JPH02151648A - Composition of diacetylene compound - Google Patents
Composition of diacetylene compoundInfo
- Publication number
- JPH02151648A JPH02151648A JP30516688A JP30516688A JPH02151648A JP H02151648 A JPH02151648 A JP H02151648A JP 30516688 A JP30516688 A JP 30516688A JP 30516688 A JP30516688 A JP 30516688A JP H02151648 A JPH02151648 A JP H02151648A
- Authority
- JP
- Japan
- Prior art keywords
- diacetylene
- viscosity
- compd
- composition
- 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
- -1 diacetylene compound Chemical class 0.000 title claims description 26
- 239000000203 mixture Substances 0.000 title claims description 16
- 229920000642 polymer Polymers 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000000962 organic group Chemical group 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 2
- LLCSWKVOHICRDD-UHFFFAOYSA-N buta-1,3-diyne Chemical group C#CC#C LLCSWKVOHICRDD-UHFFFAOYSA-N 0.000 abstract description 19
- 238000000034 method Methods 0.000 abstract description 7
- 229920005989 resin Polymers 0.000 abstract description 4
- 239000011347 resin Substances 0.000 abstract description 4
- 239000000853 adhesive Substances 0.000 abstract description 2
- 230000001070 adhesive effect Effects 0.000 abstract description 2
- 239000011248 coating agent Substances 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 239000011159 matrix material Substances 0.000 abstract description 2
- 238000002156 mixing Methods 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 238000000576 coating method Methods 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000003566 sealing material Substances 0.000 abstract 1
- 238000000465 moulding Methods 0.000 description 11
- 230000009257 reactivity Effects 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 2
- 101150065749 Churc1 gene Proteins 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 102100038239 Protein Churchill Human genes 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 238000005691 oxidative coupling reaction Methods 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Chemical group 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920000015 polydiacetylene Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、２５℃における粘度が、３０センチボイズ以
上であるジアセチレン化合物系組成物に関するものであ
り、更に詳しくは、硬化性、成形性にすぐれたジアセチ
レン化合物系組成物に関するものである。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a diacetylene compound composition having a viscosity at 25°C of 30 centivoise or more. This invention relates to an excellent diacetylene compound composition.
〔従来技術及びその問題点］
本発明者らは、ジアセチレン基を有する化合物を用いて
三次元又は二次元的に高密度に架橋させて高弾性率成形
体の製造開発を行っており、これまでに種々の機能性ジ
アセチレン系化合物を合成してきた。[Prior art and its problems] The present inventors have developed a high-modulus molded product by three-dimensionally or two-dimensionally crosslinking it with high density using a compound having a diacetylene group. Until now, various functional diacetylene compounds have been synthesized.
共有結合を用いた架橋によって三次元的に高弾性率を発
現させるために架橋基密度を可能な限り高くし、かつ架
橋基を規則的にかつ高収率で反応させねばならない。本
発明者らは、これまでに化合物の化学的安定性をそこな
うことなく、架橋基密度が高（、架橋基の反応性に冨ん
だジアセチレン系化合物をアミド基やエステル基とジア
セチレン基や炭素−炭素二重結合を組み合せることで可
能にし、これらの素材の優れた固相反応性を利用して高
弾性率化を達成してきた。しかしながら、ジアセチレン
化合物の固相反応性を利用するために、その成形方法と
しては、湿式成形や溶融成形を適用することが難しく、
そのほとんどが粉体成形であり、成形性を向上させるこ
とが非常に困難であった。In order to express high elastic modulus three-dimensionally by crosslinking using covalent bonds, the density of crosslinking groups must be made as high as possible, and the crosslinking groups must be reacted regularly and in high yield. The present inventors have so far succeeded in combining diacetylene compounds with high crosslinking group density (and high reactivity of crosslinking groups) by combining amide groups, ester groups, and diacetylene groups without impairing the chemical stability of the compound. It has been possible to achieve high elastic modulus by combining diacetylene compounds and carbon-carbon double bonds, and by taking advantage of the excellent solid-state reactivity of these materials. Therefore, it is difficult to apply wet molding or melt molding as a molding method.
