JP2002145931A - Chemical recycle process for synthetic paper - Google Patents
Chemical recycle process for synthetic paperInfo
- Publication number
- JP2002145931A JP2002145931A JP2000345330A JP2000345330A JP2002145931A JP 2002145931 A JP2002145931 A JP 2002145931A JP 2000345330 A JP2000345330 A JP 2000345330A JP 2000345330 A JP2000345330 A JP 2000345330A JP 2002145931 A JP2002145931 A JP 2002145931A
- Authority
- JP
- Japan
- Prior art keywords
- polypropylene
- synthetic paper
- calcium carbonate
- mixture
- mmhg
- 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
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
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W30/00—Technologies for solid waste management
- Y02W30/50—Reuse, recycling or recovery technologies
- Y02W30/62—Plastics recycling; Rubber recycling
Landscapes
- Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は合成紙等に含まれる
ポリプロピレンを反応性のオリゴマーとしてリサイクル
する方法に関する。The present invention relates to a method for recycling polypropylene contained in synthetic paper or the like as a reactive oligomer.
【０００２】[0002]
【従来の技術】ＰＥＴボトル、合成紙その他のプラスチ
ック製品の多くは生分解され難いため焼却処分又はリサ
イクルする必要がある。焼却処分は、資源のムダ使いで
あるだけでなく、その焼却自体に多大のエネルギーを要
し、またダイオキシン等の環境ホルモンの発生等の問題
も生起する。これに対し、リサイクルは、資源の保護の
観点から有用である。ところが、従来のプラスチックの
リサイクル手段としては、エネルギーとしての利用がほ
とんどであり、物質としてのリサイクルは、より利用価
値の低いプラスチックにリサイクルするのがほとんどで
あり、有効利用とは言えない状態である。また、別の材
料に変換するというリサイクルもほとんど行なわれてい
ない。2. Description of the Related Art Many PET bottles, synthetic papers and other plastic products are hardly biodegradable and must be incinerated or recycled. Incineration not only wastes resources but also requires a great deal of energy for incineration itself, and also causes problems such as the generation of environmental hormones such as dioxins. In contrast, recycling is useful from the viewpoint of resource protection. However, most of the conventional means of recycling plastics are used as energy, and most of the recycling as substances is recycled into lower value plastics, which is not considered an effective use. . Also, there is almost no recycling to convert to another material.
【０００３】ところで、ポリプロピレン及び他の成分を
含む合成紙は、選挙投票用紙、地図、袋類等として広く
使用されており、その生産量も増加しており、今後も増
加すると予想されている。この合成紙も、将来はリサイ
クル法により回収義務が生じると考えられるが、そのリ
サイクル手段は全く報告されていない。[0003] Incidentally, synthetic paper containing polypropylene and other components is widely used as election ballots, maps, bags, and the like, and its production is increasing, and is expected to increase in the future. This synthetic paper is considered to be required to be collected in the future under the Recycling Law, but no recycling method has been reported.
【０００４】[0004]
【発明が解決しようとする課題】従って、本発明の目的
は、合成紙に代表されるポリプロピレンと無機物の混合
物又は複合物中のポリプロピレンを反応性のオリゴマー
として効率良く回収し、また当該無機物も同時に回収す
る方法を提供することにある。SUMMARY OF THE INVENTION Accordingly, an object of the present invention is to efficiently recover a polypropylene in a mixture or a composite of a polypropylene and an inorganic substance represented by synthetic paper as a reactive oligomer, and to simultaneously recover the inorganic substance. It is to provide a method of collecting.
【０００５】[0005]
【課題を解決するための手段】本発明者は、ポリプロピ
レンを含む合成紙に代表されるポリプロピレンと無機物
との混合物又は複合物を直接熱分解できる条件について
種々検討を重ねた結果、合成紙等を直接特定の圧力、温
度及び時間で熱分解した後、有機溶媒で抽出すれば効率
良くテレケリックプロピレンオリゴマーが得られ、さら
に残部からは無機物が回収できることを見出し、本発明
を完成するに至った。Means for Solving the Problems The present inventors have conducted various studies on the conditions under which a mixture or composite of polypropylene and an inorganic substance represented by synthetic paper containing polypropylene can be directly thermally decomposed, and as a result, have found that synthetic paper and the like have been obtained. After direct pyrolysis at a specific pressure, temperature, and time, it was found that if extracted with an organic solvent, a telechelic propylene oligomer could be obtained efficiently, and further, inorganic substances could be recovered from the remainder, thus completing the present invention.
