JP3026543B2 - Phenolic resin molding material and method for producing the same - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a phenolic resin molding material and a method for producing the same, and more specifically, to the reaction of crosslinked and cured phenols with ketones and aldehydes.
More polymerized phenolic resin molding material and the cured thermosetting resin having a structure reproduced as may be cross-linked cured again by the chemical treatment was and a method of manufacturing the same.

[0002]

2. Description of the Related Art Once a thermosetting resin has been cured, it is not softened or melted by heat due to its chemical crosslinking, and therefore, waste materials of molded articles made of the cured product have been regarded as non-recyclable. For this reason, waste materials such as scraps and defective products of these thermosetting resin molded products are pulverized, and the particles and powders are used for other unreacted thermosetting materials, thermoplastic resins, organic materials such as asphalt, cements and the like. It is only used as a filler and an extender, for example, as a filler of phenolic resin, an aggregate of road surface pavement, an aggregate of artificial granite, and the like.

The technology for dissolving thermosetting resin cured products , particularly phenolic resin and epoxy resin cured products for the purpose of reuse, is described in "38th Osaka Municipal Industrial Research Institute Report" and "thermosetting resin, 4 [2] (1983) Horiuchi,
Fukuda p.63 ”. This study, general knowledge as to play and use a thermosetting resin cured product was completely dissolved, based on the idea that it is necessary to impart fluidity, cured thermosetting resin 100 weight Parts by weight of phenol in an amount of 2000 to 10000 parts by weight, and an acid catalyst at 170 to 180 ° C.
After heating for ~ 5 hours to cut the crosslinks and completely dissolve,
Further, by reacting with formalin, a regenerated novolak type phenolic resin molding material is obtained.

[0004]

In such applications as fillers, the use of virgin materials is indispensable, the product cost is high, the increase in the amount of waste materials cannot be expected, and conversely many virgin materials are used. With the use of waste, the total amount of waste continues to increase.

Further, according to the recycling method based on the report by Horiuchi et al., A large amount of phenol is required, the recycling rate of waste materials is small, and high temperature and long time heating are required. Has the disadvantage of consuming.

An object of the present invention is to treat a cured thermosetting resin which has been cross-cured using a small amount of phenol, to give the obtained material itself a property of undergoing a cross-linking reaction again, and to cure and mold it. Accordingly, it is an object of the present invention to provide a waste material recycle molding material of a cured thermosetting resin, which can prevent a cumulative increase of the molded product waste material, and a method for producing the same.

[0007]

DISCLOSURE OF THE INVENTION The present invention relates to a phenol compound.
Polymerized by reaction with ketones and aldehydes
Cured thermosetting resin having a forming, a particulate (powder) especially pulverized waste material, which trees cured thermosetting resin particles
An acid catalyst is added, if necessary, in the presence of 10 to 90 parts by weight of phenol with respect to 100 parts by weight of fat , and heated to react to solubilize at least a part of the cured resin. The present invention relates to a particulate phenolic resin molding material having fluidity and cross-linking curability required for molding and processing, and a method for producing the same.

In the present invention, any thermosetting resin having a chemical structure in which an aromatic ring is polymerized via a methylene bond or a dimethylene ether bond by reacting formalin can be recycled as a starting material. Is iso-
A resin having a bisphenol A skeleton having an aromatic ring bonded by a propylidene bond can also be recycled. Therefore, specifically, phenolic resins and epoxy resins are mentioned.

Phenols are preferred as treating agents that can be used in the reaction, and phenol is particularly preferred in view of cost. If the reaction smell Te necessary may be added the following 9 parts by weight of acid catalyst.

Conventionally, a thermosetting resin which has been cross-linked and cured is heated and
It was not thought that the material itself could react, cure, and mold again, apart from decomposing. As a result of the study, the inventors have found that even a thermosetting resin that has been cross-linked and hardened is crushed into particles (powder), and at least a portion thereof is formed.
In particular, the present inventors have found that solubilization of the surface portion that comes into contact with phenols, which are decomposition reagents, leads to the fluidity and cross-linking curability required for molding and processing, thereby completing the present invention.

[0011]

According to the present invention, an acid catalyst is added as necessary to particles obtained by pulverizing a cured thermosetting resin in the presence of phenol, and the mixture is heated and reacted to solubilize at least a part of the cured resin. Although it relates to obtaining a molding material, since the chemical structure of the crosslinked and cured thermosetting resin cannot be specified, it is not clear exactly what kind of reaction causes the solubilization in the present invention. However, since the crosslinking reaction is caused by formalin or the like, the methylene group (-C
H ₂ —) or a dimethylene ether bond (—CH ₂ —OC)
It is presumed that H _2- ) or the like is cut.

