JPH03200806A - Macrocyclic polyolefin epoxide - Google Patents
Macrocyclic polyolefin epoxideInfo
- Publication number
- JPH03200806A JPH03200806A JP34238189A JP34238189A JPH03200806A JP H03200806 A JPH03200806 A JP H03200806A JP 34238189 A JP34238189 A JP 34238189A JP 34238189 A JP34238189 A JP 34238189A JP H03200806 A JPH03200806 A JP H03200806A
- Authority
- JP
- Japan
- Prior art keywords
- macrocyclic
- polyolefin
- epoxide
- polymer
- high molecular
- 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
- 229920000098 polyolefin Polymers 0.000 title claims abstract description 29
- 150000002118 epoxides Chemical class 0.000 title claims abstract description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 230000001590 oxidative effect Effects 0.000 claims abstract description 3
- 125000003700 epoxy group Chemical group 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 abstract description 20
- 150000001875 compounds Chemical class 0.000 abstract description 15
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 abstract description 4
- 238000006116 polymerization reaction Methods 0.000 abstract description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract description 3
- 239000003054 catalyst Substances 0.000 abstract description 2
- 125000004122 cyclic group Chemical group 0.000 abstract description 2
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 abstract description 2
- 239000004913 cyclooctene Substances 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 238000005649 metathesis reaction Methods 0.000 abstract description 2
- 239000003607 modifier Substances 0.000 abstract description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 abstract description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052721 tungsten Inorganic materials 0.000 abstract description 2
- 239000010937 tungsten Substances 0.000 abstract description 2
- KPGXUAIFQMJJFB-UHFFFAOYSA-H tungsten hexachloride Chemical compound Cl[W](Cl)(Cl)(Cl)(Cl)Cl KPGXUAIFQMJJFB-UHFFFAOYSA-H 0.000 abstract description 2
- 229910003091 WCl6 Inorganic materials 0.000 abstract 1
- 230000001627 detrimental effect Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 229920000647 polyepoxide Polymers 0.000 description 5
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 4
- 229920003245 polyoctenamer Polymers 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 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
- 230000001771 impaired effect Effects 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- -1 polyoctenylene Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- CZPZWMPYEINMCF-UHFFFAOYSA-N propaneperoxoic acid Chemical compound CCC(=O)OO CZPZWMPYEINMCF-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 238000004736 wide-angle X-ray diffraction Methods 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は新規な構造を有する、高分子重合体に関するも
のである。詳しくは、種々の低分子化合物と反応可能な
、あるいは高分子化合物との反応が可能な高分子重合体
であり、機械的強度を保有しつつ他の重合体との混合が
可能な高分子重合体であるエポキシ基含有大環状ポリオ
レフィンエポキシドに関するものである。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a high molecular weight polymer having a novel structure. Specifically, it is a high-molecular polymer that can react with various low-molecular compounds or high-molecular compounds, and can be mixed with other polymers while maintaining mechanical strength. This invention relates to an epoxy group-containing macrocyclic polyolefin epoxide.
本発明のエポキシドと類似の構造を有するエポキシドは
、特開昭６３−１０５０６８号公報に開示されている。An epoxide having a structure similar to the epoxide of the present invention is disclosed in JP-A-63-105068.
併しながらこの公報に開示されている使用ポリオレフィ
ンは、平均分子量が６００〜３０００のポリオクテニレ
ン又はシクロオクテン−シクロエンコポリマーである。However, the polyolefin disclosed in this publication is a polyoctenylene or cyclooctene-cycloene copolymer having an average molecular weight of 600 to 3000.
この様に低分子量のポリオレフィンを用いるのは、使用
目的が風乾性ラッカーバインダーであり、且つ溶液時の
流動性を考慮しているためと考えられる。この公報には
本発明で用いられる高分子量ポリオレフィン、或はその
エポキシドについては些も開示されていない。The reason why such a low molecular weight polyolefin is used is considered to be because the purpose of use is as an air-drying lacquer binder and fluidity in solution is taken into consideration. This publication does not disclose anything about the high molecular weight polyolefin used in the present invention or its epoxide.
