JPS625163B2 - - Google Patents
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- Publication number
- JPS625163B2 JPS625163B2 JP54093236A JP9323679A JPS625163B2 JP S625163 B2 JPS625163 B2 JP S625163B2 JP 54093236 A JP54093236 A JP 54093236A JP 9323679 A JP9323679 A JP 9323679A JP S625163 B2 JPS625163 B2 JP S625163B2
- Authority
- JP
- Japan
- Prior art keywords
- polymerization
- polymer
- molecular weight
- water
- initiator
- 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
- 229920000642 polymer Polymers 0.000 claims description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 13
- 239000003999 initiator Substances 0.000 claims description 11
- 239000000178 monomer Substances 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 description 24
- -1 cyclic quaternary ammonium salt Chemical class 0.000 description 7
- 239000007870 radical polymerization initiator Substances 0.000 description 7
- 229920006158 high molecular weight polymer Polymers 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003505 polymerization initiator Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- NJSSICCENMLTKO-HRCBOCMUSA-N [(1r,2s,4r,5r)-3-hydroxy-4-(4-methylphenyl)sulfonyloxy-6,8-dioxabicyclo[3.2.1]octan-2-yl] 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)O[C@H]1C(O)[C@@H](OS(=O)(=O)C=2C=CC(C)=CC=2)[C@@H]2OC[C@H]1O2 NJSSICCENMLTKO-HRCBOCMUSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 150000001723 carbon free-radicals Chemical class 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000008394 flocculating agent Substances 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000005518 polymer electrolyte Substances 0.000 description 2
- 239000010865 sewage Substances 0.000 description 2
- 239000010802 sludge Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920006317 cationic polymer Polymers 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- IOMDIVZAGXCCAC-UHFFFAOYSA-M diethyl-bis(prop-2-enyl)azanium;chloride Chemical compound [Cl-].C=CC[N+](CC)(CC)CC=C IOMDIVZAGXCCAC-UHFFFAOYSA-M 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
本発明は塩化ジアリルジアルキルアンモニウム
を重合して塩化ジアリルジアルキルアンモニウム
重合体を製造する際に、水溶性アゾ系開始剤を単
量体重量当り、0.2〜1.5％使用し、55℃以下の温
度で重合させる事を特徴とする塩化ジアリルジア
ルキルアンモニウム重合体の製造法に関する。
本発明によれば、非常に高い分子量の重合体を
得ることができる。
塩化ジアリルジアルキルアンモニウムは分子内
に二重結合を２個持つ化合物であるが、ラジカル
重合開始剤を用いて重合させると、三次元網状構
造の架橋重合体を生成せずに、分子内で二重結合
即ち二つのアリル基同志で環を形成しながら重合
が進行する環化重合である事が知られている。従
つて得られる重合体はその構造単位毎に環状の第
４級アンモニウム塩を持つ水溶性の線状重合体で
ある。またこれらの重合体は、カチオン性高分子
電解質として、種々の用途に供されているが、下
水、排水処理のための沈澱凝集剤としての利用に
は高分子量の重合体が得られ難いため、限られた
用途にのみ利用されているに過ぎない。尚、一般
的に沈殿凝集剤として利用される高分子電解質は
分子量が高い程その効果が大きい事が知られてい
る。
そこで本発明者は塩化ジアリルジアルキルアン
モニウムの高い分子量の重合体を得る事を目的と
して、種々の開始剤を用いて種々の条件での重合
を検討し、おどろくべき事実を見出し、本発明を
完成するに至つた。
一般にラジカル重合開始剤を用いた重合ではラ
ジカル重合開始剤は単量体重量当り、50〜
2000ppm程度が使用されているが、特に高分子
量の重合体を得ようとするときには、重合反応の
特性として重合速度を小さくしなければならず、
ラジカル重合開始剤は50〜500ppm程度で、低温
で長時間の反応条件が採用されている。また当然
の如く、多量のラジカル重合開始剤を用いると低
分子量の重合体を得るのみである。
これはラジカル重合開始剤により生成したラジ
カルが同時に停止反応を行うという重合反応の特
性によるものである。
しかしながら塩化ジアリルジアルキルアンモニ
ウムの重合にラジカル重合開始剤として水溶性ア
ゾ系開始剤を用いた場合、50ppm〜20000ppm
（２％）の範囲で使用量の増加と共に得られた重
合体の分子量が高くなり単量体重量当り1.0％を
越えても非常に高い分子量の重合体が得られると
いうおどろくべき事実を見出した。水溶性アゾ系
開始剤に換えて、有機、無機過酸化物系開始剤を
用いた場合、一般則通りに開始剤の使用量の増加
と共に分子量の低下がみられた。尚、この水溶性
