JPS6216972B2 - - Google Patents
Info
- Publication number
- JPS6216972B2 JPS6216972B2 JP13009179A JP13009179A JPS6216972B2 JP S6216972 B2 JPS6216972 B2 JP S6216972B2 JP 13009179 A JP13009179 A JP 13009179A JP 13009179 A JP13009179 A JP 13009179A JP S6216972 B2 JPS6216972 B2 JP S6216972B2
- Authority
- JP
- Japan
- Prior art keywords
- phosphine oxide
- parts
- weight
- composition
- amount
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000203 mixture Substances 0.000 claims description 29
- 229920000642 polymer Polymers 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000004793 Polystyrene Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- -1 flame retardant compound Chemical class 0.000 claims description 8
- 238000009472 formulation Methods 0.000 claims description 8
- 229920001955 polyphenylene ether Polymers 0.000 claims description 8
- 229920002223 polystyrene Polymers 0.000 claims description 8
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 239000003063 flame retardant Substances 0.000 claims description 6
- 239000011347 resin Substances 0.000 claims description 4
- 229920005989 resin Polymers 0.000 claims description 4
- PDFFEDMPZWGYSJ-UHFFFAOYSA-N 3-[2-cyanoethyl-[(2,4,6-trimethylphenyl)methyl]phosphoryl]propanenitrile Chemical compound CC1=CC(C)=C(CP(=O)(CCC#N)CCC#N)C(C)=C1 PDFFEDMPZWGYSJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000007983 Tris buffer Substances 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
- 125000006177 alkyl benzyl group Chemical group 0.000 claims description 2
- 125000006184 2,5-dimethyl benzyl group Chemical group [H]C1=C(C([H])=C(C(=C1[H])C([H])([H])[H])C([H])([H])*)C([H])([H])[H] 0.000 claims 1
- 229920002959 polymer blend Polymers 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 239000011342 resin composition Substances 0.000 description 4
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 3
- ZKWABBRIUSNHJG-UHFFFAOYSA-N 3-[benzyl(2-cyanoethyl)phosphoryl]propanenitrile Chemical compound N#CCCP(=O)(CCC#N)CC1=CC=CC=C1 ZKWABBRIUSNHJG-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 3
- 229940073608 benzyl chloride Drugs 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- UNRGEIXQCZHICP-UHFFFAOYSA-N 2-(chloromethyl)-1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=C(CCl)C(C)=C1 UNRGEIXQCZHICP-UHFFFAOYSA-N 0.000 description 2