本発明者らは、機械的強度を保有しつつ、他の高分子化
合物との混合を可能にする高分子化合物について種々検
討した結果、分子量３０．０００以上の大環状ポリオク
テニレンを酸化して得られるポリエポキシドが、従来予
期し得なかった優れた性状を有することを見い出し、本
発明を完成するに到った。The present inventors have conducted various studies on polymer compounds that can be mixed with other polymer compounds while maintaining mechanical strength. The present inventors have discovered that polyepoxide has excellent properties that were previously unanticipated, and have completed the present invention.
本発明は、数平均分子量が３０．０００以上であり、炭
素原子８ケ当りに少なくとも１つの２重結合を規則正し
く有する大環状ポリオレフィンを酸化することにより得
られる、新規なエポキシ基含有大環状ポリオレフィンエ
ポキシドを提供するものである。The present invention is a novel epoxy group-containing macrocyclic polyolefin epoxide obtained by oxidizing a macrocyclic polyolefin having a number average molecular weight of 30,000 or more and having at least one double bond per 8 carbon atoms. It provides:
本発明に用いる好適な大環状ポリオレフィンとは、２５
０環以上の環状ポリオレフィンを意味し、タングステン
系触媒、特に六塩化タングステンと共触媒とを用いてシ
クロペンテン、シクロオクテン等をメタセシス重合する
ことにより得ることができる。この製法に関しては、例
えば西独公開特許２６１３９９９などにその技術が開示
されている。この際重合条件により、数平均分子量が変
化するが、本発明に使用する目的においては、３０．０
００以上であることが必要である。分子量が３０．００
０未満であると、得られたエポキシドが低分子化合物や
高分子化合物との反応性は有するものの、高分子化合物
との混合性、分散性が通常良くなく、混合後の機械的強
度を著しく損ねる恐れがある。The macrocyclic polyolefin suitable for use in the present invention is 25
It refers to a cyclic polyolefin having 0 or more rings, and can be obtained by metathesis polymerization of cyclopentene, cyclooctene, etc. using a tungsten-based catalyst, particularly tungsten hexachloride, and a cocatalyst. Regarding this manufacturing method, the technology is disclosed in, for example, West German Published Patent Application No. 2613999. At this time, the number average molecular weight changes depending on the polymerization conditions, but for the purpose of use in the present invention, 30.0
It needs to be 00 or more. Molecular weight is 30.00
If it is less than 0, although the obtained epoxide has reactivity with low-molecular compounds and high-molecular compounds, its miscibility and dispersibility with high-molecular compounds are usually poor, and the mechanical strength after mixing is significantly impaired. There is a fear.
また本発明に使用する大環状ポリオレフィンは、中に含
まれる二重結合が、規則正しい構造であることが望まれ
る。大環状ポリオレフィン内の二重結合の規則性は、そ
の物性に大きな影響を及ぼすものである。例えばポリブ
タジェンは主領内２重結合と主鎖の外にある２重結合の
２種類が重合時に生成するため、２重結合の繰り返しに
おける規則性は著しく低い。このような規則性の低い高
分子は、他の高分子重合体と混合する時に、混合の状態
を推測することが非常に困難であり、安定した機能性を
設計する障害になる。Further, it is desired that the double bonds contained in the macrocyclic polyolefin used in the present invention have a regular structure. The regularity of double bonds within macrocyclic polyolefins has a great influence on its physical properties. For example, in polybutadiene, two types of double bonds, double bonds within the main region and double bonds outside the main chain, are generated during polymerization, so the regularity in repeating double bonds is extremely low. When a polymer with such low regularity is mixed with other polymers, it is very difficult to predict the mixing state, which becomes an obstacle to designing stable functionality.
