WO1999049338A1 - Optical material, process for producing the same, and applied apparatus - Google Patents

Abstract

An optical material made of a resin containing a large amount of ions of a rare earth metal regardless of the kind of the metal; and a process for producing the material. The optical material is characterized by comprising an acrylic resin containing: phosphate groups derived from a monomer containing a phosphate group; optionally substituted amino groups; and a metal ion ingredient comprising rare earth metal ions. The process is characterized by comprising the step of polymerizing a monomer composition comprising a monomer containing a phosphate group and at least either of an aminated monomer and an amino compound.

Description

 Description Optical material, its manufacturing method and applied equipment

 The present invention relates to an optical material and a method for producing the same, and more specifically, can absorb light in a specific wavelength region with high efficiency, and has an anti-glare function, a high contrast function, a color purity correction function, a brightness suppression function, and the like. The present invention also relates to a synthetic resin optical material having a fluorescence emission function and a light amplification function, which can emit light in a specific wavelength range with high efficiency, and a method for manufacturing the optical material. Background technology

 Conventionally, attempts have been made to add a metal ion to a transparent material such as glass to impart specific optical characteristics to the transparent material by the metal ion.

 As a metal ion for imparting optical characteristics, a rare-earth metal ion has the property of sharply absorbing light in a specific wavelength range, and has the property of emitting a unique fluorescence, and thus is useful. Is high. For example, it is known that trivalent neodymium ions have a characteristic of sharply absorbing light near a wavelength of 580 nm, and glass optical materials containing such neodymium ions have excellent protection. As an optical material having glare, for example, it is used for anti-glare spectacle lenses, anti-glare filters used in televisions, etc., brightness adjustment filters for lighting equipment, color tone correction filters, and the like.

 In addition, rare earth metals such as erbium, neodymium, and praseodymium are considered to be useful as materials for expressing the functions of optical amplifiers in the optical communication field, and optical amplifiers obtained by introducing these rare earth metals into glass substrates have been put into practical use. ing.

Recently, a resin optical material in which a neodymium ion is contained in a resin base material such as an acrylic resin has been proposed (for example, Japanese Patent Application No. 7-232732, (See Japanese Patent Application No. 7-2889628). In such an optical material, in order to disperse metal ions in a resin material, an acrylic resin in which a phosphate group is chemically bonded in the structure of the polymer is used as the resin material.

 Therefore, in optical materials containing rare earth metal ions, it is necessary to further increase the content ratio of rare earth metal ions in order to further improve the optical function and expand the application field.

 However, in the above resin optical material, rare earth metal ions cannot be contained in the acrylic resin at a high ratio, so that when the optical material is used for an optical product having a small thickness, the optical material by the rare earth metal ion is used. However, there is a problem that the mechanical characteristics are not sufficiently exhibited.

 Also, in order to enhance the dispersibility of rare earth metal ions, it is necessary to include a high proportion of phosphate groups in the structure of the polymer constituting the acrylic resin. Because of its high water absorption, it cannot be used practically as an optical material.

 In order to solve such a problem, the present inventors have proposed an optical material in which a phosphoric acid group, an amide group, and a rare earth metal ion are contained in an acrylic resin (Japanese Patent Application No. Hei 8 (1996)). — Refer to the specification of Japanese Patent Application Publication No.

 Then, it was confirmed that by including an amide group in the acrylic resin together with the phosphoric acid group, it was possible to introduce rare earth metal ions into the acrylic resin at a relatively high rate.

 However, even with the techniques described above, a sufficient amount of rare earth metal ions cannot be introduced into the resin depending on the type of rare earth metal.

For example, according to an acrylic resin containing a phosphoric acid group and an amino-de-group, but may contain a neodymium ion in a proportion of 2 0 wt _^0/0 or more, about 5% by weight relative to Erubiumui on Can only be contained.

In addition, when erbium is dissolved in a mixture of a phosphoric acid group-containing monomer and a compound containing an amide group in order to make the acrylic resin contain erbium ions, the erbium ion must be dissolved at room temperature for a long time. Requires dissolution operation, and can be obtained after dissolution The monomer composition becomes turbid or a microgel is formed, so that a uniform monomer composition cannot be obtained. Disclosure of the invention

 [Problems to be solved by the invention]

 The present invention has been made based on the above circumstances.

 A first object of the present invention is to provide an optical material having a resin component capable of dispersing a rare earth metal ion at a high ratio regardless of the type of the rare earth metal.

 A second object of the present invention is to provide a resin optical material containing a high proportion of the rare earth metal ion regardless of the type of the rare earth metal.

 A third object of the present invention is to provide a resin optical material in which rare earth metal ions are dispersed and contained in an acrylic resin in a uniform and high ratio.

 A fourth object of the present invention is to provide a resin optical material that can absorb light in a specific wavelength range with high efficiency.

 A fifth object of the present invention is to provide a resin optical material capable of emitting light in a specific wavelength range with high efficiency and having excellent fluorescence emission function and optical amplification function. The purpose of 6 is to provide a resin optical material having low water absorption.

 A seventh object of the present invention is to provide a method for producing an optical material having a resin component capable of dispersing rare earth metal ions at a high ratio.

 An eighth object of the present invention is to provide a method for producing a resin optical material containing a high proportion of rare earth metal ions.

 [Means for solving the problem]

The present invention can increase the dispersibility of rare-earth metal ions in the acryl-based resin by including an amino group together with a phosphate group in the acrylic resin. Heading that you can do It was completed based on strong knowledge.

 That is, the optical material of the present invention contains a phosphate group derived from a phosphate group-containing monomer, a substituted or unsubstituted amino group, and a metal ion component containing a rare earth metal ion in the acrylic resin. It is characterized by being done.

