JP2896808B2 - Flame retardant oil - Google Patents
Flame retardant oilInfo
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- JP2896808B2 JP2896808B2 JP2325318A JP32531890A JP2896808B2 JP 2896808 B2 JP2896808 B2 JP 2896808B2 JP 2325318 A JP2325318 A JP 2325318A JP 32531890 A JP32531890 A JP 32531890A JP 2896808 B2 JP2896808 B2 JP 2896808B2
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Description
【発明の詳細な説明】 ［産業上の利用分野］ 本発明は、蒸気圧が低く高い誘電率を有し化学的に安
定した特性を有する難燃性に優れたホスファゼンオイル
に関するもので、コンデンサ−オイル、電圧器用オイ
ル、ケーブルオイル、電気粘性流体用オイルなどの電気
絶縁油、潤滑オイル、ブレーキオイル、ポンプオイルな
どの動力伝達油、真空オイル、離型剤、各種熱媒及び樹
脂添加剤などに用いられる。Description: BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a phosphazene oil having a low vapor pressure, a high dielectric constant, chemically stable properties, and excellent flame retardancy. For electric insulating oil such as oil, voltage unit oil, cable oil, oil for electrorheological fluid, power transmission oil such as lubricating oil, brake oil, pump oil, vacuum oil, mold release agent, various heat transfer media and resin additives Used.
［従来の技術］ 従来より高温耐久性や難燃性が要求される電気絶縁
油、動力伝達用油及び熱媒などの用途には、主鎖がSi−
Ｏ結合で構成される通称シリコーンオイルが多く使われ
ているが、近年これらの分野では、シリコーンオイルよ
りもさらに高性能なオイルへの要求が高まっている。例
えば、難燃オイルでは不十分で不燃性が求められる分
野、一層低い蒸気圧の要求される分野、あるいはさらに
高い誘電率が要求される電気絶縁オイルの分野など、従
来のシリコーンオイルでは達成不可能な性能が要求され
る用途が広がりつつある。[Prior art] For applications such as electric insulating oils, power transmission oils, and heat transfer media that require high-temperature durability and flame retardancy, the main chain is Si-
Although a so-called silicone oil composed of an O bond is often used, in these fields, a demand for an oil having higher performance than a silicone oil has recently been increasing. For example, conventional silicone oils cannot be achieved in areas where flame-retardant oils are inadequate and require noncombustibility, fields where lower vapor pressures are required, or fields where electrical insulating oils are required where dielectric constant is higher. Applications requiring high performance are expanding.
このような問題を解決するために、主成分がＰ＝Ｎ結
合で構成される環状化合物でありＰ原子上の置換基がフ
ルオロアルコキシ基であるホスファゼンオイルに関する
発明が開示された（特開昭62−265394）。この発明のオ
イルは難燃性であり、蒸気圧も低く高誘電率であるなど
従来のシリコーンオイルにはない特徴を有しており有望
なオイルである反面、高温で転移反応を起こし易く耐熱
性が劣り、さらに加水分解性があり長期耐久性が十分で
ないという欠点があるため、その用途は限られ、上記の
問題が解決されたとは言い難い現状である。In order to solve such a problem, there has been disclosed an invention relating to a phosphazene oil in which a main component is a cyclic compound composed of a P = N bond and a substituent on a P atom is a fluoroalkoxy group (Japanese Patent Application Laid-open No. Sho 62). −265394). The oil of the present invention is a promising oil that has characteristics that are not present in conventional silicone oils, such as flame retardancy, low vapor pressure, and high dielectric constant. However, its use is limited, and it is difficult to say that the above problem has been solved.
