JPH03200805A - Purification of water-soluble polyvinyl acetal - Google Patents
Purification of water-soluble polyvinyl acetalInfo
- Publication number
- JPH03200805A JPH03200805A JP34054889A JP34054889A JPH03200805A JP H03200805 A JPH03200805 A JP H03200805A JP 34054889 A JP34054889 A JP 34054889A JP 34054889 A JP34054889 A JP 34054889A JP H03200805 A JPH03200805 A JP H03200805A
- Authority
- JP
- Japan
- Prior art keywords
- water
- aqueous solution
- polyvinyl acetal
- layer
- weight
- 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
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 229920002554 vinyl polymer Polymers 0.000 title claims abstract description 27
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 title claims abstract 11
- 238000000746 purification Methods 0.000 title abstract description 3
- 239000007864 aqueous solution Substances 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 12
- 238000010438 heat treatment Methods 0.000 claims abstract description 5
- 229920005989 resin Polymers 0.000 abstract description 16
- 239000011347 resin Substances 0.000 abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 13
- 239000012535 impurity Substances 0.000 abstract description 10
- 229910001410 inorganic ion Inorganic materials 0.000 abstract description 2
- 150000001241 acetals Chemical class 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 229910001415 sodium ion Inorganic materials 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- 239000004372 Polyvinyl alcohol Substances 0.000 description 5
- 229920002451 polyvinyl alcohol Polymers 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 3
- 230000003472 neutralizing effect Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 3
- 239000011354 acetal resin Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920006324 polyoxymethylene Polymers 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003985 ceramic capacitor Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- -1 chlorine ions Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/28—Condensation with aldehydes or ketones
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、水溶性ポリビニルアセタールの精製方法に関
する。DETAILED DESCRIPTION OF THE INVENTION (Industrial Field of Application) The present invention relates to a method for purifying water-soluble polyvinyl acetal.
（従来の技術）
従来、セラミック・バインダーとしては、ポリビニルア
ルコールやアクリル系樹脂が用いられているが、前者は
硬く、脆く、後者は柔らかすぎて、共にハンドリング性
に劣る。これらに対して、ポリビニルブチラール樹脂は
、適度の硬さを有するが、従来、知られているポリビニ
ルブチラール樹脂は、多くは、ブチラール化度が５０〜
８０モル％であって、これは、水溶性でなく、有機溶剤
にのみ溶解する。(Prior Art) Conventionally, polyvinyl alcohol and acrylic resin have been used as ceramic binders, but the former is hard and brittle, and the latter is too soft, both of which have poor handling properties. In contrast, polyvinyl butyral resin has moderate hardness, but conventionally known polyvinyl butyral resins often have a degree of butyralization of 50 to 50.
80 mol%, which is not water soluble and only dissolves in organic solvents.
そこで、例えば、特開昭６２−１５６１１２号公報には
、アセタール環におけるアルキル基の平均鎖長が炭素数
０．３４〜１．７０であるポリビニルアセタール樹脂が
提案されている。しかし、このように、アセタール環に
おけるアルキル基の鎖長が短いポリビニルアセタール樹
脂は、柔軟性に欠ける。Therefore, for example, JP-A-62-156112 proposes a polyvinyl acetal resin in which the average chain length of the alkyl group in the acetal ring is 0.34 to 1.70 carbon atoms. However, polyvinyl acetal resins in which the alkyl group in the acetal ring has a short chain length lack flexibility.
（発明が解決しようとする課Ｂ）
本発明者らは、適度の柔軟性を有し、しかも、水溶性で
あるポリビニルブチラール樹脂を得るべく鋭意研究した
結果、ポリビニルアルコールの水溶液に所定量のブチル
アルデヒドを反応させて、ブチラール化度を所定の小さ
い範囲とすることによって、上記のような水溶性ポリビ
ニルブチラール樹脂を得ることができることを見出した
。(Problem B to be Solved by the Invention) As a result of intensive research to obtain a polyvinyl butyral resin that has appropriate flexibility and is water-soluble, the present inventors found that a predetermined amount of butyral resin was added to an aqueous solution of polyvinyl alcohol. It has been found that the water-soluble polyvinyl butyral resin as described above can be obtained by reacting aldehydes and controlling the degree of butyralization to a predetermined small range.
