JPH0717726B2 - Adhesive resin composition - Google Patents
Adhesive resin compositionInfo
- Publication number
- JPH0717726B2 JPH0717726B2 JP1324635A JP32463589A JPH0717726B2 JP H0717726 B2 JPH0717726 B2 JP H0717726B2 JP 1324635 A JP1324635 A JP 1324635A JP 32463589 A JP32463589 A JP 32463589A JP H0717726 B2 JPH0717726 B2 JP H0717726B2
- Authority
- JP
- Japan
- Prior art keywords
- vinyl acetate
- acetate copolymer
- partially saponified
- chlorinated
- chlorinated ethylene
- 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
Landscapes
- Adhesives Or Adhesive Processes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Adhesive Tapes (AREA)
- Polyurethanes Or Polyureas (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は、各種のプラスチックフィルム、例えばポリプ
ロピレンフィルム，ポリエステルフィルム，ポリエチレ
ンフィルムに対し優れた密着性を有する接着性樹脂組成
物に関する。更に詳しくは、エチレン−酢酸ビニル共重
合体を塩素化した後にけん化して水酸基を導入した部分
ケン化塩素化エチレン−酢酸ビニル共重合体（以下、部
分ケン化塩素化EVAと略す）と、ポリイソシアネート化
合物を混合して成る接着性樹脂組成物に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to an adhesive resin composition having excellent adhesion to various plastic films such as polypropylene film, polyester film and polyethylene film. More specifically, a partially saponified chlorinated ethylene-vinyl acetate copolymer (hereinafter abbreviated as partially saponified chlorinated EVA) in which an ethylene-vinyl acetate copolymer is chlorinated and then saponified to introduce a hydroxyl group, The present invention relates to an adhesive resin composition obtained by mixing an isocyanate compound.
近年、包装材料としてのプラスチックフィルムは包装内
容物の複雑化、包装技術の高度化に伴ない、各種のもの
が開発され、その結果内容物に適合しうるフィルムを選
択して使用されるようになった。かかる包装形態等の変
化により、例えば包装材料の高性能化のため印刷後にド
ライラミネート加工、エクストルージョンラミネート加
工などが行なわれるようになった。In recent years, various types of plastic films have been developed as the packaging material has become more complicated and the packaging technology has become more sophisticated, and as a result, the film suitable for the content should be selected and used. became. Due to such changes in the packaging form and the like, dry lamination, extrusion lamination, and the like have come to be performed after printing in order to improve the performance of packaging materials.
従来、プラスチックフィルム印刷インキ組成物のバイン
ダー成分として、ロジン変性マレイン酸樹脂，硝化綿，
ポリアミド樹脂，塩素化ポリプロピレン，ポリウレタン
樹脂，塩化ビニル−酢酸ビニル共重合樹脂，ポリエステ
ル樹脂などが単独又は混合して使用されているが，被印
刷物としてのポリプロピレン，ポリエステル及びポリエ
チレンのいずれのフィルムに対しても優れた密着性を有
するものはない。そのため必然的に使用されるフィルム
の特性に合致するインキが個々に設計されねばならず、
これらのインキの種類は多岐にわたっている。Conventionally, as a binder component of a plastic film printing ink composition, rosin-modified maleic acid resin, nitrified cotton,
Polyamide resin, chlorinated polypropylene, polyurethane resin, vinyl chloride-vinyl acetate copolymer resin, polyester resin, etc. are used alone or as a mixture, but for any film of polypropylene, polyester or polyethylene as a printing material There is no one with excellent adhesion. Therefore, inks that necessarily match the characteristics of the film used must be designed individually,
There are various types of these inks.
