JPS6247205B2 - - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for copolymerizing diallyl phthalate and triallyl isocyanurate to produce a copolymer prepolymer comprising diallyl phthalate units and triallyl isocyanurate units.

A prepolymer is a relatively low-molecular polymer that contains unsaturated bonds in its molecules. This polymer can be further molded and polymerized to produce the final polymer, or it can be added to other polymers. It is generally known as a polymerization intermediate that is produced by adding monomers, crosslinking agents, etc., molding it, and then polymerizing it to produce the final polymer.

Diallyl orthophthalate or diallyl isophthalate has been known as a polymer prepolymer of diallyl phthalate alone, and these polymer prepolymers are used as molding materials and prepregs because of their good stability. ,
In addition, the obtained polymer has particularly excellent electrical properties and heat resistance, so it can be used in various electrical parts such as connectors, switches, plugs, magnetic cores,
Used for printed wiring boards, etc.

Although these diallyl phthalate polymers have the above-mentioned properties, they have shortcomings in heat resistance, such as weight loss and rapid thermal decomposition at high temperatures, making them difficult to use under certain conditions. This results in restrictions.

The present inventor conducted research to improve the above drawbacks by adding other monomers during the production of diallyl phthalate prepolymers, and obtained a copolymer prepolymer consisting of diallyl phthalate units and triallyl isocyanurate units, and a method for producing the same. We have previously filed a patent application for this invention (Japanese Patent Application No. 142,702, 1982).

The inventor further researched the manufacturing method and completed the present invention.

That is, the present invention provides a reaction mixture containing a copolymer prepolymer comprising diallyl phthalate units and triallyl isocyanurate units by polymerizing a mixture of diallyl phthalate and triallyl isocyanurate in the presence of oxygen or a radical polymerization initiator. The gist thereof is a method for producing a copolymer prepolymer, characterized in that the reaction mixture is then treated under reduced pressure to distill off unreacted diallyl phthalate and triallyl isocyanurate. It is.

The diallyl phthalate (hereinafter referred to as DAP) of the present invention includes diallyl orthophthalate (hereinafter referred to as DAP).
ODAP) and diallyl isophthalate (hereinafter referred to as
IDAP) is used.

DAP and triallyl isocyanurate (TAIC)
As a method for radical polymerization of
A method of heating in the presence of oxygen or a method of heating in the presence of a radical generating catalyst (polymerization initiator) is employed. As the oxygen present during the radical polymerization, an oxygen-containing gas such as air, oxygen-enriched air, or oxygen is generally used, and the greater the amount of oxygen present, the faster the polymerization rate will be. As a method for causing oxygen to be present in the polymerization system, there is generally a method of blowing the above-mentioned oxygen-containing gas into the polymerization system. A method of bringing the oxygen-containing gas into contact with the liquid by stirring or the like may be adopted. In addition, the heating temperature is about 100 to 300℃, and the lower the temperature, the slower the polymerization rate, and the higher the temperature, the faster the polymerization rate, preferably 150℃.
~200℃ is used. As a method for carrying out radical polymerization in the presence of a radical generating catalyst, commonly used organic peroxides, azo compounds, etc. can be used as the radical generating catalyst. For example, lauroyl peroxide, benzoyl peroxide, t-butyl perbenzoate, dicumyl peroxide, azobisisobutyronitrile and the like are preferably used. When polymerizing in the presence of a radical generating catalyst, the presence of oxygen in the system is not preferable, and it is preferable to carry out the polymerization in an atmosphere of an inert gas such as carbon dioxide or nitrogen.

The amount of the radical generating catalyst used is not particularly limited, but if it is small, the polymerization rate will be slow, and if it is large, the polymerization rate will be fast.The amount is preferably about 0.1 to 1% by weight based on the amount of monomers charged. Further, as the heating temperature, it is preferable to adopt a decomposition temperature at which free radicals of each radical generating catalyst are generated.