- ILFYYSUCZQEGOL-UHFFFAOYSA-N 3-[bis(2-cyanoethyl)phosphoryl]propanenitrile Chemical compound N#CCCP(=O)(CCC#N)CCC#N ILFYYSUCZQEGOL-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- DSIQDXZNQNRKSD-UHFFFAOYSA-N bis(2-cyanoethyl)-oxophosphanium Chemical compound N#CCC[P+](=O)CCC#N DSIQDXZNQNRKSD-UHFFFAOYSA-N 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 229920006380 polyphenylene oxide Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- ISNICOKBNZOJQG-UHFFFAOYSA-N 1,1,2,3,3-pentamethylguanidine Chemical compound CN=C(N(C)C)N(C)C ISNICOKBNZOJQG-UHFFFAOYSA-N 0.000 description 1
- GIIKDPPVXLAAQJ-UHFFFAOYSA-N 3-(2-cyanoethylphosphonoyl)propanenitrile Chemical compound N#CCCP(=O)CCC#N GIIKDPPVXLAAQJ-UHFFFAOYSA-N 0.000 description 1
- ADBGRWDTLVXTIB-UHFFFAOYSA-N C(#N)CC[PH2]=O Chemical compound C(#N)CC[PH2]=O ADBGRWDTLVXTIB-UHFFFAOYSA-N 0.000 description 1
- 235000009781 Myrtillocactus geometrizans Nutrition 0.000 description 1
- 240000009125 Myrtillocactus geometrizans Species 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 229920005669 high impact polystyrene Polymers 0.000 description 1
- 239000004797 high-impact polystyrene Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 150000003004 phosphinoxides Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L25/00—Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
- C08L25/02—Homopolymers or copolymers of hydrocarbons
- C08L25/04—Homopolymers or copolymers of styrene
- C08L25/06—Polystyrene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5397—Phosphine oxides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
- C08G2261/312—Non-condensed aromatic systems, e.g. benzene
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
本発明はフオスフインオキサイドを遅燃性を与
えるのに有効な量含む耐焔性ポリフエニレンエー
テル樹脂組成物に関する。特に本発明は式
但し式中Ｒは炭素数約１〜12のアルキル；アル
キル部分の炭素数が約１〜８のヒドロキシアルキ
ル；ベンジル；ベンジル環が炭素数約１〜４のア
ルキル基を少くとも２個含むアルキルベンジル、
及びアルキル部分の炭素数約１〜４のω―シアノ
アルキルである、
の化合物を含む耐焔性熱可塑性樹脂組成物に関す
る。上記式の特に好適な化合物は(1)トリス（２―
シアノエチル）フオスフインオキサイド、(2)ベン
ジルビス（２―シアノエチル）フオスフインオキ
サイド、及び(3)２，４，６―トリメチルベンジル
ビス（２―シアノエチル）フオスフインオキサイ
ドである。
トリス（２―シアノエチル）フオスフインオキ
サイドは公知化合物であつて、ローハツト
（Ranhat）らのジヤーナル・オヴ・ザ・アメリカ
ン・ケミカル・ソサイアテイ（J.Am.Chem.Soc.
）誌81巻1106頁（1959年）の論文に記載されてい
る。このものは米国特許第3341625号記載のよう
にポリプロピレンを含む熱可塑性ビニル重合体の
耐焔剤として用いられた来た。ベンジルビス（２
―シアノエチルフオスフイン）オキサイド及び
２，４，６―トリメチルベンジルビス（２―シア
ノエチル）フオスフインオキサイドは塩化ベンジ
ル又は２，４，６―トリメチルベンジルクロライ
ドをビス（２―シアノエチル）フオスフインオキ
サイドと反応させることによりつくることができ
る。Ｒがアルキル又はヒドロキシアルキルの化合
物も同様につくることができる。
耐焔性のあるゴム変性ポリプロピレンエーテル
樹脂組成物は上記式の化合物の耐焔剤として効果
のある量を混入することによつてつくられる。
本発明に用いるのに適したポリフエニレンエー
テル樹脂組成物は米国特許第4024093号に記載さ
れている。好ましくはこの重合体は約50〜80重量
部のポリフエニレンエーテル樹脂と約20〜50重量
部のスチレン重合体を含んでいる。スチレン重合
