JPH07107108B2 - Thermoplastic resin composition - Google Patents
Thermoplastic resin compositionInfo
- Publication number
- JPH07107108B2 JPH07107108B2 JP61213370A JP21337086A JPH07107108B2 JP H07107108 B2 JPH07107108 B2 JP H07107108B2 JP 61213370 A JP61213370 A JP 61213370A JP 21337086 A JP21337086 A JP 21337086A JP H07107108 B2 JPH07107108 B2 JP H07107108B2
- Authority
- JP
- Japan
- Prior art keywords
- thermoplastic resin
- resin composition
- ethanol
- ester
- weight
- 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 - Fee Related
Links
Description
【発明の詳細な説明】 ［産業上の利用分野］ 本発明は、熱可塑性樹脂組成物に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a thermoplastic resin composition.
［従来の技術］ 本発明に係るフタル酸ビス［２−（N,N−ジアルキルア
ミノ）エチル］は、Rritish Journal of Pharmacology,
44（1972） P765〜778に記載のフタル酸エステルであ
る。[Prior Art] Bis [2- (N, N-dialkylamino) ethyl] phthalate according to the present invention can be prepared according to the Rritish Journal of Pharmacology,
44 (1972) Pphthalate ester described in P765-778.
［発明が解決しようとする問題点］ 本発明者らは、各種のフタル酸エステルを合成し、その
特性について鋭意検討する中で、本発明に係る化合物を
特定量配合してなる熱可塑性樹脂組成物が、機械的特性
のみならず電気的特性においても優れていることを見い
だし、この知見に基づいて本発明を完成した。[Problems to be Solved by the Invention] The present inventors have synthesized various phthalic acid esters, and, while diligently studying the characteristics thereof, a thermoplastic resin composition obtained by incorporating a specific amount of the compound according to the present invention. It was found that the product is excellent not only in mechanical properties but also in electrical properties, and the present invention has been completed based on this finding.
即ち、本発明は、新規有用な熱可塑性樹脂組成物を提供
することを目的とする。That is, the present invention aims to provide a novel and useful thermoplastic resin composition.
［問題点を解決するための手段］ 本発明に係る熱可塑性樹脂組成物は、熱可塑性樹脂100
重量部に対し、下記の一般式で表されるフタル酸エステ
ルを５〜200重量部含有することを特徴とする。[Means for Solving Problems] The thermoplastic resin composition according to the present invention comprises a thermoplastic resin 100
It is characterized by containing 5 to 200 parts by weight of a phthalic acid ester represented by the following general formula with respect to parts by weight.
（R1、R2、R3、R4は同一又は異なっていてもよい炭素数
１〜４のアルキル基を示す。） 本発明に係るフタル酸ビス［２−（N,N−ジアルキルア
ミノ）エチル］は、例えば無水フタル酸と、通常、過剰
量の２−（N,N−ジアルキルアミノ）エタノールとから
汎用のエステル化触媒、例えばパラトルエンスルホン酸
等の酸触媒、テトラアルキルチタネート等の塩基触媒、
酸化第１錫等の金属触媒を用いて、好ましくは窒素等の
不活性ガス雰囲気下、120〜250℃の温度条件下で反応さ
せることにより製造することができる。 (R 1 , R 2 , R 3 , and R 4 represent the same or different alkyl groups having 1 to 4 carbon atoms.) Bis [2- (N, N-dialkylamino) phthalate according to the present invention [Ethyl] is a general-purpose esterification catalyst such as phthalic anhydride and an excess amount of 2- (N, N-dialkylamino) ethanol, for example, an acid catalyst such as paratoluenesulfonic acid or a base such as tetraalkyl titanate. catalyst,
It can be produced by reacting with a metal catalyst such as stannous oxide, preferably in an atmosphere of an inert gas such as nitrogen under the temperature condition of 120 to 250 ° C.
更に、必要に応じて蒸留、吸着剤による精製処理等を施
すことにより高品質のものとすることもできる。Further, if necessary, a high quality product can be obtained by subjecting it to distillation, purification treatment with an adsorbent or the like.