A copolymer prepolymer is generally required to have a melting point or softening point of about 50 to 200°C, good fluidity when melted, or good solubility in a good solvent. For this purpose, the copolymer prepolymer must have a uniform copolymer composition;
Further, it is necessary that the average molecular weight is in the range of about 5,000 to 15,000, and that it does not contain microgels due to crosslinked products. In order to produce such a copolymer prepolymer, it is necessary to accurately control the polymerization rate of the copolymer prepolymer produced in the polymerization system, and
It is necessary to measure quickly and stop the polymerization reaction immediately if necessary.

According to the present invention, a mixture of DAP and TAIC is heated in the presence of oxygen or radically polymerized in the presence of a radical polymerization initiator to form DAP units and TAIC.
When producing a copolymer prepolymer consisting of units, it is advantageous to produce the copolymer prepolymer by stopping radical polymerization according to the desired refractive index, viscosity, etc. obtained from a pre-measured calibration curve. will be adopted.

In the above polymerization system, the obtained calibration curve differs depending on the ratio of DAP and TAIC used as raw materials, so when creating the calibration curve, polymerize with the same composition ratio of DAP and TAIC in advance. You can obtain a calibration curve by plotting the refractive index, viscosity, etc. versus the amount of copolymer produced, or you can add a copolymer prepolymer prepared in the same way to a specific ratio of DAP and TAIC mixture. A method of obtaining a calibration curve by plotting a graph of the amount of copolymer prepolymer, refractive index, viscosity, etc. can be adopted.

For example, the proportion (mol) of raw materials ODAP and TAIC
The refractive index (n ²⁵ _D ) on the vertical axis, calibration curve 1 in Figure 1 is obtained, and when copolymerization is carried out at a ratio (mol) of ODAP:TAIC = 1.0:1.0, calibration curve 3 in the same figure is obtained. can get. Also IDAP:TAIC=
When copolymerized at a ratio (mol) of 1.5:0.5, the calibration curve 4 in Figure 2 is similar to that in Figure 1 and IDAP:
In the case of copolymerization at a ratio (mol) of TAIC=1.0:1.0, calibration curve 5 in the same figure is similarly obtained. Also,
Draw a graph of the polymerization rate and viscosity when copolymerized at a ratio (mol) of IDAP:TAIC=1.5:0.5, with the polymerization rate (%) on the horizontal axis and the viscosity (CP/25℃) on the vertical axis. If the calibration curve 6 in Figure 3 is obtained, IDAP:TAIC
In the case of copolymerization at a ratio (mol) of =1.8:0.2, calibration curve 7 in the same figure is obtained in the same manner. material
IDAP:TAIC ratio (mol) of IDAP and TAIC
= 1.5:0.5, the polymerization rate obtained by copolymerizing by heating in the presence of a radical generating catalyst and the refractive index of the copolymerization system, and the refractive index (n ²⁵ _D ) with the polymerization rate (%) on the horizontal axis.
When a graph is plotted with the axis of ordinate, a calibration curve 8 in FIG. 4 is obtained. For example, if you want to perform copolymerization in the presence of oxygen and under heating at a ratio (mol) of ODAP:TAIC=1.5:0.5 and stop the polymerization reaction at a polymerization rate of 25%, use the calibration curve 1 in Figure 1 above. Accordingly, the polymerization may be stopped when the refractive index (n ²⁵ _D ) of the polymerization system reaches 1.5309.

By measuring the refractive index, viscosity, etc. of the polymerization system in this manner, the desired polymerization rate can be easily determined.

In the polymerization reaction of the present invention, when the polymerization reaction is carried out in the presence of oxygen and under heating, no other catalyst remains in the reaction system, so it is easy to stop the polymerization. That is, if the supply of oxygen to the polymerization system is stopped and the heating temperature is reduced to about 150° C. or lower, the polymerization reaction will hardly proceed.

The polymerization system that has stopped the polymerization reaction at the desired polymerization rate is
Unreacted DAP and TAIC are then removed. Unreacted DAP and TAIC can be easily removed by distilling the polymerization system under reduced pressure. In this case, by setting the reduced pressure to about 0.5 mmHg or less and the temperature to about 150° C. or less, unreacted DAP and TAIC can be distilled while preventing the polymerization reaction.

