JPH01226882A - Cyclic oligoarylene compound - Google Patents
Cyclic oligoarylene compoundInfo
- Publication number
- JPH01226882A JPH01226882A JP5452988A JP5452988A JPH01226882A JP H01226882 A JPH01226882 A JP H01226882A JP 5452988 A JP5452988 A JP 5452988A JP 5452988 A JP5452988 A JP 5452988A JP H01226882 A JPH01226882 A JP H01226882A
- Authority
- JP
- Japan
- Prior art keywords
- cyclic
- arylene
- residues
- compound
- group
- 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.)
- Pending
Links
- 125000004122 cyclic group Chemical group 0.000 title claims abstract description 30
- 150000001875 compounds Chemical class 0.000 title claims description 29
- 125000000732 arylene group Chemical group 0.000 claims abstract description 11
- -1 arylene sulfoxide Chemical class 0.000 claims abstract description 11
- 150000001923 cyclic compounds Chemical class 0.000 claims abstract description 11
- 239000000126 substance Substances 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 3
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 3
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 abstract description 6
- 239000003814 drug Substances 0.000 abstract description 4
- 239000003905 agrochemical Substances 0.000 abstract description 3
- 229910001385 heavy metal Inorganic materials 0.000 abstract description 3
- 150000002500 ions Chemical class 0.000 abstract description 3
- 239000002699 waste material Substances 0.000 abstract description 3
- XWUCFAJNVTZRLE-UHFFFAOYSA-N 7-thiabicyclo[2.2.1]hepta-1,3,5-triene Chemical compound C1=C(S2)C=CC2=C1 XWUCFAJNVTZRLE-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000969 carrier Substances 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 abstract description 2
- 239000007795 chemical reaction product Substances 0.000 abstract description 2
- 239000000975 dye Substances 0.000 abstract description 2
- 235000013305 food Nutrition 0.000 abstract description 2
- 238000005342 ion exchange Methods 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 abstract 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 abstract 1
- 239000000701 coagulant Substances 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 229910052938 sodium sulfate Inorganic materials 0.000 abstract 1
- 235000011152 sodium sulphate Nutrition 0.000 abstract 1
- 231100000331 toxic Toxicity 0.000 abstract 1
- 230000002588 toxic effect Effects 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 229920000858 Cyclodextrin Polymers 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000002555 ionophore Substances 0.000 description 2
- 230000000236 ionophoric effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 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 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- TXKMVPPZCYKFAC-UHFFFAOYSA-N disulfur monoxide Inorganic materials O=S=S TXKMVPPZCYKFAC-UHFFFAOYSA-N 0.000 description 1
- 239000008394 flocculating agent Substances 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical compound S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Removal Of Specific Substances (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、耐薬品性、耐熱性に優れ、種々の置換基を導
入できる新規な環状オリゴアリーレン化合物に関する。DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a novel cyclic oligoarylene compound which has excellent chemical resistance and heat resistance and into which various substituents can be introduced.
゛
（従来の技術）
クラウンエーテル類のような環状化合物は、他の化合物
に無い特殊な機能を有している。(Prior Art) Cyclic compounds such as crown ethers have special functions that other compounds do not have.
例えば、環状構造の空洞に特定の物質を取込むいわゆる
包接能を有するシクロデキストリンは、種々の分子と包
接化合物を形成しその溶解性を向上したり揮発や化学反
応を抑制できる。また同様な包接場を持つイオノフオア
は金属を選択的に取込む機能を有している。これらは、
稀薄溶液からの有用物の分離、廃液中の有害重金属の除
去あるいは医薬品、農薬、食品などに用途が拡がりつつ
おる。For example, cyclodextrin, which has the so-called clathrate ability to incorporate a specific substance into the cavity of its cyclic structure, can form clathrate compounds with various molecules to improve their solubility and suppress volatilization and chemical reactions. Ionophores with similar inclusion fields also have the ability to selectively incorporate metals. these are,
Applications are expanding to include the separation of useful substances from dilute solutions, the removal of harmful heavy metals from waste liquids, and pharmaceuticals, agricultural chemicals, and foods.
