JP2007254683A - Method for decomposition and recovery of thermosetting resin - Google Patents

Method for decomposition and recovery of thermosetting resin Download PDF

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JP2007254683A
JP2007254683A JP2006084229A JP2006084229A JP2007254683A JP 2007254683 A JP2007254683 A JP 2007254683A JP 2006084229 A JP2006084229 A JP 2006084229A JP 2006084229 A JP2006084229 A JP 2006084229A JP 2007254683 A JP2007254683 A JP 2007254683A
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thermosetting resin
organic solvent
cross
ester compound
styrene
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JP2007254683A5 (en
JP4677939B2 (en
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Naoharu Nakagawa
尚治 中川
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Panasonic Electric Works Co Ltd
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Matsushita Electric Works Ltd
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Abstract

<P>PROBLEM TO BE SOLVED: To remarkably simplify the process for the recovery of objective material. <P>SOLUTION: A thermosetting resin is decomposed with methanol at a temperature not higher than the thermal decomposition temperature of the crosslinked part to obtain a styrene maleic acid copolymer methyl ester and glycol, the styrene maleic acid copolymer methyl ester is separated from the glycol by a solid-liquid separation process to separate glycol and methanol as the liquid phase and the styrene maleic acid copolymer methyl ester as the solid phase, and styrene is added to the separated styrene maleic acid copolymer methyl ester to separate the copolymer methyl ester as a styrene solution. <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

本発明は、多価アルコールと不飽和脂肪酸からなる不飽和ポリエステルの不飽和脂肪酸に架橋材を架橋させることにより形成された、不飽和脂肪酸と架橋材の共重合体である架橋部を有する熱硬化性樹脂又はそれに無機物が含有された熱硬化性樹脂を超亜臨界有機溶媒により分解，回収する熱硬化性樹脂の分解・回収方法に関する。   The present invention is a thermosetting having a cross-linked portion, which is a copolymer of an unsaturated fatty acid and a cross-linking material, formed by cross-linking a cross-linking material to an unsaturated fatty acid of an unsaturated polyester composed of a polyhydric alcohol and an unsaturated fatty acid. The present invention relates to a method for decomposing and recovering a thermosetting resin in which a thermosetting resin or a thermosetting resin containing an inorganic substance is decomposed and recovered with a super-subcritical organic solvent.

従来、ＦＲＰ等の不飽和ポリエステル樹脂にスチレンを架橋させた熱硬化性樹脂は、リサイクルが困難であるために、埋め立て又は焼却処分されていた。しかし、熱硬化性樹脂を埋め立てると、埋め立て後の地盤が不安定となり、また埋め立て用地を確保し難いという問題があった。また、熱硬化性樹脂を焼却すると、二酸化炭素等の有害ガスや悪臭が発生し、環境汚染が懸念されるだけではなく、焼却炉が損傷してしまうという問題があった。このため、熱硬化性樹脂を再資源化するための技術の開発が急速に進められている。   Conventionally, thermosetting resins obtained by crosslinking styrene to unsaturated polyester resins such as FRP have been disposed of by landfill or incineration because they are difficult to recycle. However, when the thermosetting resin is landfilled, the ground after the landfill becomes unstable, and there is a problem that it is difficult to secure a land for landfill. Further, when the thermosetting resin is incinerated, harmful gases such as carbon dioxide and bad odors are generated, and there is a problem that not only environmental pollution is concerned but also the incinerator is damaged. For this reason, development of the technique for recycling thermosetting resin is progressing rapidly.

