JPH0576968B2 - - Google Patents
Info
- Publication number
- JPH0576968B2 JPH0576968B2 JP17766185A JP17766185A JPH0576968B2 JP H0576968 B2 JPH0576968 B2 JP H0576968B2 JP 17766185 A JP17766185 A JP 17766185A JP 17766185 A JP17766185 A JP 17766185A JP H0576968 B2 JPH0576968 B2 JP H0576968B2
- Authority
- JP
- Japan
- Prior art keywords
- vinyl chloride
- chloride resin
- parts
- thermal stability
- salt
- 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 - Lifetime
Links
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 39
- 229920005989 resin Polymers 0.000 claims description 37
- 239000011347 resin Substances 0.000 claims description 37
- -1 aminoalkyl acrylate Chemical compound 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 230000000052 comparative effect Effects 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 230000003068 static effect Effects 0.000 description 8
- 230000005611 electricity Effects 0.000 description 7
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2,2'-azo-bis-isobutyronitrile Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 3
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229940050176 methyl chloride Drugs 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 238000010557 suspension polymerization reaction Methods 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 239000003093 cationic surfactant Substances 0.000 description 2
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 229920006026 co-polymeric resin Polymers 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Landscapes
- Graft Or Block Polymers (AREA)
Description
〔産業上の利用分野〕
本発明は塩化ビニル樹脂にアミノアルキルアク
リレートの塩をグラフト共重合した帯電性に優れ
た塩化ビニル系樹脂の製造方法に関するものであ
る。
〔従来の技術〕
塩化ビニル樹脂は、いわゆる汎用樹脂としてき
わめて優秀な性質を有する有用な樹脂であるが、
プラスチツクの一般特性の一つとして静電気を帯
びやすいという欠点がある。この塩化ビニル樹脂
の帯電性を改良するために多くの方法が提案され
ている。一般に行なわれている方法は、帯電防止
に有効な極性基を有する化合物を塩化ビニル樹脂
の加工時に添加する方法、あるいは、溶剤で希釈
して成型品の表面に塗布する方法である。これに
用いる化合物の例として、ノニオン性、アニオン
性、及びカチオン性の界面活性剤があり、とくに
アミノ基を有するカチオン性界面活性剤が効果が
良好であるので広く使用されている。かゝる界面
活性剤を塩化ビニル樹脂の加工時に添加したり、
成型品の表面に塗布する方法は帯電防止に有効で
はあるが、この効果は一時的であつて、効果の持
続性がない。
つまり、界面活性剤が成型品の表面に存在して
いるかぎりにおいて帯電防止効果が発揮されるの
であるから、成型品の長期間の使用、水洗等によ
り、その表面濃度が減少すると最早帯電防止性は
認められなくなるのである。このように界面活性
剤の添加あるいは塗布による帯電防止の方法は、
帯電防止効果の持続性、永久性の点ではなはだ不
満足なものであつた。
このようなことから、帯電防止に有効な樹性基
を有するコモノマーを塩化ビニルに共重合させ、
永久帯電防止性を附与せしめようとする試みが提
案されている。この場合、やはり、アミノ基を有
するコモノマーが帯電防止に有効であると考えら
れ、アミノアルキルアクリレートを塩化ビニルに
共重合させる方法が提案されている。しかしなが
ら、この方法によると帯電防止に効果があること
は認められるが塩化ビニル樹脂の熱安定性は著し
く劣化し、実用に供しうるコポリマーはえられな
い。又、アミノアルキルアクリレートを酸類と反
応せしめた塩と塩化ビニルと共重合せしめれば、
得られたコポリマーの熱安定性はある程度は改良
されるがまだ充分でなかつた。
〔本発明が解決しようとする問題点〕
本発明の目的は、水洗処理を行なつても帯電防
止効果が失われず熱安定性が顕著にすぐれた塩化
ビニル系樹脂の製造方法を提供することにある。
〔問題点を解決するための手段〕
本発明者らは、上記目的を達成するため鋭意検
討し、遂に本発明に到つた。
即ち、本発明は、塩化ビニル樹脂100重量部に
一般式
[Industrial Field of Application] The present invention relates to a method for producing a vinyl chloride resin with excellent chargeability, which is obtained by graft copolymerizing a vinyl chloride resin with an aminoalkyl acrylate salt. [Prior Art] Vinyl chloride resin is a useful resin with extremely excellent properties as a so-called general-purpose resin.
