JPH0832753B2 - Polymer solid electrolyte - Google Patents
Polymer solid electrolyteInfo
- Publication number
- JPH0832753B2 JPH0832753B2 JP1337993A JP33799389A JPH0832753B2 JP H0832753 B2 JPH0832753 B2 JP H0832753B2 JP 1337993 A JP1337993 A JP 1337993A JP 33799389 A JP33799389 A JP 33799389A JP H0832753 B2 JPH0832753 B2 JP H0832753B2
- Authority
- JP
- Japan
- Prior art keywords
- solid electrolyte
- polymer solid
- copolymer
- molecular weight
- acid ester
- 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
- 229920000642 polymer Polymers 0.000 title claims description 17
- 239000007784 solid electrolyte Substances 0.000 title claims description 15
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 16
- 229920001577 copolymer Polymers 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- -1 diacrylic acid ester Chemical class 0.000 claims description 7
- 235000019256 formaldehyde Nutrition 0.000 claims description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 6
- 229920005604 random copolymer Polymers 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 3
- 229920001187 thermosetting polymer Polymers 0.000 claims description 3
- 229920001400 block copolymer Polymers 0.000 claims description 2
- 230000005865 ionizing radiation Effects 0.000 claims description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- PHXQIAWFIIMOKG-UHFFFAOYSA-N NClO Chemical compound NClO PHXQIAWFIIMOKG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- ZZXUZKXVROWEIF-UHFFFAOYSA-N 1,2-butylene carbonate Chemical compound CCC1COC(=O)O1 ZZXUZKXVROWEIF-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- JRRDISHSXWGFRF-UHFFFAOYSA-N 1-[2-(2-ethoxyethoxy)ethoxy]-2-methoxyethane Chemical compound CCOCCOCCOCCOC JRRDISHSXWGFRF-UHFFFAOYSA-N 0.000 description 1
- YZWVMKLQNYGKLJ-UHFFFAOYSA-N 1-[2-[2-(2-ethoxyethoxy)ethoxy]ethoxy]-2-methoxyethane Chemical compound CCOCCOCCOCCOCCOC YZWVMKLQNYGKLJ-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- CMJLMPKFQPJDKP-UHFFFAOYSA-N 3-methylthiolane 1,1-dioxide Chemical compound CC1CCS(=O)(=O)C1 CMJLMPKFQPJDKP-UHFFFAOYSA-N 0.000 description 1
- MVYGFAZZLWOFNN-UHFFFAOYSA-N 4,4-dimethyl-1,3-dioxolane Chemical compound CC1(C)COCO1 MVYGFAZZLWOFNN-UHFFFAOYSA-N 0.000 description 1
- 229910020366 ClO 4 Inorganic materials 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- 229910015015 LiAsF 6 Inorganic materials 0.000 description 1
- 229910013063 LiBF 4 Inorganic materials 0.000 description 1
- 229910013375 LiC Inorganic materials 0.000 description 1
- 229910013684 LiClO 4 Inorganic materials 0.000 description 1
- 229910013870 LiPF 6 Inorganic materials 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Inorganic materials [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 1
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 description 1
- 229910001486 lithium perchlorate Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000005518 polymer electrolyte Substances 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Polyethers (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Conductive Materials (AREA)
- Primary Cells (AREA)
- Secondary Cells (AREA)
Description
【発明の詳細な説明】 産業上の利用分野 本発明は一次電池、二次電池、エレクトロクロミック
ディスプレイ、電気化学センサー、イオントフォレーシ
ス、コンデンサーその他の電気化学的デバイスに用いる
ポリマー固体電解質に関するものである。Description: TECHNICAL FIELD The present invention relates to a solid polymer electrolyte used for primary batteries, secondary batteries, electrochromic displays, electrochemical sensors, iontophoresis, capacitors and other electrochemical devices. is there.
