JPH0588695B2 - - Google Patents
Info
- Publication number
- JPH0588695B2 JPH0588695B2 JP27763288A JP27763288A JPH0588695B2 JP H0588695 B2 JPH0588695 B2 JP H0588695B2 JP 27763288 A JP27763288 A JP 27763288A JP 27763288 A JP27763288 A JP 27763288A JP H0588695 B2 JPH0588695 B2 JP H0588695B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- calix
- arene
- compound
- 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 - Lifetime
Links
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 22
- 229920000642 polymer Polymers 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 6
- -1 propioxycarbonyl group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- 239000000178 monomer Substances 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 7
- 241001164374 Calyx Species 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 238000005979 thermal decomposition reaction Methods 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 description 3
- 238000004806 packaging method and process Methods 0.000 description 3
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229920005992 thermoplastic resin Polymers 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
- UOEYZAXKBKAKRO-UHFFFAOYSA-N 5,11,17,23,29,35-hexa-tert-butylcalix[6]arene-37,38,39,40,41,42-hexol Chemical compound C1C(C=2O)=CC(C(C)(C)C)=CC=2CC(C=2O)=CC(C(C)(C)C)=CC=2CC(C=2O)=CC(C(C)(C)C)=CC=2CC(C=2O)=CC(C(C)(C)C)=CC=2CC(C=2O)=CC(C(C)(C)C)=CC=2CC2=CC(C(C)(C)C)=CC1=C2O UOEYZAXKBKAKRO-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 150000001923 cyclic compounds Chemical group 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012567 medical material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical class O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F20/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
〔産業上の利用分野〕
本発明は、新規カリツクス［ｎ］アレーン誘導
体とその製造方法およびその誘導体からなる医療
材料、感光材料、フイルムとして有用な高分子化
合物に関する。
〔従来の技術〕
カリツクス［ｎ］アレーンは塩基性触媒下、Ｐ
−置換フエノールとホルムアルデヒドの縮合によ
つて得られる環状化合物であり、その分子量が低
くオリゴマー程度のものであるが、包接化合物と
して期待されている。
〔発明が解決しようとする課題〕
しかし、このカリツクス［ｎ］アレーンは溶媒
に溶けにくく粉末状でしか得られないため、取り
扱いにくい〔C.D.Gutsche J.Am.Chem.Soc.，
103，3782（1981）参照〕と言う欠点がある。これ
を解消するため、OH基へ置換基の導入などさま
ざまな官能基のカリツクス［ｎ］アレーンへの導
入が検討されているが、それでも未だに分子量の
低さは解決されていない〔C.D.Gutsche，TOP.
Curr，Chem.，123，１（1984）参照〕。
すなわち、カリツクス［ｎ］アレーンの優れた
包装機能を備えた高分子化合物が得られないと言
う問題があつた。
このような事情に鑑みて、この発明の目的は、
分子中にカリツクス［ｎ］アレーンの環状構造を
有し包装機能を備えた高分子化合物を得ることが
できるカリツクス［ｎ］アレーン誘導体とその製
造方法、および、前記誘導体から得られる耐熱
性、耐薬品性に優れた熱可塑性樹脂を提供するこ
とを目的としている。
〔課題を解決するための手段〕
本発明を概説すれば、その第１の発明はカリツ
クス［ｎ］アレーンに二重結合の付加され下式で
表されるカリツクス［ｎ］アレーン誘導体(A)
[Industrial Application Field] The present invention relates to a novel calix[n]arene derivative, a method for producing the same, and a polymer compound useful as a medical material, a photosensitive material, or a film comprising the derivative. [Prior art] Calix[n]arene is catalyzed by P
It is a cyclic compound obtained by the condensation of -substituted phenol and formaldehyde, and although its molecular weight is low and on the order of oligomers, it is expected to be used as an clathrate compound. [Problem to be solved by the invention] However, this calyx[n]arene is difficult to handle because it is difficult to dissolve in solvents and can only be obtained in powder form [CDGutsche J.Am.Chem.Soc.,
103, 3782 (1981)]. In order to solve this problem, the introduction of various functional groups into calix[n]arene, such as the introduction of substituents to the OH group, is being considered, but the low molecular weight still remains unsolved [CDGutsche, TOP.