体はゴムで変性した高衝撃耐性をもつポリスチレ
ンである。この樹脂は互いに可溶性で均一の重合
体組成物をつくる２種の重合体の配合物である。
耐焔剤化合物は下記に定義するような自己消火
性組成物を与えるのに十分な量で用いられる。し
かし一般には、この量は樹脂組成物に関し少くと
も約４、好ましくは少くとも約６、最も好ましく
は約８〜10重量％である。
また可塑剤、染料、顔料、熱及び光安定剤、酸
化防止剤、帯電防止剤、光着色剤等の他の成分を
混入することも本発明の範囲内に入る。
実施例 １
ベンジルビス（２―シアノエチル）フオスフイ
ンオキサイドの製造は次のようにして行なわれ
る。
500mlのジメチルフオルムアミドにビス（シア
ノエチル）フオスフインオキサイド78g（0.5モ
ル）を加える。200mlのメタノール中に水酸化カ
リウム33g（0.5モル）を含む溶液を加える。この
溶液に63g（0.5モル）の塩化ベンジルを滴下す
る。この混合物を２時間加熱還流させ、メタノー
ルを溜出させる。30分間還流を続け、冷却する。
塩化カリウムを別し、廻転蒸発器を用いてジメ
チルフオルムアミドを蒸発させて除去する。残渣
を沸騰トルエンで３回抽出する。トルエン抽出液
を一緒にして冷却し、融点118〜120℃の白色結晶
50gを得た。
実施例 ２
実施例１の方法を繰返したが、塩化ベンジルの
代りに２，４，６―トリメチルベンジルクロライ
ドを用い、対応する化合物をつくつた。
実施例 ３
１，１―ジメチルヒドロキシメチルビス（２―
シアノエチル）フオスフインオキサイドの製造
〔ジヤーナル・オヴ・オーガニツク・ケミストリ
ー（J.Org.Chem.）誌25巻4628〜4632頁、（1961
年）〕。
0.1モルのビス（２―シアノエチル）フオスフ
インオキサイドと0.1モルのアセトンとの混合物
に、1.0gのトリエチルアミンか又はペンタメチル
グアニジンを加える。この混合物を２時間水蒸気
浴の温度に加熱する。得られた固体を別し、ア
セトンから再結晶して、融点124〜125℃の生成物
を88％の収率で得た。
実施例 ４
50部のポリフエニレンエーテル／50部のゴム変
性衝撃耐性ポリスチレンの配合物に、第１表記載
の試料を10gつくるのに十分な量のトリス（２―
シアノエチル）フオスフインオキサイド
（TCEPO）を加える。これを乾式配合し、290〜
300℃で熔融係数測定器（ASTM Ｄ―1238記
載）を通して押出す。長さ３〜５インチ、直径
0.25インチの円筒形の押出物をアンダーライタ
ー・ラボラトリーズ（Under writer
Laboratories）耐焔試験UL―94、垂直試験法
3.10―3.15（1973年９月）記載の耐焔性試験に付
した。垂直位置に固定した重合体の試料を3/4イ
ンチの青色焔（メタン又は天然ガス）で10秒間燃
焼させ、焔を取除く。24秒以内で焔が消火した場
合には、試料をさらに10秒間燃焼させ、再び焔を
遠去ける。焔の消火時間を再び記録する。焔の消
火時間が、二回とも焔を近付けた時にも５秒を超
えない時には、試料の評価値はＶ―０とする。第
一回目又は第二回目に焔を近付けた時のいずれか
の消火時間が５〜25秒の時には、Ｖ―１とする。
どちらの場合にも消火時間が25秒を超えた時の試
料は自由燃焼（FB）とし、試験に不合格である
と考える。結果を第１表に示す。
第 １ 表
％TCEPO 耐焔性評価値*
なし FB；FB
６％ FB；FB
８％ Ｖ―１；Ｖ―１
＊ ２回測定結果。
実施例 ５
実施例４の方法を繰返したが70部のポリフエニ
レンオキサイドと30部のゴム変性ポリスチレンと
の配合物を用いた。UL―94試験及び酸素係数試
験の結果を第２表に示す。
The present invention relates to flame resistant polyphenylene ether resin compositions containing phosphine oxide in an amount effective to provide flame retardation. In particular, the present invention is based on the formula However, in the formula, R is alkyl having about 1 to 12 carbon atoms; hydroxyalkyl having about 1 to 8 carbon atoms in the alkyl moiety; benzyl; alkylbenzyl in which the benzyl ring contains at least two alkyl groups having about 1 to 4 carbon atoms; ,
and ω-cyanoalkyl having about 1 to 4 carbon atoms in the alkyl moiety. Particularly preferred compounds of the above formula are (1) tris(2-
(2) benzylbis(2-cyanoethyl)phosphine oxide, and (3) 2,4,6-trimethylbenzylbis(2-cyanoethyl)phosphine oxide. Tris(2-cyanoethyl)phosphine oxide is a known compound and was published by Ranhat et al. in the Journal of the American Chemical Society (J.Am.Chem.Soc.
