JP4682272B2 - Decomposition method, decomposition product and recycling method of thermosetting resin - Google Patents

Description

  The present invention relates to a thermosetting resin decomposition method, decomposition products, and a recycling method.

  Thermosetting resins such as unsaturated polyester resins and epoxy resins are widely used as materials for electric / electronic parts, automobile parts and the like because they exhibit excellent electrical insulation, heat resistance, and mechanical strength. Thermosetting resins are applied to molding materials, laminates, adhesives, paints, and the like because they can be easily blended with fillers and additives such as inorganic substances and reinforced with fibers. Once such a thermosetting resin is cured, it is not softened or melted by heat and does not dissolve in a solvent. For this reason, the decomposition process of the thermosetting resin cured product is difficult, and it has been discarded as being unsuitable for the regeneration process and reuse.

  On the other hand, as the problem of waste has attracted attention, it has become necessary to develop technology for reusing and recycling thermosetting resin cured products, and the use of raw materials by pyrolysis has begun to be studied. However, there is a problem that the advantages of the cured thermosetting resin such as hardness, strength, heat resistance, flame retardancy and chemical resistance make waste disposal difficult from the technical aspect.

  In recent years, methods for decomposing these thermosetting resin cured products in supercritical water or subcritical water have been studied. For example, a method has been proposed in which a thermosetting resin is oxidatively decomposed in supercritical water or subcritical water in the presence of oxygen, air, or hydrogen peroxide (see, for example, Patent Document 1). This method uses the fact that when the water reaches a subcritical state, the dielectric constant and ionic product are advantageous for the decomposition of the resin.

However, when only water is used as a reaction solvent, the decomposition efficiency is not improved. For this reason, a method of decomposing a thermosetting resin in a supercritical or subcritical state mononuclear phenol compound or water / mononuclear phenol compound mixture has been proposed (see, for example, Patent Document 2). ). In addition, a method of decomposing a thermosetting resin using an organic solvent having a specific solubility parameter has been proposed (see, for example, Patent Document 3).
JP-A-10-287766 (Claims) JP 2001-151933 A (Claims) JP 2002-121322 A (Claims)

  However, in the method described in Patent Document 2, since mononuclear phenol compounds are mainly used, there is a problem that the resin is limited to a resin having a benzene nucleus in the molecule, such as a phenol resin and an epoxy resin.

  Moreover, in the method described in Patent Document 3, since the thermosetting resin is decomposed using only an organic solvent, there is a problem that the handling is not easy and the cost is increased.

  That is, the present invention has been made in view of the above problems, and an object of the present invention is to provide a thermosetting resin decomposition method and a recycling method for efficiently decomposing a thermosetting resin into an organic solvent-soluble substance. It is in.

  In order to achieve the above object, in the method for decomposing a thermosetting resin of the present invention, an aliphatic monohydric alcohol having 11 to 18 carbon atoms, phenol substituted with an alkyl group having 12 to 18 carbon atoms, monoamine, amino alcohol The thermosetting resin is decomposed into an organic solvent-soluble substance in a supercritical or subcritical state using at least one selected from the group of organic compounds consisting of amino compounds and water and water.

  A feature of the present invention is that a specific organic compound is present in water that is in a supercritical state or a subcritical state and has a dielectric constant or ionic product that is advantageous for decomposition of the thermosetting resin. It has been found that the decomposition of the functional resin accelerates and accelerates. That is, according to this configuration, the thermosetting resin can be efficiently decomposed into an organic solvent-soluble substance.

  The thermosetting resin may be at least one selected from the group consisting of unsaturated polyester resins, epoxy resins, polyimide resins, melamine resins, urea resins, and urethane resins.

These thermosetting resins include —CO—, —COO—, —CH (OH) —, —NH—, —N (CO) ₂ —, —NHCH ₂ —, —NHCO—, —NHCOO in the molecule. A bond such as −. The specific organic compound and water used in the present invention are considered to cleave these binding sites. As a result, according to this configuration, the thermosetting resin can be decomposed more efficiently.