Accordingly, any thermosetting resin having a chemical structure in which an aromatic ring is polymerized via a methylene bond or a dimethylene ether bond by reacting formalin can be recycled according to the present invention.

Such phenols are converted to ketones, aldehydes
Examples of the cured thermosetting resin having a structure polymerized by reaction with a compound such as a novolak type phenol resin, a resol type phenol resin, a bisphenol A type epoxy resin, a cured product such as a novolak type epoxy resin,
The epoxy resin is not limited to an amine cured product or an acid anhydride cured product. This is because the skeleton of the epoxy resin has a structure in which an aromatic ring is reacted with formalin and bonded by a methylene bond, and if the methylene bond is cleaved,
This is because the resin is solubilized regardless of the reaction mode of the epoxy group. Bisphenol A epoxy resin has no methylene bond or dimethylene ether bond, is synthesized using acetone, and has a structure in which two benzene rings are bonded by an iso-propylidene bond.
Is used as a starting material of the present invention since this iso-propylidene bond is also cleaved by an acid decomposition reaction. Similarly, other ketones, aldehydes,
For example, a resin having a bisphenol skeleton condensed using acetaldehyde can also be used as a starting material of the present invention.

The phenolic resin-based cured product referred to in the present invention is not limited to a so-called phenolic resin in a narrow sense, but is reacted with, for example, a cresol resin, a phenolfurfural resin, a phenolic resin into which toluene is introduced, a resorcinol resin, and epichlorohydrin. Contains phenolic resin.

Generally, the phenolic resin polymerization stage is classified into three stages: A stage, B stage, and C stage. Stage A refers to the initial product stage of the reaction between phenol and formaldehyde, and is also called resol, with three-dimensional crosslinks having a very low molecular weight and soluble and fusible, that is, it dissolves in a solvent and itself becomes a liquid by heating and flows. State. In the B stage, polymerization proceeds from the state of the A stage,
The three-dimensional crosslinking progresses to some extent and swells without dissolving in solvents such as alcohol and acetone, and is not melted but softened by heating, and is also called resitol. The C stage refers to a state in which the polymerization has progressed further than the B stage and has become an insoluble and infusible three-dimensional crosslinked polymer, and is also referred to as a regit (Polymer Dictionary Editing Committee, Polymer Dictionary, Taiseisha).

The term "solubilizing" as used in the present invention means to cut methylene bridges of a C-stage thermosetting resin to a B-stage or less crosslinked state. In general,
When the particulate material reacts with the liquid reagent, the reaction proceeds inward from the surface portion, so that the reaction is more likely to proceed closer to the surface. Therefore, “solubilization” in the present invention is mainly in the state of the B stage, but the state of the A stage may be partially mixed.

Phenol used as a starting material in the present invention
Polymerized by reaction with ketones and aldehydes
The cured thermosetting resin having the above-mentioned structure may include those resins as a matrix and other fillers and reinforcing materials. Examples of these fillers and reinforcing materials include inorganic fibers such as glass fiber and asbestos, organic fibers such as cellulose fiber (paper and the like), organic fillers such as wood flour, and other inorganic fillers. Examples of such a thermosetting resin molded product include components such as an insulating plate used for electric equipment,
A housing and the like are typical examples.

The phenols used in the present invention are keto
Has a structure polymerized by reaction with aldehydes and aldehydes.
Cured thermosetting resin which is ground, preferably to be used as a particulate. This is because the solubilization reaction with phenols proceeds faster as the contact area increases, and can be used for molding directly after the reaction. The size of such particles is preferably 30 mesh or less (0.5 mm in particle diameter). If the particle diameter is larger than this, the size of the C stage of the reclaimed molding material becomes large, and problems such as not being able to reach a fine cavity during molding arise. The pulverized product may be used as it is, or when necessary, may be separated by a sieve and used as a powder having a uniform particle diameter to some extent.