One of the general characteristics of plastics is that they are easily charged with static electricity. Many methods have been proposed to improve the charging properties of vinyl chloride resin. A commonly used method is to add a compound having a polar group that is effective in preventing static electricity during processing of vinyl chloride resin, or to dilute it with a solvent and apply it to the surface of a molded product. Examples of compounds used for this purpose include nonionic, anionic, and cationic surfactants, and cationic surfactants having an amino group are particularly effective and are therefore widely used. Such surfactants are added during processing of vinyl chloride resin,
Although the method of coating the surface of a molded product is effective in preventing static electricity, this effect is temporary and does not last long. In other words, as long as the surfactant exists on the surface of the molded product, the antistatic effect is exhibited, so if the surface concentration decreases due to long-term use of the molded product, washing with water, etc., the antistatic effect will no longer be achieved. will no longer be recognized. In this way, the method of preventing static electricity by adding or coating a surfactant is as follows.
The durability and permanence of the antistatic effect were extremely unsatisfactory. For this reason, we copolymerized a comonomer with a resinous group that is effective in preventing static electricity with vinyl chloride.
Attempts have been made to impart permanent antistatic properties. In this case, it is believed that a comonomer having an amino group is effective in preventing static electricity, and a method has been proposed in which aminoalkyl acrylate is copolymerized with vinyl chloride. However, although this method is recognized to be effective in preventing static electricity, the thermal stability of the vinyl chloride resin is significantly degraded, and a copolymer that can be put to practical use cannot be obtained. Also, if aminoalkyl acrylate is copolymerized with vinyl chloride and a salt obtained by reacting with acids,
Although the thermal stability of the obtained copolymer was improved to some extent, it was still not sufficient. [Problems to be Solved by the Present Invention] An object of the present invention is to provide a method for producing a vinyl chloride resin that does not lose its antistatic effect even after washing with water and has remarkable thermal stability. be. [Means for Solving the Problems] The present inventors have made extensive studies to achieve the above object, and have finally arrived at the present invention. That is, the present invention provides 100 parts by weight of vinyl chloride resin with the general formula
【化】
（ここではR1は水素またはメチル基、R2およ
びR3は水素または炭素数１〜４のアルキル基で
ある。また、ｎは１〜４の整数である。）
で示されるアミノアルキルアクリレートの塩0.2
〜25重量部をグラフト共重合することを特徴とす
る帯電防止性、熱安定性に優れた塩化ビニル系樹
脂の製造方法である。
本発明で使用される幹ポリマーとなるべき塩化
ビニル樹脂は、塩化ビニルの単独重合により得ら
れた塩化ビニル単独樹脂、塩化ビニルと共重合可
能な他の単量体との共重合樹脂、あるいは塩化ビ
ニルと他の樹脂とのグラフト共重合樹脂等が包含
されるが、塩化ビニルの単独重合で得られた塩化
ビニル単独樹脂が実用上好ましい。幹ポリマーと
なるべき塩化ビニル樹脂の重合度は500〜5000が
適当であり好ましくは800〜1500である。また、
溶液重合、塊状重合、水性懸濁重合、水性乳化重
合等のいずれで製造されたものであつてもかまわ
ない。一般には水性懸濁重合によるものが有利で
ある。
本発明に使用されるアミノアルキルアクリレー
トは一般式[Chemical formula] (Here, R 1 is hydrogen or a methyl group, R 2 and R 3 are hydrogen or an alkyl group having 1 to 4 carbon atoms, and n is an integer of 1 to 4.) Alkyl acrylate salt 0.2