  The reusable organic solvent soluble material of the present invention comprises an aliphatic monohydric alcohol having 11 to 18 carbon atoms, phenol substituted with an alkyl group having 12 to 18 carbon atoms, a monoamine, an amino alcohol, and an amino compound. It can be obtained by decomposing a thermosetting resin in a supercritical or subcritical state using at least one selected from the group of organic compounds and water.

  The thermosetting resin recycling method of the present invention is an organic compound comprising an aliphatic monohydric alcohol having 11 to 18 carbon atoms, phenol substituted with an alkyl group having 12 to 18 carbon atoms, a monoamine, an amino alcohol, and an amino compound. In a supercritical or subcritical state, the thermosetting resin is decomposed into an organic solvent-soluble substance and reused using at least one selected from the group consisting of water and water.

  According to this configuration, the thermosetting resin is decomposed into an organic solvent-soluble substance. As a result, the decomposition product can be reused effectively.

  Moreover, the thermosetting resin recycled by the said method should just be at least 1 sort (s) selected from the group which consists of unsaturated polyester resin, an epoxy resin, a polyimide resin, a melamine resin, a urea resin, and a urethane resin.

  According to the method for decomposing a thermosetting resin of the present invention, a thermosetting resin that has been included in a large amount in industrial waste or general waste and has not been realized yet can be efficiently decomposed. be able to. Further, by using the obtained decomposition product for resynthesis of the thermosetting resin, the thermosetting resin can be effectively reused.

  The method for decomposing the thermosetting resin of the present invention is from the group consisting of an aliphatic monohydric alcohol having 11 to 18 carbon atoms, phenol substituted with an alkyl group having 12 to 18 carbon atoms, monoamine, amino alcohol, and an amino compound. Using at least one selected species and water, the thermosetting resin is decomposed into an organic solvent-soluble substance in a supercritical or subcritical state. In the present invention, it has been found that the use of a mixture of the organic compound and water as a reaction solvent is extremely effective for the decomposition of the thermosetting resin.

  FIG. 1 is a flowchart illustrating a method for decomposing a thermosetting resin according to the present invention. The following description will be made along the flowchart.

[Thermosetting resin]
The type of thermosetting resin decomposed by the method of the present invention is not particularly limited, but preferably includes unsaturated polyester resin, epoxy resin, polyimide resin, melamine resin, urea resin, urethane resin, and the like. It is done. These thermosetting resins may be used alone or in combination of two or more. Moreover, there is no restriction | limiting in particular in the manufacturing method and conditions of these thermosetting resins.

  The thermosetting resin decomposed by the method of the present invention is a cured resin, an uncured resin, a varnish containing a resin, or the like. Moreover, the thermosetting resin decomposed | disassembled by the method of this invention may not be resin single, but a thermosetting resin product etc. may be sufficient. Examples of thermosetting resin products include inorganic fine fillers such as silica fine particles and glass fibers, and molding materials containing organic fillers such as wood flour, molded articles, inorganic base materials such as glass cloth, paper, cloth, etc. Examples include laminates using an organic base material, metal-laminated laminates obtained by bonding metal foils such as copper foils to these laminates, and printed circuit boards obtained by processing metal-laminated laminates.

  The products subject to the decomposition treatment of the present invention include, for example, construction materials such as bathtubs, toilets, water storage tanks and washstands, household items such as chairs, desks and furniture, and civil engineering such as tiles, artificial marble and pipes. Examples include materials, bodies and parts of transportation equipment such as ships, automobiles, railways, and aircraft, housing equipment, decorative boards, and decorative items. Moreover, there is no restriction | limiting also in the form of the thermosetting resin in these products, a shape, etc., You may be used as a coating material, putty, an adhesive agent, etc.

  It is preferable to pulverize the product for use in the decomposition of the product using these thermosetting resins. There are no particular restrictions on the shape and size of the pulverized product, and the size can be selected as appropriate in consideration of the cost and decomposition rate for pulverization. For example, the particle diameter is 5 mm or less, preferably 1 mm or less, and more preferably 500 μm or less.

[Substances used for decomposition]
The substance used for decomposing the thermosetting resin in the present invention comprises an aliphatic monohydric alcohol having 11 to 18 carbon atoms, phenol substituted with an alkyl group having 12 to 18 carbon atoms, monoamine, amino alcohol, and an amino compound. At least one selected from the group of organic compounds and water are used. In addition, these organic compounds may be used singly or as a mixture of two or more organic compounds.

  Among the above organic compounds, the aliphatic monohydric alcohol is an aliphatic monohydric alcohol having 11 to 18 carbon atoms, preferably an aliphatic monohydric alcohol having 12 to 16 carbon atoms, more preferably 1-tetradecanol. C1-C16 aliphatic monohydric alcohols such as 1-hexadecanol. These aliphatic monohydric alcohols are not limited to linear ones, and may have branches.

  The phenol substituted with an alkyl group having 12 to 18 carbon atoms is not limited to a straight chain, and may have a branch. The substitution position of the alkyl group is preferably a para position or a meta position. Preferable phenol substituted with an alkyl group includes m-pentadecylphenol. Moreover, the substitution position is not limited to one place, and may be two or more places.

  The monoamine may be any of primary amine, secondary amine, and tertiary amine. In addition, the monoamine may be an alkylamine or an aromatic amine in which all or part of the substituents on the nitrogen atom is an aromatic hydrocarbon residue. In the case of an alkylamine, the carbon number of the alkyl substituent is 1-18, preferably 5-16.

  The amino alcohol is an amino alcohol having 1 to 18 carbon atoms, preferably an amino alcohol having 5 to 16 carbon atoms. These amino alcohols are not limited to linear ones, and may have a branch.

  Examples of the amino compound include amino acids.

  The blending ratio of the organic compound and water varies depending on the type of organic compound. In each organic compound, it is necessary to obtain an appropriate blending ratio. For example, in the case of an aliphatic monohydric alcohol, the blending ratio of the organic compound and water is 5 to 60% by mass, preferably about 7 to 50% by mass, and substituted with an alkyl group having 12 to 18 carbon atoms. In the case of phenol, 5 mass% to 55 mass%, preferably about 10 mass% to 50 mass%, and in the case of monoamine, 1 mass% to 40 mass%, preferably 1.5 mass% to 30 mass%. Degree.

  The thermosetting resin or thermosetting resin product, the organic compound and water are mixed and subjected to a decomposition reaction.

[Disassembly method]
In the present invention, the thermosetting resin is decomposed as follows. The thermosetting resin or thermosetting resin product, and the organic compound and water (hereinafter, the organic compound and water may be referred to as “reaction solvent”) are based on 100 parts by mass of the thermosetting resin cured product. The reaction solvent is preferably used at a rate of 100 to 3000 parts by mass, and more preferably at a rate of 150 to 2000 parts by mass. If the mixing ratio of the product containing the thermosetting resin cured product and the reaction solvent is smaller than the above range, the decomposition reaction of the thermosetting resin cannot proceed smoothly. On the other hand, when the mixing ratio of the product containing the thermosetting resin cured product and the reaction solvent is larger than the above range, a remarkable effect cannot be obtained as compared with the effect of the upper limit value of the preferable range. Further, the amount of heat required to heat the reaction solvent increases, which is not preferable.

  The decomposition conditions according to the decomposition method of the present invention may be adjusted to a supercritical or subcritical condition in which the temperature and pressure are usually in the range of 473 to 773K and the pressure is 1 to 60 Mpa. What is necessary is just to set temperature and pressure in temperature 523-723K and a pressure in the range of 2-40 Mpa. When the temperature is lower than the above range, since the decomposition reaction rate of the thermosetting resin is low, it becomes difficult to process in a short time. On the other hand, when the temperature is higher than the above range, the chemical structure of the resin component recovered by side reactions such as thermal decomposition is changed, so that it is difficult to reuse the thermosetting resin product as a chemical raw material.

  The reaction time can be adjusted in the range of 0.5 to 120 minutes, but the decomposition treatment is usually completed in 8 to 15 minutes.

  In a supercritical or subcritical reaction solvent, the thermosetting resin reacts with the reaction solvent and decomposes. Actually, there are those that are easily cut and those that are difficult to cut depending on the type and composition of the thermosetting resin, and the portion to be cut varies depending on the reaction conditions. Regarding the setting of the reaction conditions, if the composition is not clear such as waste, it is necessary to set the optimal reaction conditions in advance.

After decomposing a product containing a thermosetting resin cured product in a supercritical or subcritical reaction solvent, decomposition products, undecomposed products, and residues of inorganic materials such as fillers and pigments are left in the reaction solvent. It is in an included state. After cooling, the solid phase containing the residue and the liquid phase are separated by filtration. Next, the solid phase is extracted with an organic solvent to obtain a decomposition product contained in the solid phase. By this operation, decomposition products that are not soluble in the reaction solvent but are soluble in the organic solvent can be recovered. Also. The decomposition product contained in the liquid phase is extracted with an organic solvent and separated into a water-soluble substance and an organic solvent-soluble substance.
Moreover, the residue which consists of inorganic substances, such as a filler and a pigment contained in a solid layer, can also isolate | separate from the decomposition product and undecomposition thing of a thermosetting resin by performing solid separation separately.

[Organic solvent soluble substances]
The thermosetting resin decomposed by the method of the present invention is decomposed into an organic solvent-soluble substance. The organic solvent-soluble substance includes monomers and oligomers constituting the resin, and compounds derived therefrom (reacted with the organic compound in the reaction solvent). The organic solvent-soluble substance obtained varies depending on decomposition conditions such as decomposition temperature and decomposition time. The obtained organic solvent-soluble substance can be purified as necessary and reused as a chemical raw material for thermosetting resin products.

  The “organic solvent-soluble substance” in the present invention refers to the following. When decomposed using a reaction solvent in a supercritical or subcritical state, a solid phase and a liquid phase are obtained. As shown in FIG. 1, the liquid phase and the solid phase are separated by filtration. When the liquid phase is extracted with hexane, a hexane-soluble material is obtained. When the solid phase is extracted with tetrahydrofuran (hereinafter referred to as “THF”), a soluble substance dissolved in THF is obtained. When this soluble material is reprecipitated using THF and hexane, the liquid phase contains a hexane soluble material and the solid phase contains a THF soluble material. Here, the “organic solvent soluble substance” means the hexane soluble substance and the THF soluble substance. In the example of this figure, the solid phase is treated with THF and the liquid phase is treated with hexane. However, not only these organic solvents but also known organic solvents that are usually used as extraction solvents can be used.

  In order to reuse the decomposition product, it is necessary to separate each component, but various separation methods may be appropriately used depending on the composition, and various known methods may be applied. Further, if necessary, purification of the decomposition product is also necessary. A known method can be applied to the purification. The obtained decomposition product can be reused for the synthesis of a thermosetting resin.

  Hereinafter, the present invention will be described in detail with reference to examples. The present invention is not limited by these.

(Thermosetting resin)
An unsaturated polyester resin obtained by polymerizing unsaturated polyester (molar ratio: 4: 9: 14) containing maleic anhydride, phthalic anhydride and propylene glycol and styrene was used (unsaturated polyester: styrene = 2: 3). Mass ratio)).
[Evaluation of aliphatic alcohol]
(Evaluation of aliphatic monohydric alcohol)
Example 1
In a tubular reactor (inner diameter 8 mm, length 150 mm, made of SUS316L), 0.25 g of an unsaturated polyester resin and 4.75 g of a reaction solvent (water: 1-undecanol = 80: 20 (mass ratio)) were placed. Heat treatment was performed at 573 K for 10 minutes using a salt bath. Then, it cooled rapidly and isolate | separated the solid phase and the liquid phase. The solid phase was extracted with 50 ml of THF using a Soxhlet extractor. From the mass of the solid phase not dissolved in THF and the mass of the unsaturated polyester resin before decomposition, the solid residual ratio in THF was determined using the following formula, and the decomposition of the unsaturated polyester resin was evaluated. The results are shown in Table 1.

Solid residual ratio (%) = (mass of solid phase not dissolved in THF) / (mass of unsaturated polyester resin before decomposition) × 100

(Example 2)
In Example 1, it carried out similarly to Example 1 except having used 1-dodecanol instead of 1-undecanol, and evaluated decomposition | disassembly of unsaturated polyester resin. The results are shown in Table 1.

(Example 3)
In Example 1, it carried out similarly to Example 1 except having used 1-tetradecanol instead of 1-undecanol, and evaluated decomposition | disassembly of unsaturated polyester resin. The results are shown in Table 1.

Example 4
In Example 1, it carried out similarly to Example 1 except having used 1-hexadecanol instead of 1-undecanol, and evaluated decomposition of unsaturated polyester resin. The results are shown in Table 1.

(Example 5)
In Example 1, it carried out similarly to Example 1 except having used 1-octadecanol instead of 1-undecanol, and evaluated decomposition | disassembly of unsaturated polyester resin. The results are shown in Table 1.

(Comparative Example 1)
In Example 1, it carried out similarly to Example 1 except having used only water as a reaction solvent, without using 1-undecanol, and evaluated decomposition | disassembly of unsaturated polyester resin. The results are shown in Table 1.

(Comparative Example 2)
In Example 1, it carried out similarly to Example 1 except having used 1-pentanol instead of 1-undecanol, and evaluated decomposition | disassembly of unsaturated polyester resin. The results are shown in Table 1.

(Comparative Example 3)
In Example 1, it carried out similarly to Example 1 except having used 1-octanol instead of 1-undecanol, and evaluated decomposition | disassembly of unsaturated polyester resin. The results are shown in Table 1.

(Comparative Example 4)
In Example 1, it carried out similarly to Example 1 except having used 1-decanol instead of 1-undecanol, and evaluated decomposition | disassembly of unsaturated polyester resin. The results are shown in Table 1.

この表から、炭素数１１〜１８の脂肪族１価アルコールを反応溶媒の一部として用いた場合に、不飽和ポリエステル樹脂を有機溶媒可溶物質に分解する効果が大きいことがわかった。水のみ、あるいは炭素数６〜１０の低級脂肪族１価アルコールを反応溶媒の一部に用いた場合には、不飽和ポリエステル樹脂を有機溶媒可溶物質に分解する効果が小さかった。

From this table, it was found that when an aliphatic monohydric alcohol having 11 to 18 carbon atoms was used as a part of the reaction solvent, the effect of decomposing the unsaturated polyester resin into an organic solvent-soluble substance was great. When only water or a lower aliphatic monohydric alcohol having 6 to 10 carbon atoms was used as a part of the reaction solvent, the effect of decomposing the unsaturated polyester resin into an organic solvent soluble substance was small.

(Evaluation of aliphatic dihydric alcohol)
(Comparative Examples 5-14)
In Example 1, instead of 1-undecanol, ethylene glycol, propylene glycol, 1,4-butanediol, 1,6-hexanediol, 1,8-octanediol, 1,12-dodecanediol, diethylene glycol, triethylene The degradation of the unsaturated polyester resin was evaluated in the same manner as in Example 1 except that glycol, polyethylene glycol (molecular weight of about 1,000) and 1,2-tridecanediol were used. The results are shown in Table 2.

この表から、ジオールを反応溶媒として用いた場合には、水単独で分解反応を行った場合より、不溶率が大きく、ジオールは、反応溶媒として適さないことがわかった。

From this table, it was found that when diol was used as a reaction solvent, the insoluble rate was higher than when decomposition reaction was carried out with water alone, and diol was not suitable as a reaction solvent.

[Evaluation of alcohol containing benzene ring]
(Example 6)
In Example 1, it carried out similarly to Example 1 except having used m-pentadecyl phenol instead of 1-undecanol, and evaluated decomposition of unsaturated polyester resin. The results are shown in Table 3.

(Comparative Examples 15-18)
In Example 1, in place of 1-undecanol, phenol, benzyl alcohol, 4-phenyl-1-butanol and p-butylphenol were used in the same manner as in Example 1, and the degradation of the unsaturated polyester resin was evaluated. did. The results are shown in Table 3.

この表から、ベンゼン環含有アルコールは、炭素数１２〜１８のアルキル基で置換されたフェノールを反応溶媒の一部として用いた場合に、不飽和ポリエステル樹脂を有機溶媒可溶物質に分解する効果が大きいことがわかった。

From this table, the benzene ring-containing alcohol has the effect of decomposing the unsaturated polyester resin into an organic solvent-soluble substance when phenol substituted with an alkyl group having 12 to 18 carbon atoms is used as part of the reaction solvent. I found it big.

[Evaluation of the amount of alcohol added]
(Experimental example 1)
In Example 1, instead of 1-undecanol, tetradecanol was used and the concentration of tetradecanol in the reaction solvent was changed in the range of 0 to 25% by mass. The degradation of the saturated polyester resin was evaluated. The results are shown in Table 4.

(Experimental example 2)
In Example 1, instead of 1-undecanol, m-pentadecylphenol was used, and the same procedure as in Example 1 was performed except that the concentration of tetradecanol was changed in the range of 0 to 25% by mass in the reaction solvent. The degradation of the unsaturated polyester resin was evaluated. The results are shown in Table 4.

この結果から、反応溶媒への脂肪族１価アルコールの配合割合は、５質量％〜６０質量％程度であればよく、炭素数１２〜１８のアルキル基で置換されたフェノールの場合は、５質量％〜５５質量％程度であればよいことがわかった。

From this result, the blending ratio of the aliphatic monohydric alcohol to the reaction solvent may be about 5% by mass to 60% by mass, and in the case of phenol substituted with an alkyl group having 12 to 18 carbon atoms, 5% by mass. It has been found that it may be about% to 55% by mass.

[Evaluation of decomposition processing time]
(Experimental example 3)
In Example 1, instead of 1-undecanol, tetradecanol was used, and the decomposition treatment time was changed in the range of 0 to 15 minutes. evaluated. The results are shown in Table 5.

(Experimental example 4)
In Example 1, in place of 1-undecanol, m-pentadecylphenol was used and the decomposition treatment time was changed in the range of 0 to 15 minutes. Degradation was evaluated. The results are shown in Table 5.

この結果から、反応時間は、０．５〜１２０分の範囲で調製できるが、通常は８〜１５分で分解処理が終了することがわかった。

From this result, it was found that the reaction time can be adjusted in the range of 0.5 to 120 minutes, but the decomposition treatment is usually completed in 8 to 15 minutes.

[Evaluation of monoamine, diamine, amino alcohol]
(Example 7)
In Example 1, it carried out similarly to Example 1 except having used 1-tetradecylamine instead of 1-undecanol, and evaluated decomposition of unsaturated polyester resin. The results are shown in Table 6.

(Example 8)
In Example 1, it carried out similarly to Example 1 except having used N-dodecyl-N, N-dimethylamine instead of 1-undecanol, and evaluated decomposition of unsaturated polyester resin. The results are shown in Table 6.

Example 9
In Example 1, it carried out similarly to Example 1 except having used 5-amino-1-pentanol instead of 1-undecanol, and evaluated decomposition | disassembly of unsaturated polyester resin. The results are shown in Table 6.

(Comparative Example 18)
In Example 1, it carried out like Example 1 except having used 1,8-octanediamine instead of 1-undecanol, and decomposition of unsaturated polyester resin was evaluated. The results are shown in Table 6.

この表から、モノアミン、アミノアルコールを反応溶媒の一部として用いた場合に、不飽和ポリエステル樹脂を有機溶媒可溶物質に分解する効果が極めて大きいことがわかった。一方、ジアミンを反応溶媒の一部に用いた場合には、不飽和ポリエステル樹脂を有機溶媒可溶物質に分解する効果は認められなかった。

From this table, it was found that when monoamine and amino alcohol were used as a part of the reaction solvent, the effect of decomposing the unsaturated polyester resin into an organic solvent soluble substance was extremely large. On the other hand, when diamine was used as a part of the reaction solvent, the effect of decomposing the unsaturated polyester resin into an organic solvent-soluble substance was not recognized.

[Evaluation of amine carbon chain length]

(Experimental example 5)
In Example 1, 1-pentylamine was used instead of 1-undecanol, and the same as Example 1 except that the concentration of 1-pentylamine was changed in the range of 0 to 1.548% by mass in the reaction solvent. The degradation of the unsaturated polyester resin was evaluated. The results are shown in Table 7.

(Experimental example 6)
In Example 1, 1-dodecylamine was used in place of 1-undecanol, and the concentration of 1-dodecylamine was changed in the range of 0 to 0.735% by mass in the reaction solvent. The degradation of the unsaturated polyester resin was evaluated. The results are shown in Table 7.

(Experimental example 7)
In Example 1, Example 1 was used except that 1-tetradecylamine was used instead of 1-undecanol, and the concentration of 1-tetradecylamine was changed in the range of 0 to 0.633 mass% in the reaction solvent. The degradation of the unsaturated polyester resin was evaluated. The results are shown in Table 7.

(Experimental example 8)
In Example 1, 1-hexadecylamine was used in place of 1-undecanol, and the concentration of 1-hexadecylamine was changed in the range of 0 to 558% by mass in the reaction solvent. The degradation of the unsaturated polyester resin was evaluated. The results are shown in Table 7.

この表から、アミンの炭素鎖が短いと、アミンの添加量は少量でよいことがわかった。また、炭素数５〜１４のモノアミンは、不飽和ポリエステルの分解率に優れることがわかった。

From this table, it was found that if the carbon chain of the amine is short, a small amount of amine may be added. Moreover, it turned out that a C5-C14 monoamine is excellent in the decomposition | disassembly rate of unsaturated polyester.

FIG. 1 is a flowchart illustrating a method for decomposing a thermosetting resin according to the present invention.

Claims (2)

Aliphatic monohydric alcohols of 11 to 18 carbon atoms, phenols substituted with an alkyl group having 12 to 18 carbon atoms, the group of monoamines having 10 to 16 carbon atoms, and 5-amino-1-pentanol by Li Cheng organic compound A method for decomposing a thermosetting resin, comprising decomposing an unsaturated polyester resin into an organic solvent-soluble substance in a supercritical or subcritical state using at least one selected from the group consisting of water and water. Aliphatic monohydric alcohols of 11 to 18 carbon atoms, phenols substituted with an alkyl group having 12 to 18 carbon atoms, the group of monoamines having 10 to 16 carbon atoms, and 5-amino-1-pentanol by Li Cheng organic compound A method for recycling a thermosetting resin, comprising decomposing an unsaturated polyester resin into an organic solvent-soluble substance and reusing it in a supercritical or subcritical state using at least one selected from the group consisting of water and water.

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