Most of them are powder molded, and it is extremely difficult to improve moldability.
一方、エポキシ樹脂に代表される液状熱硬化性樹脂にお
いては、種々の成形方法を用いることができ、複合化も
容易に行なうことができる。On the other hand, various molding methods can be used for liquid thermosetting resins such as epoxy resins, and composites can be easily formed.
そこで、液状のジアセチレン化合物を用いれば、成形性
は向上するが、ジアセチレン化合物は、−般に液状では
、その反応性が小さいことが知られている（［ポリジア
セチレンＪ ＮＡＴＯＡＳ Ｉシリーズ Ｅ アプライ
ド サイアンス）。Therefore, if a liquid diacetylene compound is used, moldability is improved, but it is known that diacetylene compounds generally have low reactivity in liquid form ([Polydiacetylene J NATOAS I Series E Applied science).
そこで本発明者らは、液状ジアセチレン化合物を種々合
成し、その反応性、成形性を種々検討した結果、特許請
求の範囲に示した構造式を存するジアセチレン化合物が
、二重結合もジアセチレン基も良好な反応性を有するこ
とを見い出した。しかし、該ジアセチレン化合物の中に
、粘度が低すぎるために、金型やシール部からしみ出す
等の問題が生じたり、化合物によっては、反応性が高す
ぎるために、成形条件により、急激な分解反応を起こす
ものもあった。Therefore, the present inventors synthesized various liquid diacetylene compounds, and as a result of various studies on their reactivity and moldability, we found that the diacetylene compound having the structural formula shown in the claims has a double bond that is not diacetylene. It has been found that the group also has good reactivity. However, some of these diacetylene compounds have too low a viscosity, causing problems such as seeping out of molds and seals, and some compounds have too high reactivity, which can lead to sudden changes in molding conditions. Some caused decomposition reactions.
本発明の目的は、成形性及び安定性をそなえた硬化型液
状ジアセチレン化合物を提供することにある。An object of the present invention is to provide a curable liquid diacetylene compound having good moldability and stability.
すなわち本発明は、−数式（Ｉ）で示されるジアセチレ
ン化合物及び該ジアセチレン化合物の重合体から成る組
成物であって、２５°Ｃにおける粘度が３０センチポイ
ズ以上であるジアセチレン化合物系組成物
Ｒ−Ｘ−Ａ−Ｃ：：ＣＣ＝Ｃ−Ａ’ −Ｘ’ −Ｒ′（
ここで、Ｒ，Ｒ′は炭素数が２から５までの二重結合を
有する有機基であり、ｘ、Ｘ′は一〇Ｃ−又は −〇−
であり、Ａ、Ａ’は炭素数が１から６までの有機基を示
す。）を提供するものである。That is, the present invention provides - a diacetylene compound-based composition R having a viscosity at 25°C of 30 centipoise or more, which is a composition comprising a diacetylene compound represented by formula (I) and a polymer of the diacetylene compound; -X-A-C::CC=C-A'-X'-R'(
Here, R and R' are organic groups having a double bond having 2 to 5 carbon atoms, and x and X' are 10C- or -0-
, and A and A' each represent an organic group having 1 to 6 carbon atoms. ).
本発明において、Ｒ，Ｒ′は炭素数が２から５までの二
重結合を有する有機基であり、その例としては、ＣＨ２
＝ＣＨ−ＣＨｚ＝Ｃ−
ＣＨ３
ＣＨ，ＣＨ＝ＣＨ−
ＣＨ，＝ＣＨＣＨ。In the present invention, R and R' are organic groups having 2 to 5 carbon atoms and a double bond, such as CH2
=CH-CHz=C- CH3 CH, CH=CH- CH, =CHCH.
ＣＨ：ｌＣＨ＝ ＣＨＣＨｚ ＣＨ２＝ ＣＨＣＨｚＣＨｚ− ＣＨ。CH:lCH=CHCHHz CH2=CHCHzCHz- CH.
ＣＨ２＝ＣＨ。CH2=CH.
