JPH0739524B2 - Polyvinyl alcohol resin composition and use thereof - Google Patents
Polyvinyl alcohol resin composition and use thereofInfo
- Publication number
- JPH0739524B2 JPH0739524B2 JP2197450A JP19745090A JPH0739524B2 JP H0739524 B2 JPH0739524 B2 JP H0739524B2 JP 2197450 A JP2197450 A JP 2197450A JP 19745090 A JP19745090 A JP 19745090A JP H0739524 B2 JPH0739524 B2 JP H0739524B2
- Authority
- JP
- Japan
- Prior art keywords
- polyvinyl alcohol
- alcohol resin
- agent
- resin composition
- resin
- 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
Description
【発明の詳細な説明】 ポリビニルアルコール系樹脂はその水溶性、接着性、皮
膜形成性を生かして、接着剤、塗料、被覆剤、フイルム
等の用途に用いられるが、耐水性が乏しいという難点が
ある。DETAILED DESCRIPTION OF THE INVENTION Polyvinyl alcohol resins are used for adhesives, paints, coatings, films and the like by taking advantage of their water solubility, adhesiveness and film-forming property, but they have the drawback of poor water resistance. is there.
しかしてポリビニルアルコール系樹脂を耐水化するため
の一つの方法としてポリビニルアルコール系樹脂をアセ
トアセチル化し、これにジアルデヒド等の各種の架橋剤
を加えて耐水化する方法が提案されている。しかしなが
ら、従来の耐水化剤を併用する場合、水溶液の粘度が上
昇して保存安定性や塗工性に支障を生じたり、耐水化の
ために高度の熱処理が必要である等の難点がある。However, as one method for making a polyvinyl alcohol resin water resistant, a method has been proposed in which a polyvinyl alcohol resin is acetoacetylated and various crosslinking agents such as dialdehyde are added thereto to make it water resistant. However, when the conventional water-proofing agent is used in combination, there are problems that the viscosity of the aqueous solution is increased to impair the storage stability and the coating property, and a high degree of heat treatment is required for making the water resistant.
しかるに本発明者等は鋭意研究を重ねた結果、（Ａ）ア
セトアセチル化ポリビニルアルコール系樹脂に、（Ｂ）
ヘキサメチレンジアミンを添加してなる組成物は、比較
的軽度の熱処理を施すときはもとより、常温乾燥によっ
ても容易に耐水性が可能であるという新規な事実を見出
し本発明を完成するに至った。ヘキサメチレンジアミン
の使用による耐水化効果は、アセトアセチル化ポリビニ
ルアルコール系樹脂に対して飛躍的に発揮され、未変性
のポリビニルアルコールに対してヘキサメチレンジアミ
ンを使用した場合の効果をはるかに凌駕するものであ
り、本発明の効果はアセトアセチル基とアミン基との組
合わせによる相乗効果が顕著であると言わざるを得な
い。However, as a result of earnest studies by the present inventors, (A) acetoacetylated polyvinyl alcohol-based resin, (B)
The composition obtained by adding hexamethylenediamine has been found to have the novel fact that it can be easily water-resistant not only when it is subjected to a relatively mild heat treatment, but also when it is dried at room temperature, and has completed the present invention. The water resistance effect of using hexamethylenediamine is dramatically demonstrated for acetoacetylated polyvinyl alcohol resins, and far exceeds the effect of using hexamethylenediamine for unmodified polyvinyl alcohol. Therefore, it must be said that the effect of the present invention is remarkably synergistic by the combination of the acetoacetyl group and the amine group.
本発明の組成物において（Ａ）アセトアセチル化ポリビ
ニルアルコール系樹脂に対する（Ｂ）の添加量はその使
用目的、種類によって多少変動するが通常は0.1〜80重
量％、好ましくは0.5〜20重量％、特に好ましくは１〜1
0重量％の範囲である。The amount of (B) added to the acetoacetylated polyvinyl alcohol resin (A) in the composition of the present invention varies somewhat depending on the purpose of use and type, but is usually 0.1 to 80% by weight, preferably 0.5 to 20% by weight, Particularly preferably 1 to 1
It is in the range of 0% by weight.
