JPS63270648A - Polyquinone containing amino group in main chain - Google Patents
Polyquinone containing amino group in main chainInfo
- Publication number
- JPS63270648A JPS63270648A JP10447687A JP10447687A JPS63270648A JP S63270648 A JPS63270648 A JP S63270648A JP 10447687 A JP10447687 A JP 10447687A JP 10447687 A JP10447687 A JP 10447687A JP S63270648 A JPS63270648 A JP S63270648A
- Authority
- JP
- Japan
- Prior art keywords
- polyquinone
- amino group
- main chain
- ammonia
- 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.)
- Granted
Links
- 125000003277 amino group Chemical group 0.000 title description 17
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract description 12
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 abstract description 8
- 150000001875 compounds Chemical class 0.000 abstract description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract description 7
- 229910021529 ammonia Inorganic materials 0.000 abstract description 6
- 150000001412 amines Chemical class 0.000 abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 3
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 abstract description 2
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 abstract description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 abstract description 2
- 235000003704 aspartic acid Nutrition 0.000 abstract description 2
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 abstract description 2
- 235000013922 glutamic acid Nutrition 0.000 abstract description 2
- 239000004220 glutamic acid Substances 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 229920000292 Polyquinoline Polymers 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000002781 deodorant agent Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 235000019645 odor Nutrition 0.000 description 9
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 230000001877 deodorizing effect Effects 0.000 description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- DWBZUUKLOFQIGX-UHFFFAOYSA-N azane;methylsulfinylmethane Chemical compound N.CS(C)=O DWBZUUKLOFQIGX-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Abstract
Description
【発明の詳細な説明】
（発明、の技術分野）
本発明は一般式
（式中Ｒは、水素原子、無置換若しくは置換のアルキル
基又は芳香族基である。ｍ及びｎは１〜２０である。）
で表されるポリキノンに関する。Detailed Description of the Invention (Technical Field of the Invention) The present invention is based on the general formula (wherein R is a hydrogen atom, an unsubstituted or substituted alkyl group, or an aromatic group, m and n are 1 to 20) be.)
Regarding the polyquinone represented by
（発明の利用分野）
本発明の前記一般式（１）で表されるポリキノンはアミ
ン類又はメルカプタン類と反応する特徴を有し１反応性
脱臭剤として有用である。(Field of Application of the Invention) The polyquinone of the present invention represented by the general formula (1) has the characteristic of reacting with amines or mercaptans, and is useful as a monoreactive deodorizing agent.
（従来の技術）
従来、脱臭剤には活性炭が一般に用いられていた。活性
炭は臭い成分の吸着剤とし有用であるが、低分子のアミ
ン類及びメルカプタン類は吸着しにくく脱臭剤として利
用するには限界があった。(Prior Art) Activated carbon has conventionally been generally used as a deodorizer. Although activated carbon is useful as an adsorbent for odor components, it is difficult to adsorb low-molecular amines and mercaptans, and its use as a deodorizing agent is limited.
（発明が解決した問題点）
ポリキノンは、アミノ基及びメルカプト基と反応し易い
ために、悪臭の原因である低分子のアミノ基及びメルカ
プト基をもつ化合物を除去することができ、反応性脱臭
剤として有用であることを見出し本発明を完成した。(Problems solved by the invention) Since polyquinone easily reacts with amino groups and mercapto groups, it can remove compounds with low molecular weight amino groups and mercapto groups that cause bad odors, and is used as a reactive deodorizer. The present invention was completed based on the discovery that the present invention is useful as a method.
（問題点を解決するための手段）
本発明は前記一般式（１）で表される主鎖にアミン基を
有するポリキノンである。(Means for Solving the Problems) The present invention is a polyquinone having an amine group in the main chain represented by the general formula (1).
