JPS6361974B2 - - Google Patents
Info
- Publication number
- JPS6361974B2 JPS6361974B2 JP7550981A JP7550981A JPS6361974B2 JP S6361974 B2 JPS6361974 B2 JP S6361974B2 JP 7550981 A JP7550981 A JP 7550981A JP 7550981 A JP7550981 A JP 7550981A JP S6361974 B2 JPS6361974 B2 JP S6361974B2
- Authority
- JP
- Japan
- Prior art keywords
- aromatic polyester
- polyester polycarbonate
- resin composition
- aromatic
- formula
- 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
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 229920000728 polyester Polymers 0.000 claims description 18
- 229920000515 polycarbonate Polymers 0.000 claims description 12
- 239000004417 polycarbonate Substances 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 9
- 229920005668 polycarbonate resin Polymers 0.000 claims description 6
- 239000004431 polycarbonate resin Substances 0.000 claims description 6
- 229920005989 resin Polymers 0.000 claims description 4
- 239000011347 resin Substances 0.000 claims description 4
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical group 0.000 claims description 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-N terephthalic acid group Chemical group C(C1=CC=C(C(=O)O)C=C1)(=O)O KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- -1 alkali metal salt Chemical class 0.000 claims description 2
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 230000009477 glass transition Effects 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000003063 flame retardant Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 3
- 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 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- WGMBWDBRVAKMOO-UHFFFAOYSA-L disodium;4-[2-(4-oxidophenyl)propan-2-yl]phenolate Chemical compound [Na+].[Na+].C=1C=C([O-])C=CC=1C(C)(C)C1=CC=C([O-])C=C1 WGMBWDBRVAKMOO-UHFFFAOYSA-L 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 2
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical group OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Description
本発明は、難燃性の芳香族ポリエステルポリカ
ーボネート樹脂組成物に関するものである。
芳香族ポリエステルポリカーボネートは、同一
分子内にエステル結合とカーボネート結合を有す
る線状の樹脂であり、例えば、２，２−ビス（４
−ヒドロキシフエニル）プロパン（ビスフエノー
ルＡ）、テレフタロイルクロリドおよびホスゲン
を反応させることによつて製造され、すぐれた機
械的性質、耐候性、耐薬品性および透明性を有す
るものであることが知られている。（特開昭52−
128992）
このような芳香族ポリエステルポリカーボネー
トに、該樹脂が本来有するすぐれた物性を損なう
ことなく、難燃性を付与することができれば、エ
ンジニアリングプラスチツクとして、さらに価値
が大きいものとなる。
本発明者らは、芳香族ポリエステルポリカーボ
ネートの難燃化につき、鋭意研究を重ねた結果、
難燃化剤として特定の化合物を使用するときは、
少量の使用によつて十分な難燃効果を得ることが
でき、樹脂が本来有する物性を損うことがないこ
とを知得して本発明を完成した。
すなわち本発明は、難燃性で工業的価値の大き
い芳香族ポリエステルポリカーボネートを提供す
ることを目的とするものであり、その要旨とする
ところは、一般式
（式中、Ｘは２価の基を示し、芳香核は置換基を
有していてもよい。）
で表わされる構造単位と、一般式
（式中、Ｘおよび芳香核は上と同一意義を有す
る。）
で表わされる構造単位とからなり、かつジヒドロ
キシジアリール化合物残基：テレフタル酸残基：
カーボネート結合のモル比が１：0.33〜0.75：
0.67〜0.25である芳香族ポリエステルポリカーボ
ネート100重量部に対し、フタルイミドまたはナ
フタルイミドのアルカリ金属塩0.005〜0.5重量部
を配合してなる芳香族ポリエステルポリカーボネ
ート樹脂組成物である。
以下、本発明を詳細に説明する。
本発明で使用する芳香族ポリエステルポリカー
ボネートは、例えば、一般式
（式中、Ｘは、
The present invention relates to a flame retardant aromatic polyester polycarbonate resin composition. Aromatic polyester polycarbonate is a linear resin having an ester bond and a carbonate bond in the same molecule, for example, 2,2-bis(4