原料のアルコールである２−（N,N−ジアルキルアミ
ノ）エタノールは、下記一般式で表わされる化合物であ
る。2- (N, N-dialkylamino) ethanol, which is a raw material alcohol, is a compound represented by the following general formula.
（Ｒ、Ｒ′は同一又は異なっていてもよい炭素数１〜４
のアルキル基を示す。） 具体的には、２−（N,N−ジメチルアミノ）エタノー
ル、２−（N,N−ジエチルアミノ）エタノール、２−
（N,N−ジプロピルアミノ）エタノール、２−（N,N−ジ
ブチルアミノ）エタノール、２−（Ｎ−エチル,N−メチ
ルアミノ）エタノール、２−（Ｎ−メチル−Ｎ−プロピ
ルアミノ）エタノール、２−（Ｎ−ブチル−Ｎ−メチル
アミノ）エタノール、２−（Ｎ−エチル−Ｎ−プロピル
アミノ）エタノール、２−（Ｎ−ブチル−Ｎ−エチルア
ミノ）エタノール、２−（Ｎ−ブチル−Ｎ−プロピルア
ミノ）エタノール等が例示される。 (R and R'may be the same or different and have 1 to 4 carbon atoms.
Is an alkyl group. ) Specifically, 2- (N, N-dimethylamino) ethanol, 2- (N, N-diethylamino) ethanol, 2-
(N, N-dipropylamino) ethanol, 2- (N, N-dibutylamino) ethanol, 2- (N-ethyl, N-methylamino) ethanol, 2- (N-methyl-N-propylamino) ethanol , 2- (N-butyl-N-methylamino) ethanol, 2- (N-ethyl-N-propylamino) ethanol, 2- (N-butyl-N-ethylamino) ethanol, 2- (N-butyl-) Examples include N-propylamino) ethanol and the like.
こうして得られるフタル酸ビス［２−（N,N−ジアルキ
ルアミノ）エチル］は、従来のフタル酸ジアルキルがア
ルキル基が炭素原子と水素原子だけから成るのと異なり
窒素原子が加わった構造をもつため、エステル基の極性
が変化し、従来のフタル酸エステルがもつ特徴、例えば
可塑性、耐寒性、揮発性、移行性等に加えて優れた帯電
防止性、防汚性、窒素含有樹脂への相溶性等を示す。The bis [2- (N, N-dialkylamino) ethyl] phthalate thus obtained has a structure in which a nitrogen atom is added, unlike the conventional dialkyl phthalate in which the alkyl group consists only of carbon and hydrogen atoms. In addition to the characteristics of conventional phthalate esters, such as plasticity, cold resistance, volatility, and migration, the polarity of the ester group changes, and excellent antistatic properties, antifouling properties, and compatibility with nitrogen-containing resins Etc.
当該フタル酸エステルは、熱可塑性樹脂100重量部に対
し、５乃至200重量部、好ましくは20重量部以上配合す
ることにより所定の効果を得ることができ、適用に際し
ては単独若しくは他のフタル酸エステルと併用すること
ができる。The phthalate ester can obtain a predetermined effect by blending it in an amount of 5 to 200 parts by weight, preferably 20 parts by weight or more with respect to 100 parts by weight of the thermoplastic resin. It can be used together with.
本発明に係る化合物が適用される熱可塑性樹脂として
は、ポリ塩化ビニル、ポリ塩化ビニリデン、塩化ビニル
若しくは塩化ビニリデンと酢酸ビニルその他のビニル系
化合物との共重合体等の含塩素系樹脂、ポリアミド、ポ
リエチレン、ポリプロピレン、ポリメタクリレート、ポ
リビニルブチラール、ウレタン、ユリア、ポリエステ
ル、アクリロニトリル−ブタジエン共重合体等が例示さ
れる。The thermoplastic resin to which the compound according to the present invention is applied, polyvinyl chloride, polyvinylidene chloride, chlorine-containing resin such as vinyl chloride or a copolymer of vinylidene chloride and vinyl acetate and other vinyl compounds, polyamide, Examples thereof include polyethylene, polypropylene, polymethacrylate, polyvinyl butyral, urethane, urea, polyester, and acrylonitrile-butadiene copolymer.