一般に、ポリプロピレンフィルム用には、塩素化ポリプ
ロピレンなどの比較的低塩素化度の塩素化ポリオレフィ
ン樹脂を用いた印刷インキが使用されているが、ポリエ
ステルフィルムやナイロンフィルムの様な極性フィルム
に対しては十分な接着性がないため好適ではない。Generally, for polypropylene films, printing inks using chlorinated polyolefin resins with a relatively low degree of chlorination such as chlorinated polypropylene are used, but for polar films such as polyester films and nylon films It is not suitable because it does not have sufficient adhesiveness.
ポリエステルフィルム用には、熱可塑性ポリエステル樹
脂がバインダーとして使用されているが、このものは乾
燥性に劣り、ブロッキングなどのトラブルも生じやすく
印刷速度が著しく低下するため印刷物の生産性に劣る。For polyester films, a thermoplastic polyester resin is used as a binder, but this is inferior in drying property, troubles such as blocking are likely to occur, and the printing speed is remarkably reduced, resulting in inferior productivity of printed matter.
またポリエステルフィルム、ナイロンフィルムの双方に
使用するインキとして塩化ビニル−酢酸ビニル共重合樹
脂と熱可塑性ポリウレタン樹脂とを組合わせたものをバ
インダーとして使用する場合もあるが、ラミネート強度
が尚、不充分であり、より高性能のインキの開発が要望
されている。In some cases, a combination of a vinyl chloride-vinyl acetate copolymer resin and a thermoplastic polyurethane resin is used as a binder as an ink for both polyester film and nylon film, but the lamination strength is still insufficient. There is a demand for the development of higher performance inks.
一方、インキバインダーには、接着性の他に、顔料の分
散性，顔料の発色性，光沢性などインキ化適正に良好な
ものが要求される。従来から使用されている塩素化EVA
は顔料の分散性，発色性，光沢性などはすぐれている
が、接着力が十分でないため、特開昭53−104579に示さ
れる様に、塩素化ポリプロピレンを含有させて使用され
ているが、これも対象フィルムは主としてポリプロピレ
ンフィルムに限られる。また各種フィルムへの接着性を
改善したものに特開昭48−34934や特開昭56−109267,特
開昭57−46870にEVAをケン化したものにイソシアネート
等を添加した例がみられるが、常温硬化型ではなく、又
顔料分散性に劣るなどインキ化適性は良くない。On the other hand, the ink binder is required to have good dispersibility of the pigment, color developability of the pigment, glossiness, and the like, which are suitable for use as an ink, in addition to the adhesiveness. Conventionally used chlorinated EVA
Has excellent dispersibility, color developability, glossiness, etc. of the pigment, but since the adhesive strength is not sufficient, it is used by incorporating chlorinated polypropylene as shown in JP-A-53-104579. Also in this case, the target film is mainly limited to the polypropylene film. In addition, examples of improved adhesiveness to various films include JP48-34934A, JP56-109267A, JP57-46870A, and saponified EVA to which isocyanate or the like is added. However, it is not a room temperature curable type, and its pigment dispersibility is poor, and its suitability for ink formation is not good.
本発明は従来技術で解決しえなかった問題点、即ち被印
刷物としてのポリプロピレン，ポリエステル，ポリエチ
レン等のいずれのプラスチックフィルムに対しても、常
温乾燥で優れた密着性を有し、かつ顔料分散性，発色
性，光沢性などのインキ化適性の優れた印刷インキのバ
インダー樹脂として有用な、また各種ラミネーション用
の接着用樹脂としても有用な材料を提供しようとするも
のである。The present invention has a problem that cannot be solved by the prior art, that is, it has excellent adhesion to a plastic film such as polypropylene, polyester or polyethylene as an object to be printed when dried at room temperature and has a pigment dispersibility. The present invention intends to provide a material which is useful as a binder resin for a printing ink which is excellent in inkability such as color developability and glossiness, and also as an adhesive resin for various laminations.