See Curr, Chem., 123, 1 (1984)]. That is, there was a problem in that a polymer compound having the excellent packaging function of calix[n]arene could not be obtained. In view of these circumstances, the purpose of this invention is to
A calyx[n]arene derivative capable of obtaining a polymer compound having a cyclic structure of calyx[n]arene in the molecule and having a packaging function, a method for producing the same, and heat resistance and chemical resistance obtained from the derivative The purpose is to provide thermoplastic resins with excellent properties. [Means for Solving the Problems] To summarize the present invention, the first invention is a calix[n]arene derivative (A) represented by the following formula in which a double bond is added to calix[n]arene.
【化】
（式中ｎは３以上の整数、R1はアルキル基、
R2はＨ基またはアルキル基を表す。）の合成にあ
る。
また第２の発明は上記カリツクス［ｎ］アレー
ン誘導体の製造方法に関する発明であつて、下式[Chemical formula] (In the formula, n is an integer of 3 or more, R 1 is an alkyl group,
R 2 represents an H group or an alkyl group. ). The second invention is an invention relating to a method for producing the above-mentioned calyx[n]arene derivative, which comprises the following formula:
【化】
（式中ｎは３以上の整数、R1はアルキル基を
表す。）で示されるカリツクス［ｎ］アレーン(B)
と、下式、Calix [n] arene (B) represented by [Chemical formula] (where n is an integer of 3 or more, and R 1 represents an alkyl group)
And the formula below,
【式】
（式中、R2はＨ基またはアルキル基を表す。）
で示されるエポキシ基含有モノマー(C)とを、アミ
ン触媒として反応させることを特徴とする。
更に第３の発明は、前記第１の発明で得られた
カリツクス［ｎ］アレーン誘導体(A)と、下式[Formula] (In the formula, R 2 represents an H group or an alkyl group.)
It is characterized by reacting with the epoxy group-containing monomer (C) represented by as an amine catalyst. Furthermore, a third invention provides a calyx[n]arene derivative (A) obtained in the first invention, and a formula
第１の発明にかかるカリツクス［ｎ］アレーン
誘導体(A)は、上記のようにビニル基を含むので、
重合開始剤を付与すれば簡単に重合して高分子化
する。
第２の発明は、上記のように構成され、アミン
を触媒に用いると、エポキシ基含有モノマー(C)の
Ｏの片方の手が切れてα位の炭素とカリツクス
［ｎ］アレーンのフエニル基のＯが結合して誘導
体が形成される。
第３の発明にかかる高分子化合物は、分子中の
カリツクス［ｎ］アレーンの構造が、包装作用を
付与するとともに、従来の高分子化合物より物理
的性質が向上する。
〔実施例〕
以下に、この発明を、その実施例を参照しつつ
詳しく説明する。
カリツクス［ｎ］アレーン誘導体(A)を形成する
カリツクス［ｎ］アレーン(B)としては、特に限定
されないが、例えば、ｎが４〜８のものが好まし
い。
カリツクス［ｎ］アレーン(B)とエポキシ基含有
モノマー(C)とは、無溶媒中あるいはキシレン中で
アミンを触媒として用いて化合させられてカリツ
クス［ｎ］アレーン誘導体(A)が形成されるが、カ
リツクス［ｎ］アレーン(B)とエポキシ基含有モノ
マー(C)とのモル比は、１：２〜３程度、反応温度
90〜100℃程度、反応時間は20〜50時間程度が好
ましい。
カリツクス［ｎ］アレーン誘導体(A)と、前記ビ
ニルモノマー(D)との共重合体は、特に限定されな
いが、たとえば、過酸化ベンゾイルを触媒として
用いてラジカル重合させることにより得られる。
実施例 １
Ｐ−tert−ブチルカリツクス［６］アレーン3.0
ｇ、グリシジルメタクリレート９ml、および、ト
リｎ−ブチルアミン0.03ｇからなる混合物を95℃
で加熱した。反応液は最初濁つていたが、約30時
間をすぎるころから透明なつた。50時間後、反応
物を取り出すと粘稠な化合物が11.7ｇ得られた。
この化合物を水−メタノール１：５の混合溶媒で
再沈させ、再沈後、ろ過し乾燥すると白色粉末状
の次式、
Since the calix[n]arene derivative (A) according to the first invention contains a vinyl group as described above,