【０００６】すなわち、本発明はポリプロピレン及び無
機物を主成分とする混合物又は複合物を０．１〜６mmHg
条件下、３６０〜４００℃に３０〜１８０分間加熱し、
次いで有機溶媒抽出することを特徴とする当該混合物又
は複合物中のポリプロピレンをテレケリックプロピレン
オリゴマーとして回収する方法を提供するものである。
また、本発明は、ポリプロピレン及び炭酸カルシウム又
はポリプロピレン、炭酸カルシウム及びシリカを主成分
とする合成紙を、０．１〜６mmHg条件下、３６０〜４０
０℃に３０〜１８０分間加熱し、次いで有機溶媒抽出す
ることを特徴とする合成紙中のポリプロピレンをテレケ
リックプロピレンオリゴマーとして回収する方法を提供
するものである。また、本発明は、ポリプロピレン及び
無機物を主成分とする混合物又は複合物を、０．１〜６
mmHg条件下、３６０〜４００℃に３０〜１８０分間加熱
し、次いで有機溶媒抽出し、その残部を回収することを
特徴とする当該混合物又は複合物中の無機物の回収方法
を提供するものである。さらに、本発明は、ポリプロピ
レン及び炭酸カルシウム又はポリプロピレン、炭酸カル
シウム及びシリカを主成分とする合成紙を、０．１〜６
mmHg条件下、３６０〜４００℃に３０〜１８０分間加熱
し、次いで有機溶媒抽出し、残部を回収することを特徴
とする合成紙中の炭酸カルシウム及び／又はシリカの回
収方法を提供するものである。That is, the present invention provides a mixture or a composite mainly composed of polypropylene and an inorganic substance in an amount of 0.1 to 6 mmHg.
Under the conditions, heated to 360 to 400 ° C. for 30 to 180 minutes,
The present invention further provides a method for recovering the polypropylene in the mixture or the composite as a telechelic propylene oligomer, which is characterized by extracting with an organic solvent.
The present invention also relates to a synthetic paper containing polypropylene and calcium carbonate or polypropylene, calcium carbonate and silica as main components under a condition of 0.1 to 6 mmHg under 360 to 40 mmHg.
An object of the present invention is to provide a method for recovering polypropylene in synthetic paper as a telechelic propylene oligomer, wherein the polypropylene is heated to 0 ° C. for 30 to 180 minutes and then extracted with an organic solvent. Further, the present invention provides a mixture or a composite mainly composed of polypropylene and an inorganic substance in an amount of 0.1 to 6;
It is intended to provide a method for recovering inorganic substances in the mixture or the composite, wherein the method is heated at 360 to 400 ° C. for 30 to 180 minutes under mmHg conditions, then extracted with an organic solvent, and the remaining part is recovered. Further, the present invention relates to a synthetic paper containing polypropylene and calcium carbonate or polypropylene, calcium carbonate and silica as main components.
The present invention provides a method for recovering calcium carbonate and / or silica in synthetic paper, comprising heating to 360 to 400 ° C. for 30 to 180 minutes under mmHg conditions, and then extracting the organic solvent and recovering the remainder. .