Further, the optical material of the present invention contains a phosphate group-containing monomer represented by the following formula (1) and an ataryl resin obtained by copolymerizing a monomer copolymerizable therewith. It is characterized by having. Equation (1): P 0 (OH) _n R '〗 ₃ — _n

Wherein, R ^'1 _{is, H 2 C = C (X} ) C OO (R 12 - 0) m one

(X represents a hydrogen atom or a methyl group, R ′ ² represents a hydrocarbon group having 1 to 18 carbon atoms, and m is an integer of 1 to 5.)

n is 1 or 2. Further, the optical material of the present invention comprises a phosphate group-containing monomer represented by the above formula (1), an amino group-containing monomer represented by the following formula (2), and It is characterized by containing an acryl-based resin obtained by copolymerizing a monomer copolymerizable with the above.

Formula (2): R ²¹ -N-R ²³

Wherein R ²¹ , R ²² and R ²³ are each

 Hydrogen atom, alkyl group having 1 to 6 carbon atoms, phenyl group,

H ₂ C-C (X) COOR ^24-

(X represents a hydrogen atom or a methyl group, and R ²⁴ represents a hydrocarbon group having 1 to 18 carbon atoms.)

_{H 2 C = C (X)} C ONHR 25 -

(X represents a hydrogen atom or a methyl group, and R ²⁵ represents a hydrocarbon group having 1 to 18 carbon atoms.)

 These can be the same or different,

At least one is H ₂ C = C (X) CO〇R ²⁴ — or

H _z C = C (X) A group represented by CONHR ²⁵ —. Further, the optical material of the present invention is characterized by containing an amino group-containing compound represented by the following formula (3). Formula (3): R ³¹ — N— R ³³

 I

(In the formula, R ^3I and R ³³ each represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a fluorine group, which may be the same or different.)

Further, the optical material of the present invention is characterized by containing an amino group-containing compound represented by the following formula (4). Equation (4): R ⁴ '—N—R "—N—

 I I

(Wherein, R ″, RR ⁴³ and each represent a hydrogen atom, an alkyl group or a phenyl group, which may be the same or different.

 Represents an alkylene group. )

In the optical material of the present invention, the total mass of the acrylic resin and the amino group-containing compound is “R”, the mass of the phosphate group is “A”, the mass of the substituted or unsubstituted amino group is “B”, Assuming that the mass of the ionic component is “M”, it is preferable that the following conditions (a) to (c) are satisfied.

 [B] [(A + B) / R]>: The direct value of 100 must be 0.05 to 50, especially 0.1 to 40.

 [Mouth] [BZ (A + B)] X100 should be 10-70, especially 12-60.

 [C] The value of (M / R) X 100 is 0.005 to 43, especially 0.01 to 35.

 Further, in the optical material of the present invention, it is preferable that at least one rare earth metal ion selected from the group consisting of praseodymium ion, neodymium ion and erbium ion is contained in the acryl-based resin.

 The production method of the present invention comprises a monomer composition containing a phosphate group-containing monomer represented by the above formula (1) and an amino group-containing monomer represented by the above formula (2). The method includes a step of performing a polymerization treatment.

 In addition, the production method of the present invention comprises the step of preparing a phosphate group-containing monomer represented by the above formula (1), a monomer copolymerizable therewith, and a process represented by the above formula (3) or (4). And polymerizing the monomer composition containing the amino group-containing compound.

In the production method of the present invention, the monomer mixture is superposed in the presence of rare earth metal ions. It is preferable to perform a joint treatment.

 The wavelength conversion material of the present invention is characterized by comprising the optical material of the present invention. The fluorescent light emitting material of the present invention is characterized by comprising the optical material of the present invention. The anti-glare glasses of the present invention are characterized by being made of the optical material of the present invention.

 Applied equipment of the present invention (optical isolator · optical amplifier · color image display device · color image pickup device, lighting equipment) comprises the optical material of the present invention.

[Embodiment of the invention]

 Hereinafter, the present invention will be described in detail.

 In the optical material of the present invention, the acrylic resin contains a phosphate group derived from a phosphate group-containing monomer, a substituted or unsubstituted amino group, and a metal ion component containing a rare earth metal ion. It becomes.

 In the present invention, the “phosphate group” refers to a group represented by P O (OH) „— (n is 1 or 2).

In the present invention, “substituted or unsubstituted amino group” refers to a group represented by the following formula (5). Equation ^{(5): R 5 1 -} N -

R ^{5 2}

(Wherein R ⁵¹ and R ⁵² are each a hydrogen atom, a substituted or

Indicates an unsubstituted alkyl group or phenyl group. The rare earth metal ions constituting the optical material of the present invention include lanthanide ions, that is, lanthanum ions, cerium ions, praseodymium ions, neodymium ions, promethium ions, samarium ions, europium ions, gadolinium ions, terbium ions, dysprosium ions, Examples include honolemium ion, erbium ion, thulium ion, ytterbium ion, and lutetium ion. These rare earth metal ions are contained in the acrylic resin with a specific metal compound of each metal ion as a source. Examples of such a specific metal compound include an anhydride or water of a metal salt of the above-mentioned rare earth metal and an organic acid such as sulfuric acid, benzoic acid, and oxalic acid; and an inorganic acid such as sulfuric acid, hydrochloric acid, nitric acid, and hydrofluoric acid. Examples thereof include oxides of rare earth metals and oxides, but are not limited to these compounds.