本発明に使用される分子量３０．０００以上を有し、炭
素原子８ケ当りに少なくとも１ケの２重結合を規則正し
く有する大環状ポリオレフィンとしては、例えばヒュル
ス（ＨＯＩｓ）社（西ドイツ）より市販されているもの
を使用することができる。The macrocyclic polyolefin having a molecular weight of 30,000 or more and regularly containing at least one double bond per 8 carbon atoms used in the present invention is, for example, the one commercially available from HOIs (West Germany). You can use what you have.
大環状ポリオレフィン中の二重結合については、シス体
とトランス体の２つのコンホーメーション（化学結合の
位置構成）が知られている。本発明の目的に対しては、
いずれのコンホーメーションからなるものでも良いが、
得られたエポキシドの他の高分子との混合性を考慮した
場合については、トランス体が多いもの、即ち５０％以
上のトランス−ポリオクテニレンであることが望ましい
。Regarding double bonds in macrocyclic polyolefins, two conformations (positional configurations of chemical bonds) are known: cis form and trans form. For the purpose of the present invention:
It may have any conformation, but
When considering the miscibility of the obtained epoxide with other polymers, it is desirable that the epoxide has a large amount of trans isomer, that is, trans-polyoctenylene with a content of 50% or more.
本発明の大環状ポリオレフィンエポキシドは、どの様な
酸化方法によって合成されても良い。The macrocyclic polyolefin epoxide of the present invention may be synthesized by any oxidation method.
例えば、通常オレフィンをエポキシ化する方法である、
過酸、例えば過酸化水素、過酢酸、過蟻酸、過トリクロ
ル酢酸、メタ−クロロ過安息香酸、過フタル酸、過プロ
ピオン酸、過酷酸、過安息香酸、過トリプルオル酢酸な
どを用いる通常のエポキシ化方法を適用することが可能
である。For example, a method that typically epoxidizes olefins,
Conventional epoxies using peracids such as hydrogen peroxide, peracetic acid, performic acid, pertrichloroacetic acid, meta-chloroperbenzoic acid, perphthalic acid, perpropionic acid, harsh acids, perbenzoic acid, pertriolenic acid, etc. It is possible to apply the method of
本発明の大環状ポリオレフィンエポキシドとしては、エ
ポキシ基としての酸素を例えば０．５〜３０重量％含む
大環状ポリオレフィンポリエポキシドであることが望ま
しい。本発明のポリエポキシドは分子量が３０．０００
以上の新規なものであり、１）結晶化度が低下しないの
で機械的強度が向上する、２）融点をコントロールでき
る、３）耐候性が向上する等の作用効果を有する。又、
エポキシ基含量を適宜変更することにより、大環状ポリ
オレフィンエポキシドの極性が変化するので、使用目的
、用途に応じて、また混合する高分子重合体の種類によ
って最適なエポキシ含量を選択することができる。The macrocyclic polyolefin epoxide of the present invention is preferably a macrocyclic polyolefin polyepoxide containing, for example, 0.5 to 30% by weight of oxygen as an epoxy group. The polyepoxide of the present invention has a molecular weight of 30.000
This is a novel product as described above, and has the following effects: 1) mechanical strength is improved because crystallinity does not decrease, 2) melting point can be controlled, and 3) weather resistance is improved. or,
By appropriately changing the epoxy group content, the polarity of the macrocyclic polyolefin epoxide changes, so the optimal epoxy content can be selected depending on the intended use and the type of polymer to be mixed.
本発明の大環状ポリオレフィンエポキシドは、従来より
知られているポリエポキシドに比べ、高分子重合体との
混合性、分散性に優れ、従って他の高分子との混合にお
いても、強度を保持し、さらに向上させ得る。また他の
物質との反応性にも優れており、容易に低分子化合物や
高分子化合物と反応することができる。従って、本発明
の大環状ポリオレフィンエポキシドは高分子重合体の物
性の改質剤並びに低分子化合物や高分子化合物との反応
材料としても非常に有用なものである。The macrocyclic polyolefin epoxide of the present invention has excellent miscibility and dispersibility with polymers compared to conventionally known polyepoxides, and therefore retains strength even when mixed with other polymers. It can be improved. It also has excellent reactivity with other substances, and can easily react with low-molecular compounds and high-molecular compounds. Therefore, the macrocyclic polyolefin epoxide of the present invention is very useful as a modifier for the physical properties of high-molecular polymers and as a material for reaction with low-molecular compounds and high-molecular compounds.