-Hydroxyphenyl)propane (bisphenol A), terephthaloyl chloride and phosgene, and has excellent mechanical properties, weather resistance, chemical resistance and transparency. Are known. (Unexamined Japanese Patent Publication No. 52-
128992) If flame retardancy could be imparted to such an aromatic polyester polycarbonate without impairing the excellent physical properties inherent in the resin, it would become even more valuable as an engineering plastic. As a result of extensive research into flame retardant aromatic polyester polycarbonate, the present inventors found that
When using certain compounds as flame retardants,
The present invention was completed based on the knowledge that a sufficient flame retardant effect can be obtained by using a small amount and that the inherent physical properties of the resin are not impaired. That is, the purpose of the present invention is to provide an aromatic polyester polycarbonate that is flame retardant and has great industrial value, and the gist thereof is that the general formula (In the formula, X represents a divalent group, and the aromatic nucleus may have a substituent.) A structural unit represented by the following and the general formula (In the formula, X and the aromatic nucleus have the same meanings as above.) Consisting of a structural unit represented by: dihydroxydiaryl compound residue: terephthalic acid residue:
The molar ratio of carbonate bonds is 1:0.33-0.75:
This is an aromatic polyester polycarbonate resin composition prepared by blending 0.005 to 0.5 parts by weight of an alkali metal salt of phthalimide or naphthalimide to 100 parts by weight of an aromatic polyester polycarbonate having a molecular weight of 0.67 to 0.25. The present invention will be explained in detail below. The aromatic polyester polycarbonate used in the present invention has, for example, the general formula (In the formula, X is
テレフタロイルクロリドの３％塩化メチレン溶
液、ビスフエノールＡを５％水酸化ナトリウム水
溶液に溶解して調製したビスフエノールＡナトリ
ウム塩13％の水溶液および２％トリエチルアミン
水溶液を、それぞれ44.2Kg／hr、15.9Kg／hrおよ
び0.2Kg／hrの流量で、内径30mm、長さ1.5mのガ
ラス球充填塔に供給し、該塔の供給口から0.75m
の位置からホスゲン0.75Kg／hrを吹込んで反応を
行い、エステル結合を有し、末端にクロロホーメ
ート基を有するオリゴマーを製造した。
反応混合物を分液して得た上記オリゴマーの塩
化メチレン溶液44.0Kg／hr、上記と同じビスフエ
ノールＡナトリウム塩の13％水溶液17.6Kg／hr、
25％水酸化ナトリウム水溶液1.1Kg／hr、２％ト
リエチルアミンの水溶液0.67Kg／hrおよびｐ−タ
ーシヤリーブチルフエノール27ｇ／hrを、撹拌槽
に供給し、平均滞留時間が２時間となるようにし
て重縮合反応を行つた。
反応混合物を分液して得たポリマーの塩化メチ
レン溶液を、水、塩酸水溶液、次いで洗浄した
後、塩化メチレンを蒸発させて、〔η〕が0.75で
ビスフエノールＡ残基：テレフタル酸残基：カー
ボネート結合のモル比が１：0.46：0.54の芳香族
ポリエステルポリカーボネートを得た。
実施例１〜２および比較例１
上記製造例により製造した芳香族ポリエステル
ポリカーボネートの粉末100部に対し、下記表１
に示す量のフタルイミドカリウム粉末を配合し、
押出機を用いて300℃で溶融混練して押し出しペ
レツト化した。
これらのペレツトを、射出成形機（日精樹脂(株)
製、TS−100型）と、燃焼性試験片および
ASTMで規定する試験片の成形用金型を用い、
成形温度370℃、金型温度130℃、射出時間15秒、
冷却時間０秒で連続成形を行つた。
得られた成形品の燃焼性およびアイゾツト衝撃
強度は下記表１に示す通りであつた。
なお、比較のため、フタルイミドカリウム粉末
を混合しなかつた以外は実施例１〜２と同様に行
ない、その結果を表１に併記した。
（比較例 １）
実施例 ３〜４
フタルイミドカリウム粉末のかわりに、表１に
示す量のナフタルイミドカリウム粉末を配合し、
それ以外は実施例１〜２と同様に行なつた。結果
は表１に示す通りであつた。
A 3% methylene chloride solution of terephthaloyl chloride, a 13% aqueous solution of bisphenol A sodium salt prepared by dissolving bisphenol A in a 5% aqueous sodium hydroxide solution, and a 2% aqueous triethylamine solution were mixed at 44.2 Kg/hr and 15.9 kg/hr, respectively. Kg/hr and 0.2 Kg/hr flow rate to a glass bulb packed column with an inner diameter of 30 mm and a length of 1.5 m, and 0.75 m from the supply port of the column.