部分ケン化塩素化EVAとポリイソシアネート化合物を、
部分ケン化塩素化EVAの水酸基当量に対するポリイソシ
アネート化合物のイソシアネート基当量が特定の割合に
なるように混合すると各種の基材に対して優れた接着性
を有することを見い出し本発明に到達した。Partially saponified and chlorinated EVA and polyisocyanate compound,
The inventors have found that when mixed so that the isocyanate group equivalent of the polyisocyanate compound with respect to the hydroxyl group equivalent of partially saponified chlorinated EVA has a specific ratio, it has excellent adhesiveness to various base materials and arrived at the present invention.
すなわち本発明は酢酸ビニル含有量が５〜20mol％のエ
チレン−酢酸ビニル共重合体（EVA）を塩素化して得ら
れる塩素化EVA（塩素化度５〜45wt％）をケン化して得
られる、ポリビニルアルコール含有量が0.1〜10mol％の
部分ケン化塩素化EVAと、ポリイソシアネート化合物か
らなり、部分ケン化塩素化EVAの水酸基当量に対するポ
リイソシアネート化合物のイソシアネート基当量の割合
［NCO］／［OH］が0.05〜１である接着性の優れた接着
性樹脂組成物を提供するものである。That is, the present invention is obtained by saponifying a chlorinated EVA (chlorination degree of 5 to 45 wt%) obtained by chlorinating an ethylene-vinyl acetate copolymer (EVA) having a vinyl acetate content of 5 to 20 mol%. Consisting of partially saponified chlorinated EVA with an alcohol content of 0.1 to 10 mol% and a polyisocyanate compound, and the ratio of the isocyanate group equivalent of the polyisocyanate compound to the hydroxyl group equivalent of the partially saponified chlorinated EVA.
The present invention provides an adhesive resin composition having an [NCO] / [OH] of 0.05 to 1 and excellent in adhesiveness.
本発明で使用される部分ケン化塩素化EVAは、EVAを塩素
化して得られる塩素化EVAをトルエン，ベンゼン，メタ
ノール，エタノール等の有機溶剤に溶解あるいは懸濁さ
せた塩素化EVAを酸またはアルカリにより公知の方法で
ケン化する。例えば、塩素化EVAをトルエン／エタノー
ル＝3/1（重量比）に溶解し、水酸化カリウムでケン化
する。反応終了した部分ケン化塩素化EVAはメタノール
を除去した後所定濃度に調整する。また溶媒を完全に除
去し固形化することもできる。The partially saponified chlorinated EVA used in the present invention is a chlorinated EVA obtained by dissolving or suspending a chlorinated EVA obtained by chlorinating EVA in an organic solvent such as toluene, benzene, methanol, or ethanol. According to a known method. For example, chlorinated EVA is dissolved in toluene / ethanol = 3/1 (weight ratio) and saponified with potassium hydroxide. After the reaction, the partially saponified chlorinated EVA is adjusted to a predetermined concentration after removing methanol. It is also possible to completely remove the solvent and solidify.
なお、本発明で使用される塩素化EVAは、酢酸ビニル含
有量５〜20mol％のものを塩素化して得られる塩素化EVA
が使用される。その塩素化度は５〜45％が好適である。The chlorinated EVA used in the present invention is a chlorinated EVA obtained by chlorinating a vinyl acetate content of 5 to 20 mol%.
Is used. The degree of chlorination is preferably 5 to 45%.
酢酸ビニル含有量が上記の範囲外のものは、ポリプロピ
レン，ポリエステル，ポリエチレンのいずれかのフィル
ムへ接着力が低くなる。また、塩素化度が上記範囲外の
ものは、溶剤への溶解性が低下し、インキ化適性にも劣
る。If the vinyl acetate content is out of the above range, the adhesive strength to the polypropylene, polyester or polyethylene film is low. If the degree of chlorination is outside the above range, the solubility in a solvent is lowered and the suitability for ink formation is also poor.