以下に実施例で本発明をさらに詳しく説明するが、本発
明はこれらの実施例によって限定されるものではない。EXAMPLES The present invention will be explained in more detail with reference to Examples below, but the present invention is not limited by these Examples.
実施例１
トランス含量７６％である大環状ポリオクテナマー（ガ
スクロマトグラフ法にて測定した数平均分子量９４，０
００） ５．６１ｇをクロロホルム１００ｒｎｌに溶解
する。ここにメタ−クロロ過安息香酸５．０１ｇをゆっ
くりと加える。−日攪拌を続けた後、生じた白色の沈澱
を遠心分離により取り除き、溶液を大量のメタノール中
に注いでポリマーを沈澱させる。得られたポリマーは乾
燥後５．０３ｇ（収率８４％）であった。エポキシ化前
後の赤外線吸収スペクトル、および核磁気共鳴吸収スペ
クトルを図１と図２に示す。Example 1 Macrocyclic polyoctenamer with a trans content of 76% (number average molecular weight measured by gas chromatography 94.0)
00) Dissolve 5.61 g in 100 rnl of chloroform. 5.01 g of meta-chloroperbenzoic acid is slowly added thereto. After stirring for - days, the white precipitate formed is removed by centrifugation and the solution is poured into a large amount of methanol to precipitate the polymer. The obtained polymer weighed 5.03 g (yield: 84%) after drying. Infrared absorption spectra and nuclear magnetic resonance absorption spectra before and after epoxidation are shown in FIGS. 1 and 2.
また、上記反応で得られたポリマーの元素分析値は炭素
８１．２％、水素１２．０７％、酸素６．７３％であり
、大環状ポリオクテナマー中の二重結合の約４９．６％
がエポキシ化されていることが計算され、図２のＮＭＨ
の結果と一致した。さらに、ＤＳＣ（示差走査熱量計）
により大環状ポリオレフィンエポキシドの熱挙動を測定
したところ、図３に示したように、エポキシドの主融解
温度は上昇し、０℃付近に新たな別の融解ピークが認め
られた。In addition, the elemental analysis values of the polymer obtained in the above reaction were 81.2% carbon, 12.07% hydrogen, and 6.73% oxygen, which accounted for about 49.6% of the double bonds in the macrocyclic polyoctenamer.
was calculated to be epoxidized, and NMH in Figure 2
The result was consistent with that of Furthermore, DSC (differential scanning calorimeter)
When the thermal behavior of the macrocyclic polyolefin epoxide was measured using the following method, as shown in FIG. 3, the main melting temperature of the epoxide increased and a new and different melting peak was observed around 0°C.
（分子量の測定）
ゲルパーミェーションクロマトグラフィ（ＧＰＣ）を用
いて分子量を測定した。溶出液としてはテトラヒドロフ
ランを用い、検出器に屈折計を用いて数平均分子量を求
めた。反応前後のクロマトグラムを図４にあわせて示す
。図４より反応前後に於て分子量が殆ど変化しないこと
がわかる。(Measurement of molecular weight) Molecular weight was measured using gel permeation chromatography (GPC). Tetrahydrofuran was used as the eluent, and the number average molecular weight was determined using a refractometer as a detector. The chromatograms before and after the reaction are also shown in FIG. It can be seen from FIG. 4 that the molecular weight hardly changes before and after the reaction.
実施例２〜５
実施例１で使用のメタクロロ安息香酸の代りに下記の表
１に示す量で過酢酸を添加し、この際温度が０〜８０℃
の範囲にあるように添加する。Examples 2 to 5 Peracetic acid was added in place of the metachlorobenzoic acid used in Example 1 in the amount shown in Table 1 below, at a temperature of 0 to 80°C.
Add so that it is within the range of .