上記の熱可塑性樹脂組成物には、安定剤、滑剤、紫外線
吸収剤、防曇剤、帯電防止剤等各種の添加剤を適宜配合
することができる。Various additives such as a stabilizer, a lubricant, an ultraviolet absorber, an antifogging agent, and an antistatic agent can be appropriately added to the above thermoplastic resin composition.
［実施例］ 次に実施例をもって本発明を詳細に説明する。EXAMPLES Next, the present invention will be described in detail with reference to examples.
実施例１ 攪拌機、温度計、水分離機、冷却管を取付けた１の４
つ口フラスコに無水フタル酸を148g（1.0モル）、２−
（N,N−ジメチルアミノ）エタノールを267g（3.0モル）
及びエステル化触媒としてパラトルエンスルホン酸を4.
2g仕込み、系内を窒素にて置換後、150℃の反応温度で
縮合水を留去しつつ４時間エステル化反応を行なった。Example 1 1 to 4 equipped with a stirrer, a thermometer, a water separator, and a cooling pipe
Phthalic anhydride 148 g (1.0 mol) in a two-necked flask, 2-
267 g (3.0 mol) of (N, N-dimethylamino) ethanol
And paratoluenesulfonic acid as an esterification catalyst 4.
After charging 2 g of the system and replacing the inside of the system with nitrogen, an esterification reaction was carried out at a reaction temperature of 150 ° C. for 4 hours while distilling condensed water.
所定量の縮合水を留去した後、アルカリにて中和後、水
洗、蒸留することによりフタル酸ビス［２−（N,N−ジ
メチルアミノ）エチル］（以下「エステルＩ」と称す
る）を290g得た（収率94％）。After distilling off a predetermined amount of condensed water, it was neutralized with an alkali, washed with water and distilled to give bis [2- (N, N-dimethylamino) ethyl] phthalate (hereinafter referred to as "ester I"). 290 g was obtained (94% yield).
エステルＩの元素分析（第１表）、赤外吸収スペクトル
（第２表）及びNMR（第３表）の結果を夫々の表に一覧
する。The results of elemental analysis (Table 1), infrared absorption spectrum (Table 2) and NMR (Table 3) of ester I are listed in each table.
次いでエステルＩを下記の組成に従って配合して熱可塑
性樹脂組成物を調製し、その特性を評価した。得られ
た結果を第４表に示す。Next, ester I was blended according to the following composition to prepare a thermoplastic resin composition, and its characteristics were evaluated. The results obtained are shown in Table 4.
（配合組成） ポリ塩化ビニル 100重量部 （Geon 101EP:日本ゼオン（株）製） エステルＩ 50 安定剤 ステアリン酸カルシウム 0.3 ステアリン酸亜鉛 0.2 （試験片作成条件） ロール混練 163〜165℃×４分間 プレス 165℃×10分間 （物性評価方法） （１）機械的性質 :JIS K−7113 （２）電 気 特 性:JIS K−6723 （３）柔軟温度試験:JIS K−6745 （４）揮発減量、耐移行性： 各条件下での重量損失を測定 実施例２ ２−（N,N−ジエチルアミノ）エタノールと無水フタル
酸とを用いて実施例１に準拠してエステルIIを合成し、
更にこのものを配合して熱可塑性樹脂組成物を調製し
た。(Compounding composition) Polyvinyl chloride 100 parts by weight (Geon 101 EP: manufactured by Nippon Zeon Co., Ltd.) Ester I 50 stabilizer Calcium stearate 0.3 Zinc stearate 0.2 (Test piece preparation conditions) Roll kneading 163-165 ° C x 4 minutes Press 165 ℃ × 10 minutes (Physical property evaluation method) (1) Mechanical properties: JIS K-7113 (2) Electrical characteristics: JIS K-6723 (3) Flexible temperature test: JIS K-6745 (4) Volatile loss, resistance Transferability: Weight loss measured under each condition Example 2 Ester II was synthesized according to Example 1 using 2- (N, N-diethylamino) ethanol and phthalic anhydride.
Further, this was blended to prepare a thermoplastic resin composition.
