JPS6328451B2 - - Google Patents
Info
- Publication number
- JPS6328451B2 JPS6328451B2 JP11274483A JP11274483A JPS6328451B2 JP S6328451 B2 JPS6328451 B2 JP S6328451B2 JP 11274483 A JP11274483 A JP 11274483A JP 11274483 A JP11274483 A JP 11274483A JP S6328451 B2 JPS6328451 B2 JP S6328451B2
- Authority
- JP
- Japan
- Prior art keywords
- polymer
- present
- benzene
- parabis
- chloroethylmethylsilyl
- 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
Links
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 229920000642 polymer Polymers 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- MDNWOSOZYLHTCG-UHFFFAOYSA-N Dichlorophen Chemical compound OC1=CC=C(Cl)C=C1CC1=CC(Cl)=CC=C1O MDNWOSOZYLHTCG-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229920001002 functional polymer Polymers 0.000 description 4
- 239000002861 polymer material Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 238000009835 boiling Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- -1 ethylmethylethoxysilyl Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229910008045 Si-Si Inorganic materials 0.000 description 1
- 229910006411 Si—Si Inorganic materials 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- UWGJCHRFALXDAR-UHFFFAOYSA-N diethoxy-ethyl-methylsilane Chemical compound CCO[Si](C)(CC)OCC UWGJCHRFALXDAR-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
Landscapes
- Silicon Polymers (AREA)
Description
〔発明の利用分野〕
本発明は機能性高分子材料として、極めて有用
な新規な重合体に関する。
更に詳しくは、式(1)で表わされる構成単位
よりなる重合体に関するものである。
〔発明の背景〕
高分子主鎖にSi−Si結合を有する重合体として
は、式(2)で表わされる構成単位
よりなる重合体などが知られているが、感光性材
料などの電子材料として使用する場合、汎用有機
溶媒に対する溶解性に乏しいために、実用上、そ
の改善が強く望まれていた。
また、基板上に成膜して使用する場合、塗膜が
均質に形成できなかつたり、あるいは塗膜が柔軟
すぎたりして、実用に供し得ないものであつた。
〔発明の目的〕
本発明の目的は、上記した材料の欠点を補い特
に溶解性のすぐれたことを特徴とする、高分子主
鎖にSi−Si結合を有する重合体を提供することに
ある。
〔発明の概要〕
上記の目的を達成するために、本発明者は、Si
−Si結合を有する重合体を種々合体した結果、下
記一般式(1)で表わされる構成単位
よりなる重合体が上記目的を満足する有用な重合
体であることを見い出した。
本発明の重合体は、パラービス（クロロエチル
メチルシリル）ベンゼン〔３〕を金属ナトリウム
の存在下、トルエン中で加熱することにより得ら
れる。
本発明の重合体は常態では結晶であり、トルエ
ン等の有機溶媒に容易に溶解するので、この溶液
を用いて種々の成形品、例えばフイルム、繊維、
シート等に成形することができる。
また、本発明の重合体は各種の金属やガラスに
対する密着性にすぐれており、接着剤や塗料等と
しての利用にも供し得る。
更に、本発明の重合体は機能性高分子材料とし
て、極めて有用である。すなわち、本発明の重合
体は感光性材料や感放射線材料として有用に用い
られるものであり、また、耐熱性が高いために、
絶縁材料などにも利用できる。
また、本発明の重合体の数平均分子量は1000〜
1000000である。1000以下では、機能性高分子材
料として用いることは困難である。
本発明の重合体には、それ自体公知の処方に従
い、周知の配合剤、例えば酸化防止剤、熱安定
剤、着色剤、難燃剤等を配合しても良い。
〔発明の実施例〕
以下に、本発明を合成例および実施例につき具
体的に説明するが、本発明はこの実施例に限定さ
れるものではない。
合成例 １
（パラービス（エチルメチルエトキシシリル）
ベンゼン〔４〕の合成）
撹拌器、冷却器、滴下ロートを付した500mlの
三つ口フラスコに、エチルメチルジエトキシシラ
ン16.2ｇ、マグネシウム2.43ｇとテトラヒドロフ
ラン100mlを加えて撹拌し、窒素気流下で滴下ロ
ートよりＰ−ジブロムベンゼン11.8ｇのテトラヒ
ドロフラン溶液100mlを約３時間で滴下した。滴
下後、撹拌を続けながら、更に約５時間還流し
た。還流後、別し、続いて溶媒を留去し、減圧
蒸留により、パラービス（エチルメチルエトキシ
シリル）ベンゼン10.5ｇ（収率：68％）（沸点：
122〜125℃／３mmHg）を得た。
〔４〕のNMRスペクトル（CDCl3）
δ（ppm）：0.42（ｓ）、0.86〜1.08（ｍ）、1.26（ｔ
）、
3.74（ｑ）、7.56（ｓ）
合成例 ２
（パラービス（クロロエチルメチルシリル）ベ
ンゼン〔３〕の合成）
合成例１で得たパラービス（エチルメチルエト
キシシリル）ベンゼン9.3ｇとアセチルクロライ
ド12ｇとを約５時間還流することにより、98％の
収率でパラービス（クロロエチルメチルシリル）
ベンゼン8.6ｇ（沸点：131〜135℃／mmHg）を得
た。
〔５〕のNMRスペクトル（CDCl3）
δ（ppm）：0.68（ｓ）、
1.12（ｓ）、
7.68（ｓ）．
実施例 １
撹拌器、冷却器、滴下ロートを付した200mlの
三つ口フラスコに、窒素気流下でナトリウム1.2
ｇを含むトルエン約50mlのデスパージヨン溶液
に、合成例２で得たパラービス（クロロエチルメ
チルシリル）ベンゼン5.8ｇのトルエン溶液30ml
をゆつくりと滴下し、70〜80℃で約20時間加熱し
た。加熱後、得られたポリマーをベンゼン−エタ
ノール（１：1by vol）溶液で再沈し、約65％の
収率で、
なる組成のポリマーの白色粉末を得た。
得られたポリマーの性状および機器分折結果を
以下に示す。
融点：186〜189℃
数平均分子量：34000
NMRスペクトル（C6D6）δ（ppm）：0.34（ｓ）
0.94（broad ｓ）、7.28（ｓ）．
IRスペクトル：
[Field of Application of the Invention] The present invention relates to a novel polymer that is extremely useful as a functional polymer material. More specifically, the constituent unit expressed by formula (1) The present invention relates to a polymer consisting of: [Background of the Invention] As a polymer having a Si-Si bond in the polymer main chain, a structural unit represented by formula (2) is used. Polymers consisting of the following are known, but when used as electronic materials such as photosensitive materials, they have poor solubility in general-purpose organic solvents, and for practical purposes, there has been a strong desire for improvement. Further, when used by forming a film on a substrate, the coating film cannot be formed homogeneously or the coating film is too flexible, making it impossible to put it into practical use. [Object of the Invention] An object of the present invention is to provide a polymer having a Si--Si bond in its main chain, which compensates for the drawbacks of the above-mentioned materials and is characterized by particularly excellent solubility. [Summary of the Invention] In order to achieve the above object, the inventor has developed a Si
- As a result of combining various polymers having Si bonds, the structural unit represented by the following general formula (1) It has been found that a polymer consisting of the following is a useful polymer that satisfies the above objectives. The polymer of the present invention combines parabis(chloroethylmethylsilyl)benzene [3] with metallic sodium obtained by heating in toluene in the presence of The polymer of the present invention is crystalline in its normal state and easily dissolves in organic solvents such as toluene, so this solution can be used to manufacture various molded products, such as films, fibers, etc.