該組成物は各種の用途においてその使用時に（Ａ）と
（Ｂ）を混合するのが普通であるが、用途によっては一
旦（Ａ）のみを塗被したりあるいは成型した後、（Ｂ）
で後処理しても差支えない。The composition is usually mixed with (A) and (B) at the time of use in various applications, but depending on the application, only (A) is once coated or molded and then (B).
It can be post-treated with.
以下（Ａ）、（Ｂ）について更に具体的に説明する。Hereinafter, (A) and (B) will be described more specifically.
本発明における（Ａ）アセトアセチル化ポリビニルアル
コール系樹脂は任意の方法で製造され特定化されない。
代表例をあげれば、ポリビニルアルコール系樹脂にジケ
テンを付加反応するか、アセト酢酸エステルをエステル
交換反応することによって取得される。基体となるポリ
ビニルアルコール系樹脂としては、ポリ酢酸ビニルなど
ポリビニルエステルの部分又は完全ケン化物のほか、酢
酸ビニルを主体とし、これと他の共重合可能なモノマ
ー、例えば不飽和カルボン酸またはその部分又は完全エ
ステル・塩・無水物・アミド・ニトリル、不飽和スルホ
ン酸又はその塩、炭素数２〜30のα−オレフィン、ビニ
ルエーテルなどとの共重合体をケン化した「共重合変
性」ポリビニルアルコールやポリビニルアルコールをア
セタール化、ウレタン化、エーテル化、グラフト化、リ
ン酸エステル化などした「後変性」ポリビニルアルコー
ルも用いる。該ポリビニルアルコールの平均ケン化度は
60モル％以上、平均重合度は50〜3000が好ましい。The (A) acetoacetylated polyvinyl alcohol resin in the present invention is produced by any method and is not specified.
A typical example is obtained by addition reaction of polyvinyl alcohol resin with diketene or transesterification reaction of acetoacetic acid ester. The polyvinyl alcohol-based resin serving as the base is, in addition to partially or completely saponified polyvinyl ester such as polyvinyl acetate, mainly vinyl acetate and other copolymerizable monomers such as unsaturated carboxylic acid or its portion or "Copolymer-modified" polyvinyl alcohol or polyvinyl obtained by saponifying copolymers with complete esters, salts, anhydrides, amides, nitriles, unsaturated sulfonic acids or their salts, C2-C30 α-olefins, vinyl ethers, etc. "Post-modified" polyvinyl alcohol obtained by acetalizing, urethanizing, etherifying, grafting, phosphoric esterifying an alcohol is also used. The average saponification degree of the polyvinyl alcohol is
It is preferably 60 mol% or more and the average degree of polymerization is 50 to 3000.
上記樹脂に対するアセトアセチル化の割合は、0.05モル
％以上で水溶性を有する範囲内の最大限まで可能である
が、通常は0.1〜40モル％、なかんずく0.2〜20モル％の
範囲から選ぶことが多い。アセトアセチル化率が余りに
低いと耐水化の目的が達成しえなくなる。又アセトアセ
チル化率を必要以上に導入しても耐水性付与効果はそれ
以上は向上せず、かつ水溶性の範囲をはずれることが多
い。又残存する酢酸ビニル基は40モル％以下、好ましく
は30モル％以下が適当である。The ratio of acetoacetylation to the resin is 0.05 mol% or more and can be maximized within the range of having water solubility, but it is usually selected from the range of 0.1 to 40 mol%, especially 0.2 to 20 mol%. Many. If the acetoacetylation rate is too low, the purpose of water resistance cannot be achieved. Further, even if the acetoacetylation rate is introduced more than necessary, the water resistance imparting effect is not further improved, and the water solubility is often out of the range. Further, the residual vinyl acetate group is appropriately 40 mol% or less, preferably 30 mol% or less.