The phenol used as a raw material of the present invention is a ketone
Has a structure polymerized by reaction with aldehydes and aldehydes
Whether the thermosetting resin cured product is a phenolic resin or an epoxy resin, the molding material regenerated according to the present invention has a curing reaction cured by a crosslinking reaction similar to that of the phenolic resin, It belongs to phenolic resin molding materials. That is, according to the processing conditions for regeneration of the present invention, although accurate confirmation cannot be made, the methylene bond or dimethylene ether bond or the like constituting the cross-link is dissociated, and a methylol group or the like is generated to form B It is considered that a part before the stage was formed, and was swelled or dissolved in phenols. The methylol group, and the methylol group remaining in the thermosetting resin as a raw material in an unreacted state, including phenols also serving as a solvent, including aromatic rings derived from phenols as a raw material of the resin. Is crosslinked again to become a C-stage cured product.

The effects of the phenols used in the present invention are as follows:
It is presumed that it mainly acts as a solvent that swells and dissolves the resin and forms a skeleton of the remolded resin by being incorporated into the curing reaction during remolding. Furthermore, in the reaction for regeneration, it is also conceivable that it may act as a reagent that cleaves a methylene bond or the like. The phenols having such an action are not limited to phenols having one hydroxyl group bonded to an aromatic ring such as phenol and alkylphenol, and phenol compounds such as cresols, xylenols, resorcinols, and catechol. Phenol is preferred, but phenol is preferred in terms of cost.

In the present invention, an acid catalyst can be used if necessary. Acid catalysts that can be used include p-toluenesulfonic acid, xylenesulfonic acid,
Examples thereof include organic acids such as phenolsulfonic acid, and inorganic acids such as sulfuric acid, nitric acid, phosphoric acid, and condensed phosphoric acid. In particular, nonvolatile acids that do not volatilize during heating are preferable. By using these acids, the speed of the reaction for converting the C-stage resin cured product to the state before the B-stage can be increased, and the moldability of the obtained recycled phenolic resin molding material is improved. However, depending on the use of the recycled phenolic resin molding material, the use of an acid catalyst may not be preferable. In such a case, the reaction temperature may be increased and the reaction time may be increased without using a catalyst.

[0022] When using the acid catalyst, the amount is phenol
Polymerized by reaction with ketones and aldehydes
It is preferably 9 parts by weight or less based on 100 parts by weight of the cured thermosetting resin having the bent structure . 9 acid catalysts
If it exceeds the weight part, the mold used when molding the recycled resin,
This is because there is a case where a problem that an insert fitting or the like inserted into a molded article is corroded may occur. However, when phosphoric acid or condensed phosphoric acid is used, the corrosive action is small and 9 parts by weight or more can be used, which is preferable.

In the present invention, phenols are converted to ketones,
Phenols are added to pulverized material of cured thermosetting resin having a structure polymerized by reaction with aldehydes,
It is preferable that 10 to 90 parts are added to and reacted with parts. When the amount of the phenol used is 10 parts or less, the B-staged portion obtained by solubilization is small, and as a result, both fluidity and curability are insufficient for reshaping. When the amount of the phenols exceeds 90 parts, the whole proceeds to the stage A and melts. In order to form a molding material, it is necessary to further react by adding formalin and to the stage B, so that unnecessary phenol and energy are consumed. In addition to inviting the use, the number of steps is increased, and the cost is increased, which is not preferable.

The reaction temperature in the present invention is preferably
80-180 ° C. The reaction proceeds even at 80 ° C. or lower, but requires a long time. On the other hand, when the temperature is higher than 180 ° C., volatilization of phenols becomes intense, which is not preferable in working environment, and the ratio of phenols to resin cannot be controlled.
However, this reaction temperature is a case where a normal open-type reaction apparatus is used, and does not exclude the case where a pressure-resistant / closed-type apparatus is used and the reaction is performed at a higher temperature.

The reaction time depends on the type and amount of catalyst added, ketones and aldehydes used as raw materials.
Thermosetting resin having a structure polymerized by the reaction with phenols
It is necessary to adjust the temperature depending on the type of the cured product and the like.
00 minutes is appropriate. However, when a large amount of acid catalyst is used, the treatment can be performed in about 5 minutes.
When a pressure-resistant and sealed type device is used and the reaction is performed at a higher temperature, it can be further shortened.

The phenolic resin molding material obtained according to the present invention can be cured into a molded product by the same blending and technique as the virgin phenolic resin molding material.
Particularly, the use of hexamine is preferable because the molding time can be shortened.

In molding the recycled phenolic resin molding material according to the present invention, other fillers, for example, inorganic fibers such as glass fiber and asbestos, organic fibers such as cellulose fiber (paper and the like), and organic fibers such as wood powder. It is also possible to add fillers and other inorganic fillers, and if a pulverized thermosetting resin as a starting material of the present invention is added, the entire remolded product is again a recycled molding material according to the present invention. This is extremely preferable for the purpose of reducing waste.

