JP2000256377A - New phosphoric ester and mold-releasing agent comprising the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new phosphoric ester useful as a mold-releasing agent capable of providing a resin molded product excellent in transparency and mold-releasability. SOLUTION: The new compound is a phosphoric ester of formula I (R1 is a 1-20C residue after removing phenyl; R2 and R3 are each H, methyl or ethyl with the proviso that the case in which both of R2 and R3 are H is excluded), e.g. di(1-n-butoxy-2-propyl)phosphate. The compound of formula I is obtained, for example, by reacting an epoxy compound such as 1,2-propylene oxide with a hydroxy compounds such as alcohols to synthesize hydroxyalcohols, further reacting the hydroxyalcohols with a phosphorus oxyhalide to provide a halide of the phosphoric ester of formula II (X is a halogen), and hydrolyzing the obtained halide. A transparent resin obtained by adding a mold-releasing agent obtained by adding the compound of formula I to a transparent resin composition and curing the composition allows the obtained molded product therefrom to be easily released from a mold, and is useful as a transparent optical material such as a plastic lens.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a phosphoric ester useful as a mold release agent, a method for producing the same, and a transparent resin composition, a transparent resin, a transparent optical material, and a plastic lens containing the phosphoric ester.

[0002]

2. Description of the Related Art A transparent resin generally has a transparency comparable to that of glass and a higher impact strength than glass. For example, a window glass for an aircraft, a headlight cover for an automobile,
It is used in fields such as drinking water containers, sealants, liquid crystal panels, optical disks, optical fibers, and plastic lenses.

[0003] Types of general transparent resins include olefin resins such as polyvinyl chloride, polypropylene, PMMA, and (meth) acrylic resins, polyene-polythiol resins, polyester resins, polycarbonate resins, epoxy resins, and polyurethane resins. Can be

[0004] Usually, these transparent resins are molded by injection molding or cast polymerization.

[0005] In any of the molding methods, a product cannot be obtained unless the resin is released from the mold.

However, when those resins are molded without a release agent, an excessive stress is applied at the time of release, so that
In many cases, undesirable results such as deformation of the molded product, such as warpage, and generation of optical distortion inside, are given.

Further, the epoxy resin and the urethane resin are
As can be seen from the fact that it is also used as an adhesive, it is known as a resin having extremely strong adhesive force. When a metal or glass mold is used, the use of a mold release agent is usually essential.

[0008] The release agent includes an external release agent which is applied to the surface of a molding die by using a spray or the like, and an internal release agent which is previously added to a raw material monomer. As the external release agent, not only the operation is complicated, but also there is a problem that the release film is difficult to be constant and the surface accuracy is reduced. Therefore, the internal release agent is preferably used.

Conventionally known compounds as these internal release agents include aliphatic alcohols, fatty acid esters, triglycerides, fluorine-based surfactants, metal salts of higher fatty acids, and the like. There are drawbacks such as difficulty in releasing from the mold, turbidity inside the resin and on the surface, and easily impairing the original transparency of the resin.

The loss of transparency is particularly problematic in a molded article made of a transparent resin utilizing high transparency. Among them, a plastic lens which can be out of spec even with a slight cloudiness which cannot be judged by ordinary eyes. In the field of optical materials typified by, there has been a very fatal drawback.

Various methods have been proposed to solve this problem.

For example, a method using an alkoxyalkyl phosphoric acid ester (Japanese Patent Publication No. 6-20754, Japanese Patent Application Laid-Open No.
JP-A-287641), a method using a phosphinic acid ester (JP-A-58-49747), and the like. The present inventors have also proposed a method using an acid phosphate (Japanese Patent Publication No. 7-77733), a method using thiophosphates (Japanese Patent Application Laid-Open No. 5-306320), and a method using an acidic phosphonic acid derivative (Japanese Patent Application Laid-open No. -57864) and the like.