（発明が解決しようとする課題）
しかしながら、かかる従来の環状化合物は、耐薬品性や
耐熱性に劣るという大きな欠点を有していた。そのため
強酸、強アルカリなどの溶剤中や高温下での使用は不可
能で、またかかる条件で被包接物質を取出し環状化合物
を効率的に再生することもできなかった。更に置換基の
導入も、温和な反応条件を選ぶ必要があるため限界があ
った。(Problems to be Solved by the Invention) However, such conventional cyclic compounds have a major drawback of being inferior in chemical resistance and heat resistance. Therefore, it has been impossible to use it in solvents such as strong acids and strong alkalis, or at high temperatures, and it has also been impossible to extract the clathrate and efficiently regenerate the cyclic compound under such conditions. Furthermore, the introduction of substituents has been limited by the need to select mild reaction conditions.
このように従来の環状化合物では、耐薬品性や耐熱性が
劣ることが用途拡大の大きな障害となっていた。As described above, conventional cyclic compounds have poor chemical resistance and heat resistance, which has been a major obstacle to expanding their use.
一方、環状化合物の耐薬品性や耐熱性を向上する手段と
して、架橋高分子化する方法が知られているが、この場
合も十分な効果は得られず、また本来の機能を失ったり
、更に不溶化が同時に起こることもあり、かえって用途
が制限されるなどの欠点があった。On the other hand, as a means to improve the chemical resistance and heat resistance of cyclic compounds, a method of crosslinking polymerization is known, but in this case as well, sufficient effects cannot be obtained, and the original function may be lost or even worse. Insolubilization may also occur at the same time, which has the disadvantage of restricting its uses.
（課題を解決するための手段）
本発明者らはかかる現状に鑑み、従来の概念に囚われる
ことなく鋭意検討した結果、本発明に到達した。(Means for Solving the Problems) In view of the current situation, the present inventors conducted extensive studies without being bound by conventional concepts, and as a result, arrived at the present invention.
本発明は、耐薬品性、耐熱性に優れ、種々の置換基が導
入できる極めて利用範囲の広い新規な環状オリゴアリー
レン化合物の提供を目的とするものである。The object of the present invention is to provide a novel cyclic oligoarylene compound that has excellent chemical resistance and heat resistance, and can be used in a very wide range of applications into which various substituents can be introduced.
本発明は次の構成を有する。The present invention has the following configuration.
（１）下記一般式（Ｉ）で表わされる４〜１２残基の環
状化合物であって、少なくとも一部の残基がアリーレン
スルホキシド及び／またはアリーレンスルホンであるこ
とを特徴とする環状オリゴアリーレン化合物。(1) A cyclic oligoarylene compound having 4 to 12 residues represented by the following general formula (I), characterized in that at least some of the residues are arylene sulfoxide and/or arylene sulfone.
〔但し、Ａｒはアリーレン基、Ｓはイオウ原子、Ｏは酸
素原子、ＸはＯ〜２の整数を表す。〕（２）アリーレン
基が、パラフェニレン基である請求項（１）記載の環状
オリゴアリーレン化合物。[However, Ar represents an arylene group, S represents a sulfur atom, O represents an oxygen atom, and X represents an integer of O to 2. ] (2) The cyclic oligoarylene compound according to claim (1), wherein the arylene group is a paraphenylene group.
（３）環状化合物を構成する全残基の少なくとも５０％
が、アリーレンスルホン残基である請求項（１）記載の
環状オリゴアリーレン化合物。(3) At least 50% of all residues constituting the cyclic compound
The cyclic oligoarylene compound according to claim 1, wherein is an arylene sulfone residue.
（４）アリーレン基が、含水酸基、含カルボン酸基、含
スルホン酸基、含窒素置換基から選ばれた少なくとも一
種の置換基を有する請求項（１）記載の環状オリゴアリ
ーレン化合物。(4) The cyclic oligoarylene compound according to claim (1), wherein the arylene group has at least one substituent selected from a hydrous acid group, a carboxylic acid group, a sulfonic acid group, and a nitrogen-containing substituent.
以下、本発明を更に詳しく説明する。The present invention will be explained in more detail below.
本発明の環状化合物は、環状構造を有するオリゴアリー
レン化合物からなることを重要な構成要素としている。An important component of the cyclic compound of the present invention is an oligoarylene compound having a cyclic structure.