［発明が解決しようとする課題］ 本発明は、上記ホスファゼンオイルの特徴である難燃
性、低揮発性、高誘電率を保持し、しかも従来のホスフ
ァゼンオイルの欠点である耐熱性及び長期耐久性に優れ
たオイルを与える。すなわち従来のホスファゼンオイル
に比べて転移反応の生じる温度が高く、加水分解性の著
しく改良されたＰ＝Ｎ結合単位で構成された環状化合物
（以下ホスフォニトリル環化合物という）の混合体から
なる難燃性油を提供するものである。[Problems to be Solved by the Invention] The present invention maintains the flame retardancy, low volatility, and high dielectric constant, which are the characteristics of the phosphazene oil, and also has the heat resistance and long-term durability, which are the drawbacks of the conventional phosphazene oil. Give excellent oils. That is, the temperature at which the transfer reaction occurs is higher than that of conventional phosphazene oil, and the mixture is difficult to be formed of a mixture of a cyclic compound (hereinafter, referred to as a phosphonitrile ring compound) composed of P = N bond units, which has significantly improved hydrolyzability. It provides a flammable oil.
［課題を解決するための手段］ ホスファゼン誘導体の優れた難燃性に着目し耐久性に
優れたオイルを合成する研究は種々なされており、特に
ホスフォニトリル環化合物の研究が活発に行われ多くの
知見が得られてきた。すなわちホスフォニトリル環骨格
を有する化合物で、室温において流動性を示すオイルと
しては、脂肪族アルコキシ基を側鎖基とするものが知ら
れていたが、これらの化合物は一般的に高温で転移反応
が起こり易く耐加水分解性が劣ることが知られている。
一方フェノキシ基などの芳香族アルコキシ基を有するホ
スフォニトリル環化合物は、公知のように高温での安定
性や耐加水分解性は優れているものの、一般に融点が高
く室温では固体であるか又は流動性を示さないため、目
的とするオイルが得られない。[Means for Solving the Problems] There have been various studies on synthesizing oils having excellent durability by focusing on the excellent flame retardancy of phosphazene derivatives. In particular, research on phosphonitrile ring compounds has been actively conducted, and many studies have been conducted. Knowledge has been obtained. That is, as a compound having a phosphonitrile ring skeleton and having fluidity at room temperature, oils having an aliphatic alkoxy group as a side chain group have been known, but these compounds are generally subjected to a transfer reaction at a high temperature. It is known that hydrolysis easily occurs and hydrolysis resistance is inferior.
On the other hand, a phosphonitrile ring compound having an aromatic alkoxy group such as a phenoxy group is generally known to have high stability at high temperatures and excellent hydrolysis resistance, but generally has a high melting point and is solid or fluid at room temperature. The desired oil cannot be obtained due to lack of properties.
ただＰ＝Ｎ結合単位の数ｎ＝７（７量体）のみのホス
フォニトリル環化合物の物性に関しては液状であること
が知られている（Chem.Ind.,p1032［1965］）が、ホス
フォニトリル環化合物においては、７量体だけを選択的
に合成すること、あるいは７量体の精密な分離精製が著
しく、研究は余り進んでいない。又このような大員化合
物を選択的に得ることは経済的に効率が悪いので、あま
り関心を持たれていない。However, it is known that the physical property of a phosphonitrile ring compound having only n = 7 (heptamer) of P = N bond units is liquid (Chem. Ind., P1032 [1965]). In phonitrile ring compounds, the selective synthesis of only the heptamer, or the precise separation and purification of the heptamer has been remarkable, and the research has not progressed much. Also, selective access to such large compounds has been of little interest because it is economically inefficient.
発明者らはこの芳香族系側鎖基を有する化合物の優れ
た耐熱性及び耐水性に着目し、これらの化合物の優れた
特性を保持し、かつ効率よく流動点もしくは融点の低い
混合体（オイル）を得る方法について鋭意検討の結果本
発明を完成するに至った。すなわち、 分子構造が で表されるホスフォニトリル環化合物の混合体であっ
て、その化合物のＰ原子上の側鎖基のR1及びR2は芳香族
化合物誘導体であり、さらに該化合物のＰ＝Ｎ結合単位
の数ｎが３である化合物の含量が混合体中のモル分率で
１〜90％で、かつｎが７である化合物の含量が混合体中
のモル分率で１％以上である混合体によって、難燃性が
あり、揮発性が低く、かつ高誘電率で、しかも耐熱性に
優れ、さらに加水分解性の著しく改良された難燃性油が
得られることを知見した。The present inventors have focused on the excellent heat resistance and water resistance of the compound having an aromatic side group, and have efficiently maintained the excellent properties of these compounds and efficiently mixed them with a low pour point or a low melting point (oil). The present invention has been completed as a result of intensive studies on the method for obtaining (3). That is, the molecular structure Wherein R 1 and R 2 of the side chain groups on the P atom of the compound are aromatic compound derivatives, and the P = N bond unit of the compound is A mixture wherein the content of the compound wherein the number n is 3 is from 1 to 90% by mole fraction in the mixture and the content of the compound by which the number n is 7 is 1% or more by mole in the mixture; It has been found that a flame-retardant oil having flame retardancy, low volatility, high dielectric constant, excellent heat resistance and markedly improved hydrolyzability can be obtained.