 In addition, as a part of the metal ion component, other metal ions other than the metal ion due to the rare earth metal are added to the acrylic resin in a range that does not impair the object of the present invention, for example, in a proportion within 30% by mass of all metal ion components. It can be contained in a system resin. As other metal ions, copper ions, sodium ions, potassium ions, potassium ions, iron ions, manganese ions, cobalt ions, magnesium ions, nickel ions, and the like can be used. Similar to the metal ions of rare earth metals, metal compounds of other metal ions can be contained in the acrylic resin as a supply source.

 The content of the metal ion component including the rare earth metal ion is determined based on the acrylic resin (phosphate-containing monomer, amino-containing monomer, other acrylic-based monomer, and monomer copolymerizable with these. ) Is preferably 0.05 to 43 parts by mass, more preferably 0.01 to 35 parts by mass, based on 100 parts by mass of the total amount of the amino group-containing compound. . When the content of the metal ion component is less than 0.05 parts by mass, the optical function obtained cannot sufficiently exhibit the optical function of the metal ion. On the other hand, when this content exceeds 43 parts by mass, it becomes difficult to disperse the metal ion component in the acryl-based resin.

 Further, in order to contain the metal ion component at such a ratio, the metal compound serving as the supply source of the metal ion component is added in an amount of 0.1 to 100 parts by mass of the total amount of the acrylic resin and the amino group-containing compound. It is preferably used in a proportion of from 0.1 to 80 parts by mass, particularly from 0.02 to 75 parts by mass.

The optical material of the present invention contains a phosphate group as one of the components for dispersing the metal ion component. This phosphate group contains the phosphate group Included in a state of being chemically bonded to the structure of the polymer constituting the acrylic resin obtained by polymerizing a monomer composition containing a polymerizable monomer (monophosphate-containing monomer) Is done. By being contained in such a state, the dispersibility of the metal ion component is improved, and the metal ion component can be contained at a high ratio. The acrylic resin in which a phosphate group is chemically bonded in the polymer structure includes a phosphate group-containing monomer represented by the above formula (1) (hereinafter referred to as a “specific phosphate group-containing monomer”). ) And a copolymer obtained by polymerizing a monomer composition containing a monomer copolymerizable therewith (hereinafter referred to as a "copolymerizable monomer"). It is also referred to as “group-containing copolymer.”).

In the formula (1) showing the molecular structure of the specific phosphate group-containing monomer, based on the Ru represented by R ^'1, when § methacryloyl Ruo alkoxy group alkylene oxide group is bonded (X is a hydrogen atom ) Or a methacryloyloxy group (when X is a methyl group). Here, the repeating number m of the alkylene oxide group is an integer of 1 to 5. When the value of m exceeds 5, the obtained copolymer does not have practical hardness as an optical material.

 Further, in the above formula (1), the number n of the hydroxyl groups is 1 or 2, and the specific n-containing phosphoric acid group containing n is 1 depending on the properties of the obtained optical material, the molding method and the purpose of use. Either one or both of the monomer and the specific phosphate group-containing monomer having a value of n of 2 can be used, and when both are used, the mixing ratio thereof should be appropriately selected. Can be.

 Specifically, a specific phosphoric acid group-containing monomer having a value of n of 1 has two radically polymerizable unsaturated bonds bonded to a phosphorus atom and has crosslinkable polymerizability. Becomes On the other hand, the specific phosphate group-containing monomer having a value of n of 2 has the number of radically polymerizable unsaturated bonds of 1, and the number of hydroxyl groups bonded to the phosphorus atom is 2, The bondability with the metal ion component becomes large.

Therefore, when the optical material of the present invention is molded by an injection molding method or an extrusion molding method, which is a general molding method of a thermoplastic resin, a specific phosphate group-containing monomer having a value of n of 2 is used. It is preferred to use a body. When both a specific phosphate group-containing monomer having an n value of 1 and a specific phosphate group-containing monomer having an n value of 2 are used, a specific phosphate group-containing monomer is used. In the production of the copolymer, it is preferable to use a casting polymerization method capable of directly obtaining an intended shape.

 Thus, depending on the properties of the optical material to be obtained, the molding method, and the intended use, a specific phosphate group-containing monomer having a value of n of 1 and a specific phosphate group having a value of n of 2 are provided Either of the monomers can be selected, but it is preferable to use both of them. In particular, the ratio of a specific phosphate group-containing monomer having an n value of 1 to a specific phosphate group-containing monomer having an n value of 2 is approximately equimolar, for example. For example, it is preferable to use a molar ratio of 455: 55: 45 because the solubility of the metal compound as the supply source of the metal ion component in the monomer mixture is high.

 In order to obtain a specific phosphoric acid group-containing copolymer, a mixed monomer of the above specific phosphoric acid group-containing monomer and a copolymerizable monomer is used. By using such a mixed monomer, the performance of the obtained optical material such as hygroscopicity, refractive index, and hardness can be adjusted.

 Such copolymerizable monomers include: (1) homogeneously dissolving and mixing with the phosphate group-containing monomer to be used, and (2) good radical copolymerizability with the phosphate group-containing monomer to be used. (3) There is no particular limitation as long as it satisfies that an optically transparent copolymer can be obtained by copolymerization with a phosphate group-containing monomer.