【０００７】[0007]
【発明の実施の形態】本発明に用いるポリプロピレン及
び無機物を主成分とする混合物又は複合物としては、合
成紙が挙げられる。また、合成紙としては、ポリプロピ
レン及び炭酸カルシウムを主成分とするもの、又はポリ
プロピレン、炭酸カルシウム及びシリカを主成分とする
もののいずれでもよい。より具体的には、ポリプロピレ
ンと炭酸カルシウムのブレンド物を二軸延伸したもの、
又はこの表面にシリカを塗工したものが挙げられる。ま
た、合成紙には、ポリプロピレン以外に、ポリプロピレ
ンに対して２０重量％以下の範囲でポリエチレンが含ま
れていてもよい。市販品としてはエポ合成紙（王子製紙
製）等が挙げられる。BEST MODE FOR CARRYING OUT THE INVENTION As a mixture or composite containing polypropylene and an inorganic substance as main components used in the present invention, synthetic paper can be mentioned. Further, the synthetic paper may be any of those containing polypropylene and calcium carbonate as main components or those containing polypropylene, calcium carbonate and silica as main components. More specifically, a biaxially stretched blend of polypropylene and calcium carbonate,
Alternatively, a material obtained by applying silica to this surface may be used. Further, in addition to the polypropylene, the synthetic paper may contain polyethylene in a range of 20% by weight or less based on the polypropylene. Commercially available products include Epo synthetic paper (manufactured by Oji Paper).
【０００８】合成紙は、例えば選挙投票用紙、地図、袋
類等に用いられているが、本発明においてはこれら用途
に使用済であって回収された合成紙や製造段階で発生し
た裁断クズを直接熱分解に用いてもよく、必要に応じて
脱墨剤により処理して印刷を除去してから用いてもよ
い。[0008] Synthetic paper is used, for example, in election ballot papers, maps, bags and the like. In the present invention, synthetic paper that has been used for these purposes and that has been collected and cut off at the manufacturing stage is used. It may be used for direct thermal decomposition, or may be used after removing printing by treating with a deinking agent as needed.
【０００９】本発明においては前記混合物又は複合物、
例えば合成紙を直接０．１〜６mmHg条件下、３６０〜４
００℃に３０〜１８０分間加熱する。これらの圧力、温
度及び時間は、合成紙中のポリプロピレンを、工業的に
再利用可能なテレケリックプロピレンオリゴマーに効率
良く分解させるうえで極めて重要である。すなわち、こ
の圧力、温度及び時間の条件を上記範囲に制御したとき
にはじめて、合成紙中のポリプロピレンから、分子量分
布がせまい均質のテレケリックプロピレンオリゴマーが
効率良く得られる。より好ましい圧力条件は０．５〜３
mmHgであり、特に好ましくは１〜２mmHgである。好まし
い温度は３７０〜４００℃であり、特に好ましくは３８
０〜４００℃である。また、加熱時間は、３０〜１８０
分間であるが、３０〜１５０分、特に３０〜１２０分が
好ましい。なお熱分解の雰囲気は窒素ガス等の不活性ガ
ス雰囲気とする。In the present invention, the above mixture or composite,
For example, synthetic paper is directly subjected to 360-4
Heat to 00 ° C. for 30-180 minutes. These pressures, temperatures and times are extremely important for efficiently decomposing the polypropylene in the synthetic paper into telechelic propylene oligomers that can be reused industrially. That is, only when these pressure, temperature and time conditions are controlled within the above ranges, a homogeneous telechelic propylene oligomer having a narrow molecular weight distribution can be efficiently obtained from the polypropylene in the synthetic paper. More preferred pressure conditions are 0.5 to 3
mmHg, and particularly preferably 1-2 mmHg. The preferred temperature is from 370 to 400 ° C, particularly preferably 38 ° C.
0-400 ° C. The heating time is 30 to 180.
Minutes, but preferably 30 to 150 minutes, particularly 30 to 120 minutes. Note that the atmosphere for the thermal decomposition is an inert gas atmosphere such as a nitrogen gas.
【００１０】上記熱分解反応終了後、反応混合物から有
機溶媒で抽出すれば、テレケリックプロピレンオリゴマ
ーが高収率で得られる。ここで抽出溶媒としては、芳香
族炭化水素溶媒、例えばベンゼン、トルエン、キシレン
等が好ましい。After the completion of the thermal decomposition reaction, if the reaction mixture is extracted with an organic solvent, a telechelic propylene oligomer can be obtained in high yield. Here, the extraction solvent is preferably an aromatic hydrocarbon solvent, for example, benzene, toluene, xylene and the like.
【００１１】ここで得られるテレケリックプロピレンオ
リゴマーは、数平均分子量が約９０００〜１０，０００
の両末端にビニリデン基（イソプロペニル基）を有する
プロピレンオリゴマーである。本発明方法によるテレケ
リックプロピレンオリゴマーの回収率は７５％以上、約
８０％にも達する。The obtained telechelic propylene oligomer has a number average molecular weight of about 9000 to 10,000.