However, even if these methods are used,
Transparency is still strictly insufficient or colored,
If the release agent itself has a high viscosity, it is difficult to use, or it has an unpleasant odor, or if the resin has an extremely strong adhesive force, the usual amount of the resin may cause poor release properties or improve the release properties. There is a problem that the resin becomes cloudy when a large amount of the release agent is used. In addition, even with a release agent that has cleared coloring, release properties, transparency, etc., the range in which it can be used in terms of quality is extremely narrow. In some cases, it was necessary to select a suitable lot. Furthermore, problems may occur during secondary processing, such as uneven dyeing and reduced adhesion of the hard coat.

Usually, if an acidic phosphonic acid derivative is used,
Often gives better results. However, when this acidic phosphonic acid derivative is used in a special method for performing urethane polymerization uniformly and in a short time by using a Lewis acid and a tertiary amine in combination (Japanese Patent Application Laid-Open No. 8-208792), the transparency is low. It tends to be easily damaged, and it has been difficult to say that the conventional method is sufficiently satisfactory.

[0015]

That is, an object of the present invention is to provide a resin molded product having better transparency and mold releasability than a resin molded product obtained by using a conventional release agent. An object of the present invention is to provide a releasing agent that can be used and a high-quality transparent resin having excellent transparency.

[0016]

Means for Solving the Problems In view of the above problems, the present inventors have conducted intensive studies, and as a result, have found a novel compound, a phosphoric ester, and used the phosphoric ester and its composition as a releasing agent for a transparent resin. Using the above, the above problem was solved, a high-quality transparent resin was found to be obtained, and the present invention was reached.

That is, the present invention provides the following formula (1)

[0018]

Embedded image (Wherein, R ₁ represents a residue having 1 to 20 carbon atoms excluding a phenyl group, and R ₂ and R ₃ each independently represent a hydrogen atom, a methyl group or an ethyl group, provided that R ₂ and R ₃ And a method for producing the phosphoric acid ester, a releasing agent containing the phosphoric acid ester, a transparent resin composition containing the phosphoric acid ester, a transparent resin, and a transparent optical resin. It consists of a material, especially a plastic lens.

[0019]

DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below in detail. The phosphoric ester of the formula (1) according to the present invention is a phosphoric diester having an alkylethylene glycol skeleton.

R ₂ and R ₃ in the formula (1) represent hydrogen, a methyl group or an ethyl group, except that both R ₂ and R ₃ are hydrogen. When both R ₂ and R ₃ are hydrogen, the releasability is reduced as compared with the phosphoric diester of the present invention in which at least one or both are substituted with a methyl group or an ethyl group.

The R ₁ residue represented by the formula (1) is a hydrocarbon residue having 1 to 20 carbon atoms excluding a phenyl group. Phenyl groups can cause the resin to color. If the number of carbon atoms exceeds 20, transparency may decrease. Preferably it is in the range of 3 to 15.

The residue represented by R ₁ is required to have 1 to 20 carbon atoms except for the phenyl group. Therefore, typical forms of the residues will be described below, but the present invention is not limited to these forms.

Examples of the form of the residue include a linear saturated alkyl group, a linear unsaturated alkyl group, a branched saturated alkyl group, a branched unsaturated alkyl group, a linear saturated alkylaryl group, Unsaturated alkylaryl group, arylalkyl group, arylalkylene group, alkylarylalkylene group and the like. In addition, there is no problem with heteroatoms and heterostructures such as an ether bond, a thioether bond, a sulfoxy bond, a sulfone bond, an ester bond, a carbonyl bond, an amide bond, an imide bond, a hetero ring, and a cycloalkylene group ring in the residue. It may be included in the range. Further, some of the hydrogen atoms constituting these residues may be replaced with halogen atoms such as fluorine, chlorine, and bromine as far as no problem occurs.

The phosphoric diester of the formula (1) according to the present invention is synthesized, for example, by the following method.

