JPH0367061B2 - - Google Patents
Info
- Publication number
- JPH0367061B2 JPH0367061B2 JP58000424A JP42483A JPH0367061B2 JP H0367061 B2 JPH0367061 B2 JP H0367061B2 JP 58000424 A JP58000424 A JP 58000424A JP 42483 A JP42483 A JP 42483A JP H0367061 B2 JPH0367061 B2 JP H0367061B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- quaternary ammonium
- ammonium salt
- polymerization
- chloride
- 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
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 14
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 13
- -1 glycidyl quaternary ammonium salt Chemical class 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000001449 anionic compounds Chemical class 0.000 claims description 3
- 150000002891 organic anions Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000006116 polymerization reaction Methods 0.000 description 10
- 239000000178 monomer Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000004513 sizing Methods 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- PUVAFTRIIUSGLK-UHFFFAOYSA-M trimethyl(oxiran-2-ylmethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1CO1 PUVAFTRIIUSGLK-UHFFFAOYSA-M 0.000 description 3
- MPNXSZJPSVBLHP-UHFFFAOYSA-N 2-chloro-n-phenylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=CC=C1 MPNXSZJPSVBLHP-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 229940121375 antifungal agent Drugs 0.000 description 2
- 239000003429 antifungal agent Substances 0.000 description 2
- 239000002216 antistatic agent Substances 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 229920006026 co-polymeric resin Polymers 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000003623 enhancer Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229920001567 vinyl ester resin Polymers 0.000 description 2
- LTVDFSLWFKLJDQ-UHFFFAOYSA-N α-tocopherolquinone Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)(O)CCC1=C(C)C(=O)C(C)=C(C)C1=O LTVDFSLWFKLJDQ-UHFFFAOYSA-N 0.000 description 2
- DUJRJZCLDOPFGP-UHFFFAOYSA-M (3-bromo-2-hydroxypropyl)-trimethylazanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC(O)CBr DUJRJZCLDOPFGP-UHFFFAOYSA-M 0.000 description 1
- HPLFXTUAVXJDPJ-UHFFFAOYSA-M (3-chloro-2-hydroxypropyl)-triethylazanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC(O)CCl HPLFXTUAVXJDPJ-UHFFFAOYSA-M 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- HRQDDZWMEGEOOO-UHFFFAOYSA-N 2-trimethylsilylpropanoic acid Chemical compound OC(=O)C(C)[Si](C)(C)C HRQDDZWMEGEOOO-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PMUFIOHHLUVLIT-UHFFFAOYSA-M [Cl-].ClCC(CC[N+](C)(C)C)O Chemical compound [Cl-].ClCC(CC[N+](C)(C)C)O PMUFIOHHLUVLIT-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001336 alkenes Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229920006317 cationic polymer Polymers 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008394 flocculating agent Substances 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000003055 glycidyl group Chemical class C(C1CO1)* 0.000 description 1
- 150000004820 halides Chemical group 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- QVOJVKONBAJKMA-UHFFFAOYSA-M triethyl(oxiran-2-ylmethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1CO1 QVOJVKONBAJKMA-UHFFFAOYSA-M 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
本発明は重合中又は貯蔵中の安定性に優れた重
合性第４級アンモニウム塩の製造法の提供を目的
とする。
重合性第４級アンモニウム塩モノマーを（共）
重合したポリマーは、高分子凝集剤、紙力増強剤
等の製紙用薬剤、経紙サイジング用糊剤、繊維染
色性改良剤、帯電防止剤、防菌剤、防カビ剤、イ
オン交換樹脂等として有用である。
従来より重合性第４級アンモニウム塩の製造法
として次のものが開示されている。
(1) 不飽和有機酸エステル
特公昭42−14523、特公昭47−40041において
下式で示される第４級アンモニウム塩の製造
法。
An object of the present invention is to provide a method for producing a polymerizable quaternary ammonium salt having excellent stability during polymerization or storage. Polymerizable quaternary ammonium salt monomer (co)
The polymerized polymer can be used as a polymer flocculant, a papermaking agent such as a paper strength enhancer, a sizing agent for paper sizing, a fiber dyeability improver, an antistatic agent, an antibacterial agent, an antifungal agent, an ion exchange resin, etc. Useful. Conventionally, the following methods have been disclosed as methods for producing polymerizable quaternary ammonium salts. (1) Unsaturated organic acid ester A method for producing a quaternary ammonium salt represented by the following formula in Japanese Patent Publications No. 42-14523 and No. 47-40041.