本発明でいう環状オリゴアリーレン化合物のアリーレン
基とは、いわゆる芳香族炭化水素の核から、水素原子２
個を除いた残基のことである。かかるアリーレン基とし
て、本発明において特に好ましいのはパラフェニレン基
の場合である。The arylene group of the cyclic oligoarylene compound as used in the present invention refers to 2 hydrogen atoms from the so-called aromatic hydrocarbon nucleus.
It refers to the residues excluding the individual. As such an arylene group, a paraphenylene group is particularly preferred in the present invention.
更に、アリーレン基が含水酸基、含カルボン酸基、含ス
ルホン酸基、含窒素置換基などから選ばれた少なくとも
一種の置換基を有する場合は、溶剤との親和性を制御で
き、また他の多くの置換基を導入するための原体ともな
り、更に、特に包接能を利用する用途では取込む物質の
選択性が制御できるなどの点で好ましい。Furthermore, when the arylene group has at least one substituent selected from a hydrous acid group, a carboxylic acid group, a sulfonic acid group, a nitrogen-containing substituent, etc., the affinity with solvents can be controlled, and many other It also serves as a starting material for introducing a substituent, and furthermore, it is preferable in that the selectivity of the substance to be incorporated can be controlled, especially in applications that utilize inclusion ability.
更に、本発明でいう環状オリゴアリーレン化合物は、Ｓ
Ｏｘで表す含イオウ成分、即ちイオウ原子ないし酸化イ
オウ分子を残基に有する。かかるＳＯＸのＸはイオウと
結合する酸素の数を表す。Furthermore, the cyclic oligoarylene compound referred to in the present invention is S
It has a sulfur-containing component represented by Ox, that is, a sulfur atom or a sulfur oxide molecule as a residue. X in SOX represents the number of oxygens bonded to sulfur.
本発明において、イオウと結合する酸素は多いほど、環
状オリゴアリーレン化合物は耐薬品性、耐熱性に優れる
のでより好ましい。In the present invention, the more oxygen is bonded to sulfur, the more preferable the cyclic oligoarylene compound is since it has better chemical resistance and heat resistance.
即ち、本発明でいう環状オリゴアリーレン化合物は、ア
リーレンスルフィド（ｘ＝Ｏ） 、アリーレンスルホキ
シド（Ｘ＝１＞、アリーレンスルホン（ｘ＝２＞の残基
からなり、かつ少なくとも一部の残基がアリーレンスル
ホキシド及び／またはアリーレンスルホンであるものが
望ましい。特に、アリーレンスルホンの残基が全残基の
５０％以上より好ましくは７０％以上である場合は、極
めて耐薬品性、耐熱性に優れ、また良好な親水性を示し
、更に、ニトロ基を含む種々の置換基が容易に導入でき
るなど化学修飾性にも優れており特に好ましい。That is, the cyclic oligoarylene compound as used in the present invention consists of residues of arylene sulfide (x=O), arylene sulfoxide (X=1>, and arylene sulfone (x=2>), and at least some of the residues are arylene Those that are sulfoxide and/or arylene sulfone are desirable.In particular, when arylene sulfone residues account for 50% or more, preferably 70% or more of the total residues, they have excellent chemical resistance and heat resistance, and have good properties. It is particularly preferred because it exhibits excellent hydrophilicity and also has excellent chemical modification properties, such as the ability to easily introduce various substituents including a nitro group.
また、本発明でいう環状オリゴアリーレン化合物はかか
る残基が４から１２−からなるもの（４〜１２母体）が
特に好ましい。ただしかかる残基の数は環状構造内の空
洞の形と大きさを決定する主たる要因であることから、
かかる範囲であれば用途に応じて選ぶことができる。Further, the cyclic oligoarylene compound referred to in the present invention is particularly preferably one in which such residues consist of 4 to 12 groups (4 to 12 groups). However, since the number of such residues is the main factor determining the shape and size of the cavity within the cyclic structure,
As long as it is within this range, it can be selected depending on the purpose.
本発明でいう環状オリゴアリーレン化合物の製法は、特
に限定するものではないが、例えば、まず環状オリゴア
リーレンスルフィドを合成し、これを過酸化水素、過酢
酸、過マンガン酸塩などの過酸化物を用いて酸化する方
法でスルホキシド化やスルホン化する方法は有効である
。The method for producing the cyclic oligoarylene compound referred to in the present invention is not particularly limited, but for example, first, a cyclic oligoarylene sulfide is synthesized, and then a peroxide such as hydrogen peroxide, peracetic acid, permanganate, etc. is added to the cyclic oligoarylene sulfide. Sulfoxidation and sulfonation methods are effective.