エステルIIの分析結果を第１表〜第３表に、樹脂組成物
の評価結果を第４表に示す。The analysis results of ester II are shown in Tables 1 to 3, and the evaluation results of the resin composition are shown in Table 4.
実施例３ ２−（N,N−ジプロピルアミノ）エタノールと無水フタ
ル酸とを用いて実施例１に準拠してエステルIIIを合成
し、更にこのものを配合して熱可塑性樹脂組成物を調
製した。Example 3 Ester III was synthesized according to Example 1 using 2- (N, N-dipropylamino) ethanol and phthalic anhydride, and further compounded to prepare a thermoplastic resin composition. did.
エステルIIIの分析結果を第１表〜第３表に、樹脂組成
物の評価結果を第４表に示す。The analysis results of ester III are shown in Tables 1 to 3, and the evaluation results of the resin composition are shown in Table 4.
実施例４ ２−（N,N−ジブチルアミノ）エタノールと無水フタル
酸とを用いて実施例１に準拠してエステルIVを合成し、
更にこのものを配合して熱可塑性樹脂組成物を調製し
た。Example 4 An ester IV was synthesized according to Example 1 using 2- (N, N-dibutylamino) ethanol and phthalic anhydride,
Further, this was blended to prepare a thermoplastic resin composition.
エステルIVの分析結果を第１表〜第３表に、樹脂組成物
の評価結果を第４表に示す。The analysis results of ester IV are shown in Tables 1 to 3, and the evaluation results of the resin composition are shown in Table 4.
比較例 フタル酸ジ（２−エチルヘキシル）（以下「DOP」と称
する）を実施例１に準じて配合して得た樹脂組成物の物
性を第４表に示す。Comparative Example Table 4 shows the physical properties of the resin composition obtained by blending di (2-ethylhexyl) phthalate (hereinafter referred to as "DOP") according to Example 1.
Claims (3)
般式で表されるフタル酸エステルを５〜200重量部含有
することを特徴とする熱可塑性樹脂組成物。 （R1、R2、R3、R4は同一又は異なっていてもよい炭素数
１〜４のアルキル基を示す。）1. A thermoplastic resin composition comprising 5 to 200 parts by weight of a phthalate ester represented by the following general formula with respect to 100 parts by weight of a thermoplastic resin. (R 1 , R 2 , R 3 and R 4 represent the same or different alkyl groups having 1 to 4 carbon atoms.)
請求の範囲第１項に記載の熱可塑性樹脂組成物。2. The thermoplastic resin composition according to claim 1, wherein the thermoplastic resin is a chlorine-containing resin.
許請求の範囲第１項に記載の熱可塑性樹脂組成物。3. The thermoplastic resin composition according to claim 1, wherein the thermoplastic resin is polyvinyl chloride.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61213370A JPH07107108B2 (en) | 1986-09-09 | 1986-09-09 | Thermoplastic resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61213370A JPH07107108B2 (en) | 1986-09-09 | 1986-09-09 | Thermoplastic resin composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6368547A JPS6368547A (en) | 1988-03-28 |
| JPH07107108B2 true JPH07107108B2 (en) | 1995-11-15 |
Family
ID=16638058
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61213370A Expired - Fee Related JPH07107108B2 (en) | 1986-09-09 | 1986-09-09 | Thermoplastic resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH07107108B2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1490046A1 (en) * | 2001-11-22 | 2004-12-29 | Alexandru Vrabiescu | Medicine based on diethylaminoethanol derivatives and its use for the prevention and treatment of inflammatory and degenerative diseases |
| CN103145565A (en) * | 2013-03-15 | 2013-06-12 | 河南工业大学 | Preparation method of diester plasticizer containing tertiary amino |
| CN106008238B (en) * | 2016-05-24 | 2018-05-04 | 苏州科技大学 | Double Diethylaminoethanol ester citrate compounds of plant growth regulator phthalic acid and preparation method thereof |
-
1986
- 1986-09-09 JP JP61213370A patent/JPH07107108B2/en not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
| BRITISH JOURNAL OF PHARMACOLOGY=1972 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6368547A (en) | 1988-03-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |