JPH04183775A - Antistatic agent for polyester resin - Google Patents
Antistatic agent for polyester resinInfo
- Publication number
- JPH04183775A JPH04183775A JP31316890A JP31316890A JPH04183775A JP H04183775 A JPH04183775 A JP H04183775A JP 31316890 A JP31316890 A JP 31316890A JP 31316890 A JP31316890 A JP 31316890A JP H04183775 A JPH04183775 A JP H04183775A
- Authority
- JP
- Japan
- Prior art keywords
- antistatic agent
- group
- polyester resin
- present
- antistatic
- 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.)
- Granted
Links
- 239000002216 antistatic agent Substances 0.000 title abstract description 25
- 229920001225 polyester resin Polymers 0.000 title abstract description 14
- 239000004645 polyester resin Substances 0.000 title abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 229910001413 alkali metal ion Inorganic materials 0.000 claims abstract description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 6
- 239000002253 acid Substances 0.000 abstract description 3
- 150000003839 salts Chemical class 0.000 abstract description 3
- 229920005989 resin Polymers 0.000 abstract 2
- 239000011347 resin Substances 0.000 abstract 2
- 238000000034 method Methods 0.000 description 10
- -1 sodium alkylsulfonates Chemical class 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 238000004898 kneading Methods 0.000 description 5
- 229920006267 polyester film Polymers 0.000 description 5
- ZIWRUEGECALFST-UHFFFAOYSA-M sodium 4-(4-dodecoxysulfonylphenoxy)benzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCOS(=O)(=O)c1ccc(Oc2ccc(cc2)S([O-])(=O)=O)cc1 ZIWRUEGECALFST-UHFFFAOYSA-M 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 2
- DAJSVUQLFFJUSX-UHFFFAOYSA-M sodium;dodecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCS([O-])(=O)=O DAJSVUQLFFJUSX-UHFFFAOYSA-M 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は新規なポリエステル樹脂用帯電防止剤、さらに
詳しくは、特にポリエステルフィルムに対し、透明性を
損なうことなく、優れた帯電防止性を付与しうる内部練
込み型ポリエステル樹脂用帯電防止剤に関するものであ
る。[Detailed Description of the Invention] [Industrial Application Field] The present invention is a novel antistatic agent for polyester resins, more specifically, it provides excellent antistatic properties to polyester films without impairing transparency. The present invention relates to an antistatic agent for internally kneaded polyester resins that can be used in internal kneading.
［従来の技術］
従来、ポリエステルフィルムは一般に高い融点と高い結
晶性をもち、優れた寸法安定性、強度、耐薬品性、耐候
性などを有することから、例えば磁気記録テープ、メタ
ライズ用ベース、電気・電子部品材料、包装材料、印刷
製版用などに幅広く用いられている。[Prior Art] Conventionally, polyester films generally have a high melting point and high crystallinity, and have excellent dimensional stability, strength, chemical resistance, weather resistance, etc.・Widely used for electronic component materials, packaging materials, printing plates, etc.
ところが、このポリエステルフィルムは帯電しやすい性
質を有するため、加工時にトラブルが発生したり、製品
にチリやホコリが付着して美観を損ねたりするなど、し
ばしば好ましくない事態を招来する。However, this polyester film has the property of being easily electrostatically charged, which often leads to undesirable situations such as troubles occurring during processing and dirt and dust adhering to the product, which impairs its aesthetic appearance.
したがって、このような欠点を改良するために、従来適
当な帯電防止剤を表面に塗布する方法やフィルム内部に
練込む方法が取られてきた。しかしながら、前者の帯電
防止剤を塗布する方法は水洗や摩擦により容易に帯電防
止剤が消失し、効果が持続しにくいという問題がある。Therefore, in order to improve these drawbacks, conventional methods have been used to coat an appropriate antistatic agent on the surface or knead it into the film. However, the former method of applying an antistatic agent has a problem in that the antistatic agent is easily lost by washing with water or friction, and the effect is difficult to maintain.
これに対し、内部練込法は、持続性に優れた帯電防止性
能を付与することができ、好ましい方法といえる。この
内部練込法においては、帯電防止剤として、従来アルキ
ルスルホン酸ナトリウム、アルキルアリールスルホン酸
ナトリウム、ポリエチレングリコール、第四級アンモニ
ウム塩などが用いられている。しかしながら、これらの
帯電防止剤はフィルムの透明性を低下させたり、あるい
は帯電防止効果が十分でないため、多量に用いる必要が
あり、その結果フィルムの品質を低下させたりするなど
の欠点を有している。On the other hand, the internal kneading method can provide excellent long-lasting antistatic performance and can be said to be a preferable method. In this internal kneading method, sodium alkylsulfonates, sodium alkylarylsulfonates, polyethylene glycols, quaternary ammonium salts, and the like are conventionally used as antistatic agents. However, these antistatic agents have drawbacks such as reducing the transparency of the film or having insufficient antistatic effect, so they must be used in large amounts, resulting in a decrease in film quality. There is.
［発明が解決しようとする課題］
本発明は、このような従来の内部練込み型ポリエステル
樹脂用帯電防止剤が有する欠点を克服し、特にポリエス
テルフィルムに対して、透明性を損なうことなく、優れ
た帯電防止性を付与しうる内部練込み型ポリエステル樹
脂用帯電防止剤を提供することを目的としてなされｔこ
ものである。[Problems to be Solved by the Invention] The present invention overcomes the drawbacks of such conventional internally kneaded antistatic agents for polyester resins, and provides excellent antistatic agents, especially for polyester films, without impairing transparency. This invention was developed for the purpose of providing an internally kneaded antistatic agent for polyester resins that can impart antistatic properties.
［課題を解決するための手段］
本発明者らは、前記の好ましい性質を有する内部練込み
型ポリエステル樹脂用帯電防止剤を開発すべく鋭意研究
を重ねた結果、特定の構造を有するアルキルジフェニル
エーテルジスルホン酸塩がその目的に適合しうろことを
見い出し、この知見に基づいて本発明を完成するに至っ
た。[Means for Solving the Problems] As a result of intensive research to develop an internally kneaded antistatic agent for polyester resin having the above-mentioned preferable properties, the present inventors discovered an alkyl diphenyl ether disulfone having a specific structure. They discovered that acid salts are suitable for the purpose, and based on this knowledge, they completed the present invention.
すなわち、本発明は、−船蔵
（式中のＲ１は゛炭素数４〜２２のアルキル基、Ｒ１は
水素原子又は炭素数４〜２２のアルキル基、Ｍはアルカ
リ金属イオン又はアンモニウムイオンである）
で表される化合物を主成分とするポリエステル樹脂用帯
電防止剤を提供するものである。That is, the present invention provides -Shinzo (in the formula, R1 is an alkyl group having 4 to 22 carbon atoms, R1 is a hydrogen atom or an alkyl group having 4 to 22 carbon atoms, and M is an alkali metal ion or an ammonium ion). The object of the present invention is to provide an antistatic agent for polyester resins containing the represented compound as a main component.
以下、本発明の詳細な説明する。The present invention will be explained in detail below.
本発明の帯電防止剤の主成分として用いられる化合物は
、前記−船蔵（Ｉ）で表されるアルキルジフェニルエー
テルジスルホン酸塩であって、アルキル基はそれぞれの
ベンゼン環の一方に結合していてもよいし、両方に結合
していてもよく、また、アルキル基の結合位置は酸素原
子に対して〇−位、ｍ−位、ｐ−位のいずれであっても
よい。The compound used as the main component of the antistatic agent of the present invention is an alkyl diphenyl ether disulfonate represented by the above-mentioned -Funazura (I), in which the alkyl group may be bonded to one of the benzene rings. The alkyl group may be bonded to both positions, and the bonding position of the alkyl group may be any of the ○-position, m-position, and p-position with respect to the oxygen atom.
該アルキル基としては、炭素数が４〜２２の範囲にある
もの、例えばブチル基、ペンチル基、ヘキシル基、ヘプ
チル基、オクチル基、ノニル基、デ／ル基、ウンデンル
基、ドデシル基、トリデシル基、テトラデシル基、ペン
タデンル基、ヘキサデシル基、ヘプタデシル基、オクタ
デシル基、ノナデシル基、エイコンル基などが挙げられ
る。これらのアルキル基は直鎖状のものであってもよい
し、分枝鎖を有するものであってもよい。The alkyl group has a carbon number in the range of 4 to 22, such as a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a de/ru group, an undenel group, a dodecyl group, and a tridecyl group. , tetradecyl group, pentadenyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group, eikonyl group, and the like. These alkyl groups may be linear or branched.
まｔ；、該化合物のそれぞれのベンゼン環に結合してい
るスルホン酸基の位置については特に制限はなく、酸素
原子に対して〇−位、ｍ−位、ｐ−位のいずれであって
もよい。There is no particular restriction on the position of the sulfonic acid group bonded to each benzene ring of the compound, and it may be at the ○-position, m-position, or p-position with respect to the oxygen atom. good.
前記−船蔵（Ｉ）で表される化合物において、スルホン
酸塩を構成するカチオンとしては、ナトリウムイオン、
カリウムイオン、リチウムイオンなどのアルカリ金属イ
オン及びアンモニウムイオンが挙げられる。In the compound represented by Funazura (I) above, the cations constituting the sulfonate include sodium ion,
Examples include alkali metal ions such as potassium ions and lithium ions, and ammonium ions.
前記−船蔵（Ｉ）で表される化合物は、従来公知の方法
によって製造することができるが、容易に入手しうる市
販品を用いてもよい。The compound represented by Funazo (I) above can be produced by a conventionally known method, but easily available commercial products may also be used.
本発明の帯電防止剤は、前記−船蔵（１）で表される化
合物を１種用いてもよいし、２種以上を組み合わせて用
いてもよく、また、本発明の目的を損なわない範囲で、
所望に応し他の帯電防止剤を併用してもよい。In the antistatic agent of the present invention, one kind of the compound represented by the above-mentioned -Funzo (1) may be used, or two or more kinds may be used in combination. in,
Other antistatic agents may be used in combination as desired.
本発明の帯電防止剤は内部練込み型であって、ポリエス
テル樹脂に対し、通常０．１〜５重量％、好ましくは０
．５〜２重量％の割合で用いられる。The antistatic agent of the present invention is an internally kneaded type, and is usually 0.1 to 5% by weight, preferably 0% by weight, based on the polyester resin.
．． It is used in a proportion of 5 to 2% by weight.
この量が０．１重量％未満では帯電防止性の付与効果が
十分ではないし、５重量％を超えると量の割には効果の
向上が認められず、むしろポリエステル樹脂の品質が低
下する傾向がみられる。If this amount is less than 0.1% by weight, the effect of imparting antistatic properties will not be sufficient, and if it exceeds 5% by weight, no improvement in the effect will be recognized in relation to the amount, and the quality of the polyester resin will tend to deteriorate. Be looked at.
本発明の帯電防止剤をポリエステル樹脂に練込む方法に
ついては特に制限はなく、従来内部練込み型帯電防止剤
をポリエステル樹脂に練込む際に慣用されている方法を
用いることができる。There is no particular restriction on the method of kneading the antistatic agent of the present invention into the polyester resin, and any method conventionally used for kneading an internally kneaded antistatic agent into the polyester resin can be used.
このようにして本発明の帯電防止剤が練込まれたポリエ
ステル樹脂からフィルムを得るには、例えばＴダイ法や
インフレーション法などのエキストルージョン法、カレ
ンダー法、キャスティング法などの公知の方法によって
製膜したのち、所望に応じ一軸又は二軸延伸処理すれば
よい。このフィルムの厚さは用途に応じて適宜選ばれる
が、通常は３〜４００μｍの範囲で選ばれる。In order to obtain a film from the polyester resin kneaded with the antistatic agent of the present invention, a film can be formed by a known method such as an extrusion method such as a T-die method or an inflation method, a calender method, or a casting method. After that, uniaxial or biaxial stretching treatment may be performed as desired. The thickness of this film is appropriately selected depending on the application, but is usually selected in the range of 3 to 400 μm.
［実施例］
次に実施例により本発明をさらに詳細に説明するが、本
発明はこれらの例によってなんら限定されるものではな
い。[Examples] Next, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to these Examples in any way.
実施例１
ポリエチレンテレフタレートを常法に従い製造し、次い
で押出機を用いてポリエステルチップを成形した。Example 1 Polyethylene terephthalate was produced according to a conventional method, and then polyester chips were molded using an extruder.
次に、十分に乾燥したチップ１００重量部とドデシルジ
フェニルエーテルジスルホン酸ナトリウム１重量部とを
エクストルーダーにて混練し溶融押出後、二軸延伸して
厚さ６０μｍの延伸フィルムを作成し、このものの表面
抵抗値とヘイズ値を求めた。その結果を第１表に示す。Next, 100 parts by weight of the sufficiently dried chips and 1 part by weight of sodium dodecyl diphenyl ether disulfonate were kneaded in an extruder, melt-extruded, and then biaxially stretched to create a stretched film with a thickness of 60 μm. The resistance value and haze value were determined. The results are shown in Table 1.
実施例２
実施例１において、帯電防止剤としてドデシルジフェニ
ルエーテルジスルホン酸ナトリウム０．５重量部とドデ
シルベンゼンスルホン酸ナトリウム０．５重量部との混
合物を用いた以外は、実施例１と同様にして延伸フィル
ムを作成し、評価した。その結果を第１表に示す。Example 2 Stretching was carried out in the same manner as in Example 1, except that in Example 1, a mixture of 0.5 parts by weight of sodium dodecyl diphenyl ether disulfonate and 0.5 parts by weight of sodium dodecylbenzenesulfonate was used as the antistatic agent. A film was created and evaluated. The results are shown in Table 1.