上記の（Ａ）、（Ｂ）からなる組成物は次に述べる様に
種々の用途に用いられる。各用途において本組成物は特
有の効果を発揮し工業的に極めて有用である。この際該
組成物には必要に応じ充填剤、着色剤、界面活性剤、繊
維類、発泡剤、消泡剤、他の水溶性樹脂、水分散性樹脂
（例えば各種エマルジョン）、揺変性改善剤等を添加し
てもよい。又、これらの薬剤は（Ａ）と（Ｂ）の組成物
で処理した後の後処理剤としても用いられる。以下、用
途について具体的に説明する。The composition comprising (A) and (B) described above is used for various purposes as described below. In each application, the present composition exhibits unique effects and is industrially extremely useful. In this case, the composition may include a filler, a colorant, a surfactant, fibers, a foaming agent, an antifoaming agent, another water-soluble resin, a water-dispersible resin (for example, various emulsions), and a thixotropic agent, if necessary. Etc. may be added. Further, these agents are also used as a post-treatment agent after being treated with the composition of (A) and (B). The use will be specifically described below.
（１）繊維加工剤（不織布用バインダー、サイジング加
工、硬仕上げ加工、腰付け加工、防燃加工、撥水加工、
顔料捺染、防シワ加工、防縮加工、柔軟加工、寸法安定
性付与、ほつれ防止、フロッキー加工、耐摩耗性付与、
耐引裂性付与、耐汚れ性付与等） 該加工剤は各種繊維又は織物に対して柔軟性、弾力性、
耐ドライクリーニング性、機械的強度、接着性などの点
で顕著な効果を付与しうる。しかも、耐水性がすぐれて
いるから耐洗濯堅牢性が良好で、その効果が恒久的であ
る。(1) Textile processing agents (nonwoven fabric binder, sizing processing, hard finishing processing, lining processing, flameproofing processing, water repellent processing,
Pigment printing, wrinkle-proofing, shrink-proofing, softening, dimensional stability, fraying prevention, flocking, abrasion resistance,
Tear resistance imparted, stain resistance imparted, etc.) The processing agent is flexible, elastic, and
A remarkable effect can be imparted in terms of dry cleaning resistance, mechanical strength, adhesiveness and the like. Moreover, since it has excellent water resistance, it has good wash fastness and its effect is permanent.
本発明の繊維製品用処理剤を使用するにあたっては加工
すべき繊維または織物にロールコーターなどを用いて該
処理剤を塗布または噴霧するか、あるいは繊維または織
物を該組成物中に浸漬した後適宜絞って樹脂付着量を調
節し、加熱乾燥する。架橋剤・耐水化剤を添加してより
高度の処理を行う時、処理は通常100〜170℃程度の加熱
によって充分進行せしめうる。When using the treatment agent for textiles of the present invention, the treatment agent is applied or sprayed onto the fiber or fabric to be processed by using a roll coater or the fiber or fabric is appropriately dipped in the composition. Squeeze to adjust the amount of resin attached and heat dry. When a higher degree of treatment is carried out by adding a crosslinking agent / water-proofing agent, the treatment can usually be sufficiently advanced by heating at about 100 to 170 ° C.
本発明の加工の対象とする繊維としては、木綿、絹、羊
毛などの天然繊維はもとより、ポリアミド系、ポリエス
テル系、ポリアクリル系、ポリ塩化ビニル系、ポリプロ
ピレン系などの各種合成繊維も含まれる。The fibers to be processed by the present invention include not only natural fibers such as cotton, silk and wool but also various synthetic fibers such as polyamide, polyester, polyacrylic, polyvinyl chloride and polypropylene.
（２）接着剤関係 木材、紙、アルミ箔、プラスチック等の接着剤、粘着
剤、再湿剤、繊維状バインダー、石膏ボードや繊維板等
の各種建材用バインダー、各種粉体造粒用バインダー、
セメントやモルタル用添加剤、感圧接着剤、アニオン性
染料の固着剤 かかる用途においてはポリビニルアルコールに比較して
一段とすぐれた接着力が得られる。(2) Adhesives Adhesives for wood, paper, aluminum foil, plastics, adhesives, rewetting agents, fibrous binders, binders for various building materials such as gypsum board and fiber board, binders for powder granulation,
Additives for cements and mortars, pressure-sensitive adhesives, fixing agents for anionic dyes. In such applications, adhesive strength far superior to that of polyvinyl alcohol can be obtained.