If a polymerization initiator is added, it will easily polymerize and become a polymer. The second invention is constructed as described above, and when an amine is used as a catalyst, one hand of O of the epoxy group-containing monomer (C) is cut off, and the α-position carbon and the phenyl group of calix[n]arene are separated. O is bonded to form a derivative. In the polymer compound according to the third invention, the calix[n]arene structure in the molecule imparts a packaging effect and has improved physical properties than conventional polymer compounds. [Examples] The present invention will be described in detail below with reference to Examples. The calix[n]arene (B) forming the calix[n]arene derivative (A) is not particularly limited, but preferably, for example, one in which n is 4 to 8. The calix [n] arene (B) and the epoxy group-containing monomer (C) are combined in the absence of a solvent or in xylene using an amine as a catalyst to form the calix [n] arene derivative (A). , the molar ratio of calix[n]arene (B) and epoxy group-containing monomer (C) is about 1:2 to 3, and the reaction temperature is
The temperature is preferably about 90 to 100°C and the reaction time is preferably about 20 to 50 hours. The copolymer of the calix[n]arene derivative (A) and the vinyl monomer (D) is not particularly limited, but can be obtained, for example, by radical polymerization using benzoyl peroxide as a catalyst. Example 1 P-tert-butyl calix [6] arene 3.0
g, glycidyl methacrylate, 9 ml, and tri-n-butylamine 0.03 g at 95°C.
heated with. The reaction solution was cloudy at first, but became clear after about 30 hours. After 50 hours, the reaction product was taken out and 11.7 g of a viscous compound was obtained.
This compound is reprecipitated with a mixed solvent of water and methanol 1:5, and after reprecipitation, it is filtered and dried to form a white powder with the following formula:
【化】
で表される化合物（）が得られた。
この化合物の融点を測定したところ、94〜99℃
であつた。また、上記構造式は、化合物（）を
CHNレコーダー（柳本製作所製有機元素分析装
置）によりその炭素、水素、酸素の各元素の重量
比を測定し、理論上の組成式C108H144O24の重量
比と比較することにより確認した。分析の結果と
理論計算値とは、第１表に示すとおりである。A compound () represented by [chemical formula] was obtained. When the melting point of this compound was measured, it was 94-99℃.
It was hot. In addition, the above structural formula represents the compound ()
The weight ratio of each element of carbon, hydrogen, and oxygen was measured using a CHN recorder (organic elemental analyzer manufactured by Yanagimoto Seisakusho), and confirmed by comparing it with the weight ratio of the theoretical composition formula C 108 H 144 O 24 . The analysis results and theoretically calculated values are shown in Table 1.