アゾ系開始剤の使用量は重合速度と発熱量の関係
から選ばれ、単量体重量当り0.2〜1.5％の範囲が
高分子量の重合体を得るのに適当である。特に好
ましい水溶性アゾ系開始剤の使用量は0.2〜１％
である。
また重合温度については、55℃以下が高分子量
を得るための必須の条件である。55℃以上の重合
温度にすると低分子量の重合体しか得られない。
これらの相異はアゾ系の開始剤の分解による炭素
ラジカルの特異性によるものと推定され、一般的
に過酸化物系の酸素ラジカルのほうが開始反応の
能力が大きく、それと共に停止反応にも強く作用
するものと考えられ、更に炭素ラジカルでも温度
が上昇したときには同様の効果となり、分子量が
上がらないものと推定される。本発明において特
に好ましい重合温度は30〜55℃である。
また、前記した塩化ジアリルジアルキルアンモ
ニウムの重合の一般則に反する性質は重合率と重
合体の粘度の関係をみると、重合率が85％程度ま
では粘度は徐々に増加しているが90％付近から急
に粘度が増加し、高い分子量の重合体が生成する
事実から次の如く推定できる。塩化ジアリルジア
ルキルアンモニウムは環を形成しながら生長する
が連鎖停止はアリル基二つのうち一つで停止し、
もう一つのアリル基は末端あるいはペンダントに
残存するかあるいは不均斉化停止により末端に二
重結合を残し、これが高い重合率となつたときに
更に重合が起こり、高分子量の重合体を生成する
のではないかと推定される。
本発明に於いて、塩化ジアリルジアルキルアン
モニウムのアルキル基を例示すると次のようなも
のがある。メチル、エチル、ノルマルプロピル、
イソプロピル、ノルマル、イソ、セカンダリー又
はターシヤリーブチル、２−エチルヘキシル等で
ある。
また、水溶性アゾ系開始剤としては具体的に
は、２・2′−アゾビスアミジノメタン、２・2′−
アゾビスアミジノエタン、２・2′−アゾビス２−
アミジノプロパン、２・2′−アゾビス２−イミダ
ゾリジニルプロパン等及び、それぞれの塩酸塩、
硫酸塩、硝酸塩、酢酸塩等がある。
本発明を実施する場合の重合方法としては従来
公知の方法が採用出来る。例えば溶媒として水を
用いた溶液重合（水溶液重合）又は単量体水溶液
を有機溶媒中に分散させて重合を行なう油中水滴
型の逆相懸濁重合等の方法が採用出来る。
以下に実施例、比較例、応用例を掲げて、本発
明に説明する。
実施例 １
PH6.8〜7.0に調整した70重量％塩化ジアリルジ
メチルアンモニウム水溶液100部に重合開始剤と
して水溶性アゾ化合物２・2′−アゾビス２−アミ
ジノプロパンハイドロクロライドを単量体重量当
り4000ppm添加しよくかきまぜた後、窒素ガス
を導入し、溶存酸素を充分に除去し、40℃で48時
間重合を行い、ロウ状重合体を取り出し、粘度を
測定した。
In the present invention, when polymerizing diallyldialkylammonium chloride to produce a diallyldialkylammonium chloride polymer, a water-soluble azo initiator is used in an amount of 0.2 to 1.5% based on the monomer weight, and the polymerization is carried out at a temperature of 55°C or lower. The present invention relates to a method for producing a diallyldialkylammonium chloride polymer, which is characterized in that the diallyldialkylammonium chloride polymer is According to the present invention, polymers with very high molecular weights can be obtained. Diaryldialkylammonium chloride is a compound with two double bonds in the molecule, but when polymerized using a radical polymerization initiator, it does not form a crosslinked polymer with a three-dimensional network structure, but instead has two double bonds in the molecule. It is known that this is a cyclization polymerization in which polymerization proceeds while bonding, that is, two allyl groups form a ring. Therefore, the obtained polymer is a water-soluble linear polymer having a cyclic quaternary ammonium salt in each structural unit. In addition, these polymers are used for various purposes as cationic polymer electrolytes, but it is difficult to obtain high molecular weight polymers for use as sedimentation flocculants for sewage and wastewater treatment. It is only used for limited purposes. It is known that the higher the molecular weight of a polymer electrolyte generally used as a precipitant and flocculant, the greater its effect. Therefore, with the aim of obtaining a high molecular weight polymer of diallyldialkylammonium chloride, the present inventor investigated polymerization using various initiators under various conditions, discovered surprising facts, and completed the present invention. It came to this. In general, in polymerization using a radical polymerization initiator, the amount of the radical polymerization initiator is 50 to 50% per monomer weight.