本発明に使用されるイソシアネート化合物としては水酸
基と反応する少なくとも２個のイソシアネート基を含有
するジイソシアネート，トリイソシアネートなどのポリ
イソシアネートを用いる。たとえば、ヘキサメチレンン
ジイソシアネート，イソホロンジイソシアネート，ジフ
ェニルメタンジイソシアネート，トルエンジイソシアネ
ート，メチレンジイソシアネートなどのジイソシアネー
ト又は、これらの２〜３量化したポリイソシアネートが
用いられる。As the isocyanate compound used in the present invention, a polyisocyanate such as diisocyanate or triisocyanate containing at least two isocyanate groups that react with hydroxyl groups is used. For example, diisocyanates such as hexamethylene diisocyanate, isophorone diisocyanate, diphenylmethane diisocyanate, toluene diisocyanate, methylene diisocyanate or polyisocyanates obtained by dimerizing these diisocyanates are used.
部分ケン化塩素化EVAの水酸基当量に対するポリイソシ
アネート化合物のイソシアネート基当量の割合［NCO］
／［OH］が0.05〜１が好ましい。この範囲外のものは基
材との接着性が十分でない。Ratio of isocyanate group equivalent of polyisocyanate compound to hydroxyl group equivalent of partially saponified chlorinated EVA [NCO]
/ [OH] is preferably 0.05 to 1. Those outside this range do not have sufficient adhesion to the substrate.
本発明の効果は部分ケン化による水酸基の導入によっ
て、水酸基と基材との相互作用が生まれ、密着力が増大
し、且つイソシアネート化合物とエチレン−酢酸ビニル
共重合体を塩素化した後にケン化して水酸基を導入した
部分ケン化塩素化EVAの水酸基、および基材とが反応し
て、三次元構造を形成して優れた接着力を有するように
なったため発揮されたと考えられる。The effect of the present invention is that by introducing a hydroxyl group by partial saponification, interaction between the hydroxyl group and the base material is generated, the adhesion is increased, and the isocyanate compound and the ethylene-vinyl acetate copolymer are chlorinated and then saponified. It is considered that this was exhibited because the hydroxyl group of the partially saponified chlorinated EVA having the hydroxyl group introduced and the base material reacted with each other to form a three-dimensional structure and have excellent adhesive force.
以下実施例により本発明を更に説明するが、本発明はこ
れに限定されるものではない。The present invention will be further described below with reference to examples, but the present invention is not limited thereto.
実施例 １）ケン化方法 EVAを塩素化して得られる塩素化EVAをトルエン−メタノ
ール混合溶液（メタノールの混合比30vol％）にして、
触媒にKOHを用い、温度70℃でケン化した。Example 1) Saponification method A chlorinated EVA obtained by chlorinating EVA was made into a toluene-methanol mixed solution (mixing ratio of methanol 30 vol%),
KOH was used as a catalyst and saponification was performed at a temperature of 70 ° C.
実施例１ 酢酸ビニル含有量11.2mol％の塩素化EVA（塩素化度18wt
％ スーパークロンBX,山陽国策パイプ社製）を上記の
方法でケン化して得られたビニルアルコール含有量1.5m
ol％の部分ケン化塩素化EVAとポリイソシアネート化合
物（スミジュール N3500,住友バイエルウレタン社製）
を［NCO］／［OH］比0.5となるように配合した。Example 1 Chlorinated EVA with a vinyl acetate content of 11.2 mol% (chlorination degree 18 wt
% Super Clon BX, manufactured by Sanyo Kokusaku Pipe Co., Ltd., saponified by the above method, vinyl alcohol content 1.5m
ol% partially saponified and chlorinated EVA and polyisocyanate compound (Sumijour N3500, Sumitomo Bayer Urethane Co.)
Was blended so that the [NCO] / [OH] ratio was 0.5.
上記のようにして得られた樹脂45部に酸化チタン30部を
加えて練肉し、印刷インキを製造した。To 45 parts of the resin obtained as described above, 30 parts of titanium oxide was added and kneaded to prepare a printing ink.