【式】R1はＨ
またはメチル基
R2はメチル、エチル、フエニル基等
Ｘ
は陰性基
(2) 不飽和有機酸アミド
特開昭48−54020、特開昭48−56614において
下式で示される第４級アンモニウム塩。[Formula] R 1 is H or a methyl group R 2 is a methyl, ethyl, phenyl group, etc. Quaternary ammonium salt.
【式】R1はＨ
またはメチル基
R2はメチル、エチル基等
Ｘ
は陰性基
しかしながら、これらの製造法により得られる
重合性第４級アンモニウム塩モノマーは分子中に
エステル基やアミド基を有する為に加水分解を受
けやすく、貯蔵中等に不飽和酸が副生することが
多かつた。さらに他の不飽和モノマー、例えば脂
肪酸ビニルエステルと共重合した後、苛性アルカ
リを添加して加水分解あるいはカロアルコール分
解反応を行つた場合、第４級アンモニウム基がは
ずれて共重合体中にカチオン基を導入出来ない。
あるいは導入できたとしても少量しか含有せしめ
ることができないという欠点をもつていた。
本発明者はこのような従来の欠点を克服すべく
鋭意研究を重ねた結果、ここに加水分解を受けな
いエーテル結合を有する第４級アンモニウム塩の
製造法を発明するに到つた。
即ち、本発明は
アリルアルコールのアルカリ金属アルコラート
に一般式
又は
〔R1：酸素数１〜４のアルキル基
Ａ：[Formula] R 1 is H or a methyl group R 2 is a methyl, ethyl group, etc. Therefore, it is susceptible to hydrolysis, and unsaturated acids are often produced as by-products during storage. Furthermore, when copolymerizing with other unsaturated monomers, such as fatty acid vinyl esters, and then adding caustic alkali to perform hydrolysis or caroalcoholization reactions, the quaternary ammonium groups are removed and cationic groups are formed in the copolymer. cannot be introduced.
Alternatively, even if it could be introduced, it had the disadvantage that it could only be contained in a small amount. As a result of extensive research to overcome these conventional drawbacks, the present inventors have now invented a method for producing a quaternary ammonium salt having an ether bond that is not subject to hydrolysis. That is, the present invention provides an alkali metal alcoholate of allyl alcohol with the general formula or [R 1 : Alkyl group A having 1 to 4 oxygen atoms:
【式】 又は【formula】 or
【式】 Ｄ：Cl又はBr Ｅ：【formula】 D: Cl or Br E:
【式】（R2：Ｈ又はCH3−）
Ｘ
：無機又は有機アニオン〕
で表わされるハロゲン化第４級アンモニウム塩又
はグリシジル第４級アンモニウム塩を反応させて
一般式
CH2＝CH−CH2−Ｏ−CH2−Ａ−Ｂ
〔Ａ：[Formula] (R 2 : H or CH 3 − ) -O-CH 2 -A-B [A:
【式】 又は【formula】 or
【式】 Ｂ：【formula】 B:
【式】（R1：炭素数１〜４のアルキ
ル基、Ｘ
は無機又は有機アニオン）〕
で表わされる重合性第４級アンモニウム塩を製造
する方法である。
以下、本発明を詳細に説明する。
本発明の方法において用いられるアルカリ金属
は金属ナトリウム、金属カリウム、金属リチウム
等が用いられる。ハロゲン化第４級アンモニウム
塩化合物としては３−クロロ−２−ヒドロキシプ
ロピルトリメチルアンモニウムクロリド、３−ク
ロロ−２−ヒドロキシ−２−メチルプロピルトリ
メチルアンモニウムクロリド、３−ブロモ−２−
ヒドロキシプロピルトリメチルアンモニウムクロ
リド、４−クロロ−３−ヒドロキシブチルトリメ
チルアンモニウムクロリド、４−ブロモ−３−ヒ
ドロキシブチルトリメチルアンモニウムクロリ
ド、３−クロロ−２−ヒドロキシプロピルトリエ
チルアンモニウムクロリド、４−クロロ−３−ヒ
ドロキシブチルトリエチルアンモニウムクロリド
等があげられる。
グリシジル第４級アンモニウム塩化合物として
はグリシジルトリメチルアンモニウムクロリド、
β−メチルグリシジルトリメチルアンモニウムク
ロリド、グリシジルトリエチルアンモニウムクロ
リド等があげられる。
アリルアルコールをアルコラートにする場合発
熱をともなうので必要に応じて冷却することが望
ましい。反応はアルコラートに、ハロゲン化第４
級アンモニウム塩化合物、グリシジル第４級アン