原料大環状ポリオクテナマーの溶解条件は実施例１と同
じとし、添加後１００℃以下の温度で４時間、攪拌を続
けた後、溶液を大量のメタノールに注いでポリマーを沈
澱させる。得られたポリマーの物性を表１に、ＤＳＣ法
による溶融挙動を図５に、ＷＡＸＳチャートを図６に夫
々示す。The dissolution conditions for the raw material macrocyclic polyoctenamer are the same as in Example 1, and after addition, stirring is continued for 4 hours at a temperature of 100° C. or lower, and then the solution is poured into a large amount of methanol to precipitate the polymer. The physical properties of the obtained polymer are shown in Table 1, the melting behavior by DSC method is shown in FIG. 5, and the WAXS chart is shown in FIG. 6.
表 １
マー及びの）本発、明の大環状ポリオレフィンエポキシ
ドの赤外線吸収スペクトルを示す図、図２（ａ）、（ｂ
）は夫々（ａ）原料大環状ポリオクテナマー及び（ｂ）
本発明の大環状ポリオレフィンエポキシドの核磁気共鳴
スペクトルを示す図、図３は示差走査熱量計による熱分
析曲線を示す図、図４はゲルパーミェーションクロマト
グラフイーヲ示す図、図５はＤＳＣ法によるエポキシ化
大環状ポリオクテナマーの融点の変化を示す図、図６は
ＷＡＸＳによる広角Ｘ線回折を示す図である。Table 1 Figures showing the infrared absorption spectra of the macrocyclic polyolefin epoxides of the present invention, Figures 2(a) and (b)
) are respectively (a) raw material macrocyclic polyoctenamer and (b)
Figure 3 shows the nuclear magnetic resonance spectrum of the macrocyclic polyolefin epoxide of the present invention, Figure 3 shows the thermal analysis curve by differential scanning calorimeter, Figure 4 shows gel permeation chromatography, and Figure 5 shows DSC. FIG. 6 is a diagram showing wide-angle X-ray diffraction by WAXS.
Claims (1)
８ケ当りに少なくとも１つの２重結合を規則正しく有す
る大通状ポリオレフィンを酸化して得られるエポキシ基
含有大環状ポリオレフィンエポキシド。 ２ エポキシ基としての酸素含量が０．５〜３０重量％
である請求項１記載のエポキシ基含有大環状ポリオレフ
ィンエポキシド。[Scope of Claims] 1. An epoxy group-containing macrocyclic polyolefin epoxide obtained by oxidizing a large-sized polyolefin having a number average molecular weight of 30,000 or more and having at least one regular double bond per 8 carbon atoms. 2 Oxygen content as epoxy group is 0.5 to 30% by weight
The epoxy group-containing macrocyclic polyolefin epoxide according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP34238189A JP2698676B2 (en) | 1989-12-28 | 1989-12-28 | Macrocyclic polyolefin epoxide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP34238189A JP2698676B2 (en) | 1989-12-28 | 1989-12-28 | Macrocyclic polyolefin epoxide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03200806A true JPH03200806A (en) | 1991-09-02 |
| JP2698676B2 JP2698676B2 (en) | 1998-01-19 |
Family
ID=18353287
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP34238189A Expired - Lifetime JP2698676B2 (en) | 1989-12-28 | 1989-12-28 | Macrocyclic polyolefin epoxide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2698676B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3041812A4 (en) * | 2013-09-04 | 2017-08-16 | California Institute of Technology | Functionalized linear and cyclic polyolefins |
-
1989
- 1989-12-28 JP JP34238189A patent/JP2698676B2/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3041812A4 (en) * | 2013-09-04 | 2017-08-16 | California Institute of Technology | Functionalized linear and cyclic polyolefins |
| US9890239B2 (en) | 2013-09-04 | 2018-02-13 | California Institute Of Technology | Functionalized linear and cyclic polyolefins |
| US10619003B2 (en) | 2013-09-04 | 2020-04-14 | California Institute Of Technology | Functionalized linear and cyclic polyolefins |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2698676B2 (en) | 1998-01-19 |
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