1,2-propylene oxide, 1,2-
Epoxy compounds such as epoxybutane, 2,3-epoxybutane, and 3,4-epoxyhexane, and alcohols;
By reacting an oxyalcohol obtained by reacting a hydroxy compound represented by a phenol except phenol with a phosphorus oxyhalide, the following formula (2)

[0026]

Embedded image (Wherein, R ₁ represents a residue having 1 to 20 carbon atoms excluding a phenyl group, and R ₂ and R ₃ each independently represent a hydrogen atom, a methyl group or an ethyl group, provided that R ₂ and R ₃ Excluding the case where all are hydrogen atoms. X represents a halogen atom.)
Is obtained by synthesizing a phosphoric acid ester halide represented by the following formula, followed by hydrolysis. When the hydrolysis is carried out at PH = 8 or less, preferable results are obtained.

When it is desired to synthesize selectively, instead of phosphorus oxyhalide, a phosphorus trihalide such as phosphorus trichloride is reacted with an oxyalcohol to synthesize a phosphite diester. Next, by-produced oxyhalogenide is distilled off and removed from the system by a purification operation such as distillation under reduced pressure, and then reacted with halogens such as chlorine to produce a halogenophosphorous diester. It is obtained by hydrolysis in the same manner as when used.

The manufacturing method of each step will be described below with a specific example.

[0029]

Embedded image

By reacting 1,2-propylene oxide of the formula (B) with 1-butanol of the formula (A), which is an alcohol, 1-butoxy-2-propanol of the formula (C), which is an oxyalcohol, is synthesized. I do. The reaction temperature of the addition reaction for synthesizing oxyalcohols varies considerably depending on, for example, the difference in acidity, such as whether the hydroxy group is alcoholic or phenolic.
0 ° C is preferred, and 30 to 150 ° C is particularly preferred.

For the purpose of improving the reaction rate, bases such as sodium hydroxide, sodium carbonate, potassium hydroxide, potassium carbonate, triethylamine, pyridine and the like may be added as a catalyst. The addition amount is 0.001 to the reaction solution.
The range is preferably from 5 to 5% by weight, and more preferably from 0.05 to 3% by weight.

Although the reaction proceeds without using a reaction solvent, when it is used, an aprotic solvent such as acetonitrile, toluene, dichloroethane, chlorobenzene, dimethylformamide and the like is preferable.

The raw materials 1-butanol and 1-butoxy-2 were used for the purpose of improving the selectivity and suppressing a rapid rise in the internal temperature.
-Either or both of propanol and 1,2-propylene oxide may be dropped.

The thus obtained 1-butoxy-2-propanol of the formula (C) may be used as it is in the next reaction, but is usually purified by distillation in many cases.

The di (1-butoxy-2-propyl) phosphate halide of the formula (E) belonging to the phosphate halides of the formula (2) according to the present invention is a compound of the formula (C).
It is obtained by reacting propanol with phosphorus oxyhalide of the formula (D) represented by phosphorus oxychloride, phosphorus oxybromide and the like. Among the phosphorus oxyhalides, economically advantageous phosphorus oxychloride is preferably used.

The molar ratio of 1-butoxy-2-propanol of the formula (C) to phosphorus oxyhalides of the formula (D) is about 1.5 to 2.5 (C / D), particularly preferably 1 to 2.5 (C / D). .8-
2.2 (C / D).

The reaction temperature is preferably from 0 to 100 ° C.,
It is more preferable that the temperature is 60 ° C to 60 ° C. If it exceeds 100 ° C., it may be markedly colored.

For the purpose of improving the reaction rate, bases such as sodium hydroxide, sodium carbonate, potassium hydroxide, potassium carbonate, triethylamine, pyridine and the like may be added as a hydrogen halide catching agent. In particular, when a tertiary amine such as triethylamine or pyridine is used, preferable results are obtained. The amount of the base to be used is preferably 0.5 to 2.0 equivalents relative to the hydroxy group of 1-butoxy-2-propanol of the formula (C) which is an oxy alcohol.