本発明におけるホスフォニトリル環化合物のＰ原子上
の側鎖基は芳香族化合物誘導体である。The side chain group on the P atom of the phosphonitrile ring compound in the present invention is an aromatic compound derivative.
芳香族側鎖基とは、一般に芳香族環を有する化合物か
ら誘導される基であり、 などの芳香族環に官能基として水酸基を有する化合物か
ら誘導される基、あるいは、 などの芳香族環に官能基としてアミノ基を有する化合物
から誘導される基、あるいは、 などの芳香族環に官能基としてメルカプト基を有する化
合物から誘導される基などである。ホスフォニトリル環
の側鎖基の組み合わせとしては、必ずしも単一の基で構
成されていなくても良く、これらの中から複数選ばれた
組み合わせでも良い。耐熱性、耐加水分解性などを考慮
すると、アルコキシ基を有する化合物から誘導される基
から選ばれるのが好ましい。An aromatic side group is a group generally derived from a compound having an aromatic ring, A group derived from a compound having a hydroxyl group as a functional group on an aromatic ring, or A group derived from a compound having an amino group as a functional group in an aromatic ring, or And a group derived from a compound having a mercapto group as a functional group on an aromatic ring. The combination of the side chain groups of the phosphonitrile ring may not necessarily be composed of a single group, but may be a combination selected from a plurality of these groups. In consideration of heat resistance, hydrolysis resistance, and the like, it is preferable to select from groups derived from compounds having an alkoxy group.
本発明の難燃性油は上記環化合物のＰ＝Ｎ結合単位の
数ｎが３（３量体）から15（15量体）の化合物の混合体
であって、ｎが３である化合物の含量が混合体中のモル
分率で１〜90％、好ましくは１〜85％であり、かつｎが
７である化合物の含量が混合体中のモル分率で１％以
上、好ましくは５％以上であるものが用いられる。なお
ｎが３である化合物の含量がモル分率で90％を越える
か、もしくはｎが７である化合物の含量がモル分率で１
％未満の場合は、室温でオイル状とならないことがあり
好ましくない。The flame-retardant oil of the present invention is a mixture of compounds in which the number n of P = N bond units of the above-mentioned ring compound is 3 (trimer) to 15 (15-mer). The content of the compound is 1 to 90%, preferably 1 to 85% by mole fraction in the mixture, and the content of the compound in which n is 7 is 1% or more, preferably 5% by mole fraction in the mixture. The above is used. The content of the compound in which n is 3 exceeds 90% by mole fraction, or the content of the compound in which n is 7 is 1% by mole fraction.
% Is not preferable because it may not become oily at room temperature.
本発明の難燃性油の合成法において、該ホスフォニト
リル環化合物のＰ原子上の芳香族化合物誘導体がフェノ
キシ基、アルキル−フェノキシ基などである場合の混合
体の合成法を例示すれば、ハロゲン原子を含む３量体、
４量体、ｎ量体の化合物を、たとえばC6H5ONa、CH3C6H4
CNaのような求核試薬で置換して得ることができる。In the method for synthesizing the flame-retardant oil of the present invention, if the aromatic compound derivative on the P atom of the phosphonitrile ring compound is a phenoxy group, an alkyl-phenoxy group, etc. A trimer containing a halogen atom,
The tetramer or n-mer compound is converted to, for example, C 6 H 5 ONa, CH 3 C 6 H 4
It can be obtained by substitution with a nucleophile such as CNa.