比較例１ 一
実施例１において、ドデシルジフェニルエーテルジスル
ホン酸ナトリウムの代わりに、ドデシルベンゼンスルホ
ン酸ナトリウムを用いた以外は、実施例１と同様にして
延伸フィルムを作成し、評価した。その結果を第１表に
示す。Comparative Example 1 A stretched film was prepared and evaluated in the same manner as in Example 1, except that sodium dodecylbenzenesulfonate was used instead of sodium dodecyl diphenyl ether disulfonate. The results are shown in Table 1.
比較例２
実施例１において、ドデシルジフェニルエーテルジスル
ホン酸ナトリウムの代わりに、ドデシルスルホン酸ナト
リウムを用いた以外は、実施例１と同様にして延伸フィ
ルムを作成し、評価した。Comparative Example 2 A stretched film was prepared and evaluated in the same manner as in Example 1, except that sodium dodecyl sulfonate was used instead of sodium dodecyl diphenyl ether disulfonate.
その結果を第１表に示す。The results are shown in Table 1.
比較例３
実施例１において、帯電防止剤としてドデシルスルホン
酸ナトリウム０．５１！量部とポリエチレングリコール
０．５重量部との混合物を用いた以外は、実施例１と同
様にして延伸フィルムを作成し、評価した。その結果を
第１表に示す。Comparative Example 3 In Example 1, sodium dodecylsulfonate was used as an antistatic agent at 0.51! A stretched film was prepared and evaluated in the same manner as in Example 1, except that a mixture of 0.5 parts by weight of polyethylene glycol and 0.5 parts by weight of polyethylene glycol was used. The results are shown in Table 1.
（以下余白）
第 １ 表
注
１）表面抵抗値：
スタチックオネストメーターを用い、印加電圧１０００
Ｖ、温度２０℃、湿度６５％の条件で測定した。(Margin below) Table 1 Note 1) Surface resistance value: Using a static honest meter, applied voltage 1000
Measured under conditions of V, temperature of 20° C., and humidity of 65%.
２）ヘイズ値（曇り度）： ＪＩＳＫ−６７１４に準拠して求めた。2) Haze value (cloudiness): It was determined in accordance with JISK-6714.
［発明の効果］
本発明のポリエステル樹脂用帯電防止剤は、特定構造の
アルキルジフェニルエーテルジスルホン酸塩を主成分と
する内部練込み型のものであって、特にポリエステルフ
ィルムに対し、透明性を損なうことなく、優れた帯電防
止性を付与することができる。[Effects of the Invention] The antistatic agent for polyester resins of the present invention is an internally kneaded type containing an alkyldiphenyl ether disulfonate having a specific structure as a main component, and does not impair transparency, especially for polyester films. However, it is possible to impart excellent antistatic properties.
Claims (1)
は水素原子又は炭素数４〜２２のアルキル基、Ｍはアル
カリ金属イオン又はアンモニウムイオンである） で表される化合物を主成分とするポリエステル樹脂用帯
電防止剤。[Claims] 1 General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R^1 is an alkyl group having 4 to 22 carbon atoms, R^2
is a hydrogen atom or an alkyl group having 4 to 22 carbon atoms, and M is an alkali metal ion or an ammonium ion.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP31316890A JP2855370B2 (en) | 1990-11-19 | 1990-11-19 | Antistatic agent for internally kneaded polyester resin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP31316890A JP2855370B2 (en) | 1990-11-19 | 1990-11-19 | Antistatic agent for internally kneaded polyester resin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04183775A true JPH04183775A (en) | 1992-06-30 |
| JP2855370B2 JP2855370B2 (en) | 1999-02-10 |
Family
ID=18037925
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP31316890A Expired - Fee Related JP2855370B2 (en) | 1990-11-19 | 1990-11-19 | Antistatic agent for internally kneaded polyester resin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2855370B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6841598B2 (en) | 2002-08-16 | 2005-01-11 | General Electric Company | Antistatic and antidust agents, compositions thereof, and methods of manufacture |
| US6900257B2 (en) | 2002-08-06 | 2005-05-31 | General Electric Company | Antistatic agents and polymer compositions derived therefrom |
-
1990
- 1990-11-19 JP JP31316890A patent/JP2855370B2/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6900257B2 (en) | 2002-08-06 | 2005-05-31 | General Electric Company | Antistatic agents and polymer compositions derived therefrom |
| US6841598B2 (en) | 2002-08-16 | 2005-01-11 | General Electric Company | Antistatic and antidust agents, compositions thereof, and methods of manufacture |
| US7569714B2 (en) | 2002-08-16 | 2009-08-04 | Sabic Innovative Plastics Ip B.V. | Antistatic and antidust agents, compositions thereof, and methods of manufacture |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2855370B2 (en) | 1999-02-10 |
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