JP2003183507A - Asphalt-modifying agent, modified asphalt and preparation of the same - Google Patents

Asphalt-modifying agent, modified asphalt and preparation of the same

Info

Publication number
JP2003183507A
JP2003183507A JP2001387228A JP2001387228A JP2003183507A JP 2003183507 A JP2003183507 A JP 2003183507A JP 2001387228 A JP2001387228 A JP 2001387228A JP 2001387228 A JP2001387228 A JP 2001387228A JP 2003183507 A JP2003183507 A JP 2003183507A
Authority
JP
Japan
Prior art keywords
asphalt
asphalt modifier
pet
polyethylene terephthalate
molecular weight
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
Application number
JP2001387228A
Other languages
Japanese (ja)
Other versions
JP3886374B2 (en
Inventor
Yasuaki Okamoto
康昭 岡本
Daisuke Miyawaki
大祐 宮脇
Takashi Yamamoto
孝 山本
Yoji Komura
洋司 小村
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
YAMAKEN PLANT KK
Original Assignee
YAMAKEN PLANT KK
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by YAMAKEN PLANT KK filed Critical YAMAKEN PLANT KK
Priority to JP2001387228A priority Critical patent/JP3886374B2/en
Publication of JP2003183507A publication Critical patent/JP2003183507A/en
Application granted granted Critical
Publication of JP3886374B2 publication Critical patent/JP3886374B2/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • YGENERAL 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02WCLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
    • Y02W30/00Technologies for solid waste management
    • Y02W30/50Reuse, recycling or recovery technologies
    • Y02W30/62Plastics recycling; Rubber recycling

Landscapes

  • Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

<P>PROBLEM TO BE SOLVED: To provide a method of treating a large amount of discarded PET at a low cost, and to provide a method of producing value-added products. <P>SOLUTION: The asphalt-modifying agent is prepared from discarded plastics consisting of polyethylene terephthalate containing ethylene terephthalate oligomer with the weight average molecular weight (Mw) of 650-1,100 as a major component. The preparation comprises hydrolysing the PET by heating the mixture of the PET and water under the vapor pressure at a heating temperature under the condition represented by the formula; lnt=-17.9+1.01×10<SP>4</SP>/T (wherein t is the time required for the reaction (minute), T is the reaction temperature (K) and ln is natural logarithm). <P>COPYRIGHT: (C)2003,JPO

Description

【発明の詳細な説明】Detailed Description of the Invention

【0001】[0001]

【発明の属する技術分野】この発明はアスファルト改質
材、改質アスファルト及びアスファルト改質材の製造方
法に関するものである。
TECHNICAL FIELD The present invention relates to an asphalt modifier, a modified asphalt, and a method for producing an asphalt modifier.

【0002】[0002]

【従来の技術】近年、使用済みのペットボトル(以下、
「廃PET」という。)が廃棄物として社会に大量に排出
されて問題になっている。この廃PETからなる廃棄物は
各種ルートを通じて収集され、そのまま廃棄物処理場に
投棄されたり、単に燃料として燃やされたり、別の製品
として再利用されたりしている。
2. Description of the Related Art Recently, used PET bottles (hereinafter,
It is called "abandoned PET". ) Is a large amount of waste that is discharged into society, which is a problem. The waste made up of this waste PET is collected through various routes and is thrown into the waste treatment site as it is, simply burned as fuel, or reused as another product.

【0003】廃PETはポリエチレンテレフタレートから
作られており、ポリエチレンテレフタレートは石油を原
料として作られているものである。限りある石油資源を
有効に利用するという見地から考えると、これらの廃棄
物をそのまま投棄したり、単に燃料として燃やすのは好
ましくない。
Waste PET is made from polyethylene terephthalate, which is made from petroleum as a raw material. From the viewpoint of effectively utilizing limited petroleum resources, it is not preferable to discard these wastes as they are or simply burn them as fuel.

【0004】元の製品に戻すか、それができなければ別
の製品に再利用するのが好ましい。また、CO2による地
球温暖化防止という見地からも、これらの石油資源を燃
料として燃やしてしまうのは好ましくない。
It is preferable to return to the original product or reuse it for another product if this is not possible. From the viewpoint of preventing global warming by CO 2 , it is not preferable to burn these petroleum resources as fuel.