Approximately 2000 ppm is used, but when trying to obtain particularly high molecular weight polymers, the polymerization rate must be kept low due to the characteristics of the polymerization reaction.
The amount of radical polymerization initiator is about 50 to 500 ppm, and the reaction conditions are low temperature and long time. Also, as a matter of course, if a large amount of radical polymerization initiator is used, only a low molecular weight polymer will be obtained. This is due to the characteristic of the polymerization reaction that the radicals generated by the radical polymerization initiator simultaneously perform a termination reaction. However, when a water-soluble azo initiator is used as a radical polymerization initiator for the polymerization of diallyldialkylammonium chloride, the amount of 50ppm to 20000ppm
(2%), the molecular weight of the obtained polymer increases as the amount used increases, and we discovered the surprising fact that even if the amount exceeds 1.0% per monomer weight, a polymer with a very high molecular weight can be obtained. . When an organic or inorganic peroxide initiator was used instead of a water-soluble azo initiator, the molecular weight decreased as the amount of initiator used increased, as is the general rule. The amount of the water-soluble azo initiator to be used is selected based on the relationship between polymerization rate and calorific value, and a range of 0.2 to 1.5% based on the weight of the monomer is suitable for obtaining a high molecular weight polymer. The particularly preferred amount of water-soluble azo initiator used is 0.2 to 1%.
It is. Regarding the polymerization temperature, 55°C or lower is an essential condition for obtaining a high molecular weight. If the polymerization temperature is 55°C or higher, only low molecular weight polymers can be obtained.
These differences are presumed to be due to the specificity of carbon radicals caused by the decomposition of azo-based initiators; in general, peroxide-based oxygen radicals have greater ability for initiation reactions, and are also more resistant to termination reactions. Furthermore, it is presumed that carbon radicals have a similar effect when the temperature rises, and that the molecular weight does not increase. A particularly preferred polymerization temperature in the present invention is 30 to 55°C. In addition, the above-mentioned property of diallyldialkylammonium chloride that goes against the general rules of polymerization is that when looking at the relationship between the polymerization rate and the viscosity of the polymer, the viscosity gradually increases until the polymerization rate reaches about 85%, but it approaches 90%. From the fact that the viscosity suddenly increases and a high molecular weight polymer is produced, the following can be estimated. Diaryldialkylammonium chloride grows while forming a ring, but the chain is terminated at one of the two allyl groups.
