JPH0629230B2 - Novel cationic compound - Google Patents
Novel cationic compoundInfo
- Publication number
- JPH0629230B2 JPH0629230B2 JP22587187A JP22587187A JPH0629230B2 JP H0629230 B2 JPH0629230 B2 JP H0629230B2 JP 22587187 A JP22587187 A JP 22587187A JP 22587187 A JP22587187 A JP 22587187A JP H0629230 B2 JPH0629230 B2 JP H0629230B2
- Authority
- JP
- Japan
- Prior art keywords
- cationic compound
- present
- novel cationic
- bleaching
- formula
- 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
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は、アルキレンジアミン誘導体であり、分子内に 基を有する新規なカチオン化合物に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention is an alkylenediamine derivative, The present invention relates to a novel cationic compound having a group.
従来、分子内に 基を有する化合物としては、 (J.Org.Chem.1977,vol42,No.2,26〜32頁） (J.Chem.Soc.Perkin Trans.2.1978.No.8,786〜793頁） （米国特許第3281452号） （英国特許第1178371号） などが知られている。Conventionally, in the molecule As the compound having a group, (J.Org.Chem.1977, vol42, No.2, 26-32) (J. Chem. Soc. Perkin Trans.2.1978.No.8,786-793 pages) (US Patent No. 3281452) (British Patent No. 1178371) and the like are known.
しかしながら、本発明の如き分子内に２個の 基を有するアルキレンジアミン誘導体とその有用性につ
いて検討した報告はこれまで全く見当らない。However, two molecules in the molecule as in the present invention Up to now, no reports have been found on the alkylenediamine derivative having a group and its usefulness.
〔問題点を解決するための手段〕 斯かる実情において、本発明者らは分子内に 基を２個有するカチオン化合物が、漂白活性化剤、繊維
柔軟剤、帯電防止剤、殺菌剤等として優れた性質を示す
ことを見出し、本発明を完成した。[Means for Solving Problems] In such a situation, the present inventors have It was found that a cationic compound having two groups has excellent properties as a bleaching activator, a fabric softener, an antistatic agent, a bactericide, etc., and completed the present invention.
即ち、本発明は、下記の一般式（Ｉ）で表わされる新規
なカチオン化合物を提供するものである。That is, the present invention provides a novel cationic compound represented by the following general formula (I).
（式中、R1，R2，R3，R4は炭素数１〜３のアルキル基、
Ｘ は有機、あるいは無機の陰イオン、ｎは１〜９の整
数である。） このような本発明の新規な化合物の中でも、特に有用な
化合物として式（Ｉ）中のR1，R2，R3，R4がメチル基、
ｎが１〜９の整数である化合物が挙げられる。 (In the formula, R1， R2， R3， RFourIs an alkyl group having 1 to 3 carbon atoms,
X Is an organic or inorganic anion, n is an integer from 1 to 9
Is a number. ) Among such novel compounds of the present invention, particularly useful
R in formula (I) as a compound1， R2， R3， RFourIs a methyl group,
Examples include compounds in which n is an integer of 1 to 9.
本発明のカチオン化合物（Ｉ）は例えば次の方法で調製
することができる。即ち、３級のアルキレンジアミンと
アセトニトリルのハロゲン化物との反応により、通常の
アミンの４級化反応と同様にして容易に得られる。The cationic compound (I) of the present invention can be prepared, for example, by the following method. That is, it can be easily obtained by a reaction of a tertiary alkylenediamine and a halide of acetonitrile in the same manner as a usual amine quaternization reaction.
〔R1，R2，R3，R4，ｎは上記と同様、Ｘ′はハロゲンを
表わす。〕 〔発明の効果〕 以上の如くして得られる本発明の化合物（Ｉ）は凡て新
規化合物であるが、それらの中R1，R2，R3，R4及びｎが
適当に選択されたものは、繊維柔軟剤、帯電防止剤、殺
菌剤などとして使用することができる。また、漂白活性
化剤として非常に優れた効果を示す。 [R 1 , R 2 , R 3 , R 4 , and n are the same as above, and X'represents halogen. [Effects of the Invention] The compounds (I) of the present invention obtained as described above are all novel compounds, of which R 1 , R 2 , R 3 , R 4 and n are appropriately selected. Tatters can be used as a fabric softener, an antistatic agent, a bactericide, and the like. Further, it exhibits a very excellent effect as a bleach activator.