【0005】廃PETについては、別の製品に再利用する
方法の一つとして、廃PETを破砕し、これをアスファル
トに混ぜて改質アスファルトを得る方法が提案されてい
る。この方法は、廃PETを低コストで大量に処理できる
という利点がある。
Regarding waste PET, as one of the methods of recycling it to another product, a method of crushing waste PET and mixing it with asphalt to obtain modified asphalt has been proposed. This method has an advantage that a large amount of waste PET can be processed at low cost.

【0006】この方法の特許出願の例としては、例え
ば、特開昭49−25011号、特開平5−295273号、特公昭38
−18096号、特開昭59−85062号、特開昭52−74622号、
特公昭51−36283号を挙げることができる。
Examples of patent applications for this method include, for example, JP-A-49-25011, JP-A-5-295273, and JP-B-38.
-18096, JP-A-59-85062, JP-A-52-74622,
Japanese Patent Publication No. 51-36283 can be mentioned.

【0007】[0007]

【発明が解決しようとする課題】しかし、上記廃PETの
処理法も充分に満足行く方法ではなく、改良の余地は多
々有る。
However, the treatment method of waste PET is not a satisfactory method, and there is a lot of room for improvement.

【0008】本発明は廃PETをできるだけ低コストで大
量に処理でき、且つできるだけ付加価値の高い製品を得
ることができるような再利用方法を提供することを目的
とする。
An object of the present invention is to provide a recycling method capable of treating a large amount of waste PET at a low cost and obtaining a product with a high added value as much as possible.

【0009】[0009]

【課題を解決するための手段】この発明に係るアスファ
ルト改質材は、ポリエチレンテレフタレートからなる廃
プラスチックを原料としてなり、重量平均分子量(Mw)
が650〜1100のエチレンテレフタレートオリゴマーを主
成分とするものである。
The asphalt modifier according to the present invention is made of a waste plastic made of polyethylene terephthalate as a raw material and has a weight average molecular weight (Mw).
650-1100 is an ethylene terephthalate oligomer as a main component.

【0010】ここで、重量平均分子量(Mw)を650〜110
0としたのは、重量平均分子量(Mw)が650未満の場合は
テレフタル酸が多数生成し、加熱しても溶融しないの
で、改質材として使用できなくなり、1100を越えると融
点が182℃以上と高くなって、アスファルトとの混合が
良好に行えない。しかし、重量平均分子量(Mw)が650
〜1100ではそのような問題がなく、アスファルト改質材
として有効に使用できるからである。
Here, the weight average molecular weight (Mw) is 650 to 110.
The reason for 0 is that when the weight average molecular weight (Mw) is less than 650, a large amount of terephthalic acid is produced and does not melt even when heated, so it cannot be used as a modifier. It becomes too high to mix well with asphalt. However, the weight average molecular weight (Mw) is 650
The reason is that, in the case of ~ 1100, there is no such problem and it can be effectively used as an asphalt modifier.

【0011】また、発明に係るアスファルト改質材は融
点が133〜182℃が好ましい。
The asphalt modifier according to the present invention preferably has a melting point of 133 to 182 ° C.

【0012】ここで、融点を133〜182℃としたのは、融
点が133℃未満の場合は、テレフタル酸が多数生成し、
加熱しても溶融しないので、改質材として使用できなく
なるという不都合があり、182℃を越えると、アスファ
ルトとの混合が良好に行えないという不都合があるが、
融点が133〜182℃ではそのような問題がなく、アスファ
ルト改質材として有効に使用できるからである。
Here, the melting point is set to 133 to 182 ° C., because when the melting point is less than 133 ° C., a large amount of terephthalic acid is produced,
Since it does not melt even when heated, it has the inconvenience that it cannot be used as a modifier, and when it exceeds 182 ° C, there is the inconvenience that it cannot be mixed well with asphalt.
When the melting point is 133 to 182 ° C., there is no such problem and it can be effectively used as an asphalt modifier.