モニウム塩化合物の水溶液を加えて室温〜70℃で
行うことができる。好ましくは室温で反応させそ
の後40〜60℃で１時間程度熟成させることが望ま
しい。室温未満では反応速度が遅く、70℃を越え
ると重合する可能性がある。重合の可能性がある
場合は重合禁止剤を加えてもさしつかえない。反
応モル比はアルコラート１モルに対してハロゲン
化第４級アンモニウム塩化合物、グリシジル第４
級アンモニウム塩化合物1.0〜1.4モルが適当であ
るが特に1.0〜1.2モルが好ましい。反応が進行す
ると無機塩が沈澱してくるのでこの無機塩は過
により取り除く。
本発明の反応中において重合防止という点につ
いては特に必要としないが、慎重を期する為に公
知の重合禁止剤であるハイドロキノン、ハイドロ
キノンモノメチルエーテル等を添加しても何らさ
しつかえない。
本発明の製造法により得られる重合性第４級ア
ンモニウム塩モノマーは単独または他の不飽和モ
ノマーとともに公知の（共）重合法によつて重合
させることができる。その重合法としては溶液重
合、乳化重合、懸濁重合等が行なえる。その際ラ
ジカル重合開始剤、放射線、紫外線等を用いて重
合反応を開始させうる。
こうして得られたカチオン性ポリマーは高分子
凝集剤、紙力増強剤等の製紙用薬剤、経糸サイジ
ング用糊剤、繊維染色性改良剤、帯電防止剤、防
菌剤、防カビ剤、イオン交換樹脂等の幅広い用途
が期待される。
本発明の製造法により得られる重合性第４級ア
ンモニウム塩モノマーは非常に安定である為にモ
ノマーの貯蔵中、あるいは重合中等に不都合な副
反応が起きるという心配がない。また、例えば該
モノマーと脂肪酸ビニルエステルとの共重合樹脂
を苛性アルカリを用いて加水分解反応あるいは加
アルコール分解反応を行なつて得られる共重合樹
脂中の第４級アンモニウム基は、上記の反応を経
てもほとんどはずれることなく、その樹脂中に保
持される。
以下実施例をもつて本発明をさらに詳しく説明
するが、本発明はこれに限定されるものではな
い。
実施例 １
300mlの三角フラスコにアリルアルコール58ｇ
（１モル）を入れ、三角フラスコを冷却しながら
金属ナトリウム23ｇ（１モル）を加えてアルコラ
ートにした。これに室温で３−クロロ−２−ヒド
ロキシプロピルトリメチルアンモニウムクロリド
188ｇ（１モル）を水溶液状で加えて撹拌反応さ
せたのち、60℃で１時間熟成させた。反応終了後
無機塩を濾別したのち未反応アリルアルコールの
ガスクロマトグラフイーのピーク面積から求めた
反応率は98.2％であつた。
得られた生成物の核磁気共鳴スペクトル（溶
媒：D2O、基準物質：トリメチルシリルプロピオ
ン酸のd4−ナトリウム塩）の帰属、赤外線吸収ス
ペクトルの特性吸収、元素分析値（表１）より、
該生成物はＮ−（３−アリルオキシ−２−ヒドロ
キシプロピル）トリメチルアンモニウムクロリド
であることを確認した。
Γ核磁気共鳴スペクトル
This is a method for producing a polymerizable quaternary ammonium salt represented by the following formula: (R 1 is an alkyl group having 1 to 4 carbon atoms, X is an inorganic or organic anion). The present invention will be explained in detail below. The alkali metal used in the method of the present invention includes sodium metal, potassium metal, lithium metal, and the like. Examples of halogenated quaternary ammonium salt compounds include 3-chloro-2-hydroxypropyltrimethylammonium chloride, 3-chloro-2-hydroxy-2-methylpropyltrimethylammonium chloride, 3-bromo-2-
Hydroxypropyltrimethylammonium chloride, 4-chloro-3-hydroxybutyltrimethylammonium chloride, 4-bromo-3-hydroxybutyltrimethylammonium chloride, 3-chloro-2-hydroxypropyltriethylammonium chloride, 4-chloro-3-hydroxybutyl Examples include triethylammonium chloride. Examples of glycidyl quaternary ammonium salt compounds include glycidyl trimethylammonium chloride;
Examples include β-methylglycidyltrimethylammonium chloride and glycidyltriethylammonium chloride. When converting allyl alcohol into an alcoholate, it generates heat, so it is desirable to cool it as necessary. The reaction is to form an alcoholate with a quaternary halide.