When a base is not used, it is preferable not to use a reaction solvent. When a base is used, it is often convenient to use a reaction solvent.For example, a solvent that separates from water such as benzene, toluene, dichloroethane, chlorobenzene, dichlorobenzene, butyl acetate, and methyl isobutyl ketone is preferably used. Can be

For the purpose of improving selectivity and suppressing a rapid rise in internal temperature, 1-butoxy-2-propanol of the formula (C), which is an oxyalcohol, and a base are simultaneously added dropwise,
Alternatively, all three of phosphorus oxyhalides, 1-butoxy-2-propanol, and a base may be simultaneously dropped.

The di (1-butoxy-2-propyl) of the formula (F) belonging to the phosphoric diester of the formula (1) according to the present invention
Phosphoric acid is a di (1-butoxy-2-propyl) of the formula (E)
It is obtained by hydrolyzing a phosphate halide.

Hydrolysis includes aqueous sodium hydroxide, aqueous sodium carbonate, aqueous sodium hydrogen carbonate, aqueous potassium hydroxide, aqueous potassium carbonate, aqueous sodium phosphate, aqueous sodium acetate, aqueous ammonia, water, aqueous acetic acid, hydrochloric acid, sulfuric acid, and the like. Although various bases and acids can be used, the pH of the hydrolysis is 8 or less,
Further, it is preferably 7 or less. Even if hydrolysis is carried out in a state where the pH exceeds 8, the performance of the release agent is sufficiently satisfactory, but the obtained product is colored or a side reaction other than hydrolysis occurs. There is a less preferred.

As a kind of the hydrolyzing agent, water is preferable in view of economy, quality and operability. Further, it is often the case that the hydrolysis is carried out while bubbling the reaction solution with nitrogen to give a preferable result.

The reaction temperature during the hydrolysis is preferably from 0 to 100 ° C, more preferably from 30 to 70 ° C.

In the case of hydrolysis, for the purpose of, for example, suppressing a rapid increase in internal temperature, a hydrolyzing agent such as water is added to the compound of the formula (E).
The method of dropping di (1-butoxy-2-propyl) phosphoric acid halide or a reaction solution thereof often gives more preferable results.

The reaction solution thus obtained is purified, if necessary, by an adsorption treatment represented by washing, filtration, activated carbon treatment and the like, and a distillation operation such as desolvation. -Butoxy-2-propyl) phosphoric acid is obtained.

Alternatively, the phosphoric diester of the formula (1) according to the present invention forms a monoester at the same time.
It can also be obtained by reacting a hydroxy compound with diphosphorus pentoxide.

Examples of the phosphoric diester according to the present invention including the formula (F) include the following compounds.

Representative compounds include, for example, di (1-
Methoxy-2-propyl) phosphoric acid, di (1-ethoxy-2)
-Propyl) phosphoric acid, di (1-propoxy-2-propyl) phosphoric acid, di (1-butoxy-2-propyl) phosphoric acid, di (1-hexyloxy-2-propyl) phosphoric acid, di (1-octyloxy-2-propyl) ) Phosphoric acid, di (1-nonyloxy-2-propyl) phosphoric acid, di (1-decaloxy-2-propyl) phosphoric acid, di (1-dodecanoxy-2-propyl) phosphoric acid, di (1-tetradecaloxy-2-propyl) )phosphoric acid,
Di (1-hexadecaloxy-2-propyl) phosphoric acid, di (1-stearoxy-2-propyl) phosphoric acid, di (1-eicosaloxy-2-propyl) phosphoric acid, di (1-benzyloxy-2-propyl) phosphoric acid, Di (1-butylphenoxy-2-propyl) phosphoric acid, di (1-hexylphenoxy-
2-propyl) phosphoric acid, di (1-octylphenoxy-2)
-Propyl) phosphoric acid, di (1-nonylphenoxy-2-propyl) phosphoric acid, di (1-butoxy-2-butyl) phosphoric acid,
Di (2-butoxy-3-butyl) phosphoric acid, di (1-nonylphenoxy-2-butyl) phosphoric acid, di (2-nonylphenoxy-3-butyl) phosphoric acid, etc., as well as fluorine-substituted phosphoric acid diesters, Halogen-substituted products such as chlorine-substituted products and bromine-substituted products are also included. The phosphoric diester of the present invention,
It is not limited only to these listed compounds.