Is a propylene oligomer having a vinylidene group (isopropenyl group) at both ends. The recovery of telechelic propylene oligomers by the method of the present invention is 75% or more, and reaches about 80%.
【００１２】また、前記抽出操作によりテレケリックプ
ロピレンオリゴマーは有機溶媒相から回収されるが、抽
出されなかった残部には炭酸カルシウム、シリカ等の無
機物が含まれている。この混合物を塩酸処理すれば炭酸
カルシウムは塩化カルシウムとして回収され、必要に応
じて二酸化炭素処理すれば炭酸カルシウムとすることも
できる。また、塩酸処理して可溶化しなかった残部はシ
リカである。Although the telechelic propylene oligomer is recovered from the organic solvent phase by the above-mentioned extraction operation, the remainder not extracted contains inorganic substances such as calcium carbonate and silica. If this mixture is treated with hydrochloric acid, calcium carbonate is recovered as calcium chloride, and if necessary, it can be converted into calcium carbonate if treated with carbon dioxide. The remainder which was not solubilized by the hydrochloric acid treatment is silica.
【００１３】[0013]
【発明の効果】本発明によれば、埋め立てや焼却処分さ
れていた合成紙等から、テレケリックプロピレンオリゴ
マーが効率良く回収できる。当該テレケリックプロピレ
ンオリゴマーは、両末端反応性であることから、例えば
ポリプロピレン−ポリジメチルシロキサン−ブロックコ
ポリマー、ポリプロピレン−ポリアミド−ブロックコポ
リマー、ポリプロピレン−ポリエチレングリコール−ブ
ロックコポリマー等の種々のポリプロピレンブロックを
有するブロックコポリマーの原料として有用である。According to the present invention, telechelic propylene oligomers can be efficiently recovered from landfilled or incinerated synthetic paper. Since the telechelic propylene oligomer is reactive at both ends, for example, a block copolymer having various polypropylene blocks such as a polypropylene-polydimethylsiloxane-block copolymer, a polypropylene-polyamide-block copolymer, a polypropylene-polyethylene glycol-block copolymer, etc. Useful as a raw material for
【００１４】[0014]
【実施例】次に実施例を挙げて本発明を更に詳細に説明
するが、本発明はこれら実施例に何ら限定されるもので
はない。Next, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples.
【００１５】実施例１ （１）合成紙として、ＦＰＵ及びＣＰＵ（王子製紙製コ
ポ合成紙）を用いた。ＦＰＵは、ポリプロピレン及び炭
酸カルシウムのブレンド物を二軸延伸したものであり、
ＴＧ曲線から求めた組成比（重量比）は、ポリプロピレ
ン：炭酸カルシウム＝７０：３０であった。また、ＦＰ
Ｕ中のポリプロピレンの数平均分子量は４．８×１０4
程度であり、分散度は３．０であった。一方、ＣＰＵ
は、ポリプロピレン及び炭酸カルシウムのブレンド物を
二軸延伸したものの表面にシリカを塗工したものであ
り、ＴＧ曲線から求めた組成比（重量比）は、ポリプロ
ピレン：炭酸カルシウム：シリカ＝５０：２０：３０で
あった。またＣＰＵ中のポリプロピレンの数平均分子量
は、４．８×１０4程度であり、分散度は３．６であっ
た。Example 1 (1) As a synthetic paper, an FPU and a CPU (Oji Paper Copo synthetic paper) were used. FPU is obtained by biaxially stretching a blend of polypropylene and calcium carbonate,
The composition ratio (weight ratio) determined from the TG curve was polypropylene: calcium carbonate = 70: 30. Also, FP
The number average molecular weight of the polypropylene in U is 4.8 × 10 4
And the degree of dispersion was 3.0. On the other hand, CPU
Is obtained by applying silica on the surface of a blend of polypropylene and calcium carbonate that has been biaxially stretched, and the composition ratio (weight ratio) determined from the TG curve is as follows: polypropylene: calcium carbonate: silica = 50: 20: 30. The number average molecular weight of the polypropylene in the CPU was about 4.8 × 10 4 , and the degree of dispersion was 3.6.