【0013】また、発明に係る改質アスファルトは、5
〜50%のアスファルト改質材を含み、該アスファルト改
質材の重量平均分子量が650〜1100のエチレンテレフタ
レートオリゴマーを主成分とするものである。
In addition, the modified asphalt according to the invention is 5
-50 to 50% of asphalt modifier, and the main component of the asphalt modifier is ethylene terephthalate oligomer having a weight average molecular weight of 650 to 1100.

【0014】ここで、アスファルト改質材を5〜50%と
したのは、アスファルト改質材が5%未満の場合は改質
効果がみられず、50%を越えると改質アスファルトがも
ろく、堅くなって、バインダーとしての機能が果たせな
くなるが、5〜50%ではそのような問題がなく、所望の
物性の改質アスファルトが得られるからである。
Here, the asphalt modifier is set to 5 to 50% because when the asphalt modifier is less than 5%, the modifying effect is not observed, and when it exceeds 50%, the modified asphalt is fragile. This is because it becomes hard and cannot function as a binder, but if it is 5 to 50%, such a problem does not occur and a modified asphalt having desired physical properties can be obtained.

【0015】改質アスファルト中に添加するアスファル
ト改質材の重量平均分子量(Mw)を650〜1100とした理
由、融点を133〜182℃とした理由は、上述したアスファ
ルト改質材の場合と同様である。
The reason why the weight average molecular weight (Mw) of the asphalt modifier added to the modified asphalt is 650 to 1100 and the melting point is 133 to 182 ° C. is the same as in the case of the asphalt modifier described above. Is.

【0016】また、この発明に係るアスファルト改質材
の製造方法は、PETと水との混合物を、数1に示す条件下
で加熱し、該PETを加水分解させて分子量が650〜1100の
エチレンテレフタレートオリゴマーを主成分とするアス
ファルト改質材を得るものである。
Further, the method for producing an asphalt modifier according to the present invention, a mixture of PET and water is heated under the conditions shown in Formula 1, and the PET is hydrolyzed to obtain ethylene having a molecular weight of 650 to 1100. An asphalt modifier containing a terephthalate oligomer as a main component is obtained.

【0017】[0017]

【数1】 ただし、tは反応時間(分)、Tは反応温度(K)、lnは
自然対数である。
[Equation 1] However, t is a reaction time (minute), T is a reaction temperature (K), and ln is a natural logarithm.

【0018】ここで、廃PETは加熱温度における水蒸気
圧下で加水分解させるのが好ましい。また、廃PETと水
との混合物は密閉容器内で加熱するのが好ましいが、連
続容器内で反応させるようにしてもよい。
Here, the waste PET is preferably hydrolyzed under steam pressure at the heating temperature. The mixture of waste PET and water is preferably heated in a closed container, but may be reacted in a continuous container.

【0019】また、廃PETの加水分解の条件として、例
えば190〜250℃、1時間〜5分、その温度における水の水
蒸気圧下で反応させることができる。
As a condition for hydrolysis of waste PET, for example, the reaction can be carried out at 190 to 250 ° C. for 1 hour to 5 minutes under the water vapor pressure of water at that temperature.

【0020】[0020]

【発明の実施の形態】まず、フレーク状の廃PET(フレ
ークPET)と水(蒸留水)を準備した。フレークPETは廃
ペットボトルを5mm角に粉砕して得た。また、オートク
レーブ(容積:200ml、製造元:日東高圧、品番:NU−
1)と温度制御装置を準備した。
BEST MODE FOR CARRYING OUT THE INVENTION First, flake-shaped waste PET (flake PET) and water (distilled water) were prepared. Flake PET was obtained by crushing waste plastic bottles into 5 mm squares. In addition, autoclave (volume: 200 ml, manufacturer: Nitto High Pressure, product number: NU-
1) and temperature controller were prepared.

【0021】次に、オートクレーブ内に水10mlとフレー
クPET20gを入れ、圧が逃げないようにオートクレーブの
ボルトをしっかり締め、スターラを300rpmで回転させ、
オートクレーブのヒータのスイッチを入れた。
Next, 10 ml of water and 20 g of flake PET were put into the autoclave, the bolts of the autoclave were securely tightened so that the pressure did not escape, and the stirrer was rotated at 300 rpm,
The autoclave heater was switched on.

【0022】オートクレーブのヒータのスイッチを入れ
て30分後、オートクレーブ内の温度は200℃になり、圧
力は15atmとなった。そして、オートクレーブをこの温
度で更に30分間保持した。
After 30 minutes from turning on the heater of the autoclave, the temperature inside the autoclave became 200 ° C. and the pressure became 15 atm. The autoclave was then kept at this temperature for a further 30 minutes.

【0023】オートクレーブ内に入れたフレークPETの
ポリエチレンテレフタレート分子は加水分解されて分子
量が650〜1100程度のところで切れ、エチレンテレフタ
レートオリゴマー(オリゴマー化PET)になると考えら
れる。
It is considered that the polyethylene terephthalate molecule of the flake PET put in the autoclave is hydrolyzed and cut at a molecular weight of about 650 to 1100 to become an ethylene terephthalate oligomer (oligomerized PET).

【0024】その後、オートクレーブのヒータのスイッ
チを切り、2時間放冷し、常温まで冷却させた。そし
て、オートクレーブを開け、反応物を取り出して蒸留水
でろ過し、ろ過後、60℃で乾燥させ、オリゴマー化PET
を得た。
After that, the heater of the autoclave was turned off, and the autoclave was allowed to cool for 2 hours and cooled to room temperature. Then, open the autoclave, take out the reaction product, filter with distilled water, filter, and dry at 60 ° C to obtain oligomerized PET.
Got

【0025】次に、オリゴマー化PETの融点、重量平均
分子量(Mw)を調べたところ、表1〜表3に示す通りで
あった。なお、オリゴマー化する前のフレークPETの融
点は250.3℃、重量平均分子量(Mw)は65,900である。
Next, the melting point and weight average molecular weight (Mw) of the oligomerized PET were examined, and the results were as shown in Tables 1 to 3. The flake PET before oligomerization has a melting point of 250.3 ° C. and a weight average molecular weight (Mw) of 65,900.

【0026】[0026]

【表1】 [Table 1]

【0027】[0027]

【表2】 [Table 2]

【0028】[0028]

【表3】 [Table 3]

【0029】次に、これらのデータから下記数1の式を
得た。そして、この数1の式を満足する条件でPETを加水
分解させると、所望の分子量のオリゴマー化PETが得ら
れることがわかった。
Next, the following formula 1 was obtained from these data. It was found that when PET is hydrolyzed under the condition that satisfies the expression of Equation 1, oligomerized PET having a desired molecular weight can be obtained.

【0030】[0030]

【数1】 ただし、tは反応時間(分)、Tは反応温度(K)、ln
は自然対数である。
[Equation 1] Where t is reaction time (minutes), T is reaction temperature (K), ln
Is the natural logarithm.

【0031】次に、上記の加水分解で得られたオリゴマ
ー化PETをアスファルトに混ぜ、その物性を調べたとこ
ろ、オリゴマー化PETの添加量が5〜50%の範囲が好まし
かった。
Next, when the oligomerized PET obtained by the above-mentioned hydrolysis was mixed with asphalt and the physical properties thereof were examined, the addition amount of the oligomerized PET was preferably in the range of 5 to 50%.

【0032】オリゴマー化PETが5%未満の場合はアスフ
ァルトの改質効果がみられず、50%を越えると改質アス
ファルトがもろく、堅くなって、バインダーとしての機
能が果たせなくなるが、5〜50%ではそのような問題が
なく、所望の物性の改質アスファルトが得られた。
When the oligomerized PET is less than 5%, the effect of modifying the asphalt is not observed, and when it exceeds 50%, the modified asphalt becomes brittle and hard and cannot function as a binder. %, There was no such problem, and a modified asphalt having desired physical properties was obtained.