【表】
実施例 ２
メタリリル酸メチル1.6ｇ、化合物（）0.4
ｇ、過酸化ベンゾイル0.02ｇを封管中に入れ、80
℃で２時間、さらに120℃で16時間加熱すること
で共重合体２ｇを得た。得られた共重体を長さ×
幅×厚さ（mm）10×2.5×0.7に加工して、ガラス
転移温度（Tg）および熱分解温度を測定した。
実施例 ３〜10
実施例２と同様な方法で、化合物（）とメタ
クリル酸エチル、メタクリル酸ｉ−プロピル、メ
タクリル酸ｎ−ブチル、メタクリル酸ｔ−ブチ
ル、メタクリル酸２−エチルヘキシル、メタクリ
ル酸ヒドロキシエチル、スチレンとそれぞれ過酸
化ベンゾイルを触媒として、封管中80℃で２時
間、120℃で16時間、アクリロニトリルの場合、
60℃５時間、120℃16時間加熱することでそれぞ
れ共重合体を得た。得られた共重合体をそれぞれ
実施例２と同様にしてガラス転移度（Tg）およ
び熱分解温度を測定した。
また、比較として、上記実施例２〜10におい
て、化合物（）と共重合体を形成する化合物の
それぞれの単独重合体を形成し、この重合体につ
いても実施例２と同様にしてガラス転移温度
（Tg）および熱分解温度を測定した。
上記実施例２〜10の共重合体および各単独重合
体のガラス転移温度（Tg）および熱分解温度の
測定結果を第２表に示す。[Table] Example 2 Methyl methacrylate 1.6g, compound () 0.4
g, put 0.02 g of benzoyl peroxide into a sealed tube, 80
2 hours at 120° C. and then 16 hours at 120° C. to obtain 2 g of copolymer. The obtained copolymer is divided into length x
It was processed into a width x thickness (mm) of 10 x 2.5 x 0.7, and the glass transition temperature (Tg) and thermal decomposition temperature were measured. Examples 3 to 10 Compound () and ethyl methacrylate, i-propyl methacrylate, n-butyl methacrylate, t-butyl methacrylate, 2-ethylhexyl methacrylate, hydroxyethyl methacrylate were prepared in the same manner as in Example 2. , styrene and benzoyl peroxide as catalysts in a sealed tube at 80°C for 2 hours and at 120°C for 16 hours, in the case of acrylonitrile,
Copolymers were obtained by heating at 60°C for 5 hours and at 120°C for 16 hours. The glass transition degree (Tg) and thermal decomposition temperature of each of the obtained copolymers were measured in the same manner as in Example 2. In addition, for comparison, in Examples 2 to 10 above, homopolymers of each of the compounds forming the copolymer with Compound () were formed, and this polymer was also prepared in the same manner as in Example 2, so that the glass transition temperature ( Tg) and thermal decomposition temperature were measured. Table 2 shows the measurement results of the glass transition temperature (Tg) and thermal decomposition temperature of the copolymers and homopolymers of Examples 2 to 10 above.
以上のように構成されているので、第１の発明
にかかるカリツクス［ｎ］アレーン誘導体は、高
分子化することができ、包接作用を有するフイル
ムなどを形成することができる。また、従来のビ
ニルモノマーと共重合して従来のビニルモノマー
単独の高分子重合体より物性の優れた高分子化合
物を形成することができる。
第２の発明にかかる製造方法は、上記カリツク
ス［ｎ］アレーン誘導体を効率良く製造すること
ができる。
第３の発明にかかる高分子化合物は、従来のビ
ニルモノマー単独の重合による熱可塑性樹脂に比
べ、機械的強度、耐熱性、耐薬品性のすぐれた高
分子化合物となり、従来強度等の点で使用出来な
かつた構造物への使用も可能となる。また、分子
中に、カリツクス［ｎ］アレーンの環状構造を備
えているので、包接機能も備え、ガス吸収シート
などにも用いることができる。
With the structure described above, the calix[n]arene derivative according to the first invention can be made into a polymer and can form a film having an inclusion effect. In addition, by copolymerizing with conventional vinyl monomers, it is possible to form polymer compounds with better physical properties than conventional polymers made of vinyl monomers alone. The production method according to the second invention can efficiently produce the calix[n]arene derivative. The polymer compound according to the third invention has superior mechanical strength, heat resistance, and chemical resistance compared to conventional thermoplastic resins made by polymerizing vinyl monomer alone, and is used in terms of conventional strength, etc. It also becomes possible to use it for structures that were previously impossible. Furthermore, since it has a calix[n]arene cyclic structure in its molecule, it also has an inclusion function and can be used for gas absorption sheets and the like.