It can be formed into a sheet or the like. Furthermore, the polymer of the present invention has excellent adhesion to various metals and glasses, and can be used as adhesives, paints, and the like. Furthermore, the polymer of the present invention is extremely useful as a functional polymer material. That is, the polymer of the present invention can be usefully used as a photosensitive material or a radiation-sensitive material, and since it has high heat resistance,
It can also be used as an insulating material. In addition, the number average molecular weight of the polymer of the present invention is 1000 to
1000000. If it is less than 1000, it is difficult to use it as a functional polymer material. The polymer of the present invention may be blended with well-known compounding agents such as antioxidants, heat stabilizers, colorants, flame retardants, etc. according to known formulations. [Examples of the Invention] The present invention will be specifically explained below using synthesis examples and examples, but the present invention is not limited to these examples. Synthesis example 1 (parabis(ethylmethylethoxysilyl)
Synthesis of benzene [4]) Add 16.2 g of ethylmethyldiethoxysilane, 2.43 g of magnesium, and 100 ml of tetrahydrofuran to a 500 ml three-necked flask equipped with a stirrer, condenser, and dropping funnel, stir, and add P-dibrome from the dropping funnel under a nitrogen stream. A solution of 11.8 g of benzene in 100 ml of tetrahydrofuran was added dropwise over about 3 hours. After the dropwise addition, the mixture was further refluxed for about 5 hours while stirring was continued. After refluxing, the solvent was separated, and the solvent was distilled off under reduced pressure to obtain 10.5 g (yield: 68%) of parabis(ethylmethylethoxysilyl)benzene (boiling point:
122-125°C/3mmHg). NMR spectrum of [4] (CDCl 3 ) δ (ppm): 0.42 (s), 0.86-1.08 (m), 1.26 (t
),
3.74 (q), 7.56 (s) Synthesis example 2 (Synthesis of parabis(chloroethylmethylsilyl)benzene [3]) By refluxing 9.3 g of parabis(ethylmethylethoxysilyl)benzene obtained in Synthesis Example 1 and 12g of acetyl chloride for about 5 hours, parabis(chloroethylmethylsilyl) was obtained with a yield of 98%.
8.6 g of benzene (boiling point: 131-135°C/mmHg) was obtained. NMR spectrum of [5] (CDCl 3 ) δ (ppm): 0.68 (s), 1.12 (s), 7.68 (s). Example 1 In a 200 ml three-necked flask equipped with a stirrer, condenser, and dropping funnel, 1.2 ml of sodium was added under a nitrogen stream.
Add 30 ml of a toluene solution of 5.8 g of parabis(chloroethylmethylsilyl)benzene obtained in Synthesis Example 2 to about 50 ml of toluene despersion solution containing g.
was slowly added dropwise and heated at 70 to 80°C for about 20 hours. After heating, the obtained polymer was reprecipitated with a benzene-ethanol (1:1 by vol) solution, with a yield of about 65%. A white powder of a polymer having the following composition was obtained. The properties and instrumental analysis results of the obtained polymer are shown below. Melting point: 186-189°C Number average molecular weight: 34000 NMR spectrum (C 6 D 6 ) δ (ppm): 0.34 (s) 0.94 (broad s), 7.28 (s). IR spectrum:
本発明の重合体は、感光性材料等の機能性高分
子材料として極めて効用の大なるものである。
The polymer of the present invention is extremely useful as a functional polymer material such as a photosensitive material.
Claims (1)
1000000であることを特徴とする新規な重合体。 [Claims] 1 Number average molecular weight represented by formula (1) 1000~
1,000,000.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11274483A JPS604532A (en) | 1983-06-24 | 1983-06-24 | Novel polymer |
| EP84107029A EP0129834B1 (en) | 1983-06-24 | 1984-06-19 | Photo and radiation-sensitive organopolymeric material |
| DE8484107029T DE3470103D1 (en) | 1983-06-24 | 1984-06-19 | Photo and radiation-sensitive organopolymeric material |
| US06/623,168 US4544729A (en) | 1983-06-24 | 1984-06-22 | Photo and radiation-sensitive organopolymeric material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11274483A JPS604532A (en) | 1983-06-24 | 1983-06-24 | Novel polymer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS604532A JPS604532A (en) | 1985-01-11 |
| JPS6328451B2 true JPS6328451B2 (en) | 1988-06-08 |
Family
ID=14594460
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11274483A Granted JPS604532A (en) | 1983-06-24 | 1983-06-24 | Novel polymer |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS604532A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2198446B (en) * | 1986-03-11 | 1990-05-30 | Foundation Res Inst | Organopolyarysilane, process for its production, and fibers prepared therefrom |
-
1983
- 1983-06-24 JP JP11274483A patent/JPS604532A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS604532A (en) | 1985-01-11 |
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