（３）被覆剤関係 紙のクリアーコーティング剤、紙の顔料コーティング
剤、紙の内添サイズ剤、経糸糊剤、皮革仕上げ剤、塗
料、防雲剤、金属腐食防止剤、亜鉛メッキ用光沢剤、帯
電防止剤、導電剤 かかる用途においてポリビニルアルコールを使用する場
合に比較してより皮膜強度のすぐれた塗膜が得られる。(3) Coating materials Clear coating agent for paper, pigment coating agent for paper, internal sizing agent for paper, warp paste agent, leather finishing agent, paint, anti-clouding agent, metal corrosion inhibitor, brightener for zinc plating, Antistatic Agent, Conductive Agent In such applications, a coating film having better film strength can be obtained as compared with the case of using polyvinyl alcohol.
（４）成型物関係 繊維、フイルム、シート、パイプ、チューブ防漏膜、暫
定皮膜 該成型物は耐水性や機械的強度が極めて優れている。(4) Molded Articles Fibers, Films, Sheets, Pipes, Tubes Leak-Proof Films, Temporary Films The molded articles are extremely excellent in water resistance and mechanical strength.
（５）疎水性樹脂用ブレンド剤関係 疎水性樹脂の帯電防止剤、及び親水性付与剤、複合繊
維、フイルムその他成型物用添加剤 （６）凝集剤関係 水中懸濁物及び溶剤物の凝集剤、パイプスラリーの水
性向上剤 （７）土壌改良剤関係 （８）感光剤、感電子剤関係 （９）その他、イオン交換樹脂、イオン交換膜関係キレ
ート性樹脂 次に実例を挙げて本発明の組成物を具体的に説明する。(5) Hydrophobic resin blending agent Antistatic agent for hydrophobic resin, hydrophilicity-imparting agent, composite fiber, film and other additives for molded products (6) Flocculant-related flocculant of suspension in water and solvent , Water-improving agent for pipe slurry (7) Soil improving agent-related (8) Photosensitizer, electrosensitive agent-related (9) Others, ion-exchange resin, ion-exchange membrane-related chelating resin The object will be specifically described.
（Ａ）アセトアセチル化ポリビニルアルコール樹脂の調
製 ポリビニルアルコールとジケテンを酢酸溶媒中で反応さ
せて次の２種の樹脂を製造した。(A) Preparation of acetoacetylated polyvinyl alcohol resin Polyvinyl alcohol and diketene were reacted in an acetic acid solvent to produce the following two resins.
（Ａ）−1;平均重合度1700、残存酢酸基１モル％、アセ
トアセチル化ポリビニルアルコール系樹脂。(A) -1; Average degree of polymerization of 1700, residual acetic acid group of 1 mol%, acetoacetylated polyvinyl alcohol resin.
（Ａ）−2;平均重合度1100、残存酢酸基15モル％、アセ
トアセチル化度15モル％のアセトアセチル化ポリビニル
アルコール系樹脂。(A) -2; An acetoacetylated polyvinyl alcohol-based resin having an average degree of polymerization of 1100, a residual acetic acid group of 15 mol% and an acetoacetylation degree of 15 mol%.
（Ｂ）ヘキサメチレンジアミン〔（Ａ）に対し５重量％
添加〕を用いて10重量％水溶液からなる組成物を製造し
た。(B) Hexamethylenediamine [5% by weight relative to (A)
Addition] was used to produce a composition consisting of a 10% by weight aqueous solution.
実施例１ 上記の組成物について皮膜の耐水性を測定した。Example 1 The water resistance of the film was measured for the above composition.
その結果を第１表に示す。尚、対照例として、アセトア
セチル化ポリビニルアルコールに代えてポリビニルアル
コール（平均重合度1700、平均ケン化度99モル％）につ
いて又、アセトアセチル化ポリビニルアルコールを単独
使用した場合についても耐水性を測定した。The results are shown in Table 1. As a control example, the water resistance was measured for polyvinyl alcohol (average degree of polymerization 1700, average degree of saponification 99 mol%) instead of acetoacetylated polyvinyl alcohol, and also when acetoacetylated polyvinyl alcohol was used alone. .