Claims (1)
R2はＨ基またはアルキル基を表す。）で示される
カリツクス［ｎ］アレーン誘導体(A)。 ２ 請求項第１項記載のカリツクス［ｎ］アレー
ン誘導体(A)を得るにあたり、一般式、 【化】 （式中ｎは３以上の整数、R1はアルキル基を
表す。）で示される化合物(B)に、一般式、 【化】 （式中、R2はＨ基またはアルキル基を表す。）
で示される化合物(C)をアミン触媒下に反応させる
ことを特徴とするカリツクス［ｎ］アレーン誘導
体の製造方法。 ３ 一般式、 【化】 で示される化合物と一般式、 【式】 （式中、R3はＨ基またはアルキル基、R4はカ
ルボキシル基、メトキシカルボニル基、エトキシ
カルボニル基、プロピオキシカルボニル基、ｉ−
プロピオキシカルボニル基、ｎ−ブトキシカルボ
ニル基、ｉ−ブトキシカルボニル基、ｓ−ブトキ
シカルボニル基、ｔ−ブトキシカルボニル基、２
−エチルヘトキシカルボニル基、２−ヒドロキシ
エトキシカルボニル基、フエニル基、シアノ基か
ら選ばれたいずれか１つの基を表す。）で示され
る化合物(D)が共重合されてなる高分子化合物。[Claims] 1 General formula: (where n is an integer of 3 or more, R 1 is an alkyl group,
R 2 represents an H group or an alkyl group. ) Calix [n] arene derivative (A). 2. In order to obtain the calix[n]arene derivative (A) according to claim 1, a compound represented by the general formula: (where n is an integer of 3 or more, and R 1 represents an alkyl group) In (B), the general formula: [In the formula, R 2 represents an H group or an alkyl group.]
1. A method for producing a calix[n]arene derivative, which comprises reacting a compound (C) represented by the following in the presence of an amine catalyst. 3 Compounds represented by the general formula, [Formula], [Formula] (where R 3 is a H group or an alkyl group, R 4 is a carboxyl group, a methoxycarbonyl group, an ethoxycarbonyl group, a propioxycarbonyl group, i-
Propioxycarbonyl group, n-butoxycarbonyl group, i-butoxycarbonyl group, s-butoxycarbonyl group, t-butoxycarbonyl group, 2
-Represents any one group selected from an ethylhethoxycarbonyl group, a 2-hydroxyethoxycarbonyl group, a phenyl group, and a cyano group. ) A polymer compound formed by copolymerizing the compound (D) shown in (D).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27763288A JPH02124850A (en) | 1988-11-01 | 1988-11-01 | Novel calix(n)arene derivative, production thereof and high polymer compound consisting of the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27763288A JPH02124850A (en) | 1988-11-01 | 1988-11-01 | Novel calix(n)arene derivative, production thereof and high polymer compound consisting of the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02124850A JPH02124850A (en) | 1990-05-14 |
| JPH0588695B2 true JPH0588695B2 (en) | 1993-12-24 |
Family
ID=17586136
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP27763288A Granted JPH02124850A (en) | 1988-11-01 | 1988-11-01 | Novel calix(n)arene derivative, production thereof and high polymer compound consisting of the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02124850A (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0883432A1 (en) * | 1996-02-28 | 1998-12-16 | Transdiffusia S.A. | Process for the recovery of volatile low molecular compounds |
| DE102007035734A1 (en) | 2006-08-29 | 2008-03-20 | Ivoclar Vivadent Ag | Dental materials with low polymerization shrinkage |
| CN103052670B (en) * | 2010-07-30 | 2016-03-02 | 三菱瓦斯化学株式会社 | Compound, radiation sensitive composition and resist pattern forming method |
| JP6703253B2 (en) * | 2016-02-17 | 2020-06-03 | 公立大学法人 富山県立大学 | Template-forming polymerizable compound, curable composition thereof, and cured product thereof |
| CN107459606B (en) * | 2017-06-13 | 2019-04-16 | 西南石油大学 | One kind hydrophobic associated polymer containing Sulfonated calixarenes and preparation method thereof |
-
1988
- 1988-11-01 JP JP27763288A patent/JPH02124850A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH02124850A (en) | 1990-05-14 |
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