JPH03273027A - New polyamide - Google Patents
New polyamideInfo
- Publication number
- JPH03273027A JPH03273027A JP6210990A JP6210990A JPH03273027A JP H03273027 A JPH03273027 A JP H03273027A JP 6210990 A JP6210990 A JP 6210990A JP 6210990 A JP6210990 A JP 6210990A JP H03273027 A JPH03273027 A JP H03273027A
- Authority
- JP
- Japan
- Prior art keywords
- polyamide
- amino acid
- acid
- heat resistance
- present
- 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.)
- Pending
Links
- 239000004952 Polyamide Substances 0.000 title claims abstract description 15
- 229920002647 polyamide Polymers 0.000 title claims abstract description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims abstract description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 abstract description 14
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 abstract description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract description 5
- 150000004985 diamines Chemical class 0.000 abstract description 5
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 125000003275 alpha amino acid group Chemical group 0.000 abstract 1
- 229940024606 amino acid Drugs 0.000 description 11
- 235000001014 amino acid Nutrition 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 229960003767 alanine Drugs 0.000 description 2
- -1 dicarboxylic acid chlorides Chemical class 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-UWTATZPHSA-N L-Alanine Natural products C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 description 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 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、フィルム、シートおよび繊維状の形態で電子
部品、機械部品、繊維材料等として幅広く使用できる耐
熱性や風合いに優れた新規ポリアミドに関する。[Detailed Description of the Invention] <Industrial Application Field> The present invention relates to a novel polyamide with excellent heat resistance and texture that can be widely used in the form of films, sheets, and fibers as electronic parts, mechanical parts, textile materials, etc. .
〈従来の技術及び問題点〉
ポリアミドはその優れた性質からエンジニアリングプラ
スチックとして広く使用されているが、耐水性や耐熱性
の向上等更なる性質の改良が求められている。<Prior Art and Problems> Polyamide is widely used as an engineering plastic due to its excellent properties, but further improvements in properties such as improved water resistance and heat resistance are required.
また、アミノ酸ポリマーは優れた耐熱性や風合いを有す
るが熱可塑性がないという欠点かある。Furthermore, although amino acid polymers have excellent heat resistance and texture, they have the disadvantage of not being thermoplastic.
アミノ酸とジカルボン酸、ジアミンからなるポリアミド
としては、Ｒ，Ｄ 、Ｋａｔｓａｒａｖａらの研究例が
あるが（Ａｃｔａ Ｐｏｌｙｍｅｒｉｃａ ３６（１）
２９−３８（１９８５））、芳香族ジカルボン酸の例で
あり評価も生体内での分解に限定されており、ナイロン
型骨格にアミノ酸を導入した例はない。Regarding polyamides consisting of amino acids, dicarboxylic acids, and diamines, there are research examples by R, D, Katsarava et al. (Acta Polymerica 36 (1)
29-38 (1985)), which is an example of an aromatic dicarboxylic acid, and its evaluation is limited to in-vivo decomposition, and there are no examples of introducing amino acids into a nylon-type skeleton.
〈発明が解決しようとする課題〉
本発明の課題は、耐熱性等に優れた新規ポリアミドを提
供することである。<Problems to be Solved by the Invention> An object of the present invention is to provide a novel polyamide with excellent heat resistance and the like.
く課題を解決するための手段〉
本発明者らは、優れた特色を有するポリアミドに関して
鋭意検討をした結果、アミノ酸骨格を構成単位に含む新
規ポリアミドを合成する事に成功し、耐熱性や風合いが
改善される事を見いだし本発明を完成した。Means for Solving the Problems As a result of extensive research into polyamides with excellent characteristics, the present inventors succeeded in synthesizing a new polyamide containing an amino acid skeleton as a constituent unit, which has improved heat resistance and texture. They discovered that this could be improved and completed the present invention.