本発明の前記一般式（１）で表される主鎖にアミノ基を
有するポリキノンを製造するには、原料としてｐ−ベン
ゾキノン及び−級のアミノ基含有する化合物あるいはア
ンモニアと反応させることによυ行表われる。−級のア
ミン基を有する化合物としては、例えばアスパラギン酸
、グルタミン酸、グリシン等のアミノ酸、アニリンなど
の芳香族、アミン、メチルアミンなどのアルキルアミン
等を使用することができる。ポリキノンに対し一級アミ
ノ基金有する化合物あるｈはアンモニアの使用チルスル
ホキシド（ＤＭＳＯ）、 ジメチルホルムア宙ド（Ｄ
ＭＦ ’）等の溶媒を単独又は混合して用いることがで
きる。In order to produce the polyquinone having an amino group in the main chain represented by the general formula (1) of the present invention, p-benzoquinone is reacted with a -grade amino group-containing compound or ammonia as a raw material. rows appear. Examples of the compound having a -class amine group include amino acids such as aspartic acid, glutamic acid, and glycine, aromatic compounds such as aniline, amines, and alkyl amines such as methylamine. Compounds with primary amino groups for polyquinones include the use of ammonia dimethyl sulfoxide (DMSO), dimethylformate (DMSO),
Solvents such as MF') can be used alone or in combination.
反応温度は室温〜１２０℃であるが８０〜１００’Ｃ，
（Ｚ）範囲が、目的物が好率よく得られる点で好ましい
・
尚、本発明の前記一般式（１）で表わされるポリキノン
の主鎖部分はベンゾキノンタイプであることが好のまし
いが、ベンゾキノンは還元され易いこと又、アルカリ条
件では水と反応し易いために主鎖の一部はハイドロキノ
ン型又はトリヒドロキシベンゼン型を含んでいる。The reaction temperature is room temperature to 120°C, but 80 to 100°C,
The (Z) range is preferable in that the target product can be obtained with a high rate.The main chain portion of the polyquinone represented by the general formula (1) of the present invention is preferably of the benzoquinone type, but Since benzoquinone is easily reduced and reacts with water under alkaline conditions, a portion of the main chain contains a hydroquinone type or trihydroxybenzene type.
本ポリキノンを脱臭剤として使用するには、主鎖部分の
芳香環がベンゾキノンタンプであることが好ましい。In order to use this polyquinone as a deodorizing agent, it is preferable that the aromatic ring in the main chain portion is benzoquinone tamp.
（発明の効果）
本発明の前記一般式（１）で表されるポリキノンは、ア
ミノ基及びメルカプト基と反応し易いために、悪臭の原
因である低分子のアミノ基及びメルカプト基を含む化合
物を除去することができ１反応性脱臭剤として有用であ
る。(Effects of the Invention) The polyquinone of the present invention represented by the above general formula (1) easily reacts with amino groups and mercapto groups, so it does not contain compounds containing low-molecular amino groups and mercapto groups that cause bad odors. It is useful as a reactive deodorizer.
実施例１．７ミノ基を含むポリキノンの合成液を１ｍ加
え室温で５分間攪拌後、沸騰水中で３時間加熱した。冷
却後酸性にした後、沈殿物をＦ集し、蒸留水で十分洗浄
、風乾して１．１ｇのアミノ基を含むポリキノン全得た
。Example 1.7 1 m of a synthetic solution of polyquinone containing a mino group was added, stirred at room temperature for 5 minutes, and then heated in boiling water for 3 hours. After cooling and acidifying, the precipitate was collected in F, thoroughly washed with distilled water, and air-dried to obtain 1.1 g of polyquinone containing amino groups.
性状：・融点 ３００℃以上
・黒かり色粉体、ΦＤＭＳＯなどの非プロトン性溶媒、
アルカリ性水溶液に溶は易い。Properties: ・Melting point 300℃ or higher ・Dark colored powder, aprotic solvent such as ΦDMSO,
Easily soluble in alkaline aqueous solution.
・ＨＰＬＣ（高速液体クロマトグラフィー）・カラム：
ＯＤＳカラム
・溶出液ニアセトニトリル：水！６：４・流 速： １
ｄ／ｍ１ｎ
０．８２分にこのアミノ基を含むポリキノンＯピーク、
ハイドロキノン１．２４分。・HPLC (high performance liquid chromatography) column:
ODS column/eluent Niacetonitrile: Water! 6:4・Flow rate: 1
Polyquinone O peak containing this amino group at d/m1n 0.82 minutes,
Hydroquinone 1.24 minutes.