以下、実施例によって本発明を説明するが、本発明はこ
れらに限定されるものではない。Hereinafter, the present invention will be described with reference to examples, but the present invention is not limited thereto.
実施例１ クロロアセトニトリル20ｇ(172mmol)をアセトン100m
に溶解し、還流管をセットした300m二口フラスコでマ
グネティックスターラーを用いて攪拌しながら室温で39
ｇ(516mmol)のN,N,N′,N′−テトラメチルエチレンジア
ミンを100mのアセトンに溶かした溶液を滴下した。滴
下後、70℃に加熱し90分反応後、濃縮、冷却した後、生
じた結晶を濾別すると（Ｉ−ａ）が39.37ｇ得られた。
収率85.6%。Example 1 Chloroacetonitrile 20 g (172 mmol) 100 ml acetone
In a 300 m two-necked flask equipped with a reflux tube and stirred at room temperature with a magnetic stirrer at room temperature.
A solution of g (516 mmol) of N, N, N ', N'-tetramethylethylenediamine in 100 m of acetone was added dropwise. After dropping, the mixture was heated to 70 ° C., reacted for 90 minutes, concentrated and cooled, and then the resulting crystals were filtered off to obtain 39.37 g of (Ia).
Yield 85.6%.
mp. 195〜200℃分解 νKBr 3022,2944,1482,1455,1410,981,918,906,792cm
-1 1 H-NMR 3.52(12H.s)、4.33(4H,s)、4.95(4H,brs) 実施例２ 実施例１の反応でテトラメチルエチレンジアミン39ｇを
Ｎ，Ｎ，Ｎ′，Ｎ′−テトラメチル1,6ヘキサンジアミ
ン57.8(516mmol)に替えることにより（Ｉ−ｂ）白色結
晶が102.8ｇ得られた。収率80.3% mp. 201〜203℃分解 νKBr 2962,2920,1488,1455cm-1 1 H-NMR 1.05〜2.25(8H.m)、3.35(12H,s)、3.40〜3.80(4
H.m)、4.75(4H,s)、 使用例 上記のようにして得られた本発明に係る化合物Ｉ−ａ，
Ｉ−ｂについて、漂白作用に関する試験を行った。第１
表に下記の方法で漂白効果を評価した結果を示す。mp.195-200 ℃ Decomposition ν KBr 3022,2944,1482,1455,1410,981,918,906,792cm
-1 1 H-NMR 3.52 (12H.s), 4.33 (4H, s), 4.95 (4H, brs) Example 2 By replacing 39 g of tetramethylethylenediamine in the reaction of Example 1 with 57.8 (516 mmol) of N, N, N ', N'-tetramethyl1,6 hexanediamine, 102.8 g of (Ib) white crystals were obtained. Yield 80.3% mp. 201 ~ 203 ℃ Decomposition ν KBr 2962,2920,1488,1455cm -1 1 H-NMR 1.05 ~ 2.25 (8H.m), 3.35 (12H, s), 3.40 ~ 3.80 (4
Hm), 4.75 (4H, s), Examples of Use Compound Ia of the present invention obtained as described above,
Ib was tested for bleaching action. First
The table shows the results of evaluating the bleaching effect by the following method.
漂白方法 20℃の水300mに有効酸素が0.05%となるように過酸化
水素を加え、炭酸ナトリウムを１ｇ添加した。この溶液
に過酸化水素と等モルとなるようにＩ−ａ、又はＩ−ｂ
を加え、下記の方法で調製した紅茶汚染布を用いて30分
間浸漬漂白を行い、水洗い、乾燥後、下式により漂白率
を求めた。比較品の次亜塩素酸ナトリウムは有効塩素0.
06%で評価した。Bleaching method Hydrogen peroxide was added to 300 m of water at 20 ° C so that the available oxygen was 0.05%, and 1 g of sodium carbonate was added. I-a or I-b should be added to this solution so that it becomes equimolar to hydrogen peroxide.
Was added, and a black tea-contaminated cloth prepared by the following method was used for immersion bleaching for 30 minutes. After rinsing with water and drying, the bleaching rate was determined by the following formula. The comparative product, sodium hypochlorite, has no available chlorine.
