzylidene) oxalic acid hydrazide,
Isophthalic dihydrazide, N, N'-diacetal-
Adipic acid dihydrazide, N, N'-bissalicyloyl oxalic acid dihydrazide, N, N'-bissalicyloyl thiopropionic acid dihydrazide and the like can be mentioned.

The resin used in the resin composition containing the flame retardant according to the present invention includes, for example, polyethylene, polypropylene, ethylene-propylene copolymer, polybutylene, polymethylpentene, ethylene-vinyl acetate copolymer, ethylene- Polyolefins such as methyl (ethyl) acrylate copolymer, AS resin, ABS resin, P
C resin, PC / ABS alloy, polystyrene, PET,
PC / PET alloy, polyphenylene ether resin, polyphenylene sulfide resin, polybutadiene resin,
Examples thereof include polybutylene terephthalate resin, methacrylic resin, polyamide resin, epoxy resin, diallyl phthalate resin, silicone resin, and unsaturated polyester.

The resin composition of the present invention is used for various molded articles, and it is used for coatings, especially for fire protection coatings for electric wires, cables, electric parts, mechanical parts, plugs, mounts, casings, covers, and exteriors. It is useful as a material for producing.

The halogen contained in the obtained phosphazenes was analyzed by coulometric titration. In the coulometric titration method, the obtained phosphazene was thermally decomposed, captured as hydrogen halide in an absorbing solution, and when silver equivalent to halogen was electrolyzed into silver halide, the amount of halogen was determined from the amount of electricity.

Production of Flame Retardant Polyolefin Resin Composition and Evaluation of Flame Retardancy
A sample having a size of 1 mm was evaluated by an oxygen index indicating the degree of flame retardancy. Japanese Industrial Standard JISK7201
(Combustion test method of polymer material by oxygen index method). The oxygen index refers to a numerical value of a minimum oxygen concentration (% by volume) required for a material to continue burning under predetermined test conditions. For example, if there is a sample having an oxygen index of 25.0, this indicates that the oxygen concentration is 25.0%.
The above indicates that the fuel is burned when ignited, and that the fire self-extinguishes when it is 25.0% or less. Considering that the oxygen concentration in the atmosphere is about 20.9%, a substance with an oxygen index of more than 20.9 means self-extinguishing in a natural environment, and a large flame-retardant effect. I understand.

[0060]

The present invention will be described below with reference to examples.
The present invention is not limited thereby.

Example 1 41.7 g of 48% NaOH was placed in a 1 L flask equipped with a stirrer, a thermometer, a fractionation receiver for measuring moisture, and a reflux condenser.
(0.5mol), toluene 220mL, phenol 4
7.1 g (0.5 mol) was charged and heated under stirring to carry out azeotropic dehydration (recovered water 30 mL) to remove water in the flask, and phenol was salified with Na. This is 80
And cooled to 12.5 g of N, N-dimethylformamide.
(0.171 mol) was added thereto, and the mixture was added dropwise to a toluene solution of hexachlorophosphazene (58.0 g (0.167 mol), 275 mL of toluene) at 80 ° C. over 1 hour under stirring at 80 ° C., and the stirring reaction was continued at the same temperature for 5 hours went. Next, 28% was placed in a 1 L flask equipped with a stirrer, a thermometer, a fractionation receiver for measuring moisture, and a reflux condenser.
38.9 g of MeONa (MeOH solution) (0.2mo
l), 400 mL of toluene was charged and methyl alcohol (MeOH) was distilled off while heating under stirring, and then 80 ° C.
And cooled. Then, this was added dropwise over 2 hours to a reaction solution obtained by reacting chlorophosphazene and Na salt of phenol, and a stirring reaction was carried out at the same temperature for 10 hours. After the reaction,
After 200 mL of water was added to the flask to dissolve the inorganic salt, the organic layer was separated using a separating funnel. 5 organic layers
After neutralization with sulfuric acid and washing with water, toluene was distilled off to obtain 74.1 g of a chloromethoxyphenoxyphosphazene composition.
The halogen content in the obtained phosphazene was 1.89% by weight.

Example 2 A chlorophosphazene mixture [general formula (1) m = 3] was used in place of hexachlorophosphazene under the same conditions as in Example 1.
74.7%, m = 4 9.9% m = 5 or more 11.8
%, Chain phosphazenes represented by the general formula (2)
6%]. As a result, 70.2 g of a chloromethoxyphenoxyphosphazene composition was obtained. The halogen content in the obtained phosphazene was 2.23% by weight.