このような背景から、最近、亜臨界分解処理によってスチレン架橋部の熱分解温度以下の温度で熱硬化性樹脂を分解することにより、スチレン架橋部をスチレンマレイン酸共重合体として回収する方法が提案された（例えば特許文献１参照）。この方法では、始めに、ＫＯＨ等のアルカリを添加した亜臨界水を用いてグリコール，フマル不飽和脂肪酸の不飽和ポリエステルにスチレンを架橋させた熱硬化性樹脂を熱分解温度以下の温度で加水分解することにより、スチレンマレイン酸共重合体のカリウム塩とグリコール・モノマーの水溶液を生成する。次に、水溶液に塩酸等の酸を加えてｐＨ値を調整することによりカリウム塩を析出させた後、固液分離することにより固体状のスチレンマレイン酸共重合体を回収する。
国際公開第０５／９２９６２号パンフレット Against this background, a method has recently been proposed in which a styrene cross-linked part is recovered as a styrene maleic acid copolymer by decomposing a thermosetting resin at a temperature lower than the thermal decomposition temperature of the styrene cross-linked part by subcritical decomposition treatment. (See, for example, Patent Document 1). In this method, first, a thermosetting resin obtained by crosslinking styrene with an unsaturated polyester of glycol or fumar unsaturated fatty acid using subcritical water to which an alkali such as KOH is added is hydrolyzed at a temperature lower than the thermal decomposition temperature. By doing so, an aqueous solution of potassium salt of styrene maleic acid copolymer and glycol monomer is formed. Next, an acid such as hydrochloric acid is added to the aqueous solution to adjust the pH value, thereby precipitating a potassium salt, and then solid-liquid separation is performed to recover a solid styrene-maleic acid copolymer.
WO05 / 92962 pamphlet

ところで、スチレンマレイン酸共重合体は、熱硬化性樹脂を成型する際に収縮を低減する低収縮剤の原料として利用できる可能性があるが、そのためにはスチレンマレイン酸共重合体をスチレンに溶解させる必要がある。しかしながら、スチレンマレイン酸共重合体はスチレンに対して不溶性であるので、低収縮剤の原料として利用するためには、スチレンマレイン酸共重合体を形成するカルボン酸の末端をエステル化することによりスチレンマレイン酸共重合体をスチレンに可溶な状態にしなければならない。また、グリコールを回収するためには、グリコール・モノマーを蒸発乾固させることにより水と分離した後、ＫＣｌを除去するために乾固したグリコールをメタノールで溶解し、固液分離によりＫＣｌを分離除去し、グリコールのメタノール溶液として回収する必要がある。このため、従来の熱硬化性樹脂の分解・回収方法では、目的物を回収するために多くのプロセスが必要となることから、目的物を容易に回収，再利用することが困難であった。   By the way, styrene maleic acid copolymer may be used as a raw material for a low shrinkage agent that reduces shrinkage when molding a thermosetting resin. To that end, styrene maleic acid copolymer is dissolved in styrene. It is necessary to let However, since the styrene maleic acid copolymer is insoluble in styrene, in order to use it as a raw material for the low shrinkage agent, styrene is obtained by esterifying the terminal of the carboxylic acid forming the styrene maleic acid copolymer. The maleic acid copolymer must be soluble in styrene. In order to recover glycol, it is separated from water by evaporating the glycol monomer to dryness, then the dried glycol is dissolved in methanol to remove KCl, and KCl is separated and removed by solid-liquid separation. However, it must be recovered as a methanol solution of glycol. For this reason, in the conventional method for decomposing and recovering a thermosetting resin, many processes are required to recover the target object, and therefore it is difficult to easily recover and reuse the target object.

本発明は、上記課題を解決するためになされたものであり、その目的は、目的物を回収するためのプロセスを大幅に簡略化することが可能な熱硬化性樹脂の分解・回収方法を提供することにある。   The present invention has been made to solve the above-mentioned problems, and its object is to provide a method for decomposing and recovering a thermosetting resin capable of greatly simplifying a process for recovering a target product. There is to do.