Specific examples of such copolymerizable monomers include methyl § chestnut rate, Mechirumetaku Relate, Echiruakuri rate, Echirumetakuri rate, _n - Puropiruakuri les over bets, n - propyl methacrylate rate, n - butyl Atari rate, n - Buchirumeta chestnut Alkyl (meth) such as acrylate, isobutyl acrylate, isobutyl methacrylate, t-butyl acrylate, t-butyl methacrylate, n-xyl acrylate, n-xyl methacrylate, n-octyl acrylate, and n-octyl methacrylate Atari rate compounds; Glycidyl acrylate, glycidyl methacrylate, 2-hydroxyl acrylate, 2-hydroxyl methacrylate, 2-hydroxy propyl acrylate, 2-hydroxy propyl methacrylate, 2-hydroxy butyl acrylate, Modified alkyl (meth) acrylate compounds such as 2-hydroxybutyl methacrylate; ethylene glycol diacrylate, ethylene glycol dimethacrylate, diethylene glycol diatalylate, diethylene glycol dimethacrylate, polyethylene glycol diatalylate, polyethylene glycol diacrylate Methacrylate, polypropylene glyconoresatalilate, polypropylene glycoresin methacrylate, 1,3-butylene glycol 1,3-butylene glycol dimethacrylate, 1,4-butanediol dimethacrylate, 1,4 butanediol dimethacrylate, 1,6 hexanediol diatalylate, 1,6 hexanediol dimethacrylate, neopentyl Glycol diacrylate, neopentyl glycol dimethacrylate, 2 hydroxy-1,3 dimethacryloxypropane, 2,2 bis [4-1 (ataryloxyethoxy) pheninole] propane, 2, 2 bis [4_ (Methacryloxyethoxy) phenyl] propane, 2 hydroxy-1 1 atarioxy 3 -methacryloxypropane, trimethylolpropane triatalylate, trimethylolpropane trimethacrylate, pentaerythritol triacrylate, pentaerythritol tosoletri Takuri rate, Pentaerisuri Tono Les tetra Atari rate, polyfunctional (meth) § click Relate compounds such Pentaerisuri tall tetra methacrylate rates;

Carboxylic acids such as acrylic acid, methacrylic acid, 2-methacryloyloxyshethyl succinic acid, and 2-methacryloyloxyshethyl phthalic acid; styrene, _α- methylstyrene, chloronostyrene, dibromostyrene, methoxystyrene, divininolebenzene And aromatic vinyl compounds such as Bier benzoic acid, hydroxymethylstyrene, and tributylbenzene.

These exemplified compounds can be used alone or in combination of two or more. In the mixed monomer obtained from the specific phosphoric acid group-containing monomer and the copolymerizable monomer, the use ratio of the specific phosphoric acid group-containing monomer and the copolymerizable monomer is as follows. The “specific phosphoric acid group-containing monomer: copolymerizable monomer (mass)” is preferably in the range of 3:97 to 80:20, more preferably 5:95 to 7: 5: 25.

 When the proportion of the specific phosphate group-containing monomer in the mixed monomer is less than 3% by mass, it is difficult to exhibit a suitable optical function in the obtained optical material. On the other hand, when the ratio of the specific phosphoric acid group-containing monomer in the mixed monomer exceeds 80% by mass, the viscosity of the mixed monomer becomes excessive and the solubility of the rare earth metal ion is impaired. In addition, the obtained optical material may have low properties such as moisture resistance and hardness.

 Since the specific phosphoric acid group-containing monomer is rich in radical polymerizability, most of the mixed monomer is converted to a copolymer by polymerizing the mixed monomer. Therefore, by using a specific phosphoric acid group-containing monomer and a copolymerizable monomer in the above ratio, an acrylic resin in which the phosphoric acid groups are bonded in the polymer structure at the above specific ratio. Based resin (specific phosphoric acid group-containing copolymer) is obtained.

 In the optical material of the present invention, a substituted or unsubstituted amino group (hereinafter, also simply referred to as “amino group”) together with the above-mentioned phosphate group is used as a component for improving the dispersibility of the metal ion component including the rare earth metal ion. Is contained.

By including this amino group together with the phosphate group, the dispersibility of the metal ion component can be further improved as compared to the case where the phosphate group is used alone, regardless of the type of rare earth metal. The rare earth metal ion can be contained in a high ratio (for example, a ratio of 10 mass / ₀ or more for the erupium ion).

 The content ratio of the rare earth metal ion can be appropriately changed depending on the performance required for the optical material. Even in the optical material having a small content ratio of the rare earth metal ion, the content is derived from the phosphate group-containing monomer. Needless to say, the phosphoric acid group and the substituted or unsubstituted amino group are included in the scope of the present invention as long as they are contained in the acrylic resin.

The reason why the dispersibility of metal ion components is improved by introducing amino groups In other words, a salt represented by the following formula (6) is formed by the introduced amino group and the phosphate group, whereby the aggregation between the phosphate groups is suppressed, and the phosphate group and the rare earth element are formed. This is considered to be because the rapid reaction with the metal ion becomes gentle by passing through the salt, and the rare earth metal ion can be uniformly introduced.

 R

 Equation (6) RNRII

 H

 o

 〇〇p = —

 o

 When an amide group is introduced instead of an amino group, the amide group can break the hydrogen bond (aggregation) of the phosphate group, but the interaction between the amide group and the phosphate group is not strong it is conceivable that. The presence of the amide group has a great significance as a polar medium, and therefore it is considered that the effect of suppressing the rapid reaction between the phosphate group and the rare earth metal cannot be so expected.

 On the other hand, the amino group-containing monomer and the amino group-containing compound used in the present invention are typical basic compounds, and form a salt by reaction with an acid. This acid-base reaction is a well-known phenomenon.