すなわち、（PNF2）３、（PNF2）４、（PNF2）ｎ［ｎ
≦15］等の側鎖基がＦ原子の３量体、４量体、ｎ量体の
化合物、（PNCl2）３、（PNCl2）４、（PNCl2）ｎ［ｎ
≦15］等の側鎖基がCl原子の３量体、４量体、ｎ量体の
化合物、（PNBr2）３、（PNBr2）４、（PNBr2）ｎ［ｎ
≦15］等の側鎖基がBr原子の３量体、４量体、ｎ量体の
化合物、（PNI2）３、（PNI2）４、（PNI2）ｎ［ｎ≦1
5］の側鎖基がＩ原子の３量体、４量体、ｎ量体の環化
合物のハロゲン原子とC6H5ONa、CH3C6H4ONa、（C6H5O）
2Caのような芳香族有機化合物の金属塩との反応、C6H5O
Hのような水酸基を有する芳香族化合物もしくはC6H5NH2
のような芳香族アミンなどの、Ｐ原子上のハロゲン原子
と求核置換し得る芳香族化合物と、アニリンなどのアミ
ン類、水酸化ナトリウム、炭酸ナトリウムなどの塩素受
容体化合物との混合による方法を挙げることができる。That is, (PNF 2 ) 3 , (PNF 2 ) 4 , (PNF 2 ) n [n
≦ 15] and other compounds in which the side chain group is a trimer, tetramer or n-mer of an F atom, (PNCl 2 ) 3 , (PNCl 2 ) 4 , (PNCl 2 ) n [n
≦ 15] and other compounds in which the side chain group is a trimer, tetramer or n-mer of Cl atom, (PNBr 2 ) 3 , (PNBr 2 ) 4 , (PNBr 2 ) n [n
≦ 15] and other compounds in which the side chain group is a trimer, tetramer, or n-mer of a Br atom, (PNI 2 ) 3 , (PNI 2 ) 4 , (PNI 2 ) n [n ≦ 1
5] wherein the side chain group is a trimer, tetramer, or n-mer ring compound having an I atom, a halogen atom and C 6 H 5 ONa, CH 3 C 6 H 4 ONa, or (C 6 H 5 O)
Reaction of the metal salt of an aromatic organic compound such as 2 Ca, C 6 H 5 O
An aromatic compound having a hydroxyl group such as H or C 6 H 5 NH 2
By mixing an aromatic compound such as an aromatic amine capable of undergoing nucleophilic substitution with a halogen atom on a P atom and an amine such as aniline and a chlorine acceptor compound such as sodium hydroxide and sodium carbonate. Can be mentioned.
本発明におけるホスフォニトリル環化合物は一般にこ
のようにして合成されるが、置換反応を主体とする合成
方法には特に限定しない。また環状骨格中のｎの数が３
であるホスフォニトリル環化合物を混合体中のモル分率
で１〜90％、かつまた環状骨格中のｎの数が７であるホ
スフォニトリル環化合物を混合体中のモル分率で１％以
上含んでいる混合体の調製方法に関しては、置換反応を
行う前の原料であるハロゲン化ホスフォニトリル環化合
物における３量体及び７量体の含量を目的とする混合体
に合わせた後置換反応を行い油状物質を得る方法、ある
いは置換反応を行った後２種以上の環化合物を配合し油
状物質を得る方法などが考えられるが、本発明は、いず
れの方法でもその目的が達成される。ハロゲン化ホスフ
ォニトリル環化合物の合成において、単一の環状化合物
を合成する方法は一般に難しく経済的ではないことを考
えると、好ましくは置換反応前の混合比は油状物質に近
い方法が選択される。The phosphonitrile ring compound in the present invention is generally synthesized in this way, but is not particularly limited to a synthesis method mainly based on a substitution reaction. The number of n in the cyclic skeleton is 3
1 to 90% by mole fraction of the mixture in the mixture and 1% by mole of the phosphonitrile ring compound in which n in the cyclic skeleton is 7 in the mixture. Regarding the method for preparing the mixture containing the above, the substitution reaction after adjusting the trimer and heptamer content in the halogenated phosphonitrile ring compound, which is the raw material before the substitution reaction, to the desired mixture is carried out. To obtain an oily substance, or a method of blending two or more ring compounds after performing a substitution reaction to obtain an oily substance, and the present invention achieves the object by any of the methods. In the synthesis of halogenated phosphonitrile ring compounds, considering that the method of synthesizing a single cyclic compound is generally difficult and not economical, a method in which the mixing ratio before the substitution reaction is close to an oily substance is preferably selected. .