（実施例）
以下、実施例により本発明を更に詳しく説明する。なお
、本発明はこれらに限定されない。(Example) Hereinafter, the present invention will be explained in more detail with reference to Examples. Note that the present invention is not limited to these.
実施例１゜
Ｎ−メチルピロリドン中で、硫化ナトリウムと１．４−
バラジクロルベンゼンを高温加圧下で反応させ、反応生
成物から６残基の環状パラフェニレンスルフィドを分離
抽出した。Example 1 Sodium sulfide and 1,4-
Baladichlorobenzene was reacted under high temperature and pressure, and 6 residues of cyclic paraphenylene sulfide were separated and extracted from the reaction product.
次にこれを過酢酸で処理して全残基の約７０％が、アリ
ーレンスルホン残基とした（ＮＭＲにて確認）。Next, this was treated with peracetic acid to convert about 70% of all residues into arylene sulfone residues (confirmed by NMR).
１ワられた環状オリゴアリーレン化合物は、有機金属な
どと包接化合物を形成した。また′ａ硫酸中で環状オリ
ゴアリーレン化合物を効率的に再生すこともできた。The cyclic oligoarylene compound that was subjected to the first step formed a clathrate compound with an organic metal or the like. It was also possible to efficiently regenerate the cyclic oligoarylene compound in 'a' sulfuric acid.
更に、得られた環状オリゴアリーレン化合物は、ジメチ
ルアセトアミド、ジメチルホルムアミド、ジメチルスル
ホキシドなどの極性有機溶剤はもとより、濃硫酸、濃硝
酸、濃塩酸などの強酸や苛性ソーダなどの強アルカリに
も耐える耐薬品性を有し、耐熱水性および３００℃を越
える耐熱性を有していた。Furthermore, the obtained cyclic oligoarylene compound has chemical resistance that can withstand not only polar organic solvents such as dimethylacetamide, dimethylformamide, and dimethyl sulfoxide, but also strong acids such as concentrated sulfuric acid, concentrated nitric acid, and concentrated hydrochloric acid, and strong alkalis such as caustic soda. It had hot water resistance and heat resistance exceeding 300°C.
比較例１゜
シクロデキストリンと有機金属との包接化合物を合成し
、ｍ硫酸で処理したところシクロデキストリンは分解し
再生できなかった。Comparative Example 1 When an inclusion compound of cyclodextrin and an organometallic compound was synthesized and treated with sulfuric acid, the cyclodextrin was decomposed and could not be regenerated.
実施例２゜
実施例１．と同様にして得た全残基の約７０％が、アリ
ーレンスルホン残基で構成される環状オリゴアリーレン
化合物をクロルスルホン酸で処理してスルホンＩＩを導
入した後、苛性ソーダと煮沸して置換基をスルホン酸ソ
ーダに変えた。Example 2゜Example 1. A cyclic oligoarylene compound in which about 70% of the total residues are arylene sulfone residues obtained in the same manner as above was treated with chlorosulfonic acid to introduce sulfone II, and then boiled with caustic soda to remove the substituents. Changed to sodium sulfonate.
）ｑられたスルホン酸ソーダ化環状オリゴアリーレン化
合物は、実施例１．と同様な包接能、耐薬品性、耐熱性
に加え良好なイオン交換能や水溶性も示した。) The sulfonic acid sodiumated cyclic oligoarylene compound prepared in Example 1. In addition to the same clathration ability, chemical resistance, and heat resistance, it also showed good ion exchange ability and water solubility.
比較例２゜
イオノフオアであるパリノマイシンに対し、実施例２．
と同様な方法でスルホン酸ソーダ基の導入を試みたが、
パリノマイシンは分解してしまった。Comparative Example 2. In contrast to the ionophore palinomycin, Example 2.
I tried to introduce a sodium sulfonate group in the same way as above, but
Palinomycin has broken down.
（発明の効果）
本発明の環状オリゴアリーレン化合物は、以下の優れた
効果を発揮する。(Effects of the Invention) The cyclic oligoarylene compound of the present invention exhibits the following excellent effects.