一般に、水溶性樹脂の精製には、再沈法がよく用いられ
る。即ち、樹脂の水溶液に樹脂の貧溶剤としての有機溶
剤を加えて、イオン等の不純物を水中□に溶解させ、樹
脂を沈殿させて、このようにして、樹脂から不純物を分
離するのである。Generally, a reprecipitation method is often used to purify water-soluble resins. That is, an organic solvent as a poor solvent for the resin is added to an aqueous solution of the resin, impurities such as ions are dissolved in the water, and the resin is precipitated. In this way, the impurities are separated from the resin.
しかし、このような方法は、有機溶剤を用いる危険性の
みならず、水／有機溶剤混合物の後処理にも問題がある
。However, such methods have problems not only with the danger of using organic solvents, but also with the after-treatment of the water/organic solvent mixture.
そこで、本発明者らは、上記した問題を解決するために
鋭意研究した結果、水溶性ポリビニルアセタールの水溶
液から水系のままでの処理によって、特にイオン類等の
不純物を有効に除去し得る精製方法を見出して、本発明
を完成したものである。Therefore, as a result of intensive research in order to solve the above-mentioned problems, the present inventors have discovered a purification method that can effectively remove impurities, particularly ions, from an aqueous solution of water-soluble polyvinyl acetal in an aqueous system. The present invention was completed by discovering the following.
即ち、本発明は、水溶性ポリビニルアセタールの精製方
法を提供することを目的とする。That is, an object of the present invention is to provide a method for purifying water-soluble polyvinyl acetal.
（課題を解決するための手段）
本発明による水溶性ポリビニルアセタールの精製方法は
、水溶性ポリビニルアセタールを含む水溶液を加熱して
、水溶性ポリビニルアセタールの濃厚水溶液層と水層と
を形成し、この水層を前記ポリビニルアセタールの濃厚
水溶液から分離することを特徴とする。(Means for Solving the Problems) A method for purifying water-soluble polyvinyl acetal according to the present invention involves heating an aqueous solution containing water-soluble polyvinyl acetal to form a layer of a concentrated aqueous solution of water-soluble polyvinyl acetal and an aqueous layer. The method is characterized in that an aqueous layer is separated from the concentrated aqueous solution of polyvinyl acetal.
水溶性ポリビニルブチラールは、ポリビニルアルコール
を水に溶解させ、例えば、塩酸のような酸触媒の存在下
に、所定量のブチルアルデヒドを反応させた後、例えば
、水酸化ナトリウムのようなアルカリで中和することに
よって得ることができる。Water-soluble polyvinyl butyral is produced by dissolving polyvinyl alcohol in water, reacting it with a predetermined amount of butyraldehyde in the presence of an acid catalyst such as hydrochloric acid, and then neutralizing it with an alkali such as sodium hydroxide. You can get it by doing
従って、このようにして得られた水溶性ポリビニルアセ
タールの水溶液には、塩素イオンやナトリウムイオンが
不純物として含まれる。Therefore, the aqueous solution of water-soluble polyvinyl acetal thus obtained contains chloride ions and sodium ions as impurities.
本発明によれば、このような水溶性ポリビニルアセター
ルを含む水溶液を、好ましくは攪拌しながら加熱し、水
溶性ポリビニルアセタールの濃厚水溶液層（上層）と水
層（下層）とに分離させ、下層となる水層を前記水溶性
ポリビニルアセタールの濃厚水溶液層から抜き出して分
離し、必要に応じて、このような分離操作を繰り返して
行なうことによって、不純物としての塩素イオンやナト
リウムイオンが除去された高純度のポリビニルアセター
ルの水溶液を得ることができる。According to the present invention, an aqueous solution containing such water-soluble polyvinyl acetal is heated, preferably while stirring, to separate it into a concentrated aqueous solution layer (upper layer) and an aqueous layer (lower layer) of water-soluble polyvinyl acetal, and the lower layer and By extracting and separating the aqueous layer from the concentrated aqueous solution layer of the water-soluble polyvinyl acetal, and repeating this separation operation as necessary, a high-purity product with impurities such as chlorine ions and sodium ions removed. An aqueous solution of polyvinyl acetal can be obtained.