[0028]

According to the present invention, pulverized into particles.
Phenols react with ketones and aldehydes
Waste material of cured thermosetting resin having a polymerized structure ,
Rather than being used as a filler or an extender, it can be reused as a molding material that reacts and hardens itself, greatly contributing to waste reduction and effective use of resources.

[0029]

Embodiments of the present invention will be described below. Although the present example describes a phenolic resin, the basic reaction of the present invention is to form a methylene bond or the like which is a cause of three-dimensional crosslinking of a resin obtained by crosslinking and curing an aromatic ring with formaldehyde.
In addition, the cross-linking using ketones and aldehydes is performed by phenols, and is not limited to phenol resins.

In this embodiment, phenol is used as a treatment chemical, but the present invention is not limited to this. In the following, numerical values indicated as “parts” are “parts by weight”.
Means

Example 1 A known phenol formaldehyde resin molding material (flow 30 mm, gel time 55 seconds, ortho / para orientation ratio 55/45) synthesized using hydrochloric acid and oxalic acid as catalysts was heated at 120 ° C. for 90 minutes. To a B-stage, and the product of the B-stage is
The material which was pulverized to a mesh or smaller and heated at 180 ° C. for 30 minutes and completely cured was pulverized to a size of 60 mesh or less to obtain a phenol resin cured product (C stage). To 100 parts of the cured phenol resin, 10 parts of phenol and 1 part of p-toluenesulfonic acid were added and mixed well, and the mixture was uniformly heated at 150 ° C. for 30 minutes. A crosslinked state prior to the B stage was obtained to obtain a recycled phenolic resin-based molding material.

The regenerated phenolic resin-based molding material obtained as described above is used at a temperature of 16
Molding was performed at 0 ° C. and a pressure of 150 kgf / cm ^{2 for} 10 minutes.

The molded plate was used as a test piece according to JIS.
The flexural strength and flexural modulus were measured based on K-6911.

Example 2 90 parts of phenol and 9 parts of p-toluenesulfonic acid were added to 100 parts of the phenolic resin cured product of Example 1 and mixed well. The mixture was uniformly heated at 150 ° C. for 30 minutes. The phenolic resin molding material according to the object of the invention was regenerated. This was molded and evaluated in the same manner as in Example 1.

Example 3 10 parts of phenol was added to 100 parts of the phenolic resin cured product of Example 1 and mixed well. The mixture was heated uniformly at 150 ° C. for 75 minutes to obtain a phenolic resin according to the object of the present invention. Regenerated into a molding material. This was molded and evaluated in the same manner as in Example 1. In regenerating the phenolic resin molding material, no acid catalyst was added.

Example 4 90 parts of phenol was added to 100 parts of the phenol resin cured product of Example 1 and mixed well. The mixture was heated uniformly at 150 ° C. for 75 minutes to obtain a phenol resin according to the object of the present invention. Regenerated into a molding material. This was molded and evaluated in the same manner as in Example 1. In regenerating the phenolic resin molding material, no acid catalyst was added.

EXAMPLE 5 30 parts of phenol (42.8 parts of phenol per 100 parts of cured phenol resin) were added to 70 parts of the cured phenol resin of Example 1, and 5 parts of concentrated nitric acid (100 parts of cured phenol resin). 7 parts of concentrated nitric acid
Was added and mixed well, and this was uniformly heated at 150 ° C. for 20 minutes to regenerate the phenolic resin-based molding material according to the present invention. This was molded and evaluated in the same manner as in Example 1.

EXAMPLE 6 30 parts of phenol (42.8 parts of phenol per 100 parts of cured phenol resin) were added to 70 parts of the cured phenol resin of Example 1, and 3 parts of p-toluenesulfonic acid (cured phenol resin). 4.28 parts of p-toluenesulfonic acid) was added to 100 parts and mixed well, and the mixture was heated uniformly at 180 ° C. for 15 minutes to regenerate the phenolic resin molding material according to the present invention. 1
It was molded and evaluated in the same manner as described above.

EXAMPLE 7 30 parts of phenol (42.8 parts of phenol per 100 parts of cured phenol resin) were added to 70 parts of the cured phenol resin of Example 1, and 3 parts of p-toluenesulfonic acid (cured phenol resin). 4.28 parts of p-toluenesulfonic acid) was added to 100 parts and mixed well. The mixture was uniformly heated at 80 ° C. for 3 hours to regenerate the phenolic resin-based molding material according to the present invention. This was molded and evaluated in the same manner as in Example 1.