The release agent of the present invention is a phosphoric ester composition which essentially contains at least the phosphoric diester represented by the formula (1). For example, in addition to the phosphoric diester represented by the formula (1), monoesters, triesters, phosphoric acids, hydroxy compounds, water, metals, metal salts, organic metal salts, and other phosphoric esters within a range without any problem. Further, for the purpose of lowering the viscosity to improve operability and dispersibility, and increasing the solubility in monomers and polymers, for example, a hydrocarbon solvent represented by hexane or the like; Allyl) alcohol and alkoxy (allyloxy) alkyl (allyl) alcohols and their ethers and esters, benzene derivatives represented by toluene, xylene, etc., halogen solvents such as dichloromethane, chloroform, dichloroethane, chlorobenzene, dichlorobenzene, acetone , Methyl ethyl ketone, tetrahydrofuran, N,
Similarly, aprotic polar solvents represented by -dimethylformamide, N, N-dimethylimidazolidinone and the like may be similarly contained within a range without any problem.

The form of use of the release agent of the present invention may be an internal release agent method which is previously added to the monomer or an external release agent method which is previously applied to a molding die. A mold system is preferably used.

The transparent resin according to the present invention is a transparent resin containing an organic compound as a main component, for example, an olefin resin, an epoxy resin, a urethane resin, a carbonate resin,
Ester resin, olefin-thiol resin, epoxy-
Examples thereof include thiol resins and transparent resins used in combination with them. However, the present invention is not limited to only the resins listed above, but is particularly effective for polythiourethane resins.

The release agent of the present invention is used, for example, as follows. The molding modes are roughly classified into approximately three types: an injection molding method, an injection cure method, and a casting polymerization method. Operations performed for all three types will be described first.

The phosphoric diester of the present invention or a releasing agent containing the phosphoric diester is added to the raw material monomer, oligomer, or polymer pellets, and if necessary, mixed and dissolved by heating. The amount of the release agent to be added cannot be limited because it greatly varies depending on the raw material, but it is approximately 0.0001 to 3.
0% by weight.

Next, if necessary, defoaming is performed by an appropriate method such as decompression, and the resulting mixture is poured into a molding die and cured to take out a transparent resin molded product. The resulting transparent resin removes distortion,
In order to complete the polymerization more completely, usually about 100 ° C
Annealing is performed at the above temperature.

Hereinafter, each of the above-described three embodiments will be briefly described individually.

In the case of injection molding often used for olefin, polycarbonate, polyester resin, etc.,
After adding a release agent to the pellets and heating and dissolving them at about 100 to 400 ° C., the molten liquid is poured into a metal mold mainly and cooled to harden the transparent resin.

In the case of the injection cure method often used for some urethane resins and epoxy resins,
A metal mold is mainly used, a mold release agent, a curing agent, etc. are added to the monomer composition, defoaming is performed under reduced pressure, etc., and then immediately injected into the mold before the resin is cured, followed by thermosetting. Let it.

Casting polymerization often used for precision molding of most resins including urethane and olefin resins is as follows:
After adding a release agent to the monomer composition and defoaming by decompression etc., the defoaming liquid is poured into a glass mold consisting mainly of a glass mold and a resin gasket or tape, and polymerized by heat or radiation Let it cure.

The conditions for the heat polymerization are approximately 0 to 200.
The temperature is gradually raised from a low temperature to a high temperature in a temperature range of ° C., and is completed in about 1 to 100 hours.