This is a method for producing a vinyl chloride resin with excellent antistatic properties and thermal stability, which comprises graft copolymerizing up to 25 parts by weight. The vinyl chloride resin to be the backbone polymer used in the present invention is a vinyl chloride sole resin obtained by homopolymerization of vinyl chloride, a copolymer resin with other monomers copolymerizable with vinyl chloride, or a vinyl chloride resin obtained by homopolymerization of vinyl chloride, Although graft copolymer resins of vinyl and other resins are included, vinyl chloride sole resins obtained by homopolymerization of vinyl chloride are practically preferred. The degree of polymerization of the vinyl chloride resin to serve as the backbone polymer is suitably 500 to 5,000, preferably 800 to 1,500. Also,
It does not matter if it is produced by solution polymerization, bulk polymerization, aqueous suspension polymerization, aqueous emulsion polymerization, or the like. In general, preference is given to aqueous suspension polymerization. The aminoalkyl acrylate used in the present invention has the general formula
以下、実施例により本発明を説明する。
なお、実施例、比較例中に示される部は重量部
である。
実施例 １
懸濁重合法で得た重合度1050の塩化ビニルホモ
ポリマー100部、ジメチルアミノエチルメタクリ
レートにエチレンオキサイドとメチルクロライド
を反応させて得た塩10部、部分けん化ポリビニル
アルコール0.05部、２，2′−アゾビスイソブチロ
ニトリル0.3部を純水300部と共にオートクレーブ
に装入し、内部の空気を窒素で置換したのち、60
℃に昇温して反応を開始した。60℃で８時間反応
した後、オートクレーブから内容物を取出し、脱
水乾燥して粉末状の塩化ビニル系樹脂を得た。
得られた樹脂を後記の方法でプレスシートを作
成し、摩擦帯電圧および熱安定性を測定した。結
果を表に示す。
実施例 ２
アミノアルキルアクリレートの塩としてエチレ
ンオキサイドの代りにプロピレンオキサイドを用
いて得たジメチルアミノエチルアクリレートの塩
10部を用いる他は実施例１と同様にして塩化ビニ
ル系樹脂を得、プレスシートを作成して摩擦帯電
圧および熱安定性を測定した。結果を表に示す。
実施例 ３
アミノアルキルアクリレートの塩としてメチル
クロライドの代りにエチルクロライドを用いて得
たジメチルアミノエチルアクリレートの塩15部を
用いる他は実施例１と同様にして塩化ビニル系樹
脂を得、プレスシートを作成して摩擦帯電圧およ
び熱安定性を測定した。結果を表に示す。
実施例 ４
アミノアルキルアクリレートの塩として、メチ
ルクロライドの代りにジエチル硫酸を用いて得た
ジメチルアミノエチルアクリレートの塩５部を用
いる他は実施例１と同様にして塩化ビニル系樹脂
を得、プレスシートを作成して摩擦帯電圧および
熱安定性を測定した。結果を表に示す。
実施例 ５
アミノアルキルアクリレートの塩として、ジメ
チルアミノエチルアクリレートにメチルクロライ
ドを反応させて得た塩10部を用いる他は実施例１
と同様にして塩化ビニル系樹脂を得、プレスシー
トを作成して摩擦帯電圧および熱安定性を測定し
た。結果を表に示す。
実施例 ６
アミノアルキルアクリレートの塩として、ジメ
チルアミノエチルメタクリレートの過塩素酸塩５
部を用いる他は実施例１と同様にして塩化ビニル
系樹脂を得、プレスシートを作成して摩擦帯電圧
および熱安定性を測定した。結果を表に示す。
比較例 １
アミノアルキルアクリレートの塩の代りに、ジ
メチルアミノエチルアクリレート８部を用いる他
は実施例１と同様にして塩化ビニル系樹脂を得、
プレスシートを作成して摩擦帯電圧および熱安定
性を測定した。結果を表に示す。
本比較例では摩擦帯電圧は本発明と同等である
が、熱安定性に劣る。
比較例 ２
撹拌翼を装備したオートクレーブに脱イオン水
300部、ジメチルアミノエチルメタクリレートに
エチレンオキサイドとメチルクロライドを反応さ
せて得た塩7.5部、ヒドロキシプロピルメチルセ
ルローズ0.23部および２，2′−アゾビスイソブチ
ロニトリル0.15部を入れ、内部の空気を窒素で置
換した後、塩化ビニル140部を装入して激しく撹
拌しながら63℃にて、共重合反応を行なつた。15
時間後に重合機内圧が6.5Kg／cm2に低下したので
共重合反応を停止した。未反応塩化ビニルモノマ
ーを除去したのち、常法によりスラリーを脱水乾
燥し、白色粉末を得、プレスシートを作成して摩
擦帯電圧および熱安定性を測定した。結果を表に
示す。
本比較例のものは摩擦帯電圧、熱安定性共に優
れているが、熱安定性が本発明のものに比べやや
劣る。
比較例 ３
アミノアルキルアクリレートの塩の使用量を30
重量部と増す他は実施例１と同様にして塩化ビニ
ル系樹脂を得ようとしたが、反応がうまく進行せ
ず、途中で反応を中止した。
比較例 ４
アミノアルキルアクリレートの塩の使用量を
0.1重量部に減らす他は実施例１と同様にして塩
化ビニル系樹脂を得、プレスシートを作成して摩
擦帯電圧および熱安定性を測定した。結果を表に
示す。
本比較例のものでは、アミノアルキルアクリレ
ートの塩の量が不足し、ほとんど静電防止性がな
い。
比較例 ５
アミノアルキルアクリレートの塩を用いない他
は実施例１と同様の処理を行ない塩化ビニル樹脂
を回収した。回収した樹脂を用いプレスシートを
作成して摩擦帯電圧および熱安定性を測定した。
結果を表に示す。
摩擦帯電圧および熱安定性の測定
(1) 試料の作成：塩化ビニル系樹脂100部に有機
錫系安定剤（商品名ADVASTAB Ｔ−17MJ
東亜理化製）４部、ステアリン酸0.5部を添加
し、よく混合した後150℃でプレス成形して、
１mm厚のプレスシートを作製した。
(2) 摩擦帯電圧：ロータリースタチツクテスター
（興和商会製）を使用し、20℃にて60％相対湿
度の条件で綿布による摩擦３分後の帯電圧を測
定する。
なお、測定はプレスシート作成直後と、流水
中に２昼夜浸漬した後の２回である。
(3) 熱安定性（コンゴーレツド熱安定性）：JIS
Ｋ−6723による。
The present invention will be explained below with reference to Examples. Note that the parts shown in Examples and Comparative Examples are parts by weight. Example 1 100 parts of a vinyl chloride homopolymer with a degree of polymerization of 1050 obtained by suspension polymerization, 10 parts of a salt obtained by reacting dimethylaminoethyl methacrylate with ethylene oxide and methyl chloride, 0.05 part of partially saponified polyvinyl alcohol, 2. Charge 0.3 part of 2'-azobisisobutyronitrile into an autoclave together with 300 parts of pure water, replace the air inside with nitrogen, and then
The reaction was started by raising the temperature to °C. After reacting at 60° C. for 8 hours, the contents were taken out from the autoclave and dehydrated and dried to obtain a powdered vinyl chloride resin. A press sheet was prepared from the obtained resin by the method described below, and the frictional charging voltage and thermal stability were measured. The results are shown in the table. Example 2 Salt of dimethylaminoethyl acrylate obtained by using propylene oxide instead of ethylene oxide as the salt of aminoalkyl acrylate