ベンゾキノンは１．５６分にピークが認められた。この
結果、得られたアミノ基を含ム？リキノンは、ハイドロ
キノンよシ親水性が高いことがわかりた・
・窒素含量：０．０５％
・ＴＲ（ａｒｔ 、ν）、３４００，１６００，１５
００゜１２００．８２０゜
実施例２．（脱臭効果試験）
実施例１よシ得たアミノ基を含むポリキノン１．０ｇに
ＩＮ−アンモニア水１ｙｓｔ 、 ２ｍｉ、 ３ｍ／
。A peak was observed for benzoquinone at 1.56 minutes. As a result, the resulting amino group containing ? It was found that liquinone has higher hydrophilicity than hydroquinone. ・Nitrogen content: 0.05% ・TR (art, ν), 3400, 1600, 15
00°1200.820° Example 2. (Deodorizing effect test) IN-ammonia water was added to 1.0 g of the amino group-containing polyquinone obtained in Example 1 at 1yst, 2mi, 3m/
.
４ｄ、５ゴ、６ゴ、１０ゴを加え、−夜放置後アンモニ
ア臭を調べたところ１〜５プではアンモニア臭は認めら
れず、６１以上ではアンモニア臭が認められた。アミノ
基を含むポリキノン１ｇあたＤＯ，ｏｏｓＭのアンモニ
ア水を吸収できることが分った。When 4d, 5go, 6go, and 10go were added and the ammonia odor was examined after being left overnight, no ammonia odor was observed in samples 1 to 5, and ammonia odor was observed in samples 61 and above. It was found that 1 g of polyquinone containing an amino group can absorb DO, oosM of ammonia water.
実施例３゜
実施例１よル得たアミノ基を含むポリキノンの量をＨＰ
ＬＣ（カラム： Ｃ，、ＯＤＳ ） により測定し、
フェニルアラニｙの倉が１１５に減少していることが分
った。従って、アミノ基を含むポリキノン１．Ｆあたシ
０．６６．９ （０，００４Ｍ ＞のフェニルアラニン
が反応していることが分った。Example 3゜The amount of polyquinone containing an amino group obtained from Example 1 was determined by HP
Measured by LC (column: C, ODS),
It was found that the stock of Phenylalani y has decreased to 115. Therefore, polyquinones containing amino groups 1. It was found that phenylalanine with an F weight of 0.66.9 (0,004M) was reacted.
実施例４゜
実施例１よシ得たアミン基を含むポリキノンに蒸留して
精製したメルカプトエタノール０．１ Ｍ水溶液１０ｍ
／、２０ｍ、３ＱｍＡ’、４Ｑｍ、５Ｑｙｌを加え１夜
放置後、メルカプト臭をみたところ、２０ゴまでは臭い
が消えたが３０−以上では、メルカプト臭が認められた
。Example 4゜10 ml of a 0.1 M aqueous solution of mercaptoethanol purified by distillation to the polyquinone containing amine groups obtained in Example 1
/, 20m, 3QmA', 4Qm, and 5Qyl were added and left overnight, and the mercapto odor was checked.The odor disappeared up to 20g, but mercapto odor was observed at 30g and above.
Claims (1)
くは置換のアルキル基又は芳香族基である。 ｍ及びｎは１〜２０である。）。(1) Polyquinone represented by the general formula ▲ Numerical formula, chemical formula, table, etc. ▼ (wherein R is a hydrogen atom, an unsubstituted or substituted alkyl group, or an aromatic group. m and n are 1 to 20 be.).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62104476A JP2531520B2 (en) | 1987-04-30 | 1987-04-30 | Polyquinone having amino group in main chain |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62104476A JP2531520B2 (en) | 1987-04-30 | 1987-04-30 | Polyquinone having amino group in main chain |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63270648A true JPS63270648A (en) | 1988-11-08 |
| JP2531520B2 JP2531520B2 (en) | 1996-09-04 |
Family
ID=14381623
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62104476A Expired - Lifetime JP2531520B2 (en) | 1987-04-30 | 1987-04-30 | Polyquinone having amino group in main chain |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2531520B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8778320B2 (en) * | 2002-10-28 | 2014-07-15 | Takasago International Corporation | Deodorant composition |
-
1987
- 1987-04-30 JP JP62104476A patent/JP2531520B2/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8778320B2 (en) * | 2002-10-28 | 2014-07-15 | Takasago International Corporation | Deodorant composition |
| US9358191B2 (en) | 2002-10-28 | 2016-06-07 | Takasago International Corporation | Deodorant composition |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2531520B2 (en) | 1996-09-04 |
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