In the case of radiation polymerization, ultraviolet rays of 400 nm or less are mainly used. The amount of ultraviolet rays is about 1-10
In many cases, irradiation is performed at an intensity of 00 mJ / sec for 1 to 7200 seconds, and sometimes cooling or irradiation is performed several times before irradiation for the purpose of heat removal or obtaining a molded product that is optically uniform.

In some cases, thermal polymerization and radiation polymerization are combined. The present invention provides, in the case of the cast polymerization,
Be more effective.

In the above molding method, a heat catalyst, a photocatalyst,
Organic compounds and inorganic compounds other than raw materials such as UV absorbers, antioxidants, polymerization inhibitors, oil-soluble dyes, fillers, plasticizers, other release agents, and solvents can be added within a range without any problem.

Further, the obtained transparent resin, transparent optical material,
In addition, plastic lenses have surface polishing, antistatic treatment, hard coating, etc. to improve anti-reflection, high hardness, abrasion resistance, chemical resistance, anti-fog, or fashion, if necessary. Physical or chemical treatment such as treatment, anti-reflection coating treatment, and light control treatment can be performed.

[0065]

The present invention will be described below in more detail with reference to examples and comparative examples. The refractive index, Abbe number, degree of coloring, transparency, releasability, and surface state of the obtained transparent resin were evaluated by the following test methods.

Refractive index and Abbe number: Measured at 20 ° C. using a Pulfrich refractometer. Coloring degree: A 9 mm flat plate was prepared, YI was measured with a Minolta colorimeter, and 4.5 or less was evaluated as (○) and that exceeding 4.5 as (X). Transparency: A circular flat plate having a thickness of 9 mm and a diameter of 75 mm was prepared, and the measurement was performed using a light and shade image device. C average 50
The following items were evaluated as (x) and those exceeding 50 (x). -Releasability: Evaluated using a glass mold having an outer diameter of 84 mm and a height of 17 mm, an outer diameter of 84 mm and a height of 11 mm, and a convex mold made of tape. After 5 sets were charged and the polymerization was completed, the mixture was allowed to cool to room temperature, and when three or more sheets released naturally (○), three or more sheets required excessive force,
The case where the glass mold was damaged or peeled was evaluated as (x).

Example 1 (Synthesis of phosphoric acid diester-1) 300.0 g of phosphorus oxychloride was placed in a 3 liter reaction flask.
(1.96 mol) and 1200 ml of toluene
517.3 g of n-butoxy-2-propanol (3.
A mixture of 91 mol) and 680.0 g (8.60 mol) of pyridine was added dropwise over 4 hours at an internal temperature of 40 to 45 ° C while stirring under ice cooling, and the mixture was aged at 45 to 50 ° C for 2 hours. The obtained reaction solution was filtered, and the filter cake was washed with 800 ml of toluene. The mixture of the filtrate and the washing solution was desolvated under reduced pressure, and crude di (1-n-butoxy-2-propyl) phosphoric acid chloride 5
66.9 g were obtained.

Next, the resulting crude di (1-n-butoxy-2-propyl) phosphoric acid chloride was subjected to 0.1 g at an internal temperature of 50 to 60 ° C. while bubbling nitrogen into a 3 l reaction flask charged with 900 g of water. The solution was dropped in 5 hours, and aged at 60 ° C. for 5 hours (PH = 1 or less).

After nitrogen bubbling was continued until the mixture was cooled to room temperature, 1000 ml of toluene was added thereto to carry out extraction and separation. The upper organic layer was washed with 300 ml of 5% aqueous hydrochloric acid and then with 300 ml of water. Next, 10 g of activated carbon (Shirasagi C) was added to the upper organic layer, and the mixture was stirred at room temperature for 1 hour and filtered. The obtained filtrate is further added to 300 ml of water.
, And the solvent was removed under reduced pressure.

Finally, the residue was filtered (3 μm mesh) at room temperature to obtain 383.4 g (60% crude yield) of a phosphoric ester. The composition of the obtained phosphoric ester was as follows.