A vinyl chloride resin was obtained in the same manner as in Example 1 except that 10 parts of the resin was used, a press sheet was prepared, and the frictional charging voltage and thermal stability were measured. The results are shown in the table. Example 3 A vinyl chloride resin was obtained in the same manner as in Example 1, except that 15 parts of a salt of dimethylaminoethyl acrylate obtained by using ethyl chloride instead of methyl chloride was used as the salt of aminoalkyl acrylate, and a press sheet was prepared. The frictional charging voltage and thermal stability were measured. The results are shown in the table. Example 4 A vinyl chloride resin was obtained in the same manner as in Example 1, except that 5 parts of the salt of dimethylaminoethyl acrylate obtained by using diethyl sulfate instead of methyl chloride was used as the aminoalkyl acrylate salt, and a press sheet was prepared. were prepared and their frictional charging voltage and thermal stability were measured. The results are shown in the table. Example 5 Example 1 except that 10 parts of a salt obtained by reacting dimethylaminoethyl acrylate with methyl chloride was used as the aminoalkyl acrylate salt.
A vinyl chloride resin was obtained in the same manner as above, a press sheet was prepared, and the frictional charging voltage and thermal stability were measured. The results are shown in the table. Example 6 Perchlorate of dimethylaminoethyl methacrylate 5 as a salt of aminoalkyl acrylate
A vinyl chloride-based resin was obtained in the same manner as in Example 1, except that 100% of the resin was used, a press sheet was prepared, and the frictional charging voltage and thermal stability were measured. The results are shown in the table. Comparative Example 1 A vinyl chloride resin was obtained in the same manner as in Example 1 except that 8 parts of dimethylaminoethyl acrylate was used instead of the aminoalkyl acrylate salt,
A pressed sheet was prepared and its frictional charging voltage and thermal stability were measured. The results are shown in the table. In this comparative example, the frictional charging voltage is equivalent to that of the present invention, but the thermal stability is inferior. Comparative Example 2 Deionized water in an autoclave equipped with stirring blades
Add 300 parts of dimethylaminoethyl methacrylate, 7.5 parts of a salt obtained by reacting ethylene oxide and methyl chloride, 0.23 parts of hydroxypropylmethylcellulose, and 0.15 parts of 2,2'-azobisisobutyronitrile, and remove the air inside. After purging with nitrogen, 140 parts of vinyl chloride was charged and a copolymerization reaction was carried out at 63° C. with vigorous stirring. 15
After some time, the internal pressure of the polymerization machine decreased to 6.5 Kg/cm 2 and the copolymerization reaction was stopped. After removing unreacted vinyl chloride monomer, the slurry was dehydrated and dried by a conventional method to obtain a white powder, a pressed sheet was prepared, and the frictional charging voltage and thermal stability were measured. The results are shown in the table. The product of this comparative example has excellent frictional charging voltage and thermal stability, but its thermal stability is slightly inferior to that of the present invention. Comparative Example 3 The amount of aminoalkyl acrylate salt used was 30
An attempt was made to obtain a vinyl chloride resin in the same manner as in Example 1 except that the weight part was increased, but the reaction did not proceed well and the reaction was stopped midway. Comparative example 4 The amount of aminoalkyl acrylate salt used