) Journal, Volume 81, Page 1106 (1959). This product has been used as a flame retardant for thermoplastic vinyl polymers containing polypropylene as described in US Pat. No. 3,341,625. Benzyl bis(2)
-cyanoethylphosphine) oxide and 2,4,6-trimethylbenzylbis(2-cyanoethyl)phosphine oxide are prepared by reacting benzyl chloride or 2,4,6-trimethylbenzyl chloride with bis(2-cyanoethyl)phosphine oxide. It can be made by Compounds where R is alkyl or hydroxyalkyl can be similarly prepared. Flame-resistant, rubber-modified polypropylene ether resin compositions are prepared by incorporating an amount of a compound of the above formula effective as a flame-resistant agent. Polyphenylene ether resin compositions suitable for use in the present invention are described in US Pat. No. 4,024,093. Preferably, the polymer includes about 50 to 80 parts by weight polyphenylene ether resin and about 20 to 50 parts by weight styrene polymer. Styrenic polymers are high impact resistant polystyrenes modified with rubber. This resin is a blend of two polymers that are soluble in each other and create a homogeneous polymer composition. The flame retardant compound is used in an amount sufficient to provide a self-extinguishing composition as defined below. Generally, however, this amount will be at least about 4, preferably at least about 6, and most preferably about 8-10% by weight of the resin composition. It is also within the scope of this invention to incorporate other ingredients such as plasticizers, dyes, pigments, heat and light stabilizers, antioxidants, antistatic agents, photocolorants, etc. Example 1 Benzylbis(2-cyanoethyl)phosphine oxide is produced as follows. Add 78 g (0.5 mol) of bis(cyanoethyl)phosphine oxide to 500 ml of dimethyl formamide. A solution containing 33 g (0.5 mol) of potassium hydroxide in 200 ml of methanol is added. 63 g (0.5 mol) of benzyl chloride are added dropwise to this solution. The mixture is heated under reflux for 2 hours to distill off methanol. Continue refluxing for 30 minutes and cool.
Potassium chloride is separated and dimethylformamide is removed by evaporation using a rotary evaporator. The residue is extracted three times with boiling toluene. The toluene extracts were combined and cooled to form white crystals with a melting point of 118-120℃.
Got 50g. Example 2 The method of Example 1 was repeated, but using 2,4,6-trimethylbenzyl chloride instead of benzyl chloride, and the corresponding compound was prepared. Example 3 1,1-dimethylhydroxymethylbis(2-
Production of (cyanoethyl) phosphine oxide [J.Org.Chem., Vol. 25, pp. 4628-4632, (1961)
Year)〕. To a mixture of 0.1 mole bis(2-cyanoethyl)phosphine oxide and 0.1 mole acetone is added 1.0 g of triethylamine or pentamethylguanidine. The mixture is heated to steam bath temperature for 2 hours. The resulting solid was separated and recrystallized from acetone to give a product with a melting point of 124-125°C in 88% yield. Example 4 To a blend of 50 parts polyphenylene ether/50 parts rubber-modified impact-resistant polystyrene was added an amount of Tris (2-
Add cyanoethyl) phosphin oxide (TCEPO). Dry blend this, 290 ~
Extrude through a melt coefficient meter (as per ASTM D-1238) at 300°C. 3-5 inches long, diameter
The 0.25-inch cylindrical extrudates were manufactured by Underwriter Laboratories.
Laboratories) Flame resistance test UL-94, vertical test method
It was subjected to the flame resistance test described in 3.10-3.15 (September 1973). A sample of the polymer held in a vertical position is ignited with a 3/4 inch blue flame (methane or natural gas) for 10 seconds and the flame removed. If the flame is extinguished within 24 seconds, the sample is allowed to burn for an additional 10 seconds and the flame is removed again. Record the flame extinguishing time again. If the extinguishing time of the flame does not exceed 5 seconds both times when the flame is brought close, the evaluation value of the sample shall be V-0. If the extinguishing time is 5 to 25 seconds when the flame is approached for the first or second time, it is set as V-1.
In either case, if the extinguishing time exceeds 25 seconds, the sample is considered free-burning (FB) and fails the test. The results are shown in Table 1. Table 1 %TCEPO flame resistance evaluation value * None FB; FB 6% FB; FB 8% V-1; V-1 *Results of two measurements. Example 5 The method of Example 4 was repeated but using a blend of 70 parts polyphenylene oxide and 30 parts rubber modified polystyrene. The results of the UL-94 test and oxygen coefficient test are shown in Table 2.