次に参考例、実施例、比較例を用いて説明するが、本
発明は実施例に限定されるものではない。Next, reference examples, examples and comparative examples will be described, but the present invention is not limited to the examples.
［参考例］ （クロロホスフォニトリル環化合物の合成方法） 斎藤肇、梶原鳴雪：工業化学雑誌66,618（1963）に準
拠して、PCl5をテトラクロロエタンに溶解した溶液中に
大過剰のNH4Clを添加し130℃以上に加熱した。反応終了
後反応液を濾過し、未反応のNH4Clを分離した。濾液を
蒸留した後、残部を石油エーテルで処理し、ホスフォニ
トリル環化合物の混合体を得た。Reference Example (Synthesis Method of Chlorophosphonitrile Ring Compound) Hajime Saito, Naruki Kajiwara: According to Industrial Chemistry Magazine 66,618 (1963), a large excess of NH 4 Cl was dissolved in a solution of PCl 5 in tetrachloroethane. Was added and heated to 130 ° C. or higher. After completion of the reaction, the reaction solution was filtered to separate unreacted NH 4 Cl. After distilling the filtrate, the remainder was treated with petroleum ether to obtain a mixture of phosphonitrile ring compounds.
［実施例１］ フェノール24gをTHF（テトラヒドロフラン）に溶解
し、これに金属Na5.8gを加えナトリウムフェノキシドを
合成した。この溶液に前記参考例で得たクロロホスフォ
ニトリル環化合物10gを含むTHF溶液をゆっくり滴下し
た。滴下終了後THFの沸点付近の温度に加温し、１時間
還流した。反応終了後THFを留去し、エーテルと希水酸
化ナトリウム水溶液を用いて洗浄した。洗浄後エーテル
抽出を行いホスフォニトリル環混合体を含むエーテル溶
液を塩化カルシウムで乾燥した。１昼夜乾燥後エーテル
を除去すると難燃性油が得られた。[Example 1] 24 g of phenol was dissolved in THF (tetrahydrofuran), and 5.8 g of metal Na was added thereto to synthesize sodium phenoxide. A THF solution containing 10 g of the chlorophosphonitrile ring compound obtained in the above Reference Example was slowly dropped into this solution. After completion of the dropwise addition, the mixture was heated to a temperature near the boiling point of THF and refluxed for 1 hour. After completion of the reaction, THF was distilled off, and the mixture was washed with ether and a dilute aqueous sodium hydroxide solution. After washing, ether extraction was performed, and the ether solution containing the phosphonitrile ring mixture was dried with calcium chloride. After drying all day and night, the ether was removed to obtain a flame-retardant oil.
得られた難燃性油の成分は下記に示すようなホスフォ
ニトリル環化合物の混合体であり、第１表に示すよう
に、室温で液状に優れた電気絶縁性、高い誘電率を示し
た。The components of the obtained flame-retardant oil were a mixture of a phosphonitrile ring compound as shown below, and as shown in Table 1, exhibited excellent electrical insulation properties and a high dielectric constant in a liquid state at room temperature. .