ＣＨｚ＝ ＣＨＣＨｚＣＨｚＣＨ２− ＣＨ２Ｏ）ｆ＝ＣＨＣ）１２ＣＨ２− ＣＨ２ＯＨｚＣＨｚＣＨ＝ ＣＨ− ＣＨ。CHz= CHCHzCHzCH2- CH2O)f=CHC)12CH2- CH2OHzCHzCH=CH- CH.
ＣＨ２ＯＨ＝ ＣＣＨ２− ＣＨ。CH2OH=CCH2- CH.
さも考えると特にＣＨ，＝ＣＨ−１ＣＨ２＝Ｃ−が好ま
しい。In other words, CH, =CH-1CH2=C- is particularly preferred.
本発明において、ｘ、Ｘ′は、−〇Ｃ
０−であり、−０Ｃ−の場合、ＲとＡ及びＲ′とＡ′と
の結合様式には特に制限はない。In the present invention, x and X' are -0C0-, and in the case of -0C-, there is no particular restriction on the bonding mode between R and A and between R' and A'.
本発明において、Ａ、Ａ’は炭素数が１から６までの有
機基を示し、その例としては、ＣＨｚ−ｌＣＨｚ÷２、
ｌＣＨ，÷３、＋ＣＨ！＋、、−←ＣＨ２÷１、−＋Ｃ
Ｈ，→ゴ、等が挙げられ、高い反応性を有するという点
におＨｚ
いて、ＣＨ２＝ＣＨ−ＣＨ２−Ｃ−
ＣＨ２＝ＣＨＣＨ，−が好ましく、合成のしやす挙げら
れ、特に、ジアセチレン基の反応性を高め、合成しやす
いという点で＝ＣＨ，−が好ましい。In the present invention, A and A' each represent an organic group having 1 to 6 carbon atoms, such as CHz-lCHz÷2,
lCH, ÷3, +CH! +,, -←CH2÷1, -+C
In terms of high reactivity, CH2=CH-CH2-C- CH2=CHCH,- is preferred, and examples include ease of synthesis, especially for diacetylene groups. =CH,- is preferred in that it increases the reactivity of and is easy to synthesize.
本発明において、Ｒ−Ｘ−Ａ−（ｊＣＣ＝Ｃ−−Ａ’
−Ｘ’−Ｒ′の合成については、すでに本発明者らが開
示している方法、例えば特開昭６２−２６７２４８号公
報や特開昭６２−２６７２５１号公報などの方法をその
まま適用することができる。In the present invention, R-X-A-(jCC=C--A'
For the synthesis of -X'-R', methods already disclosed by the present inventors, such as those disclosed in JP-A-62-267248 and JP-A-62-267251, can be directly applied. can.
本発明のジアセチレン化合物系組成物は、−数式（Ｉ）
であられされるジアセチレン化合物及び該ジアセチレン
化合物の重合体から成る。The diacetylene compound composition of the present invention has the formula (I)
It consists of a diacetylene compound and a polymer of the diacetylene compound.
本発明の組成物を製造するには、−数式（Ｉ）であられ
されるジアセチレン化合物と該ジアセチレン化合物の重
合物を混合する方法等が挙げられるが、より容易に該組
成物を製造するには、−数式（Ｉ）であられされるジア
セチレン化合物を部分的に重合せしめ、２５°Ｃにおけ
る粘度を３０センチポイズ以上にする方法が好ましい。The composition of the present invention can be produced by a method of mixing a diacetylene compound represented by the formula (I) and a polymer of the diacetylene compound, but the composition can be produced more easily. For this purpose, it is preferable to partially polymerize the diacetylene compound represented by the formula (I) to have a viscosity of 30 centipoise or more at 25°C.
