JPS64961B2 - - Google Patents
Info
- Publication number
- JPS64961B2 JPS64961B2 JP5051681A JP5051681A JPS64961B2 JP S64961 B2 JPS64961 B2 JP S64961B2 JP 5051681 A JP5051681 A JP 5051681A JP 5051681 A JP5051681 A JP 5051681A JP S64961 B2 JPS64961 B2 JP S64961B2
- Authority
- JP
- Japan
- Prior art keywords
- ethylene
- cyanoethylated
- formula
- vinyl alcohol
- mol
- 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
- 229920000219 Ethylene vinyl alcohol Polymers 0.000 claims description 22
- RZXDTJIXPSCHCI-UHFFFAOYSA-N hexa-1,5-diene-2,5-diol Chemical class OC(=C)CCC(O)=C RZXDTJIXPSCHCI-UHFFFAOYSA-N 0.000 claims description 13
- 238000007278 cyanoethylation reaction Methods 0.000 claims description 12
- 229920001577 copolymer Polymers 0.000 claims description 11
- 230000001070 adhesive effect Effects 0.000 claims description 7
- 238000006116 polymerization reaction Methods 0.000 claims description 7
- 239000000853 adhesive Substances 0.000 claims description 5
- 239000003989 dielectric material Substances 0.000 claims description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 8
- 239000005977 Ethylene Substances 0.000 description 8
- 239000011521 glass Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 5
- 239000011888 foil Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 2
- 239000003990 capacitor Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RWPFLARVZWFRBO-DAIXLEOSSA-N (2R,3R)-2-(2,4-difluorophenyl)-1-(1,2,4-triazol-1-yl)butane-2,3-diol methanesulfonic acid Chemical compound CS(O)(=O)=O.C[C@@H](O)[C@](O)(Cn1cncn1)c1ccc(F)cc1F RWPFLARVZWFRBO-DAIXLEOSSA-N 0.000 description 1
- KXJGSNRAQWDDJT-UHFFFAOYSA-N 1-acetyl-5-bromo-2h-indol-3-one Chemical compound BrC1=CC=C2N(C(=O)C)CC(=O)C2=C1 KXJGSNRAQWDDJT-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000004715 ethylene vinyl alcohol Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229940100630 metacresol Drugs 0.000 description 1
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Adhesives Or Adhesive Processes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Insulating Materials (AREA)
Description
本発明はシアノエチル化樹脂に関する。更に詳
細にはエチレン−ビニルアルコール共重合体樹脂
をシアノエチル化することにより接着性および高
誘電率を賦与したシアノエチル化樹脂およびこの
樹脂を用いた誘電材料並びに接着剤に関する。
高分子物質の性質を変化させたり、新しい機能
を賦与する目的で各種の化学反応による改質が行
なわれている。アクリロニトリルを用いるシアノ
エチル化もその一つであり、最も代表的な例とし
てはシアノエチル化セルローズがある。シアノエ
チル化セルローズは各種の溶媒に対する溶解性
と、また高い誘電率を賦与されているので、分散
型エレクトロルミネセンス（EL）素子の発光体
のバインダーとして用いられ、またコンデンサー
フイルム等への用途も考えられている。しかしシ
アノエチルセルローズは種々の高分子や金属、ガ
ラス等への接着性に乏しく、これを単独若しくは
バインダーとして用いた成形物を誘電体材料とし
て使用する場合、電極とよく密着せず間隙を生じ
るため、その高誘電率が効果的に生かされない場
合なども屡々生じている。
本発明者等はエチレン−ビニルアルコール共重
合体のシアノエチル化を行ない、新規に得られた
シアノエチル化エチレン−ビニルアルコール共重
合体は、シアノエチル化セルローズに比しても極
めて高い誘電率を有し、また金属、ガラスは勿
論、例えば極めて他の樹脂との接着性に乏しいポ
リフツ化ビニリデンに極めて強い接着性を有する
ことを見出した。
以下本発明を詳述する。
本発明のシアノエチル化エチレン−ビニルアル
コール共重合体は、式−CH2−CH2−で示される
構造単位Ｙモル％（10Ｙ70）と、
The present invention relates to cyanoethylated resins. More specifically, the present invention relates to a cyanoethylated resin that is imparted with adhesive properties and a high dielectric constant by cyanoethylating an ethylene-vinyl alcohol copolymer resin, and to dielectric materials and adhesives using this resin. Modification through various chemical reactions is carried out to change the properties of polymeric substances or to impart new functions. Cyanoethylation using acrylonitrile is one of them, and the most typical example is cyanoethylated cellulose. Cyanoethylated cellulose is endowed with solubility in various solvents and a high dielectric constant, so it is used as a binder for the luminescent material of dispersed electroluminescence (EL) devices, and is also considered for use in capacitor films, etc. It is being However, cyanoethyl cellulose has poor adhesion to various polymers, metals, glass, etc., and when molded products using it alone or as a binder are used as dielectric materials, they do not adhere well to electrodes and create gaps. There are many cases where the high dielectric constant is not effectively utilized. The present inventors carried out cyanoethylation of ethylene-vinyl alcohol copolymer, and the newly obtained cyanoethylated ethylene-vinyl alcohol copolymer has an extremely high dielectric constant compared to cyanoethylated cellulose. It has also been found that it has extremely strong adhesiveness not only to metals and glass, but also to, for example, polyvinylidene fluoride, which has extremely poor adhesiveness to other resins. The present invention will be explained in detail below. The cyanoethylated ethylene-vinyl alcohol copolymer of the present invention has Y mol% (10Y70) of structural units represented by the formula -CH2 - CH2- ,
【式】で示される構造単位（100−Ｙ） （１−Ｘ／100）モル％（Ｘ：シアノエチル化率）と、 式Structural unit (100-Y) represented by [Formula] (1-X/100) mol% (X: cyanoethylation rate), formula
【式】で示される構造単位
（100−Ｙ）・Ｘ／100モル％とからなる線状に不規則
に配列した重合度500〜100000の共重合体であつ
て、エチレン−ビニルアルコール共重合体のシア
ノエチル化によつて得られる。
本発明で用いられるエチレンビニルアルコール
共重合体は通常酢酸ビニル−エチレンを共重合さ
せ、これをケン化することによつて得られる平均
重合度500乃至100000の高分子化合物である。こ
れらエチレン−ビニルアルコール共重合体のエチ
レン含量は任意のものが得られており、一般には
モル比で10％乃至70％であり、残り90％乃至30％
はビニルアルコールもしくは未ケン化の酢酸ビニ
ルである。酢酸ビニルのケン化度も任意である
が、一般には80％以上である。シアノエチル化率
Ｘは、シアノエチル化する前のエチレン−ビニル
アルコール共重合体分子中に含まれるOH基の数
をｍとし、エチレン−ビニルアルコール共重合体
がシアノエチル化反応後にシアノエチル化された
OH基の数をｎとするときＸ＝ｎ／ｍ×100（％）
で表わされる。シアノエチル化率は、その使用目
的、エチレン含量等によつて異なるが、エチレン
鎖が導入されている為必らずしもビニルアルコー
ル全部がシアノエチル化される必要はなく、少な
くとも10％以上シアノエチル化されたものであれ
ばよい。好ましくは30％以上である。
この様な範囲でシアノエチル化されたエチレン
−ビニルアルコール共重合体は、熱可塑性であ
り、このフイルムは極めて高い誘電率を有してい
る。
後の実施例でも明らかであるが、エチレン含量
32モル％、ビニルアルコール部へのシアノエチル
化度約90％のものは、1KHz、25℃での誘電率は
約20を示す。
本発明によるシアノエチル化されたエチレン−
ビニルアルコール共重合体の赤外線吸収曲線は第
１図（実施例１で得た共重合体）および第２図
（実施例２で得た共重合体）に示した通りであり、
原料のエチレン−ビニルアルコールの赤外線吸収
曲線（第３図）と比較して2250cm-1にＣ≡Ｎによ
る吸収の発現が生じること、3500cm-1付近のOH
による吸収スペクトルが減少すること、1100cm-1
付近のCOC（エーテル結合）による吸収スペクト
ルが増加することの点で異なる化学構造の化合物
の得られていることがわかる。
又、本発明によるシアノエチル化されたエチレ
ン−ビニルアルコール共重合体はエチレン鎖を有
する為熱溶融時の流動性にすぐれ、又、熱安定性
にも秀いでている。更に特筆すべきことは接着性
に優れていることである。例えば上述のシアノエ
チル化共重合体はガラスやアルミ板上にキヤスト
もしくは熱溶融させる場合、室温で強固に接着し
容易に剥離させることができない。
またこのシアノエチル化共重合体は水には不溶
であるが、例えばアセトン、メチルエチルケト
ン、ジメチルフオルムアミド、ジメチルアセトア
ミド、アクリロニトリル、ニトロメタンなどの極
性の溶媒に良く溶解するので、これらの溶媒の溶
液の状態で接着剤として使用されるのみならず、
またフイルム状に成形し、フイルム状接着剤とす
ることもできる。
以上本発明になるシアノエチル化樹脂はその高
誘電率、接着性、加工性に富んでおり、これ等の
特性を生かして例えばエレクトロルミネセンスの
バインダーや接着剤としてまたコンデンサ用フイ
ルムとして極めて有用である。
以下本発明を実施例で説明を加える。
実施例 １
クラレ製、エチレン−ビニルアルコール共重合
体（エバールEP−Ｆ、エチレン含量32モル％、
平均重合度1500、第３図に示す赤外線吸収曲線を
持つ）のフイルムを細かく裁断した後、この30ｇ
を苛性ソーダ0.6ｇを溶解した15c.c.の水とともに
リフラツクスコンデンサーの付いたフラスコに入
れ、50℃にバ温を保つた。
このフラスコの中にアクリロニトリル140ｇを
徐々に滴下し、フラスコ内を激しく撹拌させた。
90分後、フイルムは完全にアクリロニトリルに溶
解していた。このものを減圧下で未反応アクリロ
ニトリルを除去後、多量のアセトンに溶解させ、
これを多量の水中へ投入し、シアノエチル化エチ
レン−ビニルアルコール共重合体を析出させた。
メタノールで洗浄後、更にアセトン溶解水中再沈
を繰り返し、最後に60℃で真空乾燥させた。
こうして得られたシアノエチル化エチレン−ビ
ニルアルコール共重合体のジメチルアミド中溶液
（濃度４ｇ／）の30℃における粘度はηinh＝
0.65d／ｇ（ウベローデ氏粘度計により測定）
であり、窒素含有量（ヤナギモト社製、Ｃ−Ｎコ
ーダーMT−500により測定）は10.0重量％であ
り、シアノエチル化度（窒素含有量から計算）は
74.2％であつた。
本実施例におけるシアノエチル化エチレン−ビ
ニルアルコール共重合体を50μアルミ箔とテフロ
ン板内にはさみ、180℃でプレス成形したフイル
ムの誘電率を測定したところ、1KHz、25℃で
19.5の高い値を示した。
この共重合体はガラス、金属に対する接着性は
良好で例えばアセトン溶解させたこの共重合体を
ガラスに塗布後、80℃でアセトン除去したもの
は、ガラスに極めて良く接着しており、容易に剥
離させることができなかつた。又、アルミ板でも
同様であつた。上記フイルムの赤外線吸収曲線を
第１図に示す。
実施例 ２
エチレン−ビニルアルコール共重合体（クラレ
製、エバールEP−Ｅ、エチレン含量45モル％、
平均重合度1500）を80℃、メタクレゾールに溶解
させ、アセトン−メタノール混合溶媒中に粉末状
に析出させた。これをよく洗浄、乾燥させたもの
を実施例１と同様な方法でシアノエチル化させ、
シアノエチル化度約60％のシアノエチル化エチレ
ン−ビニルアルコール共重合体を得た。こうして
得られたシアノエチル化エチレン−ビニルアルコ
ール共重合体のジメチルアミド中溶液（濃度４
ｇ／）の30℃における粘度はηinh＝0.60d／
ｇ（ウベローデ氏粘度計により測定）であり、窒
素含有量（ヤナギモト社製、Ｃ−ＮコーダーMT
−500により測定）は10.0重量％であり、シアノ
エチル化度（窒素含有量から計算）は76.9％であ
つた。
このフイルムの誘電率（1KHz）は16を示し、
又、ガラス、金属に対する接着性は良好であり、
例えば100μ厚のAl箔間にて180℃で溶解プレス
し、Al箔を接着した試料はきわめて強い接着性
を示し、Al箔は容易に剥離せず、強いて剥離さ
せようとしたらAl箔が切断してしまつた。又、
熱安定性に優れており、100℃に１昼夜保存して
も何ら変化はなかつた。上記フイルムの赤外線吸
収曲線を第２図に示す。A copolymer with a degree of polymerization of 500 to 100,000, consisting of structural units (100-Y) and X/100 mol% represented by the formula, arranged irregularly in a linear manner, which is an ethylene-vinyl alcohol copolymer. obtained by cyanoethylation of The ethylene vinyl alcohol copolymer used in the present invention is usually a polymer compound having an average degree of polymerization of 500 to 100,000, which is obtained by copolymerizing vinyl acetate and ethylene and saponifying the copolymer. These ethylene-vinyl alcohol copolymers have an arbitrary ethylene content, and are generally 10% to 70% in molar ratio, with the remaining 90% to 30%.
is vinyl alcohol or unsaponified vinyl acetate. The degree of saponification of vinyl acetate is also arbitrary, but is generally 80% or more. The cyanoethylation rate
When the number of OH groups is n, X=n/m×100(%)
It is expressed as The cyanoethylation rate varies depending on the purpose of use, ethylene content, etc., but since an ethylene chain has been introduced, it is not necessarily necessary that all of the vinyl alcohol be cyanoethylated, but at least 10% or more. It is fine as long as it is. Preferably it is 30% or more. The ethylene-vinyl alcohol copolymer that has been cyanoethylated in such a range is thermoplastic, and the film has an extremely high dielectric constant. As is clear from the later examples, the ethylene content
A material with a degree of cyanoethylation of 32 mol% and vinyl alcohol moiety of about 90% exhibits a dielectric constant of about 20 at 1 KHz and 25°C. Cyanoethylated ethylene according to the invention
The infrared absorption curves of the vinyl alcohol copolymer are as shown in Figure 1 (copolymer obtained in Example 1) and Figure 2 (copolymer obtained in Example 2),
Compared to the infrared absorption curve of raw material ethylene-vinyl alcohol (Figure 3), absorption due to C≡N occurs at 2250 cm -1 and OH near 3500 cm -1
The absorption spectrum decreases due to 1100 cm -1
It can be seen that compounds with different chemical structures have been obtained in that the absorption spectrum due to nearby COC (ether bond) increases. In addition, the cyanoethylated ethylene-vinyl alcohol copolymer of the present invention has an ethylene chain, so it has excellent fluidity during hot melting and also has excellent thermal stability. What is also noteworthy is that it has excellent adhesive properties. For example, when the above-mentioned cyanoethylated copolymer is cast or heat-fused on a glass or aluminum plate, it adheres strongly at room temperature and cannot be easily peeled off. Although this cyanoethylated copolymer is insoluble in water, it dissolves well in polar solvents such as acetone, methyl ethyl ketone, dimethyl formamide, dimethyl acetamide, acrylonitrile, and nitromethane, so it can be used in the form of solutions of these solvents. Not only is it used as an adhesive, but
Alternatively, it can be formed into a film to form a film adhesive. As described above, the cyanoethylated resin of the present invention is rich in high dielectric constant, adhesiveness, and processability, and by taking advantage of these properties, it is extremely useful, for example, as a binder or adhesive for electroluminescence, or as a film for capacitors. . The present invention will be explained below with reference to Examples. Example 1 Ethylene-vinyl alcohol copolymer (Eval EP-F, ethylene content 32 mol%, manufactured by Kuraray)
After cutting the film (with an average degree of polymerization of 1500 and an infrared absorption curve shown in Figure 3) into pieces, 30 g of this film was cut into pieces.
was placed in a flask equipped with a reflux condenser together with 15 c.c. of water in which 0.6 g of caustic soda had been dissolved, and the temperature was maintained at 50°C. 140 g of acrylonitrile was gradually dropped into this flask, and the inside of the flask was vigorously stirred.
After 90 minutes, the film was completely dissolved in acrylonitrile. After removing unreacted acrylonitrile from this product under reduced pressure, it was dissolved in a large amount of acetone.
This was poured into a large amount of water to precipitate a cyanoethylated ethylene-vinyl alcohol copolymer.
After washing with methanol, reprecipitation in acetone-dissolved water was repeated, and finally vacuum drying was performed at 60°C. The viscosity at 30°C of the thus obtained solution of the cyanoethylated ethylene-vinyl alcohol copolymer in dimethylamide (concentration 4 g/) is ηinh=
0.65d/g (measured by Ubbelohde's viscometer)
The nitrogen content (measured using C-N Coder MT-500 manufactured by Yanagimoto Co., Ltd.) is 10.0% by weight, and the degree of cyanoethylation (calculated from the nitrogen content) is
It was 74.2%. The cyanoethylated ethylene-vinyl alcohol copolymer in this example was sandwiched between 50μ aluminum foil and a Teflon plate, and the dielectric constant of the film was press-formed at 180℃.
It showed a high value of 19.5. This copolymer has good adhesion to glass and metal. For example, if you apply this copolymer dissolved in acetone to glass and then remove the acetone at 80℃, it will adhere extremely well to glass and be easily peeled off. I couldn't let it go. The same was true for aluminum plates. The infrared absorption curve of the above film is shown in FIG. Example 2 Ethylene-vinyl alcohol copolymer (manufactured by Kuraray, EVAL EP-E, ethylene content 45 mol%,
(average degree of polymerization 1500) was dissolved in metacresol at 80°C and precipitated into a powder in an acetone-methanol mixed solvent. This was thoroughly washed and dried, and then cyanoethylated in the same manner as in Example 1.
A cyanoethylated ethylene-vinyl alcohol copolymer having a degree of cyanoethylation of about 60% was obtained. A solution of the cyanoethylated ethylene-vinyl alcohol copolymer thus obtained in dimethylamide (concentration 4
The viscosity of g/) at 30℃ is ηinh=0.60d/
g (measured using Ubbelohde's viscometer), and nitrogen content (C-N Coder MT, manufactured by Yanagimoto Co., Ltd.).
-500) was 10.0% by weight, and the degree of cyanoethylation (calculated from the nitrogen content) was 76.9%. The dielectric constant (1KHz) of this film is 16,
In addition, it has good adhesion to glass and metal,
For example, a sample that was melt-pressed between 100 μ thick Al foils at 180°C and bonded with Al foil showed extremely strong adhesion, and the Al foil did not peel off easily, and if you tried to force it to peel off, the Al foil would break. It was. or,
It has excellent thermal stability, and no change occurred even if it was stored at 100°C for one day and night. The infrared absorption curve of the above film is shown in FIG.
第１図は実施例１で製造したシアノエチル化エ
チレン−ビニルアルコール共重合体の赤外線吸収
曲線図であり、第２図は実施例２で製造したシア
ノエチル化エチレン−ビニルアルコール共重合体
の吸収曲線図であり、第３図は実施例１で使用し
た原料エチレン−ビニルアルコール共重合体の赤
外線吸収曲線図である。
FIG. 1 is an infrared absorption curve diagram of the cyanoethylated ethylene-vinyl alcohol copolymer produced in Example 1, and FIG. 2 is an absorption curve diagram of the cyanoethylated ethylene-vinyl alcohol copolymer produced in Example 2. FIG. 3 is an infrared absorption curve diagram of the raw material ethylene-vinyl alcohol copolymer used in Example 1.
Claims (1)
％（10Ｙ70）と、式【式】で示さ れる構造単位（100−Ｙ）（１−Ｘ／100）モル％ （Ｘ：シアノエチル化率）と、式
【式】で示される構造単位 （100−Ｙ）・Ｘ／100モル％とからなる線状に不規則 に配列した重合度500〜100000のシアノエチル化
エチレン−ビニルアルコール共重合体。 ２ シアノエチル化率Ｘが10％以上である特許請
求の範囲第１項に記載の共重合体。 ３ 式−CH2−CH2−で示される構造単位Ｙモル
％（10Ｙ70）と、式【式】で示さ れる構造単位（100−Ｙ）（１−Ｘ／100）モル％ （Ｘ：シアノエチル化率）と、式
【式】で示される構造単位 （100−Ｙ）・Ｘ／100モル％とからなる線状に不規則 に配列した重合度500〜100000のシアノエチル化
エチレン−ビニルアルコール共重合体からなる誘
電体材料。 ４ 式−CH2−CH2−で示される構造単位Ｙモル
％（10Ｙ70）と、式【式】で示さ れる構造単位（100−Ｙ）（１−Ｘ／100）モル％ （Ｘ：シアノエチル化率）と、式
【式】で示される構造単位 （100−Ｙ）・Ｘ／100モル％とからなる線状に不規則 に配列した重合度500〜100000のシアノエチル化
エチレン−ビニルアルコール共重合体からなる接
着剤。[Claims] 1 Y mol% (10Y70) of the structural unit represented by the formula -CH 2 -CH 2 - and (100-Y) (1-X/100) mol of the structural unit represented by the formula [Formula] % (X: cyanoethylation rate) and a structural unit (100-Y) represented by the formula [Formula] X/100 mol% Cyanoethylated ethylene with a degree of polymerization of 500 to 100,000 arranged irregularly in a linear manner -Vinyl alcohol copolymer. 2. The copolymer according to claim 1, wherein the cyanoethylation rate X is 10% or more. 3 Structural unit Y mol% (10Y70) represented by the formula -CH 2 -CH 2 - and structural unit (100-Y) (1-X/100) mol% (X: cyanoethylated cyanoethylated ethylene-vinyl alcohol copolymer with a degree of polymerization of 500 to 100,000 and randomly arranged in a linear manner, consisting of a structural unit (100-Y)/X/100 mol% represented by the formula [formula] A dielectric material made of 4 Structural unit Y mol% (10Y70) represented by the formula -CH 2 -CH 2 - and structural unit (100-Y) (1-X/100) mol% (X: cyanoethylated cyanoethylated ethylene-vinyl alcohol copolymer with a degree of polymerization of 500 to 100,000 and randomly arranged in a linear manner, consisting of a structural unit (100-Y)/X/100 mol% represented by the formula [formula] adhesive consisting of.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5051681A JPS57165406A (en) | 1981-04-06 | 1981-04-06 | Cyanoethylated ethylene-vinyl alcoholic copolymer and dielectric material and adhesive made therefrom |
| EP19820102946 EP0062351B1 (en) | 1981-04-06 | 1982-04-06 | Cyanoethylated olefin-vinyl alcohol copolymer and dielectric material and adhesive comprising the same |
| DE8282102946T DE3265547D1 (en) | 1981-04-06 | 1982-04-06 | Cyanoethylated olefin-vinyl alcohol copolymer and dielectric material and adhesive comprising the same |
| US06/366,031 US4413090A (en) | 1981-04-06 | 1982-04-06 | Cyanoethylated olefin-vinyl alcohol copolymer and dielectric material and adhesive comprising the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5051681A JPS57165406A (en) | 1981-04-06 | 1981-04-06 | Cyanoethylated ethylene-vinyl alcoholic copolymer and dielectric material and adhesive made therefrom |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57165406A JPS57165406A (en) | 1982-10-12 |
| JPS64961B2 true JPS64961B2 (en) | 1989-01-10 |
Family
ID=12861130
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5051681A Granted JPS57165406A (en) | 1981-04-06 | 1981-04-06 | Cyanoethylated ethylene-vinyl alcoholic copolymer and dielectric material and adhesive made therefrom |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57165406A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60260333A (en) * | 1984-06-08 | 1985-12-23 | 平岡織染株式会社 | Heat-seal sewing-able waterproof sheet and sewing method thereof |
| JPS6132753A (en) * | 1984-07-26 | 1986-02-15 | 平岡織染株式会社 | Heat-fusing sewing-able waterproof sheet and sewing method thereof |
| KR102405288B1 (en) | 2019-01-22 | 2022-06-07 | 주식회사 엘지화학 | Vinyl alcohol based copolymer, method for preparing the same and gas barrier film comprising the same |
-
1981
- 1981-04-06 JP JP5051681A patent/JPS57165406A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57165406A (en) | 1982-10-12 |
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