［（C6H5O）2PN］３ 45％ ［（C6H5O）2PN］６ 1％ ［（C6H5O）2PN］４ 15％ ［（C6H5O）2PN］７ 25％ ［（C6H5O）2PN］５ 12％ ８量体以上 2％ 第１図は実施例１のオイルと比較例２のオイルの耐熱
性をTGA（熱重量分析）により測定した結果を示したも
ので、横軸は温度（℃）、縦軸は重量減少率を示し、線
Ａは実施例１のデータ、線Ｂは比較例２のデータであ
る。実施例１のオイルの重量減少開始温度は175℃で、
比較例２のオイルの120℃に比し極めて優れた耐熱性を
有することがわかった。 [(C 6 H 5 O) 2 PN] 3 45% [(C 6 H 5 O) 2 PN] 6 1% [(C 6 H 5 O) 2 PN] 4 15% [(C 6 H 5 O) 2 PN] 7 25% [( C 6 H 5 O) 2 PN] 5 12% 8 -mers or more 2% Figure 1 is a heat resistance of the oil Comparative example 2 with the oil of example 1 TGA (thermogravimetric analysis ), The horizontal axis represents the temperature (° C.), the vertical axis represents the weight loss rate, line A is the data of Example 1, and line B is the data of Comparative Example 2. The temperature at which the weight of the oil of Example 1 starts to decrease is 175 ° C.
It was found that the oil of Comparative Example 2 had extremely excellent heat resistance compared to 120 ° C.
［比較例１］ 参考例により得られたホスフォニトリル環化合物を真
空蒸留を行い精製した。蒸留条件は120℃/100mmHgであ
った。蒸留精製して得られた化合物をガスクロマトグラ
フィーにより分析したところ、３量体が95％以上含まれ
ていた。またＰ−NMRにより５量体以上の化合物は含ま
れていないことが確認された。この化合物を実施例１と
同様の反応により塩素をフェノキシ基で置換した。得ら
れた化合物は第１表に示すように室温で固体であった。 Comparative Example 1 The phosphonitrile ring compound obtained in Reference Example was purified by vacuum distillation. The distillation conditions were 120 ° C / 100mmHg. Analysis of the compound obtained by distillation and purification by gas chromatography revealed that the trimer was contained in an amount of 95% or more. In addition, it was confirmed by P-NMR that a compound of pentamer or more was not contained. In this compound, chlorine was substituted with a phenoxy group by the same reaction as in Example 1. The obtained compound was a solid at room temperature as shown in Table 1.
［比較例２］ 脂肪族側鎖基のみを有するホスフォニトリル環化合物
として大塚化学（株）製ホスファロールNF46（［Ｈ（CF
2CF2）2CH2O］３（CF3CF2CH2O）３）（PN）３を用い
た。[Comparative Example 2] Phospharol NF46 ([H (CF)) manufactured by Otsuka Chemical Co., Ltd. as a phosphonitrile ring compound having only an aliphatic side chain group.
2 CF 2 ) 2 CH 2 O] 3 (CF 3 CF 2 CH 2 O) 3 ) (PN) 3 was used.
この化合物は第１表及び第１図に示すように、耐熱性
の極めて良くないものである。As shown in Table 1 and FIG. 1, this compound has extremely poor heat resistance.
［発明の効果］ 本発明の難燃性油は従来知られていたホスファゼンオ
イルの欠点であった耐熱性及び耐加水分解性を大幅に改
良したもので、しかもホスファゼンオイルの特徴である
優れた難燃性、極めて低い蒸気圧、優れた電気絶縁性、
高い誘電率、ゴムや樹脂などとの低い相互作用、潤滑性
などの特性を有しており、しかも低毒性であるため、変
圧器用、コンデンサー用、ケーブル用及び電気粘性流体
用などの電気絶縁オイル、潤滑オイル、ブレーキオイル
及びポンプオイルなどの動力伝達オイル、真空オイル、
離型剤、各種熱媒あるいは樹脂などの難燃性改良用の添
加剤などに広くしかも好適に応用される。[Effects of the Invention] The flame-retardant oil of the present invention is a material which has greatly improved the heat resistance and hydrolysis resistance, which were the drawbacks of the conventionally known phosphazene oil, and the excellent flame retardancy characteristic of the phosphazene oil. Flammability, extremely low vapor pressure, excellent electrical insulation,
It has properties such as high dielectric constant, low interaction with rubber and resin, lubricity, and low toxicity, so it is an electrically insulating oil for transformers, capacitors, cables, and electrorheological fluids. , Lubrication oil, power transmission oil such as brake oil and pump oil, vacuum oil,
It is widely and suitably applied to a release agent, various heat transfer media or additives for improving flame retardancy such as resin.