同様な手順，配合で実施例2,3及び比較例を行なった。Examples 2 and 3 and a comparative example were performed with the same procedure and formulation.
評価方法は次の通りである。The evaluation method is as follows.
１）接着性 OPPフィルム（東レ製，トレファン T2535）、PETフィ
ルム（東洋紡製,E−5100）HDPEフィルム（大倉工業
（株）製）に塗布したものを１日放置後、セロハンテー
プをはりつけ、これを急速にはがしたとき、全くはがれ
なかったものを◎、80％以上フィルムに残ったものを
○、50〜80％残ったものを△、50％以下にとどまったも
のを×として表示した。1) Adhesive OPP film (Toray, Trefan T2535), PET film (Toyobo, E-5100) HDPE film (Okura Kogyo Co., Ltd.) was applied, left for 1 day, and then attached with cellophane tape. When this was rapidly peeled off, those that did not come off at all were marked as ◎, those that remained in the film by 80% or more were marked as ○, those that remained 50 to 80% were marked as △, and those that remained below 50% were marked as ×. .
２）ヒートシール強度 上記フィルムに塗布したものを１日放置後、塗工面を重
ね、ヒートシーラーを用いて90〜110℃,1秒,1kg/cm2の
条件で熱圧着し、180℃の角度50mm/minの引張り速度で
評価した。2) Heat-sealing strength After leaving the above film coated for 1 day, the coated surfaces are overlapped and thermocompression-bonded using a heat sealer under the conditions of 90-110 ° C, 1 second, 1kg / cm 2 , and an angle of 180 ° C. It was evaluated at a pulling speed of 50 mm / min.
インキ化適性 ３）（ａ）光沢度 光沢度計をもちいて塗布面の光の反射率を測定した。Inkability 3) (a) Glossiness The light reflectance of the coated surface was measured using a gloss meter.
（ｂ）顔料分散性 印刷インキ製造後、顔料の沈降等が見られず、またフィ
ルム上への塗布後、発色性等の優れたものを◎、印刷に
支障のない程度のものを○、適性のないものを×とし
た。(B) Pigment dispersibility After production of the printing ink, no precipitation of the pigment is observed, and after coating on the film, excellent color development is indicated by ⊚, and those that do not interfere with printing are indicated by ○, aptitude Those with no mark were marked with x.
〔発明の効果〕 以上実施例に示したように、エチレン−酢酸ビニル共重
合体を塩素化した後にケン化して水酸基を導入した部分
ケン化塩素化EVAとイソシアネート化合物とを配合する
ことにより、OPP,PET,HDPEのフィルムに対する接着性，
密着性に優れ、インキ化適性にも優れた組成物が得ら
れ、本発明を完成した。 [Effect of the invention] As shown in the above examples, by blending a partially saponified chlorinated EVA in which an ethylene-vinyl acetate copolymer is chlorinated and then saponified to introduce a hydroxyl group and an isocyanate compound, OPP , PET, HDPE film adhesion,
A composition having excellent adhesion and excellent suitability for ink formation was obtained, thus completing the present invention.
Claims (5)
た後に、ケン化して水酸基を導入した分子中に少なくと
も１個の水酸基を有する部分ケン化塩素化エチレン−酢
酸ビニル共重合体及び分子中に少なくとも２個の遊離イ
ソシアネート基を有するポリイソシアネート化合物を含
むことを特徴とする接着性樹脂組成物。1. A partially saponified chlorinated ethylene-vinyl acetate copolymer having at least one hydroxyl group in a molecule obtained by chlorinating an ethylene-vinyl acetate copolymer and then saponifying the same to give a hydroxyl group. An adhesive resin composition, wherein the polyisocyanate compound having at least two free isocyanate groups is contained in.