従来技術とその問題点 従来、ポリマー固体電解質としてポリエチレンオキシ
ドの架橋ネットワーク高分子にアルカリ金属塩を含ませ
たものが用いられてきた。ポリエチレンオキシドはアル
カリ金属塩を溶解させる能力が高いが、結晶化し易いと
いう欠点がある。さらに架橋が容易なジメタクリル酸エ
ステル又はジアクリル酸エステルによる架橋は柔軟性を
欠いたものとなり、実用上問題である。柔軟性はポリエ
チレンオキシドの分子量が小さいと悪くなる。しかし従
来は、分子量が2,000よりも小さいものが用いられてお
り、特に結晶化を防ぐために、分子量が200乃至1,000程
度の小さいものを用いているので、柔軟性が悪いという
欠点があった。Conventional Technology and its Problems Conventionally, as a polymer solid electrolyte, a cross-linked network polymer of polyethylene oxide containing an alkali metal salt has been used. Polyethylene oxide has a high ability to dissolve an alkali metal salt, but has a drawback that it is easily crystallized. Further, the crosslinking with dimethacrylic acid ester or diacrylic acid ester, which is easy to crosslink, lacks flexibility, which is a practical problem. The flexibility deteriorates when the molecular weight of polyethylene oxide is small. However, conventionally, a polymer having a molecular weight of less than 2,000 has been used, and in particular, a polymer having a small molecular weight of about 200 to 1,000 is used in order to prevent crystallization, so that it has a drawback of poor flexibility.
発明の目的 本発明は上記従来の問題点に鑑みなされたものであ
り、機械的強度に優れた、イオン伝導度の高い、ポリマ
ー固体電解質を提供することを目的とするものである。SUMMARY OF THE INVENTION The present invention has been made in view of the above-described conventional problems, and has as its object to provide a polymer solid electrolyte having excellent mechanical strength and high ionic conductivity.
発明の構成 本発明は上記目的を達成するべく、 エチレンオキシドとメチレンオキシド単位CH2Oの
共重合体のジメタクリル酸エステル又は／及びジアクリ
ル酸エステルの架橋ネットワーク高分子がイオン性塩を
含むことを特徴とするポリマー固体電解質である。In order to achieve the above object, the present invention is characterized in that the crosslinked network polymer of a dimethacrylic acid ester or / and a diacrylic acid ester of a copolymer of ethylene oxide and a methylene oxide unit CH 2 O contains an ionic salt. And a polymer solid electrolyte.
又、共重合体の分子量が2,000乃至30,000である前記
のポリマー固体電解質である。Further, it is the above-mentioned polymer solid electrolyte in which the molecular weight of the copolymer is 2,000 to 30,000.
又、共重合体がランダム共重合体又は／及びブロック
共重合体である前記のポリマー固体電解質である。The above-mentioned polymer solid electrolyte in which the copolymer is a random copolymer and / or a block copolymer.
又、共重合体のメチレンオキシド単位が30モル％以下
である前記のポリマー固体電解質である。Further, it is the above-mentioned polymer solid electrolyte in which the methylene oxide unit of the copolymer is 30 mol% or less.
又、イオン性塩を相溶することができる化合物を該イ
オン性塩と共に含有する前記のポリマー固体電解質であ
る。Further, the above-mentioned polymer solid electrolyte contains a compound capable of dissolving the ionic salt together with the ionic salt.
又、架橋ネットワークの形成は、熱的、活性光線、又
は電離性放射線の照射による前記のポリマー固体電解質
である。Also, the formation of the crosslinked network is the above-mentioned polymer solid electrolyte by irradiation with heat, actinic rays, or ionizing radiation.
実施例 以下、本発明の詳細について実施例により説明する。Examples Hereinafter, details of the present invention will be described with reference to Examples.
実施例１ 先ず、オートクレーブ中にエチレンオキシドとメチレ
ンオキシドが8:2のモル比になるように仕込み、少量の
水とアルカリの共存下で反応させてエチレンオキシドと
メチレンオキシドのランダム共重合体を製造した。エチ
レンオキシドとメチレンオキシドのランダム共重合体
（メチレンオキシド20モル％含有、分子量4,000）のジ
メタクリル酸エステル100重量部と過塩素酸リチウム9.5
重量部をメチルエチルケトン100重量部に溶解した溶液
を混合し、ガラス板上にキャストした。メチルエチルケ
トンを蒸発した後、6Mradの電子線は照射して硬化し
た。得られた膜の厚味は100μｍで複素インピーダンス
法で測定したイオン伝導度は３×10-6Ｓcm-1（25℃）で
あった。Example 1 First, a random copolymer of ethylene oxide and methylene oxide was prepared by charging ethylene oxide and methylene oxide in an autoclave in a molar ratio of 8: 2 and reacting them in the presence of a small amount of water and an alkali. 100 parts by weight of dimethacrylic acid ester of a random copolymer of ethylene oxide and methylene oxide (containing 20 mol% of methylene oxide, molecular weight 4,000) and lithium perchlorate 9.5
A solution in which 100 parts by weight of methyl ethyl ketone was dissolved was mixed and cast on a glass plate. After evaporating the methyl ethyl ketone, it was cured by irradiation with an electron beam of 6 Mrad. The thickness of the obtained film was 100 μm, and the ionic conductivity measured by the complex impedance method was 3 × 10 −6 Scm −1 (25 ° C.).