A vinyl chloride resin was obtained in the same manner as in Example 1, except that the amount was reduced to 0.1 part by weight, a pressed sheet was prepared, and the frictional charging voltage and thermal stability were measured. The results are shown in the table. In this comparative example, the amount of aminoalkyl acrylate salt was insufficient, and there was almost no antistatic property. Comparative Example 5 A vinyl chloride resin was recovered by carrying out the same treatment as in Example 1 except that the aminoalkyl acrylate salt was not used. A press sheet was made using the recovered resin, and its frictional charging voltage and thermal stability were measured.
The results are shown in the table. Measurement of frictional charging voltage and thermal stability (1) Preparation of sample: 100 parts of vinyl chloride resin and organic tin stabilizer (trade name: ADVASTAB T-17MJ)
Add 4 parts (manufactured by Toa Rika) and 0.5 part of stearic acid, mix well, and then press mold at 150℃.
A press sheet with a thickness of 1 mm was produced. (2) Friction charging voltage: Using a rotary static tester (manufactured by Kowa Shokai), measure the charging voltage after 3 minutes of friction with cotton cloth at 20°C and 60% relative humidity. The measurements were taken twice: immediately after the press sheet was created, and once after it had been immersed in running water for two days and nights. (3) Thermal stability (congoled thermal stability): JIS
According to K-6723.
本発明の方法で得られる塩化ビニル系樹脂は静
電防止性、熱安定性共に良好であり、工業的にそ
の価値は大きい。
The vinyl chloride resin obtained by the method of the present invention has good antistatic properties and good thermal stability, and is of great industrial value.
Claims (1)
R3は水素または炭素数１〜４のアルキル基であ
る。また、ｎは１〜４の整数である。） で示されるアミノアルキルアクリレートの塩0.2
〜25重量部をグラフト共重合することを特徴とす
る帯電防止性、熱安定性に優れた塩化ビニル系樹
脂の製造方法。[Scope of Claims] 1 100 parts by weight of vinyl chloride resin is added with the general formula [Chemical formula] (where R 1 is hydrogen or a methyl group, R 2 and
R 3 is hydrogen or an alkyl group having 1 to 4 carbon atoms. Moreover, n is an integer of 1-4. ) Salt of aminoalkyl acrylate represented by 0.2
A method for producing a vinyl chloride resin having excellent antistatic properties and thermal stability, which comprises graft copolymerizing up to 25 parts by weight.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17766185A JPS6239609A (en) | 1985-08-14 | 1985-08-14 | Production of vinyl chloride based resin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17766185A JPS6239609A (en) | 1985-08-14 | 1985-08-14 | Production of vinyl chloride based resin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6239609A JPS6239609A (en) | 1987-02-20 |
| JPH0576968B2 true JPH0576968B2 (en) | 1993-10-25 |
Family
ID=16034890
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17766185A Granted JPS6239609A (en) | 1985-08-14 | 1985-08-14 | Production of vinyl chloride based resin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6239609A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4773188B2 (en) * | 2005-12-05 | 2011-09-14 | ライオン株式会社 | Novel ether type compound and liquid softener composition containing the compound |
| JP4970019B2 (en) * | 2006-12-19 | 2012-07-04 | ライオン株式会社 | Hair cosmetics |
| US9441123B2 (en) | 2012-08-15 | 2016-09-13 | Penn Color, Inc. | Cationic water based polymers for ink, coating, and film applications |
| US9434849B2 (en) | 2012-10-19 | 2016-09-06 | Penn Color, Inc. | Water based anionic polymers for ink, coating, and film applications |
-
1985
- 1985-08-14 JP JP17766185A patent/JPS6239609A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6239609A (en) | 1987-02-20 |
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