 When a rare earth metal compound reacts with a phosphate group, it is considered that the reaction with a phosphate group stabilized by forming a salt is more difficult than the reaction with a free phosphate group, and as a result, a reaction suppressing effect appears. Can be

The donor numbers of the amide group-containing compound and the amino group-containing compound as electron donors are about 25 to 30 for the former and about 55 to 60 for the latter [V. Gutmann, Hitoshi Otaki Translated by Isao Okada, "Donors and Axceptors" (Academic Publishing Center)], Amino group-containing compounds have an overwhelmingly high donor property, and therefore have a strong acid-binding property. As a result, the biggest difference in the solubilizing ability of the rare earth metal between the amide group-containing compound (monomer) and the amino group-containing compound (monomer) is the interaction force with this acid. It is thought to be due to the difference.

 This amino group constitutes an acrylic resin obtained by polymerizing a monomer composition containing (i) a polymerizable monomer having the amino group (amino group-containing monomer). It may be contained in the polymer structure in a chemically bonded state, or (ii) by dispersing the amino group-containing non-polymerizable compound (amino group-containing compound) in an acrylic resin. Although it may be contained, the dispersibility of the metal ion component including the rare-earth metal ion can be enhanced, and the metal ion component can be contained in a high ratio. The above-mentioned embodiment (i) is preferred in that an optical material having low deterioration and high durability is obtained, and release of amine from the resin component is suppressed and prevented.

 In the embodiment of the above, that is, when an acrylic resin having an amino group chemically bonded in the structure of the polymer is used, the acrylic resin includes a specific phosphoric acid group-containing monomer; Monomer composition containing an amino group-containing monomer represented by the formula (2) (hereinafter referred to as “specific amino group-containing monomer”) and, if necessary, a copolymerizable monomer. It is preferable to use a copolymer obtained by subjecting a product to a polymerization treatment, whereby an acrylic resin in which both a phosphate group and an amino group are chemically bonded in the polymer structure (an amino group is used). Thus, a specific phosphoric acid group-containing copolymer bonded) is obtained.

The specific amino group-containing monomer represented by the formula (2) has a (meth) acryloyl group ((meth) acryloxyalkyl group or (meth) acrylamide alkyl group) in the molecular structure, It is a monomer copolymerizable with the specific phosphoric acid group-containing monomer. Specific examples of such a specific amino group-containing monomer include N, N-dimethylaminoethyl (meth) acrylate, N, N-getylaminoethyl (meth) acrylate, N, N-dimethylamino. Amino group-containing monomers having a (meth) acryloxyalkyl group as a substituent, such as propyl (meth) acrylate, N, N-diethylaminopropyl (meth) acrylate; N— (2- Dimethylaminoethyl) (meth) acrylamide, N— (2-getylaminoethyl) (meth) acrylamide, N— (3-dimethylaminopropyl) (meth) acrylamide, N— (3 (Meth) aminopropyl) (meth) acrylamide and other amino group-containing monomers having a (meth) acrylamide alkyl group as a substituent. These may be used alone or in combination of two or more. Can be used in combination.

 In the above-mentioned embodiment (ii) for allowing the optical material to contain a phosphate group, that is, in the embodiment in which the amino group-containing compound is dispersed in the acrylic resin, the method for dispersing the amino group-containing compound is represented by the above formula ( 3) or an amino group-containing compound represented by the above formula (4) (hereinafter referred to as “specific amino group-containing compound”), a specific phosphate group-containing monomer, and a copolymerizable monomer. And a method of polymerizing a monomer composition containing

 Here, the specific amino group-containing compound represented by the above formula (3) includes carbon atoms such as methylamine, ethylamine, propylamine, butyramine, pentylamine, hexylamine, heptylamine, octylamine, decylamine, dodecylamine, and stearylamine. A monoalkylamine having a number of 1 to 18; a dialkylamine having 2 to 24 carbon atoms such as dimethylamine, getylamine, dipropylamine, dibutylamine, dipentylamine, dihexylamine, diheptylamine, dioctylamine, didecylamine, didodecylamine; Min, Triethylamine, Tripropylamine, Tributylamine, Tripentylamine, Trihexylamine, Triheptylamine, Trioctylamine, Tridede Trialkylamines having 3 to 36 carbon atoms such as luminamine and tridodecylamine; amines substituted by phenyl groups such as phenylamine, diphenylamine and triphenylamine; N, N-substituted amines having different substituents; Different N, N, N substituted amines and the like can be mentioned.

The specific amino group-containing compound represented by the above formula (4) includes ethylenediamine, trimethylenediamine, propylenediamine, tetramethylenediamine, pentamethylenediamine, and hexamethylenediamine.キ, Ν, Ν, Ν-tetramethylethylenediamine, Ν, Ν, Ν, Ν-tetramethyltrimethylenediamine, Ν, Ν, Ν, Ν-tetramethynoramine Propylenediamine, Ν, Ν, Ν, Ν -tetramethyltetramethylenediamine, Ν, Ν, Ν, Ν- Examples include N, N, N, N-tetraalkylalkylenediamines such as tetramethylpentamethylenediamine and N, N, N, N-tetramethylhexamethylenediamine.

 These specific amino group-containing compounds can be used alone or in combination of two or more.

 In the optical material of the present invention, the sum of the content of the substituted or unsubstituted amino group and the content of the phosphate group is 0.05 to 50 mass of the total amount of the acrylic resin and the amino group-containing compound. %, More preferably 0.1 to 40% by mass.

 If the total content of the amino group and the phosphate group is too small, it becomes difficult to contain the metal ion component in a sufficiently high ratio. On the other hand, when the total content of the amino group and the phosphate group is excessive, the obtained optical material tends to have high hygroscopicity and coloring property.

 In the optical material of the present invention, the ratio of the content of the substituted or unsubstituted amino group to the content of the phosphate group is such that "amino group: phosphate group (mass ratio)" is 10:90. 770: 30 is preferable, and 12: 88-60: 40 is more preferable.