別にエチレンオキシドとメチレンオキシドのランダム
共重合体（メチレンオキシド20モル％含有）の分子量が
400,1,000,2,000と10,000のものを用いて、同様の組成
比で厚み100μｍのフィルムを得た。これらの物性を表
１に示した。柔軟性は分子量の増加と共に改良すること
が認められた。尚、柔軟性が90°折り曲げ、180°折り
曲げ試験を実施し、割れにより判断した。Separately, the molecular weight of a random copolymer of ethylene oxide and methylene oxide (containing 20 mol% of methylene oxide)
A film having a thickness of 100 μm was obtained with the same composition ratio using the materials of 400, 1,000, 2,000 and 10,000. These physical properties are shown in Table 1. It was observed that the flexibility improves with increasing molecular weight. Flexibility was tested by bending at 90 ° and 180 °, and judged by cracking.
実施例２ 実施例１において、メチルエチルケトンに替えてプロ
ピレンカーボネートを用いた。又、プロピレンカーボネ
ートは蒸発させずに膜中に残した。それ以外は実施例１
と同様にした。その結果を表２に示した。 Example 2 In Example 1, propylene carbonate was used instead of methyl ethyl ketone. Further, propylene carbonate was left in the film without being evaporated. Otherwise, Example 1
Same as. The results are shown in Table 2.
実施例３ 実施例２のジメタクリル酸エステルをジアクリル酸エ
ステルに替えたものでランダム共重合体の分子量が4,00
0のものについて、100μｍの膜を作成し特性を求めた。 Example 3 The dimethacrylic acid ester of Example 2 was replaced with a diacrylic acid ester, and the random copolymer had a molecular weight of 4,000.
For 0, a film having a thickness of 100 μm was formed and the characteristics were obtained.
イオン伝導度は3.0×10-4Ｓcm-1で柔軟性は90°,180
°共に折り曲げ試験において割れなかった。Ionic conductivity is 3.0 × 10 -4 Scm -1 and flexibility is 90 °, 180
° Both did not crack in the bending test.
共重合体の分子量を上げることによって柔軟性と強度
を上げることができる。しかし分子量を上げすぎると反
応速度が低下し、生産性が悪くなる。又、結晶化し易く
なるために、伝導度の低下を招き問題である。そのため
に、分子量は2,000乃至30,000好ましくは、2,000乃至5,
000が最適である。Flexibility and strength can be increased by increasing the molecular weight of the copolymer. However, if the molecular weight is too high, the reaction rate will decrease and the productivity will deteriorate. Further, since it is easily crystallized, the conductivity is lowered, which is a problem. Therefore, the molecular weight is 2,000 to 30,000, preferably 2,000 to 5,
000 is the best.
尚、イオン性塩としてはLiClO4，LiBF4，LiAsF6，LiC
F3SO3，LiPF6,LiI,LiBr,LiSCN,NaI,Li2B10Cl10，LiCF3C
O2,NaBr,NaSCN,KSCN,MgCl2，Mg(ClO4)2，(CH3)4NBF4，
(CH3)4NBr，(C2H5)4NClO4，(C2H5)4NI、(C3H7)4NBr，(n
-C4H9)4NClO4，(n-C4H9)4NI，(n-C5H11)4NIが好ましい
が限定しない。The ionic salts are LiClO 4 , LiBF 4 , LiAsF 6 , LiC.