【0033】[0033]

【発明の効果】この発明によれば、廃PETから値段の高
いアスファルト改質材を低コストで大量に製造すること
ができるので、限りある資源を有効利用することができ
るという効果がある。
EFFECTS OF THE INVENTION According to the present invention, an expensive asphalt modifier can be mass-produced from waste PET at a low cost, so that limited resources can be effectively used.

【図面の簡単な説明】[Brief description of drawings]

【図1】この発明の一実施例を説明するための工程図で
ある。
FIG. 1 is a process drawing for explaining an embodiment of the present invention.

───────────────────────────────────────────────────── フロントページの続き (72)発明者 山本 孝 島根県簸川郡多伎町213−8 山建プラン ト株式会社内 (72)発明者 小村 洋司 島根県簸川郡多伎町213−8 山建プラン ト株式会社内 Fターム(参考) 4F301 AA25 CA09 CA23 CA24 CA32 CA41 CA65 CA71 CA72 CA73 4J002 AG001 CF062 GL00    ─────────────────────────────────────────────────── ─── Continued front page    (72) Inventor Takashi Yamamoto             213-8 Yamaken Plan, Taki-cho, Kanegawa-gun, Shimane Prefecture             Inside the corporation (72) Inventor Yoji Komura             213-8 Yamaken Plan, Taki-cho, Kanegawa-gun, Shimane Prefecture             Inside the corporation F-term (reference) 4F301 AA25 CA09 CA23 CA24 CA32                       CA41 CA65 CA71 CA72 CA73                 4J002 AG001 CF062 GL00

Claims (8)

【特許請求の範囲】[Claims] 【請求項1】 ポリエチレンテレフタレートからなる廃
プラスチックを原料としてなり、重量平均分子量(Mw)
が650〜1100のエチレンテレフタレートオリゴマ
ーを主成分とするアスファルト改質材。
1. A waste plastic made of polyethylene terephthalate is used as a raw material and has a weight average molecular weight (Mw).
Asphalt modifier containing ethylene terephthalate oligomer of 650 to 1100 as a main component.
【請求項2】 融点が133〜182℃であることを特
徴とする請求項1に記載のアスファルト改質材。
2. The asphalt modifier according to claim 1, which has a melting point of 133 to 182 ° C.
【請求項3】 5〜50%のアスファルト改質材を含
み、該アスファルト改質材が、ポリエチレンテレフタレ
ートからなる廃プラスチックを原料としてなり、重量平
均分子量(Mw)が650〜1100のエチレンテレフタ
レートオリゴマーを主成分とすることを特徴とする改質
アスファルト。
3. An ethylene terephthalate oligomer containing 5 to 50% of an asphalt modifier, the asphalt modifier being made of waste plastic consisting of polyethylene terephthalate as a raw material and having a weight average molecular weight (Mw) of 650 to 1100. Modified asphalt characterized by having it as a main component.
【請求項4】 融点が133〜182℃であることを特
徴とする請求項3に記載の改質アスファルト。
4. The modified asphalt according to claim 3, which has a melting point of 133 to 182 ° C.
【請求項5】 ポリエチレンテレフタレートと水との混
合物を、数1に示す条件下で加熱し、該ポリエチレンテ
レフタレートを加水分解させて重量平均分子量(Mw)が
650〜1100のエチレンテレフタレートオリゴマー
を主成分とするアスファルト改質材を得ることを特徴と
するアスファルト改質材の製造方法。 【数1】 ただし、tは反応時間(分)、Tは反応温度(K)、l
nは自然対数である。
5. A mixture of polyethylene terephthalate and water is heated under the conditions shown in Formula 1 to hydrolyze the polyethylene terephthalate, and an ethylene terephthalate oligomer having a weight average molecular weight (Mw) of 650 to 1100 is contained as a main component. A method for producing an asphalt modifier, which comprises obtaining the asphalt modifier. [Equation 1] Where t is reaction time (minutes), T is reaction temperature (K), l
n is a natural logarithm.
【請求項6】 前記ポリエチレンテレフタレートを加熱
温度における水蒸気圧下で加水分解させることを特徴と
する請求項5に記載のアスファルト改質材の製造方法。
6. The method for producing an asphalt modifier according to claim 5, wherein the polyethylene terephthalate is hydrolyzed under steam pressure at a heating temperature.
【請求項7】 前記ポリエチレンテレフタレートと水と
の混合物を密閉容器内で加熱することを特徴とする請求
項5又は6に記載のアスファルト改質材の製造方法。
7. The method for producing an asphalt modifier according to claim 5, wherein the mixture of polyethylene terephthalate and water is heated in a closed container.
【請求項8】 190〜250℃、1時間〜5分、その
温度における水の水蒸気圧下で反応させることを特徴と
する請求項5〜7のいずれかに記載のアスファルト改質
材の製造方法。
8. The method for producing an asphalt modifier according to claim 5, wherein the reaction is carried out at 190 to 250 ° C. for 1 hour to 5 minutes under the water vapor pressure of water at that temperature.
JP2001387228A 2001-12-20 2001-12-20 Asphalt modifier and modified asphalt Expired - Fee Related JP3886374B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2001387228A JP3886374B2 (en) 2001-12-20 2001-12-20 Asphalt modifier and modified asphalt