実施例２ （Ａ）−１とヘキサメチレンジアミンとの組合せよりな
る８重量％水溶液を調整した。〔（Ａ）に対して（Ｂ）
を10重量％配合〕 太さ３デニール、繊維長約50mmのポリエチレンテレフタ
レート単繊維をランダムウェッパーで処理した乾燥重量
100g/m2のウエブを上記液に浸漬し、マントルで絞り、
温度80℃で20分間予備乾燥後、更に温度150℃において
５分間加熱乾燥した。乾燥後の樹脂付着量は処理前のウ
エブの重量に対して固型分で30％であった。得られた不
織布の諸性質の測定結果を第２表に示す。 Example 2 An 8 wt% aqueous solution containing a combination of (A) -1 and hexamethylenediamine was prepared. [(B) for (A)
10% by weight] Dry weight of polyethylene terephthalate monofilament having a thickness of 3 denier and a fiber length of about 50 mm treated with a random webper
A 100 g / m 2 web is dipped in the above liquid, squeezed with a mantle,
After preliminary drying at a temperature of 80 ° C. for 20 minutes, heat drying was further performed at a temperature of 150 ° C. for 5 minutes. The amount of resin adhered after drying was 30% in terms of solid content with respect to the weight of the web before treatment. Table 2 shows the measurement results of various properties of the obtained nonwoven fabric.
更に上記組成の５％水溶液に30×30cmの芯地用テトロン
／綿布を浸漬し樹脂の付着量が布の重量の４％になる様
に搾液する。これを80℃で10分間乾燥させ硬仕上げを行
った。 Further, a 30 × 30 cm tetron / cotton cloth for interlining is soaked in a 5% aqueous solution of the above composition, and squeezed so that the amount of resin adhered becomes 4% of the weight of the cloth. This was dried at 80 ° C. for 10 minutes and hard-finished.
得られた芯地生地についてカンチレバー法によりその硬
度を測定した。更に該生地を家庭用電気洗濯機にて0.3
％の中性洗剤浴比1/20、40℃にて30分洗濯の後、室温で
乾燥し、硬度を測定した。又洗濯性のテストは洗濯を５
回、10回した場合についても行った。The hardness of the obtained interlining fabric was measured by the cantilever method. Further, the cloth is 0.3 in a household electric washing machine.
% Neutral detergent bath ratio 1/20, washed at 40 ° C. for 30 minutes, dried at room temperature, and measured for hardness. Also, the washability test is 5
Repeated 10 times and 10 times.
結果を第３表に示す。The results are shown in Table 3.
実施例３ （Ａ）−１に（Ｂ）を10重量％配合した組成物について
この10％水溶液を調製し、ガラス板上で流涎法によって
厚さ80μのフイルムを製造した。このフイルムについて
70℃の熱水中に１時間浸漬後、島津製オートグラフIM−
1100型（ロードセル5kg、引張速度100mm/min）にて機械
的強度を測定した。その結果を第４表に示す。 Example 3 A 10% aqueous solution of a composition obtained by blending (A) -1 with 10% by weight of (B) was prepared, and a film having a thickness of 80 μm was produced on a glass plate by a sparging method. About this film
Autograph IM- manufactured by Shimadzu after soaking in hot water at 70 ℃ for 1 hour
The mechanical strength was measured with a 1100 type (load cell 5 kg, pulling speed 100 mm / min). The results are shown in Table 4.
実施例４ （Ａ）−１に（Ｂ）を20重量％配合した組成物について
ガラス−木材接着力及び木材接着力を評価した。結果を
第５表に示す。 Example 4 The composition in which 20% by weight of (B) was mixed with (A) -1 was evaluated for glass-wood adhesion and wood adhesion. The results are shown in Table 5.
実施例５ （Ａ）−１に対して（Ｂ）を10重量％配合した組成物に
ついて紙加工を行った。 Example 5 Paper processing was performed on a composition containing 10% by weight of (B) with respect to (A) -1.
次の条件下でサイズプレス塗工を実施した。Size press coating was carried out under the following conditions.