A reaction was carried out by blowing 0.75 Kg/hr of phosgene from the position, and an oligomer having an ester bond and a chloroformate group at the end was produced. A methylene chloride solution of the above oligomer obtained by separating the reaction mixture 44.0 Kg/hr, a 13% aqueous solution of the same bisphenol A sodium salt as above 17.6 Kg/hr,
25% sodium hydroxide aqueous solution 1.1Kg/hr, 2% triethylamine aqueous solution 0.67Kg/hr and p-tert-butylphenol 27g/hr were fed into a stirring tank, and the mixture was heated so that the average residence time was 2 hours. A condensation reaction was performed. The methylene chloride solution of the polymer obtained by separating the reaction mixture was washed with water and an aqueous hydrochloric acid solution, and then the methylene chloride was evaporated to obtain bisphenol A residue: terephthalic acid residue: [η] was 0.75. An aromatic polyester polycarbonate having a molar ratio of carbonate bonds of 1:0.46:0.54 was obtained. Examples 1 to 2 and Comparative Example 1 The following table 1
Blend the amount of potassium phthalimide powder shown in
The mixture was melt-kneaded and extruded into pellets at 300°C using an extruder. These pellets are processed into an injection molding machine (Nissei Plastics Co., Ltd.).
TS-100), flammability test pieces and
Using a test piece mold specified by ASTM,
Molding temperature 370℃, mold temperature 130℃, injection time 15 seconds,
Continuous molding was performed with a cooling time of 0 seconds. The flammability and Izod impact strength of the obtained molded article were as shown in Table 1 below. For comparison, the same procedures as in Examples 1 and 2 were conducted except that potassium phthalimide powder was not mixed, and the results are also shown in Table 1. (Comparative Example 1) Examples 3 to 4 Instead of potassium phthalimide powder, potassium naphthalimide powder was blended in the amount shown in Table 1,
Other than that, the same procedure as in Examples 1 and 2 was carried out. The results were as shown in Table 1.
Claims (1)
有していてもよい。） で表わされる構造単位と、一般式 （式中、Ｘおよび芳香核は上記と同一意義を有す
る。） で表わされる構造単位とからなり、かつジヒドロ
キシジアリール化合物残基：テレフタル酸残基：
カーボネート結合のモル比が１：0.33〜0.75：
0.67〜0.25である芳香族ポリエステルポリカーボ
ネート100重量部に対し、フタルイミドまたはナ
フタルイミドのアルカリ金属塩0.005〜0.5重量部
を配合してなる芳香族ポリエステルポリカーボネ
ート樹脂組成物。 ２ 芳香族ポリエステルポリカーボネートの固有
粘度が0.4〜1.5である特許請求の範囲第１項記載
の芳香族ポリエステルポリカーボネート樹脂組成
物。 ３ 芳香族ポリエステルポリカーボネートのガラ
ス転移点が、160〜190℃である特許請求の範囲第
１項記載の芳香族ポリエステルポリカーボネート
樹脂組成物。 ４ 芳香族ポリエステルポリカーボネートの末端
カルボキシル基が10μ当量／ｇ樹脂以下である特
許請求の範囲第１項記載の芳香族ポリエステルポ
リカーボネート樹脂組成物。[Claims] 1. General formula (In the formula, X represents a divalent group, and the aromatic nucleus may have a substituent.) A structural unit represented by the following and the general formula (In the formula, X and the aromatic nucleus have the same meanings as above.) Consisting of a structural unit represented by: dihydroxydiaryl compound residue: terephthalic acid residue:
The molar ratio of carbonate bonds is 1:0.33-0.75:
An aromatic polyester polycarbonate resin composition comprising 0.005 to 0.5 parts by weight of an alkali metal salt of phthalimide or naphthalimide to 100 parts by weight of an aromatic polyester polycarbonate having a molecular weight of 0.67 to 0.25. 2. The aromatic polyester polycarbonate resin composition according to claim 1, wherein the aromatic polyester polycarbonate has an intrinsic viscosity of 0.4 to 1.5. 3. The aromatic polyester polycarbonate resin composition according to claim 1, wherein the aromatic polyester polycarbonate has a glass transition point of 160 to 190°C. 4. The aromatic polyester polycarbonate resin composition according to claim 1, wherein the aromatic polyester polycarbonate has a terminal carboxyl group of 10 μ equivalent/g resin or less.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7550981A JPS57190039A (en) | 1981-05-19 | 1981-05-19 | Aromatic polyester polycarbonate resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7550981A JPS57190039A (en) | 1981-05-19 | 1981-05-19 | Aromatic polyester polycarbonate resin composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57190039A JPS57190039A (en) | 1982-11-22 |
| JPS6361974B2 true JPS6361974B2 (en) | 1988-11-30 |
Family
ID=13578274
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7550981A Granted JPS57190039A (en) | 1981-05-19 | 1981-05-19 | Aromatic polyester polycarbonate resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57190039A (en) |
-
1981
- 1981-05-19 JP JP7550981A patent/JPS57190039A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57190039A (en) | 1982-11-22 |
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