合体の水酸基に対するポリイソシアネート化合物のイソ
シアネート基当量の割合［NCO］／［OH］が0.05〜１で
ある請求項１記載の組成物。2. The composition according to claim 1, wherein the ratio [NCO] / [OH] of the isocyanate group equivalent of the polyisocyanate compound to the hydroxyl groups of the partially saponified chlorinated ethylene vinyl acetate copolymer is 0.05 to 1.
合体のビニルアルコール含有量が0.1〜10mol％である請
求項１記載の組成物。3. The composition according to claim 1, wherein the vinyl alcohol content of the partially saponified chlorinated ethylene vinyl acetate copolymer is 0.1 to 10 mol%.
合体の塩素化度が５〜45wt％、酢酸ビニル含有量が５〜
20mol％である請求項１記載の組成物。4. A partially saponified chlorinated ethylene vinyl acetate copolymer having a chlorination degree of 5 to 45 wt% and a vinyl acetate content of 5 to 5.
The composition according to claim 1, which is 20 mol%.
ン−酢酸ビニル共重合体を塩素化した塩素化度が５〜45
％の塩素化エチレン−酢酸ビニル共重合体をケン化して
得られる、ビニルアルコール含有量が0.1〜10mol％の部
分ケン化塩素化エチレン−酢酸ビニル共重合体と、部分
ケン化塩素化エチレン−塩酸ビニル共重合体の水酸基に
対するポリイソシアネート化合物のイソシアネート基当
量の割合［NCO］／［OH］が0.05〜１であるポリイソシ
アネート化合物からなる請求項１記載の組成物。5. An ethylene-vinyl acetate copolymer having a vinyl acetate content of 5 to 20 mol% and having a chlorination degree of 5 to 45.
% Of chlorinated ethylene-vinyl acetate copolymer obtained by saponification, vinyl alcohol content of 0.1-10 mol% partially saponified chlorinated ethylene-vinyl acetate copolymer and partially saponified chlorinated ethylene-hydrochloric acid The composition according to claim 1, comprising a polyisocyanate compound having a ratio [NCO] / [OH] of the isocyanate group equivalent of the polyisocyanate compound to the hydroxyl groups of the vinyl copolymer of 0.05 to 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1324635A JPH0717726B2 (en) | 1989-12-14 | 1989-12-14 | Adhesive resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1324635A JPH0717726B2 (en) | 1989-12-14 | 1989-12-14 | Adhesive resin composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03185087A JPH03185087A (en) | 1991-08-13 |
| JPH0717726B2 true JPH0717726B2 (en) | 1995-03-01 |
Family
ID=18168032
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1324635A Expired - Fee Related JPH0717726B2 (en) | 1989-12-14 | 1989-12-14 | Adhesive resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0717726B2 (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013253192A (en) * | 2012-06-08 | 2013-12-19 | Tosoh Corp | Two-component polyurethane-based adhesive, laminate using the same, and protective sheet for solar battery |
| JP5998660B2 (en) * | 2012-06-08 | 2016-09-28 | 東ソー株式会社 | Two-component polyurethane adhesive, laminate using the same, and protective sheet for solar cell |
| JP2014125632A (en) * | 2012-12-27 | 2014-07-07 | Tosoh Corp | Two-liquid polyurethane-based adhesive, and laminated body and protective sheet for solar battery using the same |
| JP7767889B2 (en) * | 2021-12-09 | 2025-11-12 | 東ソー株式会社 | Hydroxyl-containing chlorosulfonated polyolefin |
| JP2023132945A (en) * | 2022-03-11 | 2023-09-22 | 東ソー株式会社 | Urethane resin forming composition and two-component adhesive |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5219451B2 (en) * | 1971-07-22 | 1977-05-27 | ||
| JPS58141274A (en) * | 1982-02-17 | 1983-08-22 | Dainippon Ink & Chem Inc | Adhesive composition |
-
1989
- 1989-12-14 JP JP1324635A patent/JPH0717726B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH03185087A (en) | 1991-08-13 |
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| LAPS | Cancellation because of no payment of annual fees |