【表】
実施例 ６
実施例５の方法を繰返したが、材料を280℃で
処理し、各試料の酸素係数のみを決定した。結果
は次の通り。
試 料 酸素係数
対 照 18.5
２％TCEPO 20.1
４％ 〃 20.7
６％ 〃 22.3
８％ 〃 22.8
10％ 〃 23.2
実施例 ７
実施例４の方法を繰返したが、トリス（２―シ
アノエチル）フオスフインオキサイドの代りにベ
ンジルビス（２―シアノエチル）フオスフインオ
キサイド（BBCEPO）を用いた。UL―94及び酸
素係数の試験結果を第３表に示す。Table: Example 6 The method of Example 5 was repeated, but the material was treated at 280°C and only the oxygen coefficient of each sample was determined. The results are as follows. Sample oxygen coefficient control 18.5 2% TCEPO 20.1 4% 〃 20.7 6% 〃 22.3 8% 〃 22.8 10% 〃 23.2 Example 7 The method of Example 4 was repeated, but with the addition of tris(2-cyanoethyl)phosphine oxide. Benzylbis(2-cyanoethyl)phosphine oxide (BBCEPO) was used instead. Table 3 shows the test results for UL-94 and oxygen coefficient.
【表】
実施例 ８
実施例４の方法により、６重量％の下記化合物
を用い自己消火性重合体、即ちＶ―０又はＶ―１
の重合体組成物を得た。
対照例
実施例４の方法に従い、20重量％のTCEPOを
含む高衝撃耐性ポリスチレンの耐焔性評価値を決
定した。UL―94試験法によれば、試料は自由燃
焼（FB）であつた。
上記実施例によれば、(1)70／30ポリフエニレン
オキサイド配合物に対しては、TCEPOは自己消
火性を与えるためには約４重量％の臨界濃度をも
ち、(2)50／50配合物に対しては耐焔剤は約６重量
％が必要であり、(3)TCPEOは高衝撃耐性ポリス
チレンに対しては20％の高濃度でも耐焔剤とはな
らないことがわかる。[Table] Example 8 A self-extinguishing polymer, namely V-0 or V-1, was prepared using 6% by weight of the following compound according to the method of Example 4.
A polymer composition was obtained. Control Example According to the method of Example 4, the flame resistance evaluation value of high impact resistant polystyrene containing 20% by weight of TCEPO was determined. According to the UL-94 test method, the sample was free burning (FB). According to the above examples, (1) for a 70/30 polyphenylene oxide formulation, TCEPO has a critical concentration of about 4% by weight to provide self-extinguishing properties; It can be seen that approximately 6% by weight of flame retardant is required for the formulation and (3) TCPEO is not a flame retardant for high impact polystyrene even at concentrations as high as 20%.
Claims (1)
脂、約90〜10重量部のポリスチレン、及び式 但し式中Ｒは炭素数約１〜12のアルキル；アル
キル部分の炭素数約１〜８のヒドロキシアルキ
ル；ベンジル；ベンジル環が炭素数約１〜４のア
ルキル基を少くとも２個含むアルキルベンジル；
及びアルキル部分の炭素数約１〜４のω―シアノ
アルキルを表わす、 の化合物を耐焔性を与えるのに有効な量含有する
均一な重合体配合物であることを特徴とする耐焔
剤組成物。 ２ 該配合物は約50〜80部のポリフエニレンエー
テル樹脂と約50〜20部のポリスチレンを含む特許
請求の範囲第１項記載の組成物。 ３ 耐焔剤化合物がトリス（２―シアノエチル）
フオスフインオキサイドである特許請求の範囲第
１項記載の組成物。 ４ 配合物は約70部のポリフエニレンエーテルと
約30部のポリスチレンを含み、フオスフインオキ
サイドは重合体配合物に関し少くとも４重量％の
量で混入されている特許請求の範囲第３項記載の
組成物。 ５ 配合物は約50部のポリフエニレンエーテルと
約50部のポリスチレンとの配合物であり、フオス
フインオキサイドは重合体配合物に関し少くとも
６重量％混入されている特許請求の範囲第３項記
載の組成物。 ６ 耐焔剤化合物が２，４，６―トリメチルベン
ジルビス（２―シアノエチル）フオスフインオキ
サイドである特許請求の範囲第１項記載の組成
物。 ７ フオスフインオキサイドは重合体配合物に関
し少くとも約６重量％の量で混入されている特許
請求の範囲第６項記載の組成物。 ８ フオスフインオキサイドは重合体配合物に関
し少くとも約６重量％の量で混入されている特許
請求の範囲第１項記載の組成物。 ９ フオスフインオキサイドは重合体配合物の量
に関し約８〜10重量％の量で混入されている特許
請求の範囲第１項記載の組成物。 １０ Ｒはベンジル；ペンタメチルベンジル；
２，５―ジメチルベンジル；ｎ―オクチル；及び
１，１―ジメチルヒドロキシメチルから撰ばれる