Example 8 Paper was used as a base material, and a prepreg impregnated with a varnish of virgin phenolic resin was compression-molded on the paper, and an electric consisting of 50 parts of the obtained phenolic resin and 50 parts of paper was obtained. The insulating plate was pulverized to 30 mesh or less to obtain paper composite phenol resin cured product particles. 5 parts of phenol (10 parts of resin in the cured paper composite phenol resin particles) was added to 100 parts of the cured paper composite phenol resin particles.
0 parts by weight of phenol (10 parts by weight) and p-toluenesulfonic acid (0.5 part by weight (1 part of acid to 100 parts of resin in the cured paper composite phenol resin particles)) and mixed well. The phenolic resin molding material according to the object of the present invention was regenerated under the same conditions as described above.

This phenolic resin molding material was molded into a plate under the same molding conditions as in Example 1, and this plate was used as a test piece to determine the Charpy impact value in order to confirm the paper reinforcing effect. The measurement of the bending strength, the bending elastic modulus, and the flowability was performed in the same manner as in Example 1.

Example 9 Using the paper composite phenolic resin cured product particles of Example 8, 45 parts of phenol was added to 100 parts of the particle material (based on 100 parts of resin in the paper composite phenolic resin cured product particles). Phenol 90 parts) and p-
4.5 parts of toluenesulfonic acid (9 parts of acid to 100 parts of resin in the cured paper composite phenol resin particles) were added and mixed well, and the phenol according to the object of the present invention was obtained under the same conditions as in Example 1. Regenerated into resin molding material. This phenolic resin molding material was molded and evaluated in the same manner as in Example 8.

Example 10 The paper composite phenolic resin cured product particles of Example 8 were used, and 100 parts of the particle material were used.
Add 5 parts of phenol (10 parts of phenol to 100 parts of resin in the cured paper composite phenolic resin particles), mix well, and heat uniformly at 150 ° C. for 75 minutes to obtain the object of the present invention. Regenerated into phenolic resin molding material.
When regenerating this phenolic resin molding material,
No acid catalyst was added. This phenolic resin molding material was molded and evaluated in the same manner as in Example 8.

Example 11 Using the paper composite phenolic resin cured product particles of Example 8, this phenolic resin cured product 1
For 00 parts, 45 parts of phenol (90 parts of phenol for 100 parts of cured resin in cured paper composite phenolic resin)
And mix well.
The mixture was heated uniformly for a minute to regenerate the phenolic resin molding material according to the object of the present invention. No acid was added in regenerating the phenolic resin molding material. This phenolic resin molding material was molded and evaluated in the same manner as in Example 8.

Comparative Example 1 The phenol resin oligomer used in Example 1 was B-staged at 120 ° C. for 90 minutes and molded under the molding conditions of Example 1 (virgin phenol resin molded ) Was evaluated in the same manner as in Example 1. This comparative example is for comparing the physical properties of a recycled phenolic resin-based molding material with a molded article using a virgin material.

Comparative Example 2 The cured phenolic resin of Example 1 was molded without any treatment under the same molding conditions as in Example 1. However, in this case, a molded article formed on a plate could not be obtained.

[Comparative Example 3] 100 parts of phenol and 10 parts of p-toluenesulfonic acid were added to 100 parts of the phenol resin cured product of Example 1 and mixed well.
Heated uniformly for 0 minutes. However, in this case, a large amount of unreacted phenol was obtained, and when the heating was further continued, the mixture was brought into the A stage and melted, and the desired particulate molding material could not be obtained.

[Comparative Example 4] 9 parts of phenol and 0.9 part of p-toluenesulfonic acid were added to 100 parts of the phenol resin cured product particles of Example 1 and mixed well, and the mixture was uniformly heated at 150 ° C for 30 minutes. did. However, in this case, there were few solubilized portions, and molding was performed under the same molding conditions as in Example 1. However, the strength of the molded product was extremely low, and physical characteristics could not be measured.

[Comparative Example 5] 30 parts of phenol (42.8 parts of phenol based on 100 parts of cured phenol resin) were added to 70 parts of the cured phenol resin particles of Example 1, and 3 parts of p-toluenesulfonic acid (phenol resin). 4.28 parts) was added to 100 parts of the cured product and mixed well.
When heated at ℃, phenol as a solvent volatilized much, and there was a problem in workability. Because of the volatilization of the phenol, the molded product obtained by molding under the molding conditions of Example 1 did not have sufficient strength.

Comparative Example 6 30 parts of phenol (70 parts of cured phenol resin, 42.8 parts of phenol per 100 parts of cured phenol resin) and 3 parts of p-toluenesulfonic acid (cured phenol resin) 4.28 parts) was added to the mixture, and the mixture was mixed well and heated at 70 ° C .. The time required for solubilization was 3 hours or more, and there was a lot of time loss in production, and it was practical. Did not. (I stopped halfway.)

Comparative Example 7 50 parts of phenol was added to 100 parts of the paper composite phenolic resin cured product particles of Example 8 (100 parts of phenol to 100 parts of resin in the cured paper composite phenolic resin), and p-toluene sulfone was used. 5 parts of acid (100 parts of resin in cured phenolic resin composite paper)
0 part) and mixed well, and the mixture was uniformly heated at 150 ° C. for 30 minutes. However, in this case, there was much unreacted phenol, and when heating was continued, the stage was changed to the A stage, and the desired particulate molding material could not be obtained.

Comparative Example 8 4.5 parts of phenol was added to 100 parts of the paper composite phenol resin cured product particles of Example 8 (9 parts of phenol to 100 parts of the resin in the cured paper composite phenol resin), 0.45 parts of toluenesulfonic acid (0.9 parts of acid per 100 parts of resin in the cured paper composite phenolic resin) are added and mixed well, and the mixture is mixed at 150 ° C.
For 30 minutes. However, in this case, although there were few solubilized portions and molding was performed under the same molding conditions as in Example 1, a molded product having sufficient strength to measure physical properties could not be obtained.

The conditions of the above Examples and Comparative Examples are shown in Table 1 using only phenol resin as a starting material, and Table 2 using phenol resin molded products using paper as a reinforcing material.
Are summarized below.

The fluidity of the recycled phenolic resin molding material produced in this example was evaluated by the following method. 1 g of the recycled phenolic resin molding material is dropped on an iron plate heated to 160 ° C., deposited in a conical shape, compressed on a flat hot plate with a total load of 5000 kg, and molded into a disk shape. The obtained disk is composed of a highly transparent resin cured region near the center and an opaque resin cured region outside the region. R is the diameter of the cured resin region having high transparency, and r is the diameter including the opaque resin cured region.
(R / r) × 100 (%) was used as an index of fluidity. R /
The larger r is, the larger the fluidity and the better the moldability.

[0055]

[Table 1]

[0056]

[Table 2] Table 3 shows the evaluation results of the recycled molding materials of Examples and Comparative Examples using only phenolic resin as a starting material, and Table 4 shows the evaluation results using phenolic resin molded products using paper as a reinforcing material.
Are summarized below.

[0057]

[Table 3]

[0058]

[Table 4]

Continuation of the front page (72) Inventor Ryutaro Nishimura 2-9-1-11 Takaidanaka, Higashiosaka-shi, Osaka (56) References “Thermosetting resin” Vol. 4, No. 2 (1983) Horiuchi, Fukuda p. 63-68 (58) Field surveyed (Int.Cl. ⁷ , DB name) C08J 11/00-11/28 B29B 17/00

Claims (5)

(57) [Claims] 1. A phenol, which is a ketone or an aldehyde.
Cured thermosetting resin particles having at least a portion of thermosetting resin particles having a structure polymerized by the reaction with
A particulate phenolic resin molding material solubilized in the presence of 10 to 90 parts by weight of a phenol relative to 100 parts by weight of the resin component. Wherein said thermosetting resin cured product according to claim 1, wherein a cured product of a phenolic resin or epoxy resin
Particulate phenolic resin molding material. 3. A phenol, which is a ketone or an aldehyde.
Cured thermosetting resin particles having at least a portion of thermosetting resin particles having a structure polymerized by the reaction with
A method for producing a particulate phenolic resin molding material which is solubilized by heating in the presence of 10 to 90 parts by weight of phenol relative to 100 parts by weight of the resin component. 4. A particle according to claim 3, wherein the cured thermosetting resin is a cured product of a phenolic resin or an epoxy resin
A method for producing a phenolic resin molding material. 5. The method for producing a particulate phenolic resin molding material according to claim 3, wherein at least a part of the cured thermosetting resin particles is solubilized by heating in the presence of a phenol using an acid catalyst.