本発明の方法は、樹脂濃度が２０重量％以下のポリビニ
ルアセタールの水溶液の精製に好適である。また、水溶
液の加熱温度は、通常、５０〜１００°Ｃの範囲である
が、好ましくは８０〜１００°Ｃの範囲である。The method of the present invention is suitable for purifying an aqueous solution of polyvinyl acetal having a resin concentration of 20% by weight or less. Moreover, the heating temperature of the aqueous solution is usually in the range of 50 to 100°C, preferably in the range of 80 to 100°C.
（発明の効果）
以上のように、本発明によれば、特に、無機イオンを不
純物として含む水溶性ポリビニルアセタールの水溶液か
らそれら不純物を効果的に除去することができる。特に
、本発明によれば、水系で水溶性ポリビニルアセタール
を製造し、水系のままでの処理によって不純物を除去し
て、精製されたポリビニルアセタールの水溶液を得るこ
とができる。(Effects of the Invention) As described above, according to the present invention, in particular, impurities can be effectively removed from an aqueous solution of water-soluble polyvinyl acetal containing inorganic ions as impurities. In particular, according to the present invention, water-soluble polyvinyl acetal is produced in an aqueous system, and impurities are removed by treatment in the aqueous system to obtain a purified aqueous solution of polyvinyl acetal.
このようにして得られた不純物イオンを含まない精製ポ
リビニルアセタール水溶液は、例えば、電子工業におい
て、セラミック・コンデンサー製造用のセラ、ξツク・
グリーン・シートのための水性バインダーとして好適に
用いることができる。The thus obtained purified polyvinyl acetal aqueous solution containing no impurity ions is used, for example, in the electronics industry as a ceramic for manufacturing ceramic capacitors,
It can be suitably used as an aqueous binder for green sheets.
また、水性インクジェット記録紙用コーティング剤や親
水性付与添加剤等に用いることができる。It can also be used as a coating agent for water-based inkjet recording paper, an additive for imparting hydrophilicity, and the like.
（実施例）
以下に実施例を挙げて本発明の方法を具体的に説明する
。(Example) The method of the present invention will be specifically explained with reference to Examples below.
実施例！
重合度５００、ケン化度８８モル％のポリビニルアルコ
ール７９０重量部を純水２１２０重量部に加え、９０℃
で約２時間攪拌して、溶解させた。Example! 790 parts by weight of polyvinyl alcohol with a degree of polymerization of 500 and a degree of saponification of 88 mol% was added to 2120 parts by weight of pure water, and the mixture was heated at 90°C.
The mixture was stirred for about 2 hours and dissolved.
この後、４５℃に冷却し、３５重量％塩酸２７重量部を
加えて、３５℃まで冷却した。次いで、これに純度９９
重量％のブチルアルデヒド６２重量部を２時間かけて滴
下した後、３５゛Ｃで３時間反応させたところ、白濁し
た溶液を得た。Thereafter, the mixture was cooled to 45°C, 27 parts by weight of 35% by weight hydrochloric acid was added, and the mixture was cooled to 35°C. Next, this is given a purity of 99
After 62 parts by weight of butyraldehyde (wt%) was added dropwise over 2 hours, the mixture was reacted at 35°C for 3 hours to obtain a cloudy white solution.
攪拌下にこれに１０重量％水酸化ナトリウム水溶液６６
重量部を加え、中和した後、２０℃まで冷却して、透明
な溶液を得た。Add 10% by weight aqueous sodium hydroxide solution 66 to this while stirring.