特許請求の範囲第１項記載の組成物。[Scope of Claims] 1. About 10 to 90 parts by weight of polyphenylene ether resin, about 90 to 10 parts by weight of polystyrene, and the formula However, in the formula, R is alkyl having about 1 to 12 carbon atoms; hydroxyalkyl having about 1 to 8 carbon atoms in the alkyl moiety; benzyl; alkylbenzyl in which the benzyl ring contains at least two alkyl groups having about 1 to 4 carbon atoms;
and omega-cyanoalkyl having about 1 to 4 carbon atoms in the alkyl moiety, in an amount effective to impart flame resistance. thing. 2. The composition of claim 1, wherein the formulation comprises about 50 to 80 parts polyphenylene ether resin and about 50 to 20 parts polystyrene. 3 The flame retardant compound is tris(2-cyanoethyl)
The composition according to claim 1, which is phosphine oxide. 4. The formulation comprises about 70 parts of polyphenylene ether and about 30 parts of polystyrene, and the phosphine oxide is incorporated in an amount of at least 4% by weight with respect to the polymer formulation. Composition of. 5. The blend is a blend of about 50 parts polyphenylene ether and about 50 parts polystyrene, and the phosphine oxide is incorporated at least 6% by weight with respect to the polymer blend. Compositions as described. 6. The composition according to claim 1, wherein the flame retardant compound is 2,4,6-trimethylbenzylbis(2-cyanoethyl)phosphine oxide. 7. The composition of claim 6, wherein the phosphine oxide is incorporated in an amount of at least about 6% by weight with respect to the polymer formulation. 8. The composition of claim 1, wherein the phosphine oxide is incorporated in an amount of at least about 6% by weight with respect to the polymer formulation. 9. The composition of claim 1, wherein the phosphine oxide is incorporated in an amount of about 8 to 10% by weight relative to the amount of polymer formulation. 10 R is benzyl; pentamethylbenzyl;
The composition of claim 1 selected from 2,5-dimethylbenzyl; n-octyl; and 1,1-dimethylhydroxymethyl.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US95120278A | 1978-10-13 | 1978-10-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5552348A JPS5552348A (en) | 1980-04-16 |
| JPS6216972B2 true JPS6216972B2 (en) | 1987-04-15 |
Family
ID=25491412
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13009179A Granted JPS5552348A (en) | 1978-10-13 | 1979-10-11 | Flame resisting composition |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS5552348A (en) |
| DE (1) | DE2941464A1 (en) |
| NL (1) | NL7907579A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3731607A1 (en) * | 1987-09-19 | 1989-03-30 | Hoechst Ag | STABILIZED MIXTURE CONTAINING AROMATIC POLYETHERKETONE AND THE USE THEREOF FOR THE PRODUCTION OF MOLDED PARTS |
-
1979
- 1979-10-11 JP JP13009179A patent/JPS5552348A/en active Granted
- 1979-10-12 NL NL7907579A patent/NL7907579A/en not_active Application Discontinuation
- 1979-10-12 DE DE19792941464 patent/DE2941464A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| NL7907579A (en) | 1980-04-15 |
| DE2941464A1 (en) | 1980-04-24 |
| JPS5552348A (en) | 1980-04-16 |
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