従来の環状化合物にない耐薬品性、耐熱性を発揮し、ま
た種々の置換基を導入できることから極めて利用範囲が
拡がった。It exhibits chemical resistance and heat resistance not found in conventional cyclic compounds, and the ability to introduce various substituents has greatly expanded its range of use.
特に包接能を持つので、稀薄溶液からの有用物の分離、
廃液中の有害重金属の除去、医薬品、農薬、食料品、選
択的触媒、イオンキャリヤ、分子センサなどの様々な用
途で利用できる。In particular, it has inclusion ability, so it can be used to separate useful substances from dilute solutions.
It can be used in a variety of applications, including the removal of hazardous heavy metals from waste liquids, pharmaceuticals, agricultural chemicals, foodstuffs, selective catalysts, ion carriers, and molecular sensors.
更に種々の置換基を導入すれば、上記以外の医薬品、染
料、凝集剤、イオン交換体などとして利用できる化合物
の原体となる。Furthermore, by introducing various substituents, it becomes a raw material for compounds that can be used as pharmaceuticals, dyes, flocculants, ion exchangers, etc. other than those mentioned above.
Claims (1)
環状化合物であって、少なくとも一部の残基がアリーレ
ンスルホキシド及び／またはアリーレンスルホンである
ことを特徴とする環状オリゴアリーレン化合物。 ▲数式、化学式、表等があります▼…………（ I ） 〔但し、Ａｒはアリーレン基、Ｓはイオウ原子、Ｏは酸
素原子、ｘは０〜２の整数を表す。〕（２）アリーレン
基が、パラフェニレン基である請求項（１）記載の環状
オリゴアリーレン化合物。 （３）環状化合物を構成する全残基の少なくとも５０％
が、アリーレンスルホン残基である請求項（１）記載の
環状オリゴアリーレン化合物。 （４）アリーレン基が、含水酸基、含カルボン酸基、含
スルホン酸基、含窒素置換基から選ばれた少なくとも一
種の置換基を有する請求項（１）記載の環状オリゴアリ
ーレン化合物。[Scope of Claims] (1) A cyclic compound having 4 to 12 residues represented by the following general formula (I), characterized in that at least some of the residues are arylene sulfoxide and/or arylene sulfone. A cyclic oligoarylene compound. ▲There are mathematical formulas, chemical formulas, tables, etc.▼…………(I) [However, Ar is an arylene group, S is a sulfur atom, O is an oxygen atom, and x is an integer from 0 to 2. ] (2) The cyclic oligoarylene compound according to claim (1), wherein the arylene group is a paraphenylene group. (3) At least 50% of all residues constituting the cyclic compound
The cyclic oligoarylene compound according to claim 1, wherein is an arylene sulfone residue. (4) The cyclic oligoarylene compound according to (1), wherein the arylene group has at least one substituent selected from a hydrous acid group, a carboxylic acid group, a sulfonic acid group, and a nitrogen-containing substituent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5452988A JPH01226882A (en) | 1988-03-07 | 1988-03-07 | Cyclic oligoarylene compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5452988A JPH01226882A (en) | 1988-03-07 | 1988-03-07 | Cyclic oligoarylene compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01226882A true JPH01226882A (en) | 1989-09-11 |
Family
ID=12973191
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5452988A Pending JPH01226882A (en) | 1988-03-07 | 1988-03-07 | Cyclic oligoarylene compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01226882A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008087967A1 (en) * | 2007-01-16 | 2008-07-24 | Hodogaya Chemical Co., Ltd. | Process for production of oxidized cyclic phenol sulfide |
-
1988
- 1988-03-07 JP JP5452988A patent/JPH01226882A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008087967A1 (en) * | 2007-01-16 | 2008-07-24 | Hodogaya Chemical Co., Ltd. | Process for production of oxidized cyclic phenol sulfide |
| CN101636394A (en) * | 2007-01-16 | 2010-01-27 | 保土谷化学工业株式会社 | Process for production of oxidized cyclic phenol sulfide |
| JP5239872B2 (en) * | 2007-01-16 | 2013-07-17 | 保土谷化学工業株式会社 | Method for producing oxidized cyclic phenol sulfide |
| US8624065B2 (en) | 2007-01-16 | 2014-01-07 | Hodogaya Chemical Co., Ltd. | Methods for producing oxidized cyclic phenol sulfides |
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