上記課題を解決するために、本発明に係る熱硬化性樹脂の分解・回収方法の特徴は、多価アルコールと不飽和脂肪酸からなる不飽和ポリエステルの不飽和脂肪酸に架橋材を架橋させることにより形成された不飽和脂肪酸と架橋材の共重合体である架橋部を有する熱硬化性樹脂を、架橋部の熱分解温度以下の超亜臨界状態の水酸基を有する有機溶媒によって分解することにより、架橋部の有機溶媒エステル化合物と多価アルコールを生成するステップと、有機溶媒エステル化合物と多価アルコールを固液分離することにより、多価アルコールと有機溶媒を液相、架橋物の有機溶媒エステル化合物を固相として分離するステップと、分離された架橋部の有機溶媒エステル化合物に架橋材を加えることにより有機溶媒エステル化合物の架橋材溶液として回収するステップとを有することにある。   In order to solve the above problems, the thermosetting resin decomposition / recovery method according to the present invention is characterized by forming a cross-linking material on an unsaturated fatty acid of an unsaturated polyester composed of a polyhydric alcohol and an unsaturated fatty acid. By decomposing the thermosetting resin having a crosslinked part, which is a copolymer of the unsaturated fatty acid and the crosslinking material, with an organic solvent having a super subcritical hydroxyl group that is equal to or lower than the thermal decomposition temperature of the crosslinked part, A step of producing an organic solvent ester compound and a polyhydric alcohol, and solid-liquid separation of the organic solvent ester compound and the polyhydric alcohol, whereby the polyhydric alcohol and the organic solvent are in a liquid phase, and the crosslinked organic solvent ester compound is solidified. Separating as a phase, and adding a crosslinking agent to the organic solvent ester compound of the separated crosslinking part, In that a step of recovering Te.

本発明に係る熱硬化性樹脂の分解・回収方法によれば、目的物を回収するための大幅に簡略化し、目的物を容易に回収，再利用することができる。   According to the method for decomposing and recovering a thermosetting resin according to the present invention, it is possible to greatly simplify the process for recovering the target object, and to easily recover and reuse the target object.

以下、図１，２を参照して、熱硬化性樹脂が無機物を含有しない場合と含有する場合とに分けて本発明の実施形態となる熱硬化性樹脂の分解・回収方法について説明する。なお、本発明において、分解の対象となる熱硬化性樹脂は、多価アルコールと不飽和脂肪酸からなる不飽和ポリエステルの不飽和脂肪酸に架橋材を架橋させることにより形成された不飽和脂肪酸と架橋材の共重合体である架橋部を有する熱硬化性樹脂である。また、上記多価アルコールとしては、エチレングリコールやプロピレングリコール，ジエチレングリコール，ジブロピレングリコール等のグリコール類を例示することができるが、これらに限定されるものではない。また、上記不飽和脂肪酸としては、無水マレイン酸，マレイン酸，フマル酸，フタル酸等を例示することができるが、これらに限定されるものではない。また、上記架橋剤としては、スチレン，メタクリル酸メチル等の重合性ビニルモノマーを例示することができるが、これらに限定されるものではない。また、上記無機物としては、ガラス繊維や炭酸カルシウム，水酸化アルミニウム等の無機充填材を例示することができるが、これらに限定されてるものではない。また、本実施形態では、水酸基を有する有機溶媒としてメタノール、架橋材としてスチレンを用いるが、これに限定されるものではない。   Hereinafter, with reference to FIGS. 1 and 2, a method for decomposing and recovering a thermosetting resin according to an embodiment of the present invention will be described separately for a case where the thermosetting resin does not contain an inorganic substance and a case where the thermosetting resin contains. In the present invention, the thermosetting resin to be decomposed is an unsaturated fatty acid and a cross-linking material formed by cross-linking a cross-linking material to an unsaturated fatty acid of an unsaturated polyester composed of a polyhydric alcohol and an unsaturated fatty acid. It is a thermosetting resin which has a crosslinked part which is a copolymer. Examples of the polyhydric alcohol include, but are not limited to, glycols such as ethylene glycol, propylene glycol, diethylene glycol, and dipropylene glycol. Examples of the unsaturated fatty acid include, but are not limited to, maleic anhydride, maleic acid, fumaric acid, and phthalic acid. Moreover, as said crosslinking agent, polymeric vinyl monomers, such as styrene and methyl methacrylate, can be illustrated, However, It is not limited to these. Moreover, as said inorganic substance, although inorganic fillers, such as glass fiber, a calcium carbonate, and aluminum hydroxide, can be illustrated, it is not limited to these. In this embodiment, methanol is used as the organic solvent having a hydroxyl group, and styrene is used as the cross-linking material. However, the present invention is not limited to this.