F 3 SO 3 , LiPF 6 , LiI, LiBr, LiSCN, NaI, Li 2 B 10 Cl 10 , LiCF 3 C
O 2 , NaBr, NaSCN, KSCN, MgCl 2 , Mg (ClO 4 ) 2 , (CH 3 ) 4 NBF 4 ,
(CH 3 ) 4 NBr, (C 2 H 5 ) 4 NClO 4 , (C 2 H 5 ) 4 NI, (C 3 H 7 ) 4 NBr, (n
-C 4 H 9 ) 4 NClO 4 , (nC 4 H 9 ) 4 NI, (nC 5 H 11 ) 4 NI are preferred but not limited.
又、イオン性塩を溶解することができる化合物とは、
テトラヒドロフラン、２−メチルテトラヒドロフラン、
1,3−ジオキソラン、4,4−ジメチル−1,3−ジオキソラ
ン、γ−ブチロラクトン、エチレンカーボネート、プロ
ピレンカーボネート、ブチレンカーボネート、スルホラ
ン、３−メチルスルホラン、tert.−ブチルエーテル、i
so−ブチルエーテル、1,2ジメトキシエタン、1,2−エト
キシメトキシエタン、メチルジグライム、メチルトリグ
ライム、メチルテトラグライム、エチルグライム、エチ
ルジグライム等があるが限定はしない。Further, the compound capable of dissolving the ionic salt,
Tetrahydrofuran, 2-methyltetrahydrofuran,
1,3-dioxolane, 4,4-dimethyl-1,3-dioxolane, γ-butyrolactone, ethylene carbonate, propylene carbonate, butylene carbonate, sulfolane, 3-methylsulfolane, tert.-butyl ether, i
Examples include, but are not limited to, so-butyl ether, 1,2 dimethoxyethane, 1,2-ethoxymethoxyethane, methyl diglyme, methyl triglyme, methyl tetraglyme, ethyl glyme, ethyl diglyme.
発明の効果 上述した如く、機械的強度に優れた、イオン伝導度の
高いポリマー固体電解質を提供できるので、その工業的
価値は極めて大である。EFFECTS OF THE INVENTION As described above, since a polymer solid electrolyte having excellent mechanical strength and high ionic conductivity can be provided, its industrial value is extremely large.
Claims (5)
−（CH2O）−の共重合体のジメタクリル酸エステル又は
／及びジアクリル酸エステル架橋ネットワーク高分子が
イオン性塩を含むことを特徴とするポリマー固体電解
質。1. A polymer solid electrolyte characterized in that the dimethacrylic acid ester and / or diacrylic acid ester crosslinked network polymer of a copolymer of ethylene oxide and a methylene oxide unit-(CH 2 O)-contains an ionic salt. .
請求項１記載のポリマー固体電解質。2. The polymer solid electrolyte according to claim 1, wherein the molecular weight of the copolymer is 2000 to 30,000.
ロック共重合体である請求項１記載のポリマー固体電解
質。3. The polymer solid electrolyte according to claim 1, wherein the copolymer is a random copolymer and / or a block copolymer.
を該イオン性塩と共に含有する請求項１記載のポリマー
固体電解質。4. The polymer solid electrolyte according to claim 1, which contains a compound capable of compatibilizing an ionic salt together with the ionic salt.
線、又は電離性放射線の照射による請求項１又は２記載
のポリマー固体電解質。5. The polymer solid electrolyte according to claim 1, wherein the crosslinked network is formed by irradiation with heat, actinic rays, or ionizing radiation.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1337993A JPH0832753B2 (en) | 1989-12-25 | 1989-12-25 | Polymer solid electrolyte |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1337993A JPH0832753B2 (en) | 1989-12-25 | 1989-12-25 | Polymer solid electrolyte |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03196409A JPH03196409A (en) | 1991-08-27 |
| JPH0832753B2 true JPH0832753B2 (en) | 1996-03-29 |
Family
ID=18313933
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1337993A Expired - Lifetime JPH0832753B2 (en) | 1989-12-25 | 1989-12-25 | Polymer solid electrolyte |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0832753B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100393181B1 (en) * | 1996-06-28 | 2003-11-28 | 삼성전자주식회사 | Polymer solid electrolyte composition |
-
1989
- 1989-12-25 JP JP1337993A patent/JPH0832753B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH03196409A (en) | 1991-08-27 |
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