It was evaluated by 06%.
紅茶汚染布の漂白率： 反射率は日本電色工業（株）製NDR-101DPで460nmフィル
ターを使用して測定した。Bleaching rate of black tea cloth: The reflectance was measured by NDR-101DP manufactured by Nippon Denshoku Industries Co., Ltd. using a 460 nm filter.
紅茶汚染布： 日東紅茶（黄色パッケージ）80ｇを３のイオン交換水
にて約15分間煮沸後、糊抜きしたサラシ木綿でこし、こ
の液に木綿金布＃2003布を浸し、約15分間煮沸する。そ
のまま火よりおろし、２時間程度放置後自然乾燥させ、
洗液に色のつかなくなるまで水洗し、脱水、プレス後、
10cm×10cmの試験片とし、実験に供した。Black tea-contaminated cloth: 80g of Nitto black tea (yellow package) is boiled with ion-exchanged water of 3 for about 15 minutes, then rubbed with desalted cotton and soaked in cotton gold cloth # 2003 cloth and boiled for about 15 minutes. . Remove from heat as it is, let stand for about 2 hours and let it air dry,
Rinse with water until the washing liquid is no longer colored, dehydrate, press,
A test piece of 10 cm × 10 cm was used for the experiment.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.5 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ｄ０６Ｍ 13/46 ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 5 Identification code Office reference number FI technical display location D06M 13/46
Claims (2)
Ｘ は有機、あるいは無機の陰イオン、ｎは１〜９の整
数である。） で表わされるカチオン化合物。1. The following general formula (I):(In the formula, R1， R2， R3， RFourIs an alkyl group having 1 to 3 carbon atoms,
X Is an organic or inorganic anion, n is an integer from 1 to 9
Is a number. ) A cationic compound represented by.
メチル基である特許請求の範囲第１項記載のカチオン化
合物。2. The cationic compound according to claim 1 , wherein in the general formula (I), R 1 , R 2 , R 3 and R 4 are methyl groups.
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22587187A JPH0629230B2 (en) | 1987-09-09 | 1987-09-09 | Novel cationic compound |
| US07/229,913 US4915863A (en) | 1987-08-14 | 1988-08-08 | Bleaching composition |
| MYPI88000908A MY103600A (en) | 1987-08-14 | 1988-08-09 | Bleaching composition |
| DK451488A DK451488A (en) | 1987-08-14 | 1988-08-12 | BLEACH |
| NZ233651A NZ233651A (en) | 1987-08-14 | 1988-08-12 | N,n'-(cyanomethyl)-n,n,n',n',-tetraalkyl alkylene diamine salts and their preparation |
| NO883581A NO171564C (en) | 1987-08-14 | 1988-08-12 | BLEACH MIXING |
| NZ225815A NZ225815A (en) | 1987-08-14 | 1988-08-12 | Bleaching composition with peroxide and a peracid precursor of an ammonium nitrile compound |
| AU20920/88A AU617686B2 (en) | 1987-08-14 | 1988-08-12 | Bleaching composition |
| DE3889165T DE3889165T2 (en) | 1987-08-14 | 1988-08-15 | Bleach composition. |
| ES88307558T ES2063040T3 (en) | 1987-08-14 | 1988-08-15 | WHITENING COMPOUND. |
| EP88307558A EP0303520B1 (en) | 1987-08-14 | 1988-08-15 | Bleaching composition |
| KR1019880010409A KR910005027B1 (en) | 1987-08-14 | 1988-08-16 | Bleaching composition |
| US07/502,335 US4978770A (en) | 1987-08-14 | 1990-03-30 | Quaternary ammonium salts of dicyano substituted teriary alkylene diamines as bleach activators |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22587187A JPH0629230B2 (en) | 1987-09-09 | 1987-09-09 | Novel cationic compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6468347A JPS6468347A (en) | 1989-03-14 |
| JPH0629230B2 true JPH0629230B2 (en) | 1994-04-20 |
Family
ID=16836157
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22587187A Expired - Fee Related JPH0629230B2 (en) | 1987-08-14 | 1987-09-09 | Novel cationic compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0629230B2 (en) |
-
1987
- 1987-09-09 JP JP22587187A patent/JPH0629230B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6468347A (en) | 1989-03-14 |
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