After adding parts by weight and neutralizing, the solution was cooled to 20° C. to obtain a transparent solution.
この溶液５重量部をアルミニウム皿に分取し、７０℃で
３時間真空乾燥したところ、上記溶液は約２５重量％の
固形物を含んでおり、この固形物は、その赤外線吸収ス
ペクトルからポリビニルブチラール樹脂であることを確
認した。ＪＩＳ Ｋ ６７２Ｂの方法によって測定した
樹脂のブチラール化度は、約１０モル％であった。When 5 parts by weight of this solution was placed in an aluminum dish and vacuum-dried at 70°C for 3 hours, the solution contained about 25% by weight of solids, and this solid was determined by its infrared absorption spectrum to be polyvinyl butyral. It was confirmed that it was resin. The degree of butyralization of the resin measured by the method of JIS K 672B was about 10 mol%.
また、上記溶液中のナトリウムイオン濃度は、原子吸光
装置で測定した結果、２０００ｐｐｍ、イオンクロマト
グラフィーで測定した塩素イオン濃度は約３０００ｐｐ
ｍであった。In addition, the sodium ion concentration in the above solution was measured using an atomic absorption spectrometer to be 2000 ppm, and the chloride ion concentration measured using ion chromatography was approximately 3000 ppm.
It was m.
そこで、上記溶液５００重量部を純水４５００重量部に
加え、全体を５０００重量部とし、これを攪拌しながら
、９５°Ｃまで加熱したところ、不透明で粘稠な上層と
透明な下層とに分離した。高温下で下層を分離し、粘稠
な上層約５００重量部を得た。この層は、２０°Ｃまで
冷却すると、透明な溶液となった。Therefore, 500 parts by weight of the above solution was added to 4,500 parts by weight of pure water to make a total of 5,000 parts by weight, and when this was heated to 95°C while stirring, it separated into an opaque and viscous upper layer and a transparent lower layer. did. The lower layer was separated at high temperature to obtain about 500 parts by weight of a viscous upper layer. This layer became a clear solution upon cooling to 20°C.
この溶液中の固形物の含有量を前述したと同様にして測
定したところ、２３重量％であって、この固形物は、ブ
チラール化度約１０モル％のポリビニルブチラール樹脂
であった。また、溶液中のナトリウムイオン濃度は約２
００ｐｐｍ、塩素イオン濃度は約３１０ ｐｐｍにそれ
ぞれ低減していることが確認された。The content of solid matter in this solution was measured in the same manner as described above, and was found to be 23% by weight, and this solid matter was polyvinyl butyral resin with a degree of butyralization of about 10 mol%. Also, the sodium ion concentration in the solution is approximately 2
It was confirmed that the chlorine ion concentration was reduced to about 00 ppm and about 310 ppm.
実施例２
重合度１０００、ケン化度９８．５モル％のポリビニル
アルコール２５５重量部を純水２７００重量部に加え、
９０°Ｃで約２時間攪拌して、溶解させた。この後、４
５°Ｃに冷却し、３５重量％塩酸２０重量部を加えて、
３５°Ｃまで冷却した。次いで、これに純度９９重量％
のブチルアルデヒド１６重量部を２時間かけて滴下した
後、３５°Ｃで３時間反応させたところ、白濁した溶液
を得た。Example 2 255 parts by weight of polyvinyl alcohol with a degree of polymerization of 1000 and a degree of saponification of 98.5 mol% was added to 2700 parts by weight of pure water,
The mixture was stirred at 90°C for about 2 hours to dissolve. After this, 4
Cool to 5°C, add 20 parts by weight of 35% hydrochloric acid,
Cooled to 35°C. Next, this was added with a purity of 99% by weight.
After 16 parts by weight of butyraldehyde was added dropwise over 2 hours, the mixture was reacted at 35°C for 3 hours to obtain a cloudy solution.