[0071]

[Table 1]

The identification data of the diester obtained by purification by silica gel column chromatography is described below. <MS spectrum (FD (Pos.))> M / z = 327 (M + 1) + < ^13C -NMR> See FIG.

Example 2 m-xylylene diisocyanate (364 g, 1.93 mol) and dibutyltin dichloride 0.070 g (100 pp)
0.70 g of the phosphoric ester of Example 5 in the mixture of m)
(1000 ppm) and mixed and dissolved under nitrogen. Next, 336 g (1.29 mol) of 1,2-bis (2-mercaptoethylthio) -3-propanethiol was added to this solution.
Was added and mixed, and mixed and defoamed under reduced pressure. After defoaming, inject into the prepared mold beforehand,
The temperature was gradually increased from room temperature to 120 ° C., and the composition was cured by heating for 20 hours.

After cooling, the lens obtained by releasing the mold was colorless and transparent, and had a refractive index Nd = 1.660 and an Abbe number νd = 32. Table 2 shows the evaluation results of the release agents.

Examples 3 to 6 and Comparative Examples 1 to 7 The same tests as in Example 2 were carried out by changing the amount and type of the release agent. Table 7 shows the results.

[0076]

[Table 2]

Release agent (a): "Zelek U" manufactured by DuPont
N "Lot 26 Release Agent (b):" XELEC UN "Lot 4 manufactured by DuPont
97 Release agent (c): "Zelek UN" lot 5 manufactured by DuPont
48 Release agent (d): "JP-506H" manufactured by Johoku Chemical Release agent (e): "Plysurf A212" manufactured by Daiichi Kogyo Chemical
E "

[0078]

Embedded image

[0079]

[Table 3]

[0080]

Embedded image

[0081]

According to the present invention, a transparent resin is easily released from a molding die, and a product having extremely high transparency can be obtained.

[Brief description of the drawings]

FIG. 1 is a ¹³ C-NMR chart of the phosphoric diester of the present invention obtained in Example 1.

 ────────────────────────────────────────────────── ─── Continuing on the front page (72) Inventor Yoshinobu Kanemura 30 Asamuta-cho, Omuta-shi, Fukuoka Prefecture F-term (reference) 4F202 AA03 AA28 AB07 AH74 CA11 CB01 CM55 4H050 AA01 AA02 AA03 AB48 WA15 WA23 4J002 BB121 BD041 BG041 BG051 BG061 CD001 CF031 CG001 CK021 EW046 EW056 FD166 GG01 GN00 GP01 GP02 GQ05 GS02

Claims (8)

[Claims] [Claim 1] The following formula (1) (Wherein, R ₁ represents a residue having 1 to 20 carbon atoms excluding a phenyl group, and R ₂ and R ₃ each independently represent a hydrogen atom, a methyl group or an ethyl group, provided that R ₂ and R ₃ Except when both are hydrogen atoms). 2. The following formula (2): (Wherein, R ₁ represents a residue having 1 to 20 carbon atoms excluding a phenyl group, and R ₂ and R ₃ each independently represent a hydrogen atom, a methyl group or an ethyl group, provided that R ₂ and R ₃ Excluding the case where all are hydrogen atoms. X represents a halogen atom.)
The method for producing a phosphate according to claim 1, wherein the phosphate halide represented by the formula is hydrolyzed. 3. A release agent containing the phosphoric ester according to claim 1. 4. A transparent resin composition containing the release agent according to claim 3. 5. A transparent resin obtained by curing the transparent resin composition according to claim 4. 6. A transparent resin obtained by using the release agent according to claim 3 as an external release agent and curing the transparent resin composition. 7. The transparent optical material according to claim 5, wherein the transparent resin is a transparent optical material.
Or the transparent resin according to 6. 8. The transparent resin according to claim 7, wherein the transparent optical material is a plastic lens.