The other allyl group remains at the terminal or pendant, or leaves a double bond at the terminal due to disproportionation termination, and when the polymerization rate is high, further polymerization occurs to produce a high molecular weight polymer. It is presumed that this is the case. In the present invention, examples of the alkyl group of diallyldialkylammonium chloride include the following. Methyl, ethyl, normal propyl,
Isopropyl, normal, iso, secondary or tertiary butyl, 2-ethylhexyl and the like. In addition, specific examples of water-soluble azo initiators include 2,2'-azobisamidinomethane, 2,2'-
Azobisamidinoethane, 2,2'-azobis2-
amidinopropane, 2,2′-azobis2-imidazolidinylpropane, etc. and their respective hydrochlorides,
There are sulfates, nitrates, acetates, etc. Conventionally known methods can be employed as the polymerization method when carrying out the present invention. For example, methods such as solution polymerization using water as a solvent (aqueous solution polymerization) or water-in-oil reverse phase suspension polymerization in which polymerization is carried out by dispersing an aqueous monomer solution in an organic solvent can be employed. The present invention will be explained below with reference to Examples, Comparative Examples, and Application Examples. Example 1 A water-soluble azo compound 2,2'-azobis2-amidinopropane hydrochloride was added as a polymerization initiator to 100 parts of a 70% by weight diallyldimethylammonium chloride aqueous solution adjusted to pH 6.8 to 7.0 at 4000 ppm per monomer weight. After thoroughly stirring, nitrogen gas was introduced to sufficiently remove dissolved oxygen, polymerization was carried out at 40°C for 48 hours, and the waxy polymer was taken out and its viscosity was measured.
【表】
実施例 ２
実施例１の条件のうち、重合開始剤として水溶
性アゾ化合物２・2′−アゾビス２−イミダゾリジ
ニルプロパンハイドロクロライドを単量体重量当
り4000ppm添加し、他は全く同一条件で重合
し、得られたロウ状重合体を取り出し、粘度を測
定した。[Table] Example 2 Under the conditions of Example 1, 4000 ppm of water-soluble azo compound 2,2'-azobis2-imidazolidinylpropane hydrochloride was added per monomer weight as a polymerization initiator, and the other conditions were exactly the same. Polymerization was carried out under the following conditions, and the obtained waxy polymer was taken out and its viscosity was measured.
【表】
実施例 ３
PH6.8〜7.0に調整した70重量％塩化ジアリルジ
エチルアンモニウム水溶液100部に重合開始剤と
して水溶性アゾ化合物２・2′−アゾビス２−アミ
ジノプロパンハイドロクロライドを単量体重量当
り4000ppm添加し、他は実施例１と全く同一条
件で重合し、得られたロウ状重合体を取り出し粘
度を測定した。[Table] Example 3 A water-soluble azo compound 2,2'-azobis2-amidinopropane hydrochloride was added as a polymerization initiator to 100 parts of a 70% by weight diallyldiethylammonium chloride aqueous solution adjusted to pH 6.8 to 7.0 by monomer weight. Polymerization was carried out under exactly the same conditions as in Example 1, except that 4000 ppm was added, and the obtained waxy polymer was taken out and its viscosity was measured.
【表】
比較例 １、２
PH6.8〜7.0に調整した70重量％塩化ジアリルジ
メチルアンモニウム水溶液100部に重合開始剤と
してｔ−ブチルハイドロパーオキサイドを単量体
重量当り150ppm（比較例１）及び水溶性アゾ化
合物２・2′−アゾビス２−アミジノプロパンハイ
ドロクロライドを単量体重量当り1000ppm（比
較例２）添加し、よくかきまぜた後、窒素ガスを
導入し、溶存酸素を充分に除去し35℃で24時間、
更に45℃に昇温し24時間重合を行つた。得られた
ロウ状重合体を取り出し、粘度を測定した。[Table] Comparative Examples 1 and 2 t-Butyl hydroperoxide was added as a polymerization initiator to 100 parts of a 70% by weight diallyldimethylammonium chloride aqueous solution adjusted to pH 6.8 to 7.0 at 150 ppm per monomer weight (Comparative Example 1) and A water-soluble azo compound 2,2'-azobis2-amidinopropane hydrochloride was added at 1000 ppm per monomer weight (Comparative Example 2), and after stirring well, nitrogen gas was introduced to thoroughly remove dissolved oxygen. ℃ for 24 hours,
The temperature was further raised to 45°C and polymerization was carried out for 24 hours. The obtained waxy polymer was taken out and its viscosity was measured.