該ジアセチレン化合物を部分的に反応させる場合、反応
する官能基としては、二重結合でもジアセチレン基でも
よく、その反応量、反応形式、分子量、分子量分布につ
いても特に制限はない。また、これらの二重結合又は／
及びジアセチレン基を部分的に反応させる方法としては
、通常の塊状重合、溶液重合、乳化重合、懸濁重合、固
相重合を用いることができる。（例えば、新実験化学講
座、１９巻 高分子化学（Ｉ）丸善に開示されている方
法を適用することができる。）
二重結合及び／又は、ジアセチレン基の一部又は全部を
反応させる際、該ジアセチレン化合物と該ジアセチレン
化合物の重合体のモル比は、反応時間、反応温度、開始
剤や抑制剤の種類や量等の反応条件を変化させることで
容易に達成される。When the diacetylene compound is partially reacted, the functional group to be reacted may be a double bond or a diacetylene group, and there are no particular limitations on the reaction amount, reaction format, molecular weight, or molecular weight distribution. In addition, these double bonds or/
As a method for partially reacting diacetylene groups, ordinary bulk polymerization, solution polymerization, emulsion polymerization, suspension polymerization, and solid phase polymerization can be used. (For example, the method disclosed in New Experimental Chemistry Course, Volume 19, Polymer Chemistry (I) Maruzen can be applied.) When reacting some or all of the double bonds and/or diacetylene groups The molar ratio of the diacetylene compound and the polymer of the diacetylene compound can be easily achieved by changing reaction conditions such as reaction time, reaction temperature, type and amount of initiator and inhibitor.
本発明において、該組成物中の該ジアセチレン化合物の
重量分率については、特に制限はないが、該組成物の流
動性に由来する成形性を上げるためには、７０％以下、
より好ましくは６０％以下、さらに製造のしやすさから
５０〜５％の範囲が好ましい。In the present invention, the weight fraction of the diacetylene compound in the composition is not particularly limited;
It is more preferably 60% or less, and more preferably in the range of 50 to 5% for ease of production.
本発明において、該組成物の粘度が低い場合に、金型か
らしみ出したり、複合化の際に補強剤との分散性がうま
（いかない等の成形上の問題を解決するために、又、厳
しい成形条件において、しばしば起こる分解反応を低下
させるために、該組成物の２５°Ｃでの粘度は、２５“
Ｃで３０センチポイズ以上が好ましく、さらに好ましく
は、８０センチポイズ以上、特に好ましくは、１００セ
ンチポイズ以上である。In the present invention, when the viscosity of the composition is low, in order to solve molding problems such as seepage from the mold or poor dispersibility with the reinforcing agent during compounding, , the viscosity of the composition at 25°C is 25" to reduce the decomposition reactions that often occur under harsh molding conditions.
C is preferably 30 centipoise or more, more preferably 80 centipoise or more, particularly preferably 100 centipoise or more.
本発明の組成物は、必要に応じ、他の溶媒安定剤、重合
禁止剤、増粘剤、増量剤、モノマー、ポリマー、充填剤
等を含んでいてもよい。The composition of the present invention may contain other solvent stabilizers, polymerization inhibitors, thickeners, extenders, monomers, polymers, fillers, etc., as necessary.
本発明の液状ジアセチレン化合物系組成物は、成形性、
反応性に優れた硬化型樹脂であり、コーティング剤、マ
トリックス樹脂、封止剤、接着剤の原料等に極めて有用
である。The liquid diacetylene compound composition of the present invention has moldability,
It is a curable resin with excellent reactivity and is extremely useful as a raw material for coating agents, matrix resins, sealants, adhesives, etc.
以下、実施例を挙げて本発明の説明を行うが、言うまで
もなく、本発明が以下の実施例に限定されるものではな
い。The present invention will be described below with reference to examples, but it goes without saying that the present invention is not limited to the following examples.
〔実施例１〕 （Ｉ〕が９５％の収率で得られた。[Example 1] (I) was obtained with a yield of 95%.
得られた化合物（Ｉ）の構造は、ＮＭＲ，ＩＲ，元素分
析、マススペクトル等で確認した。The structure of the obtained compound (I) was confirmed by NMR, IR, elemental analysis, mass spectrum, etc.
こうして合成した化合物（Ｉ）を、Ｎ２ガス雰囲気下、
１００℃で一定時間熱処理した（この時、開始剤、溶媒
は、用いなかった）。Compound (I) synthesized in this way was prepared under an N2 gas atmosphere.