The reaction can be carried out at room temperature to 70°C by adding an aqueous solution of a quaternary ammonium salt compound or a glycidyl quaternary ammonium salt compound. It is preferable to react at room temperature and then age at 40 to 60°C for about 1 hour. Below room temperature, the reaction rate is slow, and above 70°C, polymerization may occur. If there is a possibility of polymerization, a polymerization inhibitor may be added. The reaction molar ratio is 1 mol of alcoholate to halogenated quaternary ammonium salt compound, glycidyl quaternary
The amount of the ammonium salt compound is suitably 1.0 to 1.4 mol, particularly preferably 1.0 to 1.2 mol. As the reaction progresses, inorganic salts precipitate and are removed by filtration. Although it is not particularly necessary to prevent polymerization during the reaction of the present invention, there is no harm in adding known polymerization inhibitors such as hydroquinone, hydroquinone monomethyl ether, etc. for the sake of caution. The polymerizable quaternary ammonium salt monomer obtained by the production method of the present invention can be polymerized alone or together with other unsaturated monomers by a known (co)polymerization method. As the polymerization method, solution polymerization, emulsion polymerization, suspension polymerization, etc. can be performed. At that time, the polymerization reaction can be initiated using a radical polymerization initiator, radiation, ultraviolet light, or the like. The cationic polymers thus obtained are polymer flocculants, paper-making agents such as paper strength enhancers, sizing agents for warp sizing, fiber dyeability improvers, antistatic agents, antibacterial agents, antifungal agents, and ion exchange resins. It is expected to have a wide range of applications such as Since the polymerizable quaternary ammonium salt monomer obtained by the production method of the present invention is very stable, there is no fear that undesirable side reactions will occur during storage of the monomer or during polymerization. Furthermore, for example, quaternary ammonium groups in a copolymer resin obtained by subjecting a copolymer resin of the monomer and a fatty acid vinyl ester to a hydrolysis reaction or an alcohololysis reaction using caustic alkali, It is retained in the resin without coming off even after a long period of time. The present invention will be explained in more detail below with reference to Examples, but the present invention is not limited thereto. Example 1 58g of allyl alcohol in a 300ml Erlenmeyer flask
(1 mol) was added thereto, and while cooling the Erlenmeyer flask, 23 g (1 mol) of metallic sodium was added to form an alcoholate. Add 3-chloro-2-hydroxypropyltrimethylammonium chloride to this at room temperature.
After adding 188 g (1 mole) in the form of an aqueous solution and causing a stirring reaction, it was aged at 60°C for 1 hour. After the reaction was completed, the inorganic salt was filtered off, and the reaction rate determined from the peak area of unreacted allyl alcohol in gas chromatography was 98.2%. Based on the nuclear magnetic resonance spectrum (solvent: D 2 O, reference material: d 4 -sodium salt of trimethylsilylpropionic acid) of the obtained product, the characteristic absorption of the infrared absorption spectrum, and the elemental analysis values (Table 1),
The product was confirmed to be N-(3-allyloxy-2-hydroxypropyl)trimethylammonium chloride. Γ nuclear magnetic resonance spectrum
【式】
（アリルアルコールのオレフインプロトンの吸
収位置を参考に構造を決定した。）
−Ｎ
（CH3）3
Cl3.22ppm
（化合物中、最多プロトンを有するので、
3.22ppmの帰属に決定した。他のプロトンの吸
収は３〜5ppmに重なりあつている。）
Γ赤外線吸収スペクトル
CH2＝CH− 1635cm-1、1415cm-1、910cm-1
−OH 3350cm-1
−CH2−Ｏ−CH2− 1100cm-1
（これらの構造は中西香爾著「赤外線吸収スペ
クトル」南江堂を参考として決定した。）