【表】
応用例
実施例１、比較例１で得られた重合体0.5重量
％水溶液について凝集剤としての性能評価を行つ
た。評価方法としては、300mlを500ml容器にと
り、250rpmで撹拌しながら所定量の薬剤を加
え、30秒間撹拌した。フロツクの大きさ、清澄性
を測定後、フロツク強度をみるため、500rpmで
15秒撹拌し、フロツクの大きさ、過試験、小型
遠心過器で脱水し、ケーキ水分を測定し、以下
の如く、本発明の優秀さが証明された。
汚泥 Ｍ下水処理場 混合汚泥 SS（懸濁物
質）2.22％[Table] Application Example The 0.5% by weight aqueous solutions of the polymers obtained in Example 1 and Comparative Example 1 were evaluated for their performance as flocculants. As an evaluation method, 300 ml was placed in a 500 ml container, a predetermined amount of the drug was added while stirring at 250 rpm, and the mixture was stirred for 30 seconds. After measuring the floc size and clarity, the machine was run at 500 rpm to check the floc strength.
After stirring for 15 seconds, floc size, overtesting, dehydration in a small centrifuge, and cake moisture content, the superiority of the present invention was demonstrated as follows. Sludge M sewage treatment plant Mixed sludge SS (suspended solids) 2.22%
【表】【table】
【表】
乾燥前のケ
ーキ重量
[Table] Before drying
key weight
Claims (1)
して塩化ジアリルジアルキルアンモニウム重合体
を製造する際に、水溶性アゾ系開始剤を単量体重
量当り、0.2〜1.5％使用し、55℃以下の温度で重
合させる事を特徴とする塩化ジアリルジアルキル
アンモニウム重合体の製造法。1. When polymerizing diallyldialkylammonium chloride to produce a diallyldialkylammonium chloride polymer, use a water-soluble azo initiator in an amount of 0.2 to 1.5% per monomer weight and polymerize at a temperature of 55°C or lower. A method for producing a diallyldialkylammonium chloride polymer characterized by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9323679A JPS5618611A (en) | 1979-07-24 | 1979-07-24 | Production of diallyldialkylammonium chloride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9323679A JPS5618611A (en) | 1979-07-24 | 1979-07-24 | Production of diallyldialkylammonium chloride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5618611A JPS5618611A (en) | 1981-02-21 |
| JPS625163B2 true JPS625163B2 (en) | 1987-02-03 |
Family
ID=14076887
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9323679A Granted JPS5618611A (en) | 1979-07-24 | 1979-07-24 | Production of diallyldialkylammonium chloride |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5618611A (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH677857B5 (en) * | 1986-07-02 | 1992-01-15 | Sandoz Ag | |
| US5248744A (en) * | 1992-04-20 | 1993-09-28 | Nalco Chemical Company | Process of polymerizing diallyldialkyl ammonium compounds with azo catalyst |
| US5422408A (en) * | 1992-04-20 | 1995-06-06 | Nalco Chemical Company | Polymerization of diallyldialkyl ammonium halide compounds with azo compound and inorganic salt |
| CA2125545C (en) * | 1993-06-10 | 2005-11-01 | Manian Ramesh | Hydrophobic dispersants used in forming polymer dispersions |
| US6083497A (en) * | 1997-11-05 | 2000-07-04 | Geltex Pharmaceuticals, Inc. | Method for treating hypercholesterolemia with unsubstituted polydiallylamine polymers |
| JP4149795B2 (en) * | 2002-11-18 | 2008-09-17 | ハイモ株式会社 | Sludge dewatering agent |
| CN100357501C (en) * | 2006-04-21 | 2007-12-26 | 北京科技大学 | Poly-diallyldimethyl ammonium chloride single-chain single crystal and method for preparing same |
| JP5846387B2 (en) * | 2010-04-19 | 2016-01-20 | 日東紡績株式会社 | Method for producing diallylamine acetate polymer |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5035279A (en) * | 1973-06-12 | 1975-04-03 | ||
| JPS5157793A (en) * | 1974-11-15 | 1976-05-20 | Nitto Boseki Co Ltd | JIARIRUAMIN JUDOTAINO JUGOTAIO SEIZOSURU HOHO |
-
1979
- 1979-07-24 JP JP9323679A patent/JPS5618611A/en active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5035279A (en) * | 1973-06-12 | 1975-04-03 | ||
| JPS5157793A (en) * | 1974-11-15 | 1976-05-20 | Nitto Boseki Co Ltd | JIARIRUAMIN JUDOTAINO JUGOTAIO SEIZOSURU HOHO |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5618611A (en) | 1981-02-21 |
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