攪拌下にこれに１０重量％水酸化ナトリウム水溶液６６
重量部を加え、中和した後、２０″Ｃまで冷却して、透
明な溶液を得た。Add 10% by weight aqueous sodium hydroxide solution 66 to this while stirring.
After adding parts by weight and neutralizing, it was cooled to 20''C to obtain a clear solution.
実施例１と同様にして、この溶液は、ブチラール化度約
８モル％のポリビニルブチラール樹脂を約８重量％含ん
でいることが確認された。また、溶液中のナトリウムイ
オン濃度は約１５００ｐｐｍ、塩素イオン濃度は約２２
００ｐｐｍであった。In the same manner as in Example 1, it was confirmed that this solution contained about 8% by weight of polyvinyl butyral resin with a degree of butyralization of about 8 mol%. Also, the sodium ion concentration in the solution is about 1500 ppm, and the chlorine ion concentration is about 22
It was 00 ppm.
そこで、上記溶液５００重量部を純水４５００重量部に
加え、全体を５０００重量部とし、これを攪拌しながら
、９５℃まで加熱したところ、不透明で粘稠な上層と透
明な下層とに分離した。高温下で下層を分離し、粘稠な
上層約２００重量部を得た。この層は、２０″Ｃまで冷
却すると、透明な？容液となった。Therefore, 500 parts by weight of the above solution was added to 4,500 parts by weight of pure water to make a total of 5,000 parts by weight, and when this was heated to 95°C while stirring, it was separated into an opaque and viscous upper layer and a transparent lower layer. . The lower layer was separated at high temperature to obtain about 200 parts by weight of a viscous upper layer. This layer became a clear liquid upon cooling to 20''C.
この溶液中の固形物の含有量を前述したと同様にして測
定したところ、約２１重量％であって、この固形物は、
ブチラール化度約８モル％のポリビニルブチラール樹脂
であった。また、溶液中のナトリウムイオン濃度は約６
０ｐｐｍ、塩素イオン濃度は約９０ｐｐｍにそれぞれ低
減していることが確認された。When the content of solids in this solution was measured in the same manner as described above, it was approximately 21% by weight, and the solids were:
It was a polyvinyl butyral resin with a degree of butyralization of about 8 mol%. Also, the sodium ion concentration in the solution is about 6
It was confirmed that the chlorine ion concentration was reduced to 0 ppm and about 90 ppm.
Claims (1)
して、水溶性ポリビニルアセタールの濃厚水溶液層と水
層とを形成し、この水層を前記ポリビニルアセタールの
濃厚水溶液から分離することを特徴とする水溶性ポリビ
ニルアセタールの精製方法。(1) An aqueous solution comprising heating an aqueous solution containing a water-soluble polyvinyl acetal to form a layer of a concentrated aqueous solution of the water-soluble polyvinyl acetal and an aqueous layer, and separating this aqueous layer from the concentrated aqueous solution of the polyvinyl acetal. Method for purifying polyvinyl acetal.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP34054889A JPH0699499B2 (en) | 1989-12-28 | 1989-12-28 | Purification method of water-soluble polyvinyl acetal |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP34054889A JPH0699499B2 (en) | 1989-12-28 | 1989-12-28 | Purification method of water-soluble polyvinyl acetal |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03200805A true JPH03200805A (en) | 1991-09-02 |
| JPH0699499B2 JPH0699499B2 (en) | 1994-12-07 |
Family
ID=18338043
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP34054889A Expired - Lifetime JPH0699499B2 (en) | 1989-12-28 | 1989-12-28 | Purification method of water-soluble polyvinyl acetal |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0699499B2 (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003028143A1 (en) | 2001-09-21 | 2003-04-03 | Sekisui Chemical Co., Ltd. | Modified polyvinyl acetal resin |
| WO2004087773A1 (en) * | 2003-03-28 | 2004-10-14 | Az Electronic Materials (Japan) K.K. | Auxiliary for forming fine pattern and process for producing the same |