 If the proportion of the amino group is too small, the effect of including the amino group, that is, the effect of increasing the dispersibility of the metal ion component, cannot be sufficiently obtained. On the other hand, even if the ratio of the amino group is excessive, the effect corresponding to the ratio of the amino group cannot be obtained. A monomer mixture containing a monomer and / or a specific amino group-containing compound is preferably polymerized by a radical polymerization method in the presence of a rare earth metal compound which is a source of rare earth metal ions. Can be manufactured.

Specifically, before the radical polymerization of the polymerizable component in the monomer mixture is performed, the metal compound is added to the monomer mixture to be dissolved or dispersed, whereby a specific phosphoric acid group-containing monomer is added. And a specific amino group-containing monomer and / or a specific A monomer composition containing a mino group-containing compound and a rare earth metal compound is prepared, and this monomer composition is subjected to radical polymerization treatment.

In the monomer mixture, the total content of the phosphoric acid group in the specific phosphoric acid group-containing monomer and the total amino acid content in the specific amino group-containing monomer and the specific amino group-containing compound is simply 0.05-50 mass in the monomer mixture. /. And more preferably 0.1 to 40 mass. / ₀ .

 Further, it is preferable that the ratio between the amino group and the phosphate group is 10:90 to 70:30 by mass. In order to prepare such a monomer mixture, the aforementioned copolymerizable monomer may be used as needed.

 The amount of the metal compound containing the rare earth metal compound used is such that the content of the metal ion component constituting the metal compound is 0.005 to 43 parts by mass with respect to 100 parts by mass of the monomer mixture. Preferably, the amount is 0.01 to 35 parts by mass.

 By satisfying such conditions, the metal compound (rare earth metal compound) can be surely dissolved or dispersed in the monomer mixture, and the metal compound containing a phosphate group, an amino group, and a rare earth metal ion can be dissolved. An optical material can be obtained in which the components are contained in the above-described specific ratios, respectively.

 Also, in the preparation of the monomer mixture, by using a specific amino group-containing monomer, an acryl-based resin in which an amino group is chemically bonded in a polymer structure (a specific resin having an amino group bonded thereto). (Phosphate-containing copolymer).

 In the polymerization treatment of the monomer mixture, the radical polymerization method is not particularly limited, and a bulk (cast) polymerization method, a suspension polymerization method, an emulsion polymerization method, and a solution using a usual radical polymerization initiator are used. A known method such as a polymerization method can be used. The optical material of the present invention can be advantageously produced by the above-mentioned method, but the method of producing the optical material of the present invention is not limited to this. For example, the optical material can also be produced by the following method. be able to.

(1) A method in which a specific metal compound as a supply source of a metal ion component is added to an acryl-based resin obtained by subjecting the above monomer mixture to radical polymerization treatment and mixed. In the method (1), specifically, a) a method in which an acrylic resin is heated and melted, and the above-mentioned metal compound is added thereto and mixed; b) a method in which the acrylic resin is dissolved in an organic solvent or the like; And a method of adding and mixing the above metal compound.

 (2) A specific phosphate group-containing copolymer is obtained by radical polymerization of a mixed monomer of a specific phosphate group-containing monomer and a copolymerizable monomer, and the specific phosphate group-containing copolymer is obtained. A method in which a specific amino group-containing compound and a metal compound that is a supply source of a metal ion component are added to a copolymer and mixed.

 In the method (2), a method according to the above (1) can be used. The optical material thus obtained is used for various applications as it is or by shaping and polishing into a plate-like, column-like, lens-like, etc. shape according to the purpose of use. be able to.

 Also, as a result of the metal ion component being supplied from the metal compound and the metal ion component being bonded to a phosphate group or an amino group, an acid derived from the specific metal compound is contained in the acrylic resin as a by-product. However, it is more preferable to remove the acid by an appropriate method, for example, a method of filtering crystals, a method of evaporating at a high temperature, a solvent extraction method, and a method of washing with water.

 Since the optical material of the present invention is a resin-made optical material containing a high proportion of rare-earth metal ions, the optical function of rare-earth metal ions (the function of absorbing light in a specific wavelength region with high efficiency) Function that emits light in the wavelength range with high efficiency) Power It is much better than conventional resin-made optical materials.

 Since the rare earth metal ions are contained at a high concentration, the functional efficiency is high, and the size and the size of the optical device can be reduced.

The optical material of the present invention has an excellent optical function, and has an anti-glare spectacle lens (sun glass), an anti-glare filter, a screen cover, an anti-glare display filter, a color purity correction filter, a color tone correction filter. First, it is extremely useful as a component of optical filters such as brightness adjustment filters for lighting equipment, optical communication function devices, Faraday elements, optical amplification elements, wavelength conversion elements, etc. Examples thereof include a color display (color image display device), a color image capturing camera (power image capturing device), an illuminating light (illumination device), a laser, a communication optical amplifier, a communication optical isolator, and an optical switch. it can. BEST MODE FOR CARRYING OUT THE INVENTION

 Hereinafter, examples of the present invention will be described, but the present invention is not limited thereto.

 In the following, “parts” means “parts by mass”.

<Example 1>

 According to the formulation shown in Table 1 below, 20.0 parts of a specific phosphate group-containing monomer represented by the following formula (7) and a specific phosphate group-containing monomer represented by the following formula (8) A monomer mixture consisting of 12.0 parts, 25.3 parts of N, N-dimethylaminoethyl methacrylate (specific amino group-containing monomer), and 42.7 parts of methyl methacrylate was prepared. The content of the phosphoric acid group and the amino group in this monomer mixture was 11.52% by mass of the phosphoric acid group, 2.25% by mass of the amino group, 13.77% by mass in total, and The ratio of the phosphoric acid group to the phosphoric acid group is amino group: phosphate group 16:84 by mass ratio.