【００１６】（２）図１に示す反応器に合成紙１kgを入
れ、窒素２ｌ／min気流下、内圧１〜２mmHg条件下、３
９０℃で９０分間熱分解反応を行った。反応器残存物を
キシレンによるソックスレー抽出器で抽出した。一方、
抽出残部には塩酸を加えて水相を残部に分離し、炭酸カ
ルシウムを塩化カルシウムに変換して水相に移行させ
た。残部はシリカであった。(2) 1 kg of synthetic paper is put into the reactor shown in FIG. 1 and the internal pressure is set to 1 to 2 mmHg under an air flow of 2 l / min.
The thermal decomposition reaction was performed at 90 ° C. for 90 minutes. The reactor residue was extracted with a Soxhlet extractor with xylene. on the other hand,
Hydrochloric acid was added to the remainder of the extraction to separate the aqueous phase into the remainder, and calcium carbonate was converted to calcium chloride and transferred to the aqueous phase. The balance was silica.
【００１７】（３）キシレン抽出物について、ＧＰＣ、
熱分析、ＩＲ及びＮＭＲにより分析した。その結果、図
２に示すように、ポリマー成分はイソタクチッソポリプ
ロピレン以外に少量のポリエチレンを含んでいることが
明らかとなった。また、図２から明らかなように、得ら
れたオリゴマーは、両末端にビニリデン基を有するテレ
ケリックプロピレンオリゴマーであることがわかる。こ
れらのシグナル強度比から、オリゴマー一分子当たりの
末端ビニリデン二重結合の平均数（fTVD）値を求めた。
得られたオリゴマーの数平均分子量及び回収率も求め
た。その結果、表１に示すように、オリゴマーの回収率
はＦＰＵで８５．８重量％、ＣＰＵで７９．５重量％で
あり、得られたオリゴマーの数平均分子量はＦＰＵで約
９５００、ＣＰＵで約９０００であり、分散度はＦＰＵ
で１．８８、ＣＰＵで７．５２となった。また上記fTVD
値はＦＰＵで１．７１、ＣＰＵで１．６９であった。(3) For the xylene extract, GPC,
Analyzed by thermal analysis, IR and NMR. As a result, as shown in FIG. 2, it was found that the polymer component contained a small amount of polyethylene in addition to isotactic polypropylene. In addition, as is apparent from FIG. 2, the obtained oligomer is a telechelic propylene oligomer having vinylidene groups at both ends. From these signal intensity ratios, the average number of terminal vinylidene double bonds per oligomer (f TVD ) value was determined.
The number average molecular weight and recovery of the obtained oligomer were also determined. As a result, as shown in Table 1, the recovery of the oligomer was 85.8% by weight in the FPU and 79.5% by weight in the CPU, and the number average molecular weight of the obtained oligomer was about 9500 in the FPU and about 9500 in the CPU. 9000 and the degree of dispersion is FPU
At 1.88 and CPU at 7.52. Also above f TVD
The value was 1.71 for FPU and 1.69 for CPU.
【００１８】[0018]
【表１】 [Table 1]
【図１】熱分解装置の概略図である。FIG. 1 is a schematic diagram of a thermal decomposition apparatus.
【図２】得られたオリゴマーの13C-NMRスペクトルを示
す図である。FIG. 2 is a view showing a 13 C-NMR spectrum of the obtained oligomer.
フロントページの続き (72)発明者 鈴木 義弘 埼玉県三郷市戸ヶ崎３丁目302 株式会社 三栄興業内 Ｆターム(参考） 4F301 AA13 AA14 AB02 BA25 BA29 CA04 CA12 CA24 CA26 CA42 CA51 CA72 CA73 4J100 AA03P BD00H CA01 HA51 JA00 Continued on the front page (72) Inventor Yoshihiro Suzuki 3-302 Togasaki, Misato-shi, Saitama F-term within Sanei Kogyo Co., Ltd. 4F301 AA13 AA14 AB02 BA25 BA29 CA04 CA12 CA24 CA26 CA42 CA51 CA72 CA73 4J100 AA03P BD00H CA01 HA51 JA00
Claims (7)
る混合物又は複合物を０．１〜６mmHg条件下、３６０〜
４００℃に３０〜１８０分間加熱し、次いで有機溶媒抽
出することを特徴とする当該混合物又は複合物中のポリ
プロピレンをテレケリックプロピレンオリゴマーとして
回収する方法。1. A mixture or composite containing polypropylene and an inorganic material as main components is prepared under the conditions of 0.1 to 6 mmHg for 360 to
A method for recovering polypropylene as a telechelic propylene oligomer in the mixture or the composite, wherein the mixture is heated to 400 ° C. for 30 to 180 minutes and then extracted with an organic solvent.