〔熱硬化性樹脂が無機物を含有しない場合の処理〕
熱硬化性樹脂が無機物を含有しない場合、本発明の実施形態となる熱硬化性樹脂の分解・回収方法では、始めに、図１に示すように、超亜臨界状態（超臨界状態又は亜臨界状態を意味する）のメタノールによって熱硬化性樹脂を架橋部の熱分解温度以下の温度で分解することにより、架橋部の有機溶媒エステル化合物であるスチレンマレイン酸共重合体メチルエステルと多価アルコールであるグリコールを生成する。次に、スチレンマレイン酸共重合体メチルエステルとグリコールを固液分離することにより、グリコールのメタノール溶液を液相、スチレンマレイン酸共重合体メチルエステルを固相として分離する。そして最後に、スチレンマレイン酸共重合体メチルエステルに架橋材としてのスチレンを加えることによりスチレンマレイン酸共重合体メチルエステルを低収縮剤として利用可能なスチレンマレイン酸共重合体メチルエステルのスチレン溶液として回収する。なお、グリコールのメタノール溶液は、不飽和ポリエステル樹脂原料として樹脂化の製造プロセスにおいて再利用することができる。 [Treatment when the thermosetting resin does not contain inorganic substances]
When the thermosetting resin does not contain an inorganic substance, in the thermosetting resin decomposition / recovery method according to the embodiment of the present invention, first, as shown in FIG. 1, a supersubcritical state (supercritical state or subcritical state) is used. By decomposing the thermosetting resin with methanol at a temperature equal to or lower than the thermal decomposition temperature of the cross-linking portion, and by using the styrene-maleic acid copolymer methyl ester, which is an organic solvent ester compound of the cross-linking portion, and a polyhydric alcohol. Produces a glycol. Next, the styrene-maleic acid copolymer methyl ester and the glycol are separated into solid and liquid, so that the methanol solution of glycol is separated as a liquid phase and the styrene-maleic acid copolymer methyl ester is separated as a solid phase. Finally, styrene maleic acid copolymer methyl ester can be used as a low shrinkage agent by adding styrene as a crosslinking agent to styrene maleic acid copolymer methyl ester as a styrene solution of styrene maleic acid copolymer methyl ester. to recover. The methanol solution of glycol can be reused as an unsaturated polyester resin raw material in the production process of resinization.