すなわち、本発明は一般式（Ｉ）
Ｈ
０
○
（Ｉ）
（ただし１は１０から１０００まで
の整数、ｍは１から１０の整数、ｎは１から８の整数、
Ｒは水素原子、メチル基１、イソプロピル基、イソブチ
ル基、ベンジル基を表す。）の構造を有する新規ポリア
ミドに関する。That is, the present invention is based on the general formula (I) H 0 ○ (I) (where 1 is an integer from 10 to 1000, m is an integer from 1 to 10, n is an integer from 1 to 8,
R represents a hydrogen atom, a methyl group, an isopropyl group, an isobutyl group, or a benzyl group. ) relates to a new polyamide having the structure.
この新規ポリアミドは、ジカルボン酸の両端にアミノ酸
をアミド結合し、これとジアミンを重縮合させて得られ
る。本発明に用いられるアミノ酸はアラニンやロイシン
、フェニルアラニンのような中性アミノ酸が用いられる
。This novel polyamide is obtained by amide bonding amino acids at both ends of dicarboxylic acid and polycondensing this with diamine. The amino acids used in the present invention are neutral amino acids such as alanine, leucine, and phenylalanine.
ジカルボン酸としてはコハク酸、グルタル酸やアジピン
酸が用いられる。また、シアミンとしてはテトラメチレ
ンジアミンやヘキサメチレンジアミンが用いられる。Succinic acid, glutaric acid and adipic acid are used as the dicarboxylic acid. Further, as the cyamine, tetramethylene diamine and hexamethylene diamine are used.
本発明の新規ポリアミドの製法は、特に限定されないが
例えばジカルボンサンのアミノ酸ジアシル体とジアミン
を重縮合することにより行われる。The method for producing the novel polyamide of the present invention is not particularly limited, but may be carried out, for example, by polycondensing an amino acid diacyl form of dicarbonane with a diamine.
ジカルボン酸のアミノ酸ジアシル体は、ジカルボン酸ク
ロライドでアミノ酸をアシル化することにより容易に得
られる。Amino acid diacyl derivatives of dicarboxylic acids can be easily obtained by acylating amino acids with dicarboxylic acid chlorides.
ジアミンとの重縮合は常法により行われる。Polycondensation with diamines is carried out by conventional methods.
例えば、縮合剤としてトリフェニルホスファイト、ピリ
ジン等が用いられる。For example, triphenyl phosphite, pyridine, etc. are used as the condensing agent.
本発明によって得られた新規ポリアミドはアミノ酸の種
類によりことなるが耐熱性の向上や風合いの改善が認め
られる。The novel polyamide obtained by the present invention has improved heat resistance and improved texture, although this varies depending on the type of amino acid.
以下に具体例で本発明を説明するが、これらは例示であ
り本発明はこれらに限定されるものではない。The present invention will be explained below using specific examples, but these are merely illustrative and the present invention is not limited thereto.
〈実施例〉
実施例１゜
Ｌ−アラニン９３・５ｇを水酸化ナトリウム４２ｇと水
３７０ｍ１にン古かしアセトン１６５ｍｌを加え水冷下
激しく撹はんした。アジポイルクロライド９］、、５ｇ
と１０％水酸化ナトリウム水溶７１に約４５０ｇをｐＨ
１０〜１１．５に保ちながら約６０分かけて適下した。<Example> Example 1 93.5 g of L-alanine was added to 42 g of sodium hydroxide and 165 ml of aged acetone to 370 ml of water, and the mixture was stirred vigorously under water cooling. Adipoyl chloride 9], 5g
and about 450 g in 10% sodium hydroxide aqueous solution 71 to pH
It was applied over about 60 minutes while maintaining the temperature at 10 to 11.5.
史に６０分攪はん後、？＋、１硫酸を加えｐ Ｈ２にす
ると白色の固体が析出した。After stirring for 60 minutes,? When the pH was adjusted to 2 by adding +1 sulfuric acid, a white solid was precipitated.
これを濾別、約２００ｍ１の水で洗浄し減圧下に６０〜
７０℃で乾燥した。This was separated by filtration, washed with about 200ml of water, and heated under reduced pressure for 60~
It was dried at 70°C.