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP2001387228A JP3886374B2 (en) 2001-12-20 2001-12-20 Asphalt modifier and modified asphalt

Publications (2)

Publication Number Publication Date
JP2003183507A true JP2003183507A (en) 2003-07-03
JP3886374B2 JP3886374B2 (en) 2007-02-28

Family

ID=27596133

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JP2006096799A (en) * 2004-09-28 2006-04-13 Yamaken Plant Kk Method for producing plastic composition for pavement material
KR100674127B1 (en) 2005-03-09 2007-01-24 황익현 Material to improve quality of asphalt concrete, and the manufacturing method thereof
WO2007102488A1 (en) * 2006-03-07 2007-09-13 Koichi Nakamura Process for the decomposition and reclamation of synthetic resins having ester-linkage structures
JP2012219210A (en) * 2011-04-12 2012-11-12 As R&D合同会社 Method for producing low-molecular polymer, low-molecular polymer obtained by the method, and coating material, powder coating material, adhesive, fiber and nonwoven fabric using the polymer
WO2015137366A1 (en) * 2014-03-11 2015-09-17 日東電工株式会社 Polyester resin hydrolyzate production method
WO2015137365A1 (en) * 2014-03-11 2015-09-17 日東電工株式会社 Polyester resin hydrolyzate production method
JP2016089008A (en) * 2014-11-04 2016-05-23 昭和瀝青工業株式会社 Additive for recycled asphalt
WO2016111289A1 (en) * 2015-01-06 2016-07-14 日東電工株式会社 Method for producing terephthalic acid and method for producing recycled polyethylene terephthalate

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006096799A (en) * 2004-09-28 2006-04-13 Yamaken Plant Kk Method for producing plastic composition for pavement material
KR100674127B1 (en) 2005-03-09 2007-01-24 황익현 Material to improve quality of asphalt concrete, and the manufacturing method thereof
WO2007102488A1 (en) * 2006-03-07 2007-09-13 Koichi Nakamura Process for the decomposition and reclamation of synthetic resins having ester-linkage structures
US7985778B2 (en) 2006-03-07 2011-07-26 Koichi Nakamura Method for decomposing and reclaiming synthetic resin having ester bond in the composition structure
JP2012219210A (en) * 2011-04-12 2012-11-12 As R&D合同会社 Method for producing low-molecular polymer, low-molecular polymer obtained by the method, and coating material, powder coating material, adhesive, fiber and nonwoven fabric using the polymer
WO2015137366A1 (en) * 2014-03-11 2015-09-17 日東電工株式会社 Polyester resin hydrolyzate production method
WO2015137365A1 (en) * 2014-03-11 2015-09-17 日東電工株式会社 Polyester resin hydrolyzate production method
JP2016089008A (en) * 2014-11-04 2016-05-23 昭和瀝青工業株式会社 Additive for recycled asphalt
WO2016111289A1 (en) * 2015-01-06 2016-07-14 日東電工株式会社 Method for producing terephthalic acid and method for producing recycled polyethylene terephthalate

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