| EP1369439A4 (en) * | 2001-01-25 | 2005-04-06 | Sekisui Chemical Co Ltd | Polyvinyl acetal, polyvinyl acetal composition, ink, coating material, dispersant, heat-developable photosensitive material, ceramic green sheet, primer for plastic lens, recording agent for water-based ink, and adhesive for metal foil |
| JP2007206728A (en) * | 2007-04-24 | 2007-08-16 | Az Electronic Materials Kk | Auxiliary agent for forming fine pattern |
| US7745077B2 (en) | 2008-06-18 | 2010-06-29 | Az Electronic Materials Usa Corp. | Composition for coating over a photoresist pattern |
| US7923200B2 (en) | 2007-04-09 | 2011-04-12 | Az Electronic Materials Usa Corp. | Composition for coating over a photoresist pattern comprising a lactam |
| WO2013002292A1 (en) * | 2011-06-28 | 2013-01-03 | 株式会社クラレ | Solar cell sealing material and laminated glass interlayer |
-
1989
- 1989-12-28 JP JP34054889A patent/JPH0699499B2/en not_active Expired - Lifetime
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1369439A4 (en) * | 2001-01-25 | 2005-04-06 | Sekisui Chemical Co Ltd | Polyvinyl acetal, polyvinyl acetal composition, ink, coating material, dispersant, heat-developable photosensitive material, ceramic green sheet, primer for plastic lens, recording agent for water-based ink, and adhesive for metal foil |
| WO2003028143A1 (en) | 2001-09-21 | 2003-04-03 | Sekisui Chemical Co., Ltd. | Modified polyvinyl acetal resin |
| WO2004087773A1 (en) * | 2003-03-28 | 2004-10-14 | Az Electronic Materials (Japan) K.K. | Auxiliary for forming fine pattern and process for producing the same |
| JP2004294992A (en) * | 2003-03-28 | 2004-10-21 | Clariant (Japan) Kk | Auxiliary agent for forming fine pattern and its manufacturing method |
| CN1328295C (en) * | 2003-03-28 | 2007-07-25 | Az电子材料（日本）株式会社 | Auxiliary for forming fine pattern and process for producing the same |
| KR101059378B1 (en) * | 2003-03-28 | 2011-08-26 | 에이제토 엘렉토로닉 마티리알즈 가부시키가이샤 | Fine patterning aid and preparation method thereof |
| US7598320B2 (en) | 2003-03-28 | 2009-10-06 | Az Electronic Materials Usa Corp. | Protected polyvinyl alcohol auxiliary for forming fine pattern and process for producing the same |
| US7923200B2 (en) | 2007-04-09 | 2011-04-12 | Az Electronic Materials Usa Corp. | Composition for coating over a photoresist pattern comprising a lactam |
| JP4610578B2 (en) * | 2007-04-24 | 2011-01-12 | Ａｚエレクトロニックマテリアルズ株式会社 | Fine pattern formation aid |
| JP2007206728A (en) * | 2007-04-24 | 2007-08-16 | Az Electronic Materials Kk | Auxiliary agent for forming fine pattern |
| US7745077B2 (en) | 2008-06-18 | 2010-06-29 | Az Electronic Materials Usa Corp. | Composition for coating over a photoresist pattern |
| WO2013002292A1 (en) * | 2011-06-28 | 2013-01-03 | 株式会社クラレ | Solar cell sealing material and laminated glass interlayer |
| JP5179681B2 (en) * | 2011-06-28 | 2013-04-10 | 株式会社クラレ | Solar cell encapsulant and laminated glass interlayer |
| JP2013100225A (en) * | 2011-06-28 | 2013-05-23 | Kuraray Co Ltd | Solar cell sealing material and laminated glass interlayer |
| EP2728625A4 (en) * | 2011-06-28 | 2014-12-10 | Kuraray Co | Solar cell sealing material and laminated glass interlayer |
| KR101491707B1 (en) * | 2011-06-28 | 2015-02-09 | 가부시키가이샤 구라레 | Solar cell sealing material and laminated glass interlayer |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0699499B2 (en) | 1994-12-07 |
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