シアラニルアシビン酸１２１ｇを得た。121 g of cyanylacibic acid was obtained.
ジアラニルアシビン酸、１・４４ｇ、ヘキサメチレンジ
アミン０．５８ｇ、）・リフェニルホスファイト３．５
ｇ、 ピリジン５ｍｌをＮ−メチルピロリドン１５ｍ
１に加え室温で２時間、８５°Ｃで５時間撹はんした。Dialanylacibic acid, 1.44g, hexamethylenediamine 0.58g, )・Riphenyl phosphite 3.5
g, 5 ml of pyridine to 15 ml of N-methylpyrrolidone
1 and stirred at room temperature for 2 hours and at 85°C for 5 hours.
得られた重合液をアセトン中に分散させポリマ−を沈澱
させた。The obtained polymerization solution was dispersed in acetone to precipitate the polymer.
減圧下に乾燥させ１．４ｇを得た。It was dried under reduced pressure to obtain 1.4 g.
得られたポリマーのギ酸中での極限粘度は０゜９、ＤＳ
Ｃにより測定した融点は２４３℃であった。The intrinsic viscosity of the obtained polymer in formic acid was 0°9, DS
The melting point measured by C was 243°C.
〈 発明の効果〉
本発明により得られた新規ポリアミドはアミノ酸を１１
６造単位に含む耐熱性や風合いにに優れたｍ合物であり
、各種用途への利用が可能である。<Effects of the invention> The novel polyamide obtained by the present invention has 11 amino acids.
It is a m-compound containing excellent heat resistance and texture, and can be used for various purposes.
実施例２゜
実施例１．と同様の方法で得たジフェニルアラニルアジ
ピン酸２．２ｇ、 テトラメチレンジアミン０． ４
４ｇ、 トリフェニルホスファイト３．５ｇ、ピリジ
ン５ｍｌをＮ−メチルピロリドン２０ｍ１に加え８０℃
で６時間攪はんした。Example 2゜Example 1. 2.2 g of diphenylalanyl adipic acid obtained in the same manner as above, 0.0 g of tetramethylenediamine. 4
4 g, triphenyl phosphite 3.5 g, and pyridine 5 ml were added to 20 ml of N-methylpyrrolidone at 80°C.
The mixture was stirred for 6 hours.
同様にポリマーを沈澱、乾燥させ１．７ｇを得た。Similarly, the polymer was precipitated and dried to obtain 1.7 g.
ギ酸中での極限粘度は０，７５、ＤＳＣによる融点は２
５０℃であった。Intrinsic viscosity in formic acid is 0.75, melting point by DSC is 2
The temperature was 50°C.
Claims (1)
Ｒは水素原子、メチル基、、イソプロピル基、イソブチ
ル基、ベンジル基を表す。） で示される新規ポリアミド。[Claims] 1) General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (where 1 is an integer from 10 to 1000, m is an integer from 1 to 10, and n is 1 to 8 an integer of
R represents a hydrogen atom, a methyl group, an isopropyl group, an isobutyl group, or a benzyl group. ) A new polyamide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6210990A JPH03273027A (en) | 1990-03-13 | 1990-03-13 | New polyamide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6210990A JPH03273027A (en) | 1990-03-13 | 1990-03-13 | New polyamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03273027A true JPH03273027A (en) | 1991-12-04 |
Family
ID=13190560
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6210990A Pending JPH03273027A (en) | 1990-03-13 | 1990-03-13 | New polyamide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03273027A (en) |
Cited By (8)
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|---|---|---|---|---|
| WO2013002074A1 (en) * | 2011-06-27 | 2013-01-03 | 三菱瓦斯化学株式会社 | Multi-layer direct blow bottle |
| WO2013002073A1 (en) * | 2011-06-27 | 2013-01-03 | 三菱瓦斯化学株式会社 | Multilayer injection-molded body |