24.5 parts of erbium acetate tetrahydrate (9.84 parts of erbium ion based on 100 parts of monomer mixture) and t-butyl peroxycineodecanoate (polymerization initiator) 2.0 parts was added, and the mixture was sufficiently stirred and mixed to prepare a monomer composition. The monomer composition thus prepared is poured into a disc molding mold (for molding a 2 mm-thick disc), and is heated at 35 ° C for 1 hour and from 35 ° C to 60 ° C for 6 hours. In the present invention, the temperature is raised from 60 ° C to 80 ° C in 2 hours, from 80 ° C to 100 ° C in 1 hour, and heated at 100 ° C for 2 hours to perform cast polymerization. A 2 mm thick transparent disk made of the above optical material was obtained. Equation (7): (CH ₂ = CCH ₃ C〇〇C ₂ H ₄ 〇) ₂ P〇 (〇H)

Equation (8): CH ₂ = CCH ₃ C〇〇C ₂ H ₄₀ P〇 (〇H) ₂

<Example 2>

According to the recipe shown in Table 1 below, 20.0 parts of the specific phosphate group-containing monomer represented by the above formula (7) and the specific phosphate group-containing monomer represented by the above formula (8) 12. A monomer mixture consisting of 0 parts, 30.3 parts of N- (3-dimethylaminopropyl) methacrylamide (a monomer containing a specific amino group), and 37.7 parts of methyl methacrylate Was prepared. The content of phosphate groups Contact Yopi Amino groups in this monomer mixture, 1 1.52% by weight phosphoric acid, Amino group. 2. 49 wt _^0/0, total 01 wt% 14. The ratio of amino groups to phosphate groups is 18:82 by mass ratio of amino groups: phosphate groups.

 24.5 parts of erbium acetate tetrahydrate (9.84 parts of erbium ion with respect to 100 parts of monomer mixture) were added to this monomer mixture, and t-butyl vinyloxynedecanoate (polymerization (Initiator) 2.0 parts, and the mixture was sufficiently stirred and mixed to prepare a monomer composition. The monomer composition thus prepared was poured into a disk molding mold, and subjected to casting polymerization under the same conditions as in Example 1 to obtain a 2 mm thick optical material of the present invention. A transparent disc was obtained. <Example 3>

According to the formulation shown in Table 1 below, 33.1 parts of the specific phosphate group-containing monomer represented by the above formula (7) and the specific phosphate group-containing monomer represented by the above formula (8) A monomer mixture consisting of 19.9 parts and 47.0 parts of N, N-dimethylaminoethyl methacrylate (specific amino group-containing monomer) was prepared. The content of phosphate groups and amino groups in the monomer mixture was 19.08% by mass for phosphate groups and 4.19% for amino groups. The total is 23.27 mass. / ₀ , and the ratio between the amino group and the phosphate group is In this case, the ratio by mass is amino group: phosphate group 18:82.

 This monomer mixture was mixed with 40.0 parts of erbium acetate tetrahydrate (the content of erbium ion was 16.1 parts based on 100 parts of the monomer mixture) and t-butyl vinyloxynedecanoate (polymerization). (Initiator) 2.0 parts, and the mixture was sufficiently stirred and mixed to prepare a monomer composition. The monomer composition thus prepared was poured into a disk molding mold, and subjected to casting polymerization under the same conditions as in Example 1 to obtain a 2 mrn thick optical material of the present invention. A transparent disc was obtained. Example 4>

According to the formulation shown in Table 1 below, 0.13 parts of the specific phosphate group-containing monomer represented by the above formula (7) and the specific phosphate group-containing monomer represented by the above formula (8) A monomer mixture composed of 0.05 parts, 0.1 part of N, N-dimethylaminoethyl methacrylate (specific amino group-containing monomer) and 99.72 parts of methyl methacrylate was prepared. The content of phosphate and Amino groups in this monomer mixture is-phosphate group 0.0648 mass _^0/0, Amino groups 0.00891 wt%, total 0.0

7371% by mass, and the ratio of the amino group to the phosphoric acid group was amino group: phosphoric acid group 21:88 in mass ratio.

 0.1 part of erbium acetate tetrahydrate (0.04 part of erbium ion content per 100 parts of monomer mixture) was added to this monomer mixture, and t-butyl vinyloxy neodecanoate (polymerization initiator) 2. The monomer composition was prepared by adding 0 parts and adding and stirring thoroughly. The monomer composition thus prepared was poured into a disk molding mold (for molding a disk having a thickness of 2 Omm) and subjected to casting polymerization under the same conditions as in Example 1 to obtain the present invention. Thickness of optical material

A 20 mm transparent disc was obtained.

 <Example 5>

According to the recipe shown in Table 1 below, 125 parts of the specific phosphate group-containing monomer represented by the above formula (7) and the specific phosphate group-containing monomer represented by the above formula (8) A monomer mixture consisting of 7.5 parts of the compound, 70.0 parts of N, N-dimethylaminoethyl methacrylate (specific amino group-containing monomer), and 10.0 parts of methyl methacrylate Key Made. The content of the phosphoric acid group and the amino group in this monomer mixture was as follows: phosphoric acid group: 7.20% by mass; amino group: 6.24% by mass; total: 13.44% by mass; The ratio of the amino acid to the phosphoric acid group is amino group: phosphate group = 46.4: 53.6 by mass ratio.

 Into this monomer mixture, 18.8 parts of erbium acetate tetrahydrate (7.23 parts of erbium ion based on 100 parts of monomer mixture) and t-butyl peroxycineodecanoate (polymerization start) 2.0 parts), and the resulting mixture was thoroughly stirred and mixed to prepare a monomer composition. The monomer composition thus prepared was poured into a mold for disk molding, and cast polymerization was carried out under the same conditions as in Example 1 to obtain a thickness comprising the optical material of the present invention. A 2 mm clear disk was obtained. <Example 6>

According to the formulation shown in Table 1 below, 21.8 parts of a specific phosphate group-containing monomer represented by the above formula (7) and a specific phosphate group-containing monomer represented by the above formula (8) 13.0 parts, N, N-dimethylaminoethyl methacrylate (specific amino group-containing monomer) 30.1 part, methyl methacrylate 10.0 parts, and phenoxyshetyl methacrylate 25.1 parts Was prepared. The content of phosphate groups and amino groups in the monomer mixture, phosphoric acid group is 1 2.5 mass ⁰ I amino groups 2.68 wt%, the total is 1 5.1 8 wt% The ratio of the amino group to the phosphate group is amino group: phosphate group = 17.7: 82.3 in mass ratio.

 To this monomer mixture were added 15.0 parts of neodymium acetate monohydrate (the content of neodymium ion was 6.37 parts per 100 parts of the monomer mixture), and 7.0 parts of praseodymium acetate dihydrate ( 2.79 parts of praseodymium ion based on 100 parts of the monomer mixture) and 2.0 parts of t-butyl peroxy neodecanoate (polymerization initiator) are added, and mixed with sufficient stirring. As a result, a monomer composition was prepared. The monomer composition thus prepared was poured into a disk molding mold, and subjected to casting polymerization under the same conditions as in Example 1 to obtain a 2 mm thick optical material of the present invention. A transparent disc was obtained.

Example 7> According to the formulation shown in Table 1 below, 14.7 parts of the specific phosphate group-containing monomer represented by the above formula (7) and the specific phosphate group-containing monomer represented by the above formula (8) A monomer mixture consisting of 8.8 parts, 20.0 parts of triethylamine (a specific amino group-containing compound), and 56.5 parts of methyl methacrylate was prepared. The content of the phosphoric acid group and the amino group in this monomer mixture was 8.46% by mass for the phosphoric acid group, 2.77% by mass for the amino group, and 11.23% by mass in total. The ratio of the amino group to the phosphate group is amino group: phosphate group = 24.7: 75.3 by mass ratio.

 To this monomer mixture, 18.0 parts of erbium acetate tetrahydrate (7.23 parts of erbium ion based on 100 parts of monomer mixture) and t-butyl peroxycineodecanoate (polymerization initiator) 2.0 parts) was added to the mixture, and the mixture was sufficiently stirred and mixed to prepare a monomer composition. The monomer composition thus prepared was poured into a disk molding mold, and subjected to casting polymerization under the same conditions as in Example 1 to obtain a 2 mm thick optical material of the present invention. A transparent disc was obtained. <Comparative Example 1>

 20.0 parts of a specific phosphate group-containing monomer represented by the above formula (7), 12.0 parts of a specific phosphate group-containing monomer represented by the above formula (8), and methyl methacrylate A monomer mixture consisting of 68.0 parts was prepared.

 24.5 parts of erbium nitrate tetrahydrate (9.84 parts of erbium ion with respect to 100 parts of the monomer mixture) was added to the monomer mixture, and the mixture was stirred. The hydrate was not completely dissolved, and the resulting monomer composition was cloudy and heterogeneous.

 In addition, when erbium acetate tetrahydrate was gradually added to the above monomer mixture and stirred, the amount added was 1 part (the erbium ion content was 0.4 parts per 100 parts of the monomer mixture). Then, a microgel was generated in the monomer composition. <Comparative Example 2>

According to the recipe shown in Table 1 below, 20.0 parts of the specific phosphate group-containing monomer represented by the above formula (7) and the specific phosphate group-containing monomer represented by the above formula (8) A monomer mixture consisting of 12.0 parts and 68.0 parts of methyl methacrylate was prepared. To this monomer mixture, 0.1 part of erbium acetate tetrahydrate (0.04 part of erbium ion content per 100 parts of monomer mixture) and t-butyl peroxy neodecanoate (polymerization initiator) 2.0 And the mixture was sufficiently stirred and mixed to prepare a monomer composition. The monomer composition thus prepared was poured into a disk molding mold and subjected to cast polymerization under the same conditions as in Example 1 to obtain a 2 mm thick optical material for comparison. A transparent disc was obtained. Reference Example 1>

 20.0 parts of a specific phosphate group-containing monomer represented by the above formula (7), 12.0 parts of a specific phosphate group-containing monomer represented by the above formula (8), A monomer mixture consisting of 25.3 parts of N-dimethylacrylamide (monomer containing an amide group) and 42.7 parts of methyl methacrylate was prepared.

 When 24.5 parts of erbium acetate tetrahydrate (the content of erbium ion relative to 100 parts of the monomer mixture was 9.84 parts) was added to the monomer mixture, and the mixture was stirred, a microgel was obtained. It was not possible to obtain a monomer composition in which erbium acetate tetrahydrate was uniformly dissolved.

 Also, when erbium acetate tetrahydrate was gradually added to the above monomer mixture and stirred, the added amount was 13 parts (the erbium ion content was 5.2 parts per 100 parts of the monomer mixture). At the point where no microgel was generated in the monomer composition.

According to the recipe shown in Table 1 below, 20.0 parts of the specific phosphate group-containing monomer represented by the above formula (7) and the specific phosphate group-