Example 3 Phenoxyphosphazene composition obtained in Example 1
2% by weight, 32.3% by weight of magnesium hydroxide, and 64.5% by weight of polypropylene as a polyolefin resin were inserted into a mixer and kneaded at 180 ° C. The resulting mixture was molded by a compression molding machine (185 ° C., 3 minutes), and the sheet obtained was evaluated for flame retardancy. Table 1 shows the results.

Example 4 In the same manner as in Example 3, the phosphazene composition obtained in Example 2 was used in place of the phenoxyphosphazene composition obtained in Example 1, and the flame retardancy was evaluated. Table 1 shows the results.

Comparative Example 1 In the same manner as in Example 3, without adding the phenoxyphosphazene composition obtained in Example 1, only magnesium hydroxide was added, and the flame retardancy was evaluated. Table 1 shows the results.

[0066]

[Table 1]

[0067]

According to the present invention, by using a phosphazene composition containing a small amount of halogen, the flame retardancy of the phosphazene composition can be remarkably improved.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int. Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) C08L 101/00 C08L 101/00 C09K 21/12 C09K 21/12 21/14 21/14 (72) Inventor Masayuki Nishimatsu 1-3-3 Higashikawasaki-cho, Chuo-ku, Kobe City, Hyogo Prefecture Inside the Chemipro Kasei Co., Ltd. Inventor Yoshinori Omae 1-3-3 Higashikawasaki-cho, Chuo-ku, Kobe-shi, Hyogo F-term (reference) 4K028 AA10 AA38 AA39 AA40 AA42 AA48 BA06 4H050 AA01 AA02 AA03 AB80 AC40 BA69 WA15 WA23 4J0021 BB021 BB071 BB111 BB151 BB171 BC021 BC061 BE051 BG061 BL011 BN151 CD001 CF061 CF071 CF211 CG001 CH071 CL001 CN011 CP031 CQ012 CQ013 EW156 EW157 FD030 FD040 FD07 0 FD132 FD133 FD136 FD137 GH00 GM00 GQ00 GQ01 4J030 CB43 CB47 CB48 CB51 CB54

Claims (7)

[Claims] [Claim 1] The following general formula (1) (In the formula, m is an integer of 3 to 10, and Q is a halogen, an aryloxy group, an alkoxy group, an amino group, an aryloxy group having a halogen, an alkoxy group having a halogen, and an amino group having a halogen. Each independently selected group, at least one of Q
Phosphazene compounds having a halogen content of at least 1% by weight based on the total amount of all the cyclic phosphazene compounds. 2. The following general formula (1): (In the formula, m is an integer of 3 to 10, and Q is a halogen, an aryloxy group, an alkoxy group, an amino group, an aryloxy group having a halogen, an alkoxy group having a halogen, and an amino group having a halogen. Each independently selected group, at least one of Q
And a mixture of cyclic phosphazene compounds represented by the following general formula (2): (In the formula, n is an integer of 1 to 20, and Q is independently selected from the group consisting of halogen, an aryloxy group, an alkoxy group, an amino group, an alkoxy group having a halogen, and an amino group having a halogen. And at least one of Q is an alkoxy group) and a mixture of linear phosphazene compounds of formula (I), wherein the halogen content is all cyclic phosphazene compounds and all linear phosphazene compounds. A phosphazene composition, which is 1% by weight or more based on the total amount of the compound. (A) The following general formula (3): (Wherein, X is a halogen, m is an integer of 3 to 10), (B) phenols, alcohols, amines, phenols having a halogen, alcohols having a halogen, 2. The production of a phosphazene composition according to claim 1, wherein at least one compound selected from the group consisting of amines having halogen and an amine is reacted with an alcohol (C) in the presence of an alkali. Method. (A ′) The following general formula (3): (Wherein X is a halogen and m is an integer of 3 to 10), and a cyclic halogenated phosphazene represented by the following general formula (4): (Wherein, X is a halogen, and n is an integer of 1 to 20).
(B) at least one compound selected from the group consisting of phenols, alcohols, amines, phenols having a halogen, alcohols having a halogen and amines having a halogen, and (C) alcohols;
3. The method of producing a phosphazene composition according to claim 2, wherein the reaction is carried out in the presence of an alkali. 5. A flame retardant comprising the phosphazene composition according to claim 1 as an active ingredient. 6. A resin composition comprising the phosphazene composition according to claim 1 or 2. 7. A molded article comprising the resin composition according to claim 6.