Heat treatment was performed at 100° C. for a certain period of time (no initiator or solvent was used at this time).
表１に、反応時間と反応物の粘度の関係を示す。Table 1 shows the relationship between reaction time and viscosity of the reactant.
表１
ＣＨｚ＝ＣＨＣＯＯＣＨｇＣ＝ＣＨ１ｍｏｌをＣｕ Ｃ
ｌ Ｏ，０１モルと共に、ピリジン２００ｍｊ！中、
４ｈｒ、酸素ガスを導入しながら室温で反応させた。Table 1 CHz=CHCOOCHgC=CH1mol CuC
200 mj of pyridine with 0,01 mole of l O! During,
The reaction was carried out for 4 hours at room temperature while introducing oxygen gas.
反応後、冷濃塩酸に反応物を注ぎ、エーテルを用いて抽
出した後、ボウ硝で乾燥し、目的の化合物熱処理して得
た４種の粘度の異なるエステルを図１に示す金型で２０
０ｋｇ／ａａ、 １６０°Ｃ，５分間の加圧成形処理
を行なった。この時、粘度が３０．９０センチボイズの
場合には、硬い成形体が得られたが、５．１５センチポ
イズの場合には金型の下部のすきまよりエステルが流れ
出して形の整った成形体を得ることができなかった。ま
た、成形温度を２２０℃にしたところ、３０．９０セン
チボイズの場合には硬い成形体が得られたが、５，１５
センチポイズの場合にはエステルの流れ出しと共に急激
な反応よる分解が生じた。After the reaction, the reactants were poured into cold concentrated hydrochloric acid, extracted with ether, dried with sulfur salt, and heat-treated to obtain the desired compound.
Pressure molding treatment was performed at 0 kg/aa, 160°C, and 5 minutes. At this time, when the viscosity was 30.90 centipoise, a hard molded body was obtained, but when the viscosity was 5.15 centipoise, the ester flowed out from the gap at the bottom of the mold, resulting in a well-shaped molded body. I couldn't. In addition, when the molding temperature was set to 220°C, a hard molded product was obtained in the case of 30.90 cm voids, but 5.15 cm
In the case of centipoise, the ester flowed out and decomposition occurred due to rapid reaction.
熱処理したエステルの！Ｒスペクトルを見ると二重結合
に基づ＜１６３１ｃｍ−’の吸収が大巾に減少していた
。又、ジアセチレン基の吸収も若干減少していた。又、
熱処理したエステルをエーテルで洗うと、二重結合が反
応した重合物を単離することができた。Of heat-treated ester! Looking at the R spectrum, absorption at <1631 cm-' due to double bonds was greatly reduced. Moreover, the absorption of diacetylene groups was also slightly reduced. or,
By washing the heat-treated ester with ether, it was possible to isolate the polymer in which the double bonds had reacted.
また、比較のために
（Ｃｔ Ｈｓ ＣＯＯＣＨｚ Ｃ＝Ｃ−ｈ と（ＣＨｚ
＝ ＣＨＣ００ＣＨｚ ＣＨｚ ＣＨｚ ＋−１を用
いて熱処理したが、いずれも２５°Ｃにおける粘度は３
０センチボイズ以下であり、さらに金型で圧縮しても液
状のままであった。Also, for comparison, (Ct Hs COOCHz C=Ch and (CHz
= CHC00CHz CHz CHz +-1, but the viscosity at 25°C was 3
The particle size was 0 centivoise or less, and it remained liquid even when compressed with a mold.
〔実施例２〜７〕
ＣＨｚ ＝ ＣＨＣＯＯＣＨｔ Ｃ＝ＣＨの代りに表２
に示したモノマーを用い、酸化カップリングして得られ
たジアセチレン化合物を１００°Ｃで一定時間アニーリ
ング（必要に応じてベンゾイルパーオキシドを開始剤と
して用いた）し、実施例１と同様にして成形を行った。[Examples 2 to 7] CHz = CHCOOCHt Table 2 instead of C=CH
Using the monomer shown in Example 1, the diacetylene compound obtained by oxidative coupling was annealed at 100 °C for a certain period of time (benzoyl peroxide was used as an initiator if necessary), and the diacetylene compound obtained by oxidative coupling was annealed in the same manner as in Example 1. I did the molding.