| WO2013002076A1 (en) * | 2011-06-27 | 2013-01-03 | 三菱瓦斯化学株式会社 | Multi-layer sheet |
| WO2013002078A1 (en) * | 2011-06-27 | 2013-01-03 | 三菱瓦斯化学株式会社 | Laminate and paper container |
| WO2013002079A1 (en) * | 2011-06-27 | 2013-01-03 | 三菱瓦斯化学株式会社 | Laminate and paper container |
| WO2013002069A1 (en) * | 2011-06-27 | 2013-01-03 | 三菱瓦斯化学株式会社 | Multi-layer film and film packaging container |
| WO2013002071A1 (en) * | 2011-06-27 | 2013-01-03 | 三菱瓦斯化学株式会社 | Multilayer injection-molded body |
| CN102985464A (en) * | 2010-06-29 | 2013-03-20 | 三菱瓦斯化学株式会社 | Polyamide compound |
-
1990
- 1990-03-13 JP JP6210990A patent/JPH03273027A/en active Pending
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|---|---|---|---|---|
| CN102985464A (en) * | 2010-06-29 | 2013-03-20 | 三菱瓦斯化学株式会社 | Polyamide compound |
| JP5867391B2 (en) * | 2010-06-29 | 2016-02-24 | 三菱瓦斯化学株式会社 | Polyamide compound |
| CN102985464B (en) * | 2010-06-29 | 2015-04-01 | 三菱瓦斯化学株式会社 | Polyamide compound |
| EP2589616A4 (en) * | 2010-06-29 | 2014-05-14 | Mitsubishi Gas Chemical Co | Polyamide compound |
| EP2589616A1 (en) * | 2010-06-29 | 2013-05-08 | Mitsubishi Gas Chemical Company, Inc. | Polyamide compound |
| JPWO2013002073A1 (en) * | 2011-06-27 | 2015-02-23 | 三菱瓦斯化学株式会社 | Multi-layer injection molding |
| JPWO2013002079A1 (en) * | 2011-06-27 | 2015-02-23 | 三菱瓦斯化学株式会社 | Laminate and paper container |
| WO2013002069A1 (en) * | 2011-06-27 | 2013-01-03 | 三菱瓦斯化学株式会社 | Multi-layer film and film packaging container |
| WO2013002079A1 (en) * | 2011-06-27 | 2013-01-03 | 三菱瓦斯化学株式会社 | Laminate and paper container |
| WO2013002078A1 (en) * | 2011-06-27 | 2013-01-03 | 三菱瓦斯化学株式会社 | Laminate and paper container |
| WO2013002074A1 (en) * | 2011-06-27 | 2013-01-03 | 三菱瓦斯化学株式会社 | Multi-layer direct blow bottle |
| JPWO2013002078A1 (en) * | 2011-06-27 | 2015-02-23 | 三菱瓦斯化学株式会社 | Laminate and paper container |
| WO2013002071A1 (en) * | 2011-06-27 | 2013-01-03 | 三菱瓦斯化学株式会社 | Multilayer injection-molded body |
| JPWO2013002069A1 (en) * | 2011-06-27 | 2015-02-23 | 三菱瓦斯化学株式会社 | Multilayer film and film packaging container |
| JPWO2013002071A1 (en) * | 2011-06-27 | 2015-02-23 | 三菱瓦斯化学株式会社 | Multi-layer injection molding |
| JPWO2013002076A1 (en) * | 2011-06-27 | 2015-02-23 | 三菱瓦斯化学株式会社 | Multilayer sheet |
| WO2013002076A1 (en) * | 2011-06-27 | 2013-01-03 | 三菱瓦斯化学株式会社 | Multi-layer sheet |
| WO2013002073A1 (en) * | 2011-06-27 | 2013-01-03 | 三菱瓦斯化学株式会社 | Multilayer injection-molded body |
| US9718259B2 (en) | 2011-06-27 | 2017-08-01 | Mitsubishi Gas Chemical Company, Inc. | Multilayer injection-molded body |
| US9731482B2 (en) | 2011-06-27 | 2017-08-15 | Mitsubishi Gas Chemical Company, Inc. | Multilayer injection-molded body |
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