第１図は実施例１のオイルと比較例２のオイルの耐熱性
をTGA（熱重量分析）により測定した結果を示したもの
で、横軸は温度（℃）、縦軸は重量減少率を示し、線Ａ
は実施例１のデータ、線Ｂは比較例２のデータである。FIG. 1 shows the results of measuring the heat resistance of the oil of Example 1 and the oil of Comparative Example 2 by TGA (thermogravimetric analysis). The horizontal axis represents temperature (° C.), and the vertical axis represents the weight loss rate. Show, line A
Represents data of Example 1, and line B represents data of Comparative Example 2.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 ＦＩ Ｃ１０Ｎ 40:06 40:08 40:16 40:36 (58)調査した分野(Int.Cl.6，ＤＢ名) C10M 105/74 C10M 137/12 H01B 3/20 C09K 21/12 C10N 30:00 C10N 30:08 C10N 40:06 C10N 40:08 C10N 40:16 C10N 40:36 ──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. 6 identification code FI C10N 40:06 40:08 40:16 40:36 (58) Investigated field (Int.Cl. 6 , DB name) C10M 105 / 74 C10M 137/12 H01B 3/20 C09K 21/12 C10N 30:00 C10N 30:08 C10N 40:06 C10N 40:08 C10N 40:16 C10N 40:36
Claims (1)
て、その化合物のＰ原子上の側鎖基のR1及びR2は芳香族
化合物誘導体であり、さらに該化合物のＰ＝Ｎ結合単位
の数ｎが３である化合物の含量が混合体中のモル分率で
１〜90％で、かつｎが７である化合物の含量が混合体中
のモル分率で１％以上であることを特徴とする難燃性
油。1. The molecular structure is Wherein R 1 and R 2 of the side chain groups on the P atom of the compound are aromatic compound derivatives, and the P = N bond unit of the compound is The content of the compound having the number n of 3 is 1 to 90% by mole fraction in the mixture, and the content of the compound having the number n is 7 by mole or more in the mixture is 1% or more. And flame-retardant oils.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2325318A JP2896808B2 (en) | 1990-11-29 | 1990-11-29 | Flame retardant oil |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2325318A JP2896808B2 (en) | 1990-11-29 | 1990-11-29 | Flame retardant oil |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04198189A JPH04198189A (en) | 1992-07-17 |
| JP2896808B2 true JP2896808B2 (en) | 1999-05-31 |
Family
ID=18175485
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2325318A Expired - Fee Related JP2896808B2 (en) | 1990-11-29 | 1990-11-29 | Flame retardant oil |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2896808B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1308418C (en) * | 2002-09-13 | 2007-04-04 | 旭化成化学株式会社 | Phosphazene composition |
| WO2009055993A1 (en) * | 2007-11-02 | 2009-05-07 | Dow Global Technologies Inc. | Substituted phosphazene compounds and their use as flame resistance additives for organic polymers |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7060744B2 (en) | 2002-09-13 | 2006-06-13 | Asahi Kasei Chemicals Corporation | Phosphazene composition |
| DE102008038939B3 (en) | 2008-08-13 | 2010-04-15 | Kraussmaffei Berstorff Gmbh | extruding |
-
1990
- 1990-11-29 JP JP2325318A patent/JP2896808B2/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1308418C (en) * | 2002-09-13 | 2007-04-04 | 旭化成化学株式会社 | Phosphazene composition |
| WO2009055993A1 (en) * | 2007-11-02 | 2009-05-07 | Dow Global Technologies Inc. | Substituted phosphazene compounds and their use as flame resistance additives for organic polymers |
| CN101842379A (en) * | 2007-11-02 | 2010-09-22 | 陶氏环球技术公司 | Substituted phosphazene compounds and their use as flame resistance additives for organic polymers |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH04198189A (en) | 1992-07-17 |
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