表２にその結果を併せて示した。いずれも２５°Ｃにお
ける粘度が３０センチポイズ以上であり、金型からしみ
出すこともなく、又分解することもなく成形体を製造す
ることができた。１００°Ｃで熱処理したものはすべて
ＩＲスペクトルで二重結合に基づく吸収が大巾に減少し
ていた。Table 2 also shows the results. All of them had a viscosity of 30 centipoise or more at 25°C, and molded products could be produced without seeping out of the mold or decomposing. The IR spectra of all samples heat-treated at 100°C showed a significant decrease in absorption based on double bonds.
以下余白
図１は、本発明のジアセチレン化合物系組成物を成形す
るための成形用金型（斜線部にサンプルを入れ上下より
プレスで圧縮する）である。Figure 1 below shows a mold for molding the diacetylene compound composition of the present invention (a sample is placed in the shaded area and compressed with a press from above and below).
Claims (1)
アセチレン化合物の重合体から成る組成物であって、２
５℃における粘度が３０センチポイズ以上であるジアセ
チレン化合物系組成物 Ｒ−Ｘ−Ａ−Ｃ≡ＣＣ≡Ｃ−Ａ′−Ｘ′−Ｒ′・・・（
I ） （ここで、Ｒ、Ｒ′は炭素数が２から５までの二重結合
を有する有機基であり、Ｘ、Ｘ′は▲数式、化学式、表
等があります▼又は−Ｏ−であり、Ａ、Ａ′は炭素数が
１から６までの有機基を示す。）[Scope of Claims] A composition comprising a diacetylene compound represented by general formula (I) and a polymer of the diacetylene compound, comprising:
Diacetylene compound composition R-X-A-C≡CC≡C-A'-X'-R'...(
I) (Here, R and R' are organic groups with a double bond of 2 to 5 carbon atoms, and X and X' are ▲There are numerical formulas, chemical formulas, tables, etc.▼ or -O- , A, and A' represent organic groups having 1 to 6 carbon atoms.)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30516688A JPH02151648A (en) | 1988-12-03 | 1988-12-03 | Composition of diacetylene compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30516688A JPH02151648A (en) | 1988-12-03 | 1988-12-03 | Composition of diacetylene compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02151648A true JPH02151648A (en) | 1990-06-11 |
| JPH0378426B2 JPH0378426B2 (en) | 1991-12-13 |
Family
ID=17941860
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP30516688A Granted JPH02151648A (en) | 1988-12-03 | 1988-12-03 | Composition of diacetylene compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02151648A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0337213A (en) * | 1989-07-04 | 1991-02-18 | Asahi Chem Ind Co Ltd | Diacetylene composition |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6396144A (en) * | 1986-10-13 | 1988-04-27 | Agency Of Ind Science & Technol | Diacetylene compound having double bond |
| JPS63295612A (en) * | 1987-05-28 | 1988-12-02 | Agency Of Ind Science & Technol | Highly rigid molded product which comprises diacetylene compound with double bond |
| JPS63295639A (en) * | 1987-05-28 | 1988-12-02 | Agency Of Ind Science & Technol | Molding prepared from double bond-containing diacetylene compound |
-
1988
- 1988-12-03 JP JP30516688A patent/JPH02151648A/en active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6396144A (en) * | 1986-10-13 | 1988-04-27 | Agency Of Ind Science & Technol | Diacetylene compound having double bond |
| JPS63295612A (en) * | 1987-05-28 | 1988-12-02 | Agency Of Ind Science & Technol | Highly rigid molded product which comprises diacetylene compound with double bond |
| JPS63295639A (en) * | 1987-05-28 | 1988-12-02 | Agency Of Ind Science & Technol | Molding prepared from double bond-containing diacetylene compound |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0337213A (en) * | 1989-07-04 | 1991-02-18 | Asahi Chem Ind Co Ltd | Diacetylene composition |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0378426B2 (en) | 1991-12-13 |
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