ポリプロピレン、炭酸カルシウム及びシリカを主成分と
する合成紙を、０．１〜６mmHg条件下、３６０〜４００
℃に３０〜１８０分間加熱し、次いで有機溶媒抽出する
ことを特徴とする合成紙中のポリプロピレンをテレケリ
ックプロピレンオリゴマーとして回収する方法。2. A method in which polypropylene and calcium carbonate or synthetic paper containing polypropylene, calcium carbonate and silica as main components is treated under a condition of 0.1 to 6 mmHg at 360 to 400 mmHg.
A method for recovering polypropylene in synthetic paper as a telechelic propylene oligomer, which comprises heating to 30 ° C. for 30 to 180 minutes and then extracting with an organic solvent.
る請求項１又は２記載の回収方法。3. The method according to claim 1, wherein the organic solvent is an aromatic hydrocarbon solvent.
ピレンに対し２０重量％以下含有するものである請求項
２又は３記載の回収方法。4. The recovery method according to claim 2, wherein the synthetic paper further contains polyethylene in an amount of 20% by weight or less based on the polypropylene.
数平均分子量約９０００〜１０，０００の両末端にビニ
リデン基を有するテレケリックプロピレンオリゴマーで
ある請求項１〜４のいずれか１項記載の回収方法。5. A telechelic propylene oligomer comprising:
The method according to any one of claims 1 to 4, which is a telechelic propylene oligomer having a number average molecular weight of about 9000 to 10,000 and having vinylidene groups at both ends.
る混合物又は複合物を、０．１〜６mmHg条件下、３６０
〜４００℃に３０〜１８０分間加熱し、次いで有機溶媒
抽出し、その残部を回収することを特徴とする当該混合
物又は複合物中の無機物の回収方法。6. A mixture or composite containing polypropylene and an inorganic substance as main components is prepared under the conditions of 0.1 to 6 mmHg for 360 minutes.
A method for recovering an inorganic substance in the mixture or the composite, wherein the mixture or the composite is heated at a temperature of about 400 ° C. for about 30 to 180 minutes, then extracted with an organic solvent, and the remaining part is recovered.
ポリプロピレン、炭酸カルシウム及びシリカを主成分と
する合成紙を、０．１〜６mmHg条件下、３６０〜４００
℃に３０〜１８０分間加熱し、次いで有機溶媒抽出し、
残部を回収することを特徴とする合成紙中の炭酸カルシ
ウム及び／又はシリカの回収方法。7. Polypropylene and calcium carbonate or a synthetic paper containing polypropylene, calcium carbonate and silica as main components are treated under a condition of 0.1 to 6 mmHg for 360 to 400 mmHg.
C. for 30-180 minutes, then extract with organic solvent,
A method for recovering calcium carbonate and / or silica in synthetic paper, comprising recovering the remainder.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008255159A (en) * | 2007-04-02 | 2008-10-23 | Sanei Kogyo:Kk | Method for synthesizing oligomer having on its one end vinylidene-type double bond and/or oligomer having on its both ends vinylidene-type double bonds |
| WO2017154098A1 (en) * | 2016-03-08 | 2017-09-14 | 日立化成株式会社 | Inorganic material separation method, reprocessed material production method, and organic substance removal method |
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| JPWO2017154098A1 (en) * | 2016-03-08 | 2019-01-10 | 日立化成株式会社 | Method for separating inorganic material, method for producing recycled material, and method for removing organic substance |
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| Publication number | Publication date |
|---|---|
| JP4639394B2 (en) | 2011-02-23 |
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