〔熱硬化性樹脂が無機物を含有する場合の処理〕
熱硬化性樹脂が無機物を含有する場合、本発明の実施形態となる熱硬化性樹脂の分解・回収方法では、始めに、図２に示すように、超亜臨界状態のメタノールによって無機物を含有する熱硬化性樹脂を架橋部の熱分解温度以下の温度で分解することにより、スチレンマレイン酸共重合体メチルエステル，無機物，及びグリコールを生成する。次に、スチレンマレイン酸共重合体メチルエステル及び無機物とグリコールを固液分離することにより、グリコールのメタノール溶液を液相、スチレンマレイン酸共重合体メチルエステル及び無機物を固相として分離する。次に、架橋材としてのスチレンをスチレンマレイン酸共重合体メチルエステルと無機物に加えることによりスチレンマレイン酸共重合体メチルエステルをスチレンに溶解させた後、固液分離することにより、スチレンマレイン酸共重合体メチルエステルのスチレン溶液を液相、無機物を固相として回収する。 [Treatment when the thermosetting resin contains an inorganic substance]
When the thermosetting resin contains an inorganic substance, in the thermosetting resin decomposition / recovery method according to the embodiment of the present invention, first, as shown in FIG. 2, the inorganic substance is contained by methanol in a super subcritical state. By decomposing the thermosetting resin at a temperature equal to or lower than the thermal decomposition temperature of the cross-linked part, styrene maleic acid copolymer methyl ester, inorganic substance, and glycol are generated. Next, the styrene-maleic acid copolymer methyl ester and the inorganic substance are separated from the glycol by solid-liquid separation, thereby separating the methanol solution of glycol as the liquid phase and the styrene-maleic acid copolymer methyl ester and the inorganic substance as the solid phase. Next, styrene maleic acid copolymer methyl ester is dissolved in styrene by adding styrene as a cross-linking material to the styrene maleic acid copolymer methyl ester and the inorganic substance, and then solid-liquid separation is performed, whereby styrene maleic acid copolymer is obtained. A polymer methyl ester styrene solution is recovered as a liquid phase and an inorganic substance as a solid phase.

以上、本発明者らによってなされた発明を適用した実施の形態について説明したが、この実施の形態による本発明の開示の一部をなす論述及び図面により本発明は限定されることはない。すなわち、上記実施の形態に基づいて当業者等によりなされる他の実施の形態、実施例及び運用技術等は全て本発明の範疇に含まれることは勿論であることを付け加えておく。   As mentioned above, although embodiment which applied the invention made by the present inventors was described, this invention is not limited by the description and drawing which make a part of indication of this invention by this embodiment. That is, it should be added that other embodiments, examples, operation techniques, and the like made by those skilled in the art based on the above-described embodiments are all included in the scope of the present invention.

本発明の実施形態となるプラスチックの分解・回収方法の流れを示す図である。It is a figure which shows the flow of the decomposition | disassembly and collection | recovery method of the plastics used as embodiment of this invention. 本発明の実施形態となるプラスチックの分解・回収方法の応用例の流れを示す図である。It is a figure which shows the flow of the application example of the decomposition | disassembly and collection | recovery method of the plastics used as embodiment of this invention.

Claims (4)