塗工条件；速度90m/min,ニップ圧11kg/cm,乾燥115℃2mi
n 原紙；テスト用抄造紙 （坪量64g/m2,サイズ度3sec,密度0.67） キャレンダー仕上げ;80℃,50kg/cm,2poss塗工濃度;3％ 得られた塗工紙の物性値を第６表に示す。Coating conditions; speed 90m / min, nip pressure 11kg / cm, dry 115 ℃ 2mi
n Base paper; paper for testing (grammage 64g / m 2 , size 3sec, density 0.67) Calendar finish; 80 ℃, 50kg / cm, 2poss coating concentration; 3% Physical properties of the obtained coated paper It is shown in Table 6.
Claims (5)
ール系樹脂及び（Ｂ）ヘキサメチレンジアミンとからな
るポリビニルアルコール系樹脂組成物。1. A polyvinyl alcohol resin composition comprising (A) an acetoacetylated polyvinyl alcohol resin and (B) hexamethylene diamine.
ール系樹脂及び（Ｂ）ヘキサメチレンジアミンとからな
るポリビニルアルコール系樹脂組成物を主剤とする繊維
加工剤。2. A fiber processing agent containing a polyvinyl alcohol resin composition comprising (A) an acetoacetylated polyvinyl alcohol resin and (B) hexamethylenediamine as a main component.
ール系樹脂及び（Ｂ）ヘキサメチレンジアミンとからな
るポリビニルアルコール系樹脂組成物を主剤とする接着
剤。3. An adhesive containing a polyvinyl alcohol resin composition comprising (A) an acetoacetylated polyvinyl alcohol resin and (B) hexamethylene diamine as a main component.
ール系樹脂及び（Ｂ）ヘキサメチレンジアミンとからな
るポリビニルアルコール系樹脂組成物を主剤とする被覆
剤。4. A coating agent comprising a polyvinyl alcohol resin composition comprising (A) an acetoacetylated polyvinyl alcohol resin and (B) hexamethylenediamine as a main component.
ール系樹脂及び（Ｂ）ヘキサメチレンジアミンとからな
るポリビニルアルコール系樹脂組成物を主剤とする成形
物。5. A molded product comprising a polyvinyl alcohol resin composition comprising (A) an acetoacetylated polyvinyl alcohol resin and (B) hexamethylenediamine as a main component.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2197450A JPH0739524B2 (en) | 1982-05-21 | 1990-07-25 | Polyvinyl alcohol resin composition and use thereof |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57087051A JPS58204040A (en) | 1982-05-21 | 1982-05-21 | Polyvinyl alcohol resin composition and its application |
| JP2197450A JPH0739524B2 (en) | 1982-05-21 | 1990-07-25 | Polyvinyl alcohol resin composition and use thereof |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57087051A Division JPS58204040A (en) | 1982-05-21 | 1982-05-21 | Polyvinyl alcohol resin composition and its application |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03243643A JPH03243643A (en) | 1991-10-30 |
| JPH0739524B2 true JPH0739524B2 (en) | 1995-05-01 |
Family
ID=26428369
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2197450A Expired - Lifetime JPH0739524B2 (en) | 1982-05-21 | 1990-07-25 | Polyvinyl alcohol resin composition and use thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0739524B2 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001247738A (en) * | 2000-03-06 | 2001-09-11 | Unitika Chem Co Ltd | Polyvinyl alcohol-based resin composition and paper coating agent consisting essentially of the same |
| CA2649840A1 (en) * | 2006-04-21 | 2007-11-01 | Next21 K.K. | Figure-forming composition, method for forming three-dimensional figures and three-dimensional structures by using the same |
| WO2009092698A1 (en) * | 2008-01-22 | 2009-07-30 | Basf Se | Coated polyoxymethylenes |
| DE102020128713A1 (en) * | 2019-12-04 | 2021-06-10 | Fischerwerke Gmbh & Co. Kg | Michael addition-curing hybrid system for chemical fastening technology |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4878218A (en) * | 1972-01-21 | 1973-10-20 | ||
| JPS56125446A (en) * | 1980-03-06 | 1981-10-01 | Nippon Synthetic Chem Ind Co Ltd:The | Resin solution |
-
1990
- 1990-07-25 JP JP2197450A patent/JPH0739524B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH03243643A (en) | 1991-10-30 |
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