Γ元素分析値[Formula] (The structure was determined with reference to the absorption position of the olefin proton of allyl alcohol.) -N (CH 3 ) 3 Cl3.22ppm (Since it has the largest number of protons among the compounds,
The attribution was determined to be 3.22ppm. The absorption of other protons overlaps at 3 to 5 ppm. ) Γ Infrared absorption spectrum CH 2 = CH− 1635cm -1 , 1415cm -1 , 910cm -1 -OH 3350cm -1 -CH 2 -O-CH 2 - 1100cm -1 (These structures are based on the infrared absorption spectrum written by Kaji Nakanishi. Determined with reference to "Spectrum" Nankodo.) Γ elemental analysis value
【表】
実施例 ２
実施例１に準じてアリルアルコール58ｇ（１モ
ル）、金属ナトリウム23ｇ（１モル）を用いて得
たアルコラートに、グリシジルトリメチルアンモ
ニウムクロリド151ｇ（１モル）を水溶液状で加
えて撹拌反応させた。未反応のグリシジルトリメ
チルアンモニウムクロリドのエポキシを定量して
求めた反応率は99.1％であつた。
元素分析値は表２のとおりであり、生成物は実
施例１と同様にしてＮ−（３−アリルオキシ−２
−ヒドロキシプロピル）トリメチルアンモニウム
クロリドであることを確認した。[Table] Example 2 To an alcoholate obtained according to Example 1 using 58 g (1 mol) of allyl alcohol and 23 g (1 mol) of metallic sodium, 151 g (1 mol) of glycidyltrimethylammonium chloride was added in the form of an aqueous solution. The reaction was stirred. The reaction rate determined by quantifying the amount of epoxy in unreacted glycidyltrimethylammonium chloride was 99.1%. The elemental analysis values are shown in Table 2, and the product was prepared in the same manner as in Example 1 to obtain N-(3-allyloxy-2
-Hydroxypropyl)trimethylammonium chloride.
Claims (1)
トに一般式 又は 〔R1：炭素数１〜４のアルキル基 Ａ：【式】【式】 又は【式】 Ｄ：Cl又はBr Ｅ：【式】（R2：Ｈ又はCH3−） Ｘ ：無機又は有機アニオン〕 で表わされるハロゲン化第４級アンモニウム塩又
はグリシジル第４級アンモニウム塩を反応させて
一般式 CH2＝CH−CH2−Ｏ−CH2−Ａ−Ｂ 〔Ａ：【式】【式】 又は【式】 Ｂ：【式】（R1：炭素数１〜４のアルキ ル基、Ｘ は無機又は有機アニオン）〕 で表わされる重合性第４級アンモニウム塩を製造
する方法。[Claims] 1. General formula for the alkali metal alcoholate of allyl alcohol or [R 1 : Alkyl group having 1 to 4 carbon atoms A: [Formula] [Formula] or [Formula] D: Cl or Br E: [Formula] (R 2 : H or CH 3 -) X: Inorganic or organic anion ] A halogenated quaternary ammonium salt or a glycidyl quaternary ammonium salt represented by the general formula CH 2 =CH-CH 2 -O-CH 2 -A-B [A: [Formula] [Formula] or [Formula] B: [Formula] (R 1 : C1-C4 alkyl group, X is an inorganic or organic anion)] A method for producing a polymerizable quaternary ammonium salt represented by the following formula.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP42483A JPS59128362A (en) | 1983-01-07 | 1983-01-07 | Polymerizable quaternary ammonium salt and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP42483A JPS59128362A (en) | 1983-01-07 | 1983-01-07 | Polymerizable quaternary ammonium salt and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59128362A JPS59128362A (en) | 1984-07-24 |
| JPH0367061B2 true JPH0367061B2 (en) | 1991-10-21 |
Family
ID=11473420
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP42483A Granted JPS59128362A (en) | 1983-01-07 | 1983-01-07 | Polymerizable quaternary ammonium salt and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59128362A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4967292B2 (en) * | 2005-03-07 | 2012-07-04 | 住友ベークライト株式会社 | Composition, ion conductive electrolyte obtained therefrom, and secondary battery using the same |
| KR100757666B1 (en) | 2006-07-14 | 2007-09-11 | 단국대학교 산학협력단 | Anti-static adhesive and method for manufacturing the same |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53130610A (en) * | 1977-04-19 | 1978-11-14 | Nippon Oil & Fats Co Ltd | Preparation of quaternary ammonium salt |
-
1983
- 1983-01-07 JP JP42483A patent/JPS59128362A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53130610A (en) * | 1977-04-19 | 1978-11-14 | Nippon Oil & Fats Co Ltd | Preparation of quaternary ammonium salt |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59128362A (en) | 1984-07-24 |
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