多価アルコールと不飽和脂肪酸からなる不飽和ポリエステルの不飽和脂肪酸に架橋材を架橋させることにより形成された、不飽和脂肪酸と架橋材の共重合体である架橋部を有する熱硬化性樹脂を、架橋部の熱分解温度以下の超亜臨界状態の水酸基を有する有機溶媒によって分解することにより、架橋部の有機溶媒エステル化合物と多価アルコールを生成するステップと、
有機溶媒エステル化合物と多価アルコールを固液分離することにより、多価アルコールと有機溶媒を液相、架橋物の有機溶媒エステル化合物を固相として分離するステップと、
分離された架橋部の有機溶媒エステル化合物に架橋材を加えることにより有機溶媒エステル化合物を有機溶媒エステル化合物の架橋材溶液として回収するステップと
を有することを特徴とする熱硬化性樹脂の分解・回収方法。 A thermosetting resin having a cross-linked portion, which is a copolymer of an unsaturated fatty acid and a cross-linking material, formed by cross-linking a cross-linking material to an unsaturated fatty acid of an unsaturated polyester composed of a polyhydric alcohol and an unsaturated fatty acid, A step of generating an organic solvent ester compound and a polyhydric alcohol in the crosslinked portion by decomposing with an organic solvent having a super-subcritical hydroxyl group at a temperature equal to or lower than the thermal decomposition temperature of the crosslinked portion;
Separating the organic solvent ester compound and the polyhydric alcohol into a solid phase by separating the polyhydric alcohol and the organic solvent as a liquid phase, and the crosslinked organic solvent ester compound as a solid phase; and
A step of recovering the organic solvent ester compound as a cross-linking material solution of the organic solvent ester compound by adding a cross-linking material to the organic solvent ester compound of the separated cross-linking portion, and decomposing and recovering the thermosetting resin Method. 請求項１に記載の熱硬化性樹脂の分解・回収方法であって、前記架橋材はスチレンであることを特徴とする熱硬化性樹脂の分解・回収方法。   The method for decomposing / recovering a thermosetting resin according to claim 1, wherein the crosslinking material is styrene. 請求項１又は請求項２に記載の熱硬化性樹脂の分解・回収方法であって、前記有機溶媒エステル化合物の架橋材溶液を熱硬化性樹脂用の低収縮剤として再利用することを特徴とする熱硬化性樹脂の分解・回収方法。   The method for decomposing / recovering a thermosetting resin according to claim 1 or 2, wherein the organic solvent ester compound crosslinking material solution is reused as a low shrinkage agent for the thermosetting resin. To disassemble and recover thermosetting resin. 請求項１乃至請求項３のうち、いずれか１項に記載の熱硬化性樹脂の分解・回収方法であって、前記熱硬化性樹脂は無機物を含有し、前記固液分離処理後、架橋材を加えることにより架橋部の有機溶媒エステル化合物を溶解した後に再度固液分離し、無機物と有機溶媒エステル化合物の架橋材溶液を回収することを特徴とする熱硬化性樹脂の分解・回収方法。
The thermosetting resin decomposition / recovery method according to any one of claims 1 to 3, wherein the thermosetting resin contains an inorganic substance, and after the solid-liquid separation treatment, a crosslinking material. A method for decomposing and recovering a thermosetting resin, comprising: dissolving an organic solvent ester compound in a cross-linked portion by adding a solid, followed by solid-liquid separation again to recover a cross-linking material solution of an inorganic substance and an organic solvent ester compound.
JP2006084229A 2006-03-24 2006-03-24 Decomposition and recovery method of thermosetting resin Expired - Fee Related JP4677939B2 (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
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JP2009155404A (en) * 2007-12-25 2009-07-16 Panasonic Electric Works Co Ltd Decomposition/recovery method of thermosetting resin
EP3178874A1 (en) * 2015-12-11 2017-06-14 Korea Institute of Science and Technology Method and apparatus for recovering fiber assembly from thermosetting resin composite materials and recovered fiber assembly thereby

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JP2000297053A (en) * 1999-04-13 2000-10-24 Asahi Chem Ind Co Ltd Production of alcohols by hydrogenation of ester
JP2005336323A (en) * 2004-05-26 2005-12-08 Matsushita Electric Works Ltd Method for recovering inorganic substance from plastic
JP2006219640A (en) * 2005-02-14 2006-08-24 Yamaguchi Prefecture Method for decomposition-treating thermosetting resin, and method for decomposition-treating waste material of fiber-reinforced plastic obtained by using thermosetting resin as parent material

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JP2000297053A (en) * 1999-04-13 2000-10-24 Asahi Chem Ind Co Ltd Production of alcohols by hydrogenation of ester
JP2005336323A (en) * 2004-05-26 2005-12-08 Matsushita Electric Works Ltd Method for recovering inorganic substance from plastic
JP2006219640A (en) * 2005-02-14 2006-08-24 Yamaguchi Prefecture Method for decomposition-treating thermosetting resin, and method for decomposition-treating waste material of fiber-reinforced plastic obtained by using thermosetting resin as parent material

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009155404A (en) * 2007-12-25 2009-07-16 Panasonic Electric Works Co Ltd Decomposition/recovery method of thermosetting resin
EP3178874A1 (en) * 2015-12-11 2017-06-14 Korea Institute of Science and Technology Method and apparatus for recovering fiber assembly from thermosetting resin composite materials and recovered fiber assembly thereby

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