Since a small amount of unreacted DAP and TAIC still remain in the crude copolymer prepolymer from which unreacted DAP and TAIC have been distilled off by the above method, it is necessary to further remove these unreacted DAP and TAIC. is necessary. Therefore, unreacted DAP and TAIC
A solvent was then added to the crude copolymer prepolymer from which unreacted DAP and TAIC were removed by distillation, but the copolymer prepolymer was not dissolved to extract unreacted DAP and TAIC.
A copolymer prepolymer consisting of DAP units and TAIC units is recovered.

Examples of the solvent used in the present invention include lower alcohols such as methyl alcohol, ethyl alcohol, and propyl alcohol; and aliphatic hydrocarbons such as pentane and hexaneheptane.

In addition, when the polymerization reaction is carried out in the presence of a radical generating catalyst in the present invention, the polymerization reaction is stopped at the desired polymerization rate and immediately cooled to dissolve the above-mentioned DAP or TAIC, but the copolymer Unreacted DAP and TAIC can be removed by adding a solvent that does not dissolve the prepolymer.
can be extracted and the copolymer prepolymer formed from DAP units and TAIC units can be recovered.

Unreacted DAP distilled off as described above and
The composition ratio of TAIC or unreacted DAP and TAIC recovered by distilling off the solvent after extraction can be easily determined by measuring its refractive index. In other words, DAP and TAIC used in the copolymerization system
remain in the copolymerization system because their reactivity ratios are different.
DAP and TAIC have different composition ratios than those used initially. Therefore, when using the recovered material as a reaction raw material or copolymerizing it with a different composition ratio, it is necessary to know the correct proportion of DAP and TAIC, and then adjust the ratio before using it as a copolymerization reaction raw material. Must be.

In the present invention, the composition ratio and refractive index of DAP and TAIC can be adjusted very easily by further adding DAP and/or TAIC to the desired composition ratio using a calibration curve measured in advance. You can adjust the recovery
DAP and TAIC can be easily reused.

For example, as shown in Figure 5, on the left side of the vertical axis
A calibration curve 9 can be drawn in which the number of moles of TAIC is plotted on the horizontal axis and the refractive index (n ²⁵ _D ) is plotted on the right side of the vertical axis. Similarly, by plotting the mixing ratio with IDAP and the refractive index (n ²⁵ _D ), the calibration curve 12 in FIG. 7 can be obtained. For example, according to calibration curve 9
A mixed solution of 1.3 moles of ODAP and 0.7 moles of TAIC has a refractive index (n ²⁵ _D ) at point 10 in the figure, that is, 1.5149, and the copolymer prepolymer is produced from this raw material and the recovered ODAP and The refractive index (n ²⁵ _D ) of the TAIC mixture is 11 points in the figure, that is, 1.5150. This means that the molar ratio of ODAP:TAIC is approximately 0.675:
It is clearly understood from the calibration curve 9 that the value is 0.325. Therefore, this recovered ODAP and TAIC are used as the above copolymer raw material (ODAP:TAIC=1.3:0.7).
When used as a liquid, TAIC may be added until the liquid has a refractive index of 1.5149.

In this way, according to the refractive index measurement method of the present invention,
Conventionally known method of measuring saponification value of DAP or quantitative analysis of nitrogen atoms of TAIC
Compared to the method of measuring the composition ratio of DAP and TAIC, the composition ratio of DAP and TAIC can be measured very easily, quickly and accurately.

Next, the present invention will be explained with reference to examples, but the present invention is not limited to the following examples.

Example 1 369.4 g (1.5 mol) of ODAP and
124.5 g (0.5 mol) of TAIC was added, and the reaction was carried out at 160° C. while stirring and blowing air at a rate of 150 ml/min. After 95 minutes, the refractive index (n ²⁵ _D ) of the reaction solution reached 1.5309, which is a polymerization rate of about 25%, based on the calibration curve 1 in Figure 1 obtained in advance by a similar reaction, so the supply of air was stopped. It was cooled to 140° C. and distilled under reduced pressure of 0.3 mmHg to recover 230 g of ODAP and TAIC mixture. After cooling the distillation residue, 800 ml of methyl alcohol was injected with stirring to precipitate the copolymer prepolymer as a solid, the resulting solid was filtered with suction, and the solid was diluted with 50 ml of methyl alcohol three times
After washing twice and drying, 123.5 g of copolymer prepolymer was obtained. The obtained prepolymer has a number average molecular weight
9000, bromine number 56, melting point 130-148℃,
It was a copolymer prepolymer having a composition ratio (mol) of ODAP:TAIC=0.684:0.316.

On the other hand, the above copolymer prepolymer (solid) was separated and washed, and methyl alcohol was distilled off from the liquid to obtain 140.4 g of a mixture of ODAP and TAIC.

ODAP and TAIC previously recovered by vacuum distillation
and the mixture of ODAP and TAIC obtained by distilling off the methyl alcohol, totaling 370.4g.
was recovered as a mixture of unreacted ODAP and TAIC. The refractive index ( ^n25D ₎ of this mixture is 1.5156, and from the calibration curve 9 in Figure 5, ODAP:TAIC=0.772:
It was found that the ratio (mol) was 0.228.

Example 2 ODAP320.1g (1.3
mol) and 174.3 g of TAIC were added, and the reaction was carried out in the same manner as in Example 1. Refractive index of reaction solution (n ²⁵ _D ) after 115 minutes
Figure 1 is the calibration curve 2 obtained in advance by a similar reaction.
When the polymerization rate reached 1.5284, which is about 22%, the air supply was stopped and the mixture was cooled to 140°C. ODAP and TAIC were distilled under reduced pressure of 0.3 mmHg and 190 g was recovered. It was treated in the same manner as in Example 1, and 109 g of copolymer prepolymer was obtained. This prepolymer has a number average molecular weight of 10,000, a bromine number of 63, a melting point of 135-143℃,
It was a copolymer prepolymer having a composition ratio of ODAP:TAIC=0.562:0.438, and contained no unreacted ODAP or TAIC. When the refractive index (n ²⁵ _D ) of the mixture of ODAP and TAIC collected in the same manner as in Example 1 was measured, it was 1.5148.
This mixture is calculated from the calibration curve 9 in Figure 5 by ODAP:TAIC
It was found that the ratio (mol) was 0.675:0.325.

Add 384 g of the recovered mixture of ODAP and TAIC to the original reaction solution composition (mol) and amount.
By adding 61.9 g of ODAP and 48.5 g of TAIC and repeating the same reaction and operation, 110 g of prepolymer was obtained. This prepolymer has a number average molecular weight
9800, bromine number 63, melting point 136-144℃, TAIC content
It was 44.0%.

For comparison, a similar reaction was carried out without distilling unreacted ODAP and TAIC from the reaction product.
When 2500ml of methyl alcohol was injected with stirring, a sticky solid precipitated, and when it was left to stand, the solid coagulated and precipitated, so the supernatant liquid was removed by decanting.
Furthermore, 500 ml of methyl alcohol was added and stirred to break up the aggregated solids. After standing still, the supernatant liquid was removed by decanting, 500 ml of methyl alcohol was added, stirred, and suctioned.
After washing twice, 113.3 g of prepolymer was obtained.
This prepolymer was analyzed as ODAP and TAIC.
It contained 3.8%.

Example 3 ODAP246.2g (1.0
mol) and 249 g (1.0 mol) of TAIC were added and heated to 170°C while stirring and blowing air at a rate of 150 ml/min.
I reacted. Refractive index of reaction solution after 100 minutes (n ²⁵ _D )
However, when the polymerization rate reached 1.5287, which is 24% from the calibration curve 3 in Figure 1 obtained in advance from a similar reaction, the air supply was stopped, the temperature was cooled to 140°C, and the ODAP and ODAP were distilled under reduced pressure of 0.3 mmHg. 260g of TAIC was recovered.

After cooling the distillation residue, 700 ml of methyl alcohol was injected with stirring, and the precipitated solid was filtered off by suction, and the solid was washed three times with 50 ml of methyl alcohol to obtain 118.9 g of prepolymer. The obtained prepolymer was a copolymer prepolymer having a number average molecular weight of 9400, a bromine number of 74, a melting point of 175 to 200°C, and a composition ratio (mol) of ODAP:TAIC=0.419:0.581.

When the mixture of ODAP and TAIC collected in the same manner as in Example 1 was combined and the refractive index (n ²⁵ _D ) was measured,
1.5142, and this mixture is calculated from the calibration curve 9 in Figure 5.
It was found that the ratio (mol) of ODAP:TAIC=0.526:0.474.

Example 4 369.3 g of IDAP (1.5
mol) and 124.5 g (0.5 mol) of TAIC were added, and the reaction was carried out in the same manner as in Example 1. After 90 minutes, the refractive index (n ²⁵ _D ) of the reaction solution was determined by the second
From the calibration curve 4 in the figure, the polymerization rate reached 1.5341, which is about 25%, so the air supply was stopped, the temperature was cooled to 140℃, and the polymerization rate was 0.3%.
IDAP and 250 g of TAIC were recovered by distillation under reduced pressure of mmHg. After cooling the distillation residue, 750 ml of methyl alcohol was poured into it while stirring, and the precipitated solid was filtered off by suction. The solid was washed three times with 100 ml of methyl alcohol each time, and then dried to obtain 123 g of prepolymer. The obtained prepolymer had a number average molecular weight of 9200, a bromine number of 66, a melting point of 101-113°C, and an IDAP:
It was a copolymer prepolymer having a composition ratio (mol) of TAIC=0.699:0.301, and did not contain any unreacted IDAP or TAIC.

IDAP and TAIC collected in the same manner as Example 1
The refractive index (n ²⁵ _D ) of the mixture with
1.5187, and this mixture was found to have a composition ratio (mol) of IDAP:TAIC=0.767:0.233 from the calibration curve 12 in FIG.

Add 370 g of the recovered IDAP and TAIC mixture to the original reaction solution composition (moles) and amount.
111.5 g of IDAP and 12.3 g of TAIC were added and the same reaction and operation were repeated to obtain 123 g of prepolymer.

This prepolymer has a number average molecular weight of 9400 and a bromine number
66, melting point 102-110℃, IDAP:TAIC=0.699:
It was a copolymer prepolymer having a composition ratio (mol) of 0.301.

Example 5 IDAP246.2g (1.0
The reaction was carried out in the same manner as in Example 1, except that 249 g (1.0 mol) of TAIC and 249 g (1.0 mol) of TAIC were added and the reaction temperature was 170°C. After 90 minutes, the refractive index of the reaction solution was determined to be 25.5% based on the calibration curve 5 in Figure 2, which was previously obtained by a similar reaction.
When it reached 1.5310, the air supply was stopped and 140
The mixture was cooled to 0.degree. C. and distilled under reduced pressure of 0.3 mmHg to recover 260 g of IDAP and TAIC.

After cooling the distillation residue, 700 ml of methyl alcohol was injected with stirring, and the precipitated solid was filtered off by suction. The solid was washed three times with 100 ml of methyl alcohol and dried to obtain 126.3 g of prepolymer.

The obtained prepolymer had a number average molecular weight of 9500, a bromine number of 79, a melting point of 132 to 150°C, and IDAP:TAIC=
It was a copolymer prepolymer having a composition ratio (mol) of 0.443:0.557.

When the mixed solution of IDAP and TAIC collected in the same manner as in Example 1 was combined and the refractive index (n ²⁵ _D ) was measured,
1.5154, and it was found from the calibration curve 12 in FIG. 6 that this mixture had a composition ratio (mol) of IDAP:TAIC=0.520:0.480.

Example 6 Into a reactor similar to Example 1, 369.3 g of IDAP (1.5
mol) and 124.5 g (0.5 mol) of TAIC were added, and the reaction was carried out in the same manner as in Example 1. After 90 minutes, the viscosity of the reaction solution reached 1800 (CP/25℃), which indicates a polymerization rate of about 25%, based on the calibration curve 6 in Figure 3 obtained in advance by a similar reaction, so the air supply was stopped and the temperature was lowered to 140℃. cooled, 0.3mm
Mixture of IDAP and TAIC distilled under reduced pressure of Hg 250
g was collected. Three times the weight of methyl alcohol is poured into the distillation residue with stirring, and the precipitated solid is filtered off and dried to form a powdered prepolymer.
128.5g was obtained. This prepolymer is the result of analysis
It contained 4% IDAP and TAIC.

For comparison, similar reactions were performed with IDAP and
5 of the reaction solution without distilling TAIC.
When twice the amount of methyl alcohol was injected with stirring, a viscous liquid precipitated. Remove the supernatant by decanting and
After removing methyl alcohol from the remaining viscous liquid under reduced pressure and drying it, 143g of sticky semi-solid material was obtained.
was obtained, and analysis revealed that it contained 13.5% IDAP and TAIC.

Example 7 In a reactor similar to Example 1, 295.5 g of IDAP (1.2
A reaction was carried out in the same manner as in Example 1 by adding 199.2 g (0.8 mol) of TAIC and 199.2 g (0.8 mol) of TAIC. After 120 minutes, the viscosity of the reaction solution was 540 (CP/25°C), at which the polymerization rate was approximately 22%, based on the calibration curve 7 in Figure 3 obtained in advance by a similar reaction.
When the temperature reached 0.3, the air supply was stopped and the temperature was cooled to 140℃.
Mixture of IDAP and TAIC distilled under reduced pressure of mmHg
280g was recovered. Three times the weight of methyl alcohol was poured into the distillation residue with stirring, and the precipitated solid was suctioned off and dried to obtain 113.3 g of a powdered prepolymer. This prepolymer was analyzed to contain 3.8% IDAP and TAIC.

For comparison, similar reactions were performed and IDAP and TAIC
When methyl alcohol in an amount five times the amount of the reaction solution was directly injected with stirring without distilling it, a viscous liquid precipitated. The supernatant liquid was decanted, and the remaining viscous liquid was dried to remove methyl alcohol under reduced pressure, yielding 123.6 g of a sticky semi-solid substance, which was analyzed to contain 11.8% IDAP and TAIC. .

Example 8 369.4 g of IDAP (1.5
mol), 124.5 g (0.5 mol) of TAIC, and 2.47 g of benzoyl peroxide were added, and nitrogen gas was introduced using the oxygen introduction tube in Example 1 to create a nitrogen atmosphere.
The reaction was carried out at 80°C. After 120 minutes, the refractive index (n
^25D ) reached a polymerization rate of _1.5308 , which is about 22%, based on the calibration curve 8 in FIG. 4 obtained in advance by a similar reaction, and was cooled to room temperature. This reaction solution was poured into 2,500 ml of methyl alcohol with stirring, and the precipitated solid was filtered off by suction. The solid was washed three times with 100 ml of methyl alcohol and dried to obtain 98.8 g of prepolymer. This prepolymer has a number average molecular weight
11000, bromine number 65, melting point 113-119℃, IDAP:
It was a copolymer prepolymer having a composition ratio (mol) of TAIC=0.694:0.306.

[Brief explanation of the drawing]

Figure 1 shows a calibration curve showing the polymerization rate (%) and refractive index when diallyl orthophthalate and triallyl isocyanurate are polymerized in the presence of oxygen and under heating. The vertical axis is the refractive index (n ²⁵ _D ) and the horizontal axis is the polymerization rate (%). Figure 2 shows a calibration curve showing the polymerization rate (%) and refractive index when diallyl isophthalate and triallyl isocyanurate are polymerized in the presence of oxygen and under heating. The vertical axis is the refractive index (n ²⁵ _D) . )
and the horizontal axis is the polymerization rate (%). Figure 3 is a diagram showing a calibration curve showing the polymerization rate and viscosity when diallyl isophthalate and triallyl isocyanurate are polymerized in the presence of oxygen and under heating, and the vertical axis is 25°C.
Viscosity (CP/25℃) in centipoise at
The horizontal axis is the polymerization rate (%). Figure 4 shows a calibration curve showing the polymerization rate and refractive index when diallyl isophthalate and triallyl isocyanurate are polymerized in the presence of a radical generating catalyst (polymerization initiator), and the vertical axis is the refractive index (n ²⁵ _D ), and the horizontal axis is the polymerization rate (%). FIG. 5 is a diagram showing the relationship between the mixing ratio of diallyl orthophthalate and triallyl isocyanurate and the refractive index, where the left vertical axis represents the number of moles of diallyl orthophthalate, the horizontal axis represents the number of moles of triallyl isocyanurate, and The right side of the vertical axis is the refractive index (n ²⁵ _D ). FIG. 6 is a diagram showing the relationship between the mixing ratio of diallyl isophthalate and triallyl isocyanurate and the refractive index, where the left vertical axis represents the number of moles of diallyl isophthalate, and the horizontal axis represents the number of moles of triallyl isocyanurate. The right side of the vertical axis is the refractive index (n
^25D ₎ . In Figures 1 to 6, 1, 2, 3, 4, 5,
6, 7, 8, 9 and 12 are calibration curves. Fifth
In the figure, 10 indicates that the refractive index (n ²⁵ _D ) of a mixed solution of 1.3 mol of diallyl orthophthalate and 0.7 mol of triallyl isocyanurate is 1.5149, and 11 indicates diallyl orthophthalate:
The molar proportion of triallyl isocyanurate is approximately
This point shows that 0.675:0.325.

Claims (1)

[Claims] 1. A copolymer prepolymer comprising diallyl phthalate units and triallyl isocyanurate units obtained by polymerizing a mixture of diallyl phthalate and triallyl isocyanurate in the presence of oxygen or a radical polymerization initiator. A method for producing a copolymer prepolymer, which comprises producing a reaction mixture, and then treating the reaction mixture under reduced pressure to distill off unreacted diallyl phthalate and triallyl isocyanurate. 2. In the method for producing a copolymer prepolymer according to claim 1, the polymerization reaction is carried out at 150 to 200°C in the presence of oxygen, and then the reaction mixture is treated under reduced pressure of 0.5 mmHg or less. A method characterized by distilling off unreacted diallyl phthalate and triallyl isocyanurate. 3. In the method for producing a copolymer prepolymer according to claim 1 or 2, the refractive index or viscosity of the reaction mixture is measured, and when the measured value reaches a predetermined value, the polymerization reaction is started. A method characterized by stopping. 4. A method for producing a copolymer prepolymer according to any one of claims 1 to 3, characterized in that diallyl phthalate is diallyl orthophthalate or diallyl isophthalate. 5 A mixture of diallyl phthalate and triallyl isocyanurate was polymerized in the presence of oxygen or a radical polymerization initiator to produce a reaction mixture containing a copolymer prepolymer consisting of diallyl phthalate units and triallyl isocyanurate units. After that, the reaction mixture is treated under reduced pressure to distill off unreacted diallyl phthalate and triallyl isocyanurate, and then the copolymer prepolymer that has undergone the reduced pressure treatment is treated to dissolve diallyl phthalate and triallyl isocyanurate. A method for producing a copolymer prepolymer, which comprises treating the copolymer prepolymer with a solvent that does not dissolve the copolymer prepolymer to extract and remove unreacted diallyl phthalate and triallyl isocyanurate in the copolymer prepolymer. 6. In the method for producing a copolymer prepolymer according to claim 5, the polymerization reaction is carried out at 150 to 200°C in the presence of oxygen, and then the reaction mixture is treated under reduced pressure of 0.5 mmHg or less. A method characterized by distilling off unreacted diallyl phthalate and triallyl isocyanurate. 7. In the method for producing a copolymer prepolymer according to claim 5 or 6, the refractive index or viscosity of the reaction mixture is measured, and when the measured value reaches a predetermined value, the polymerization reaction is started. A method characterized by stopping. 8. A method for producing a copolymer prepolymer according to any one of claims 5 to 7, characterized in that diallyl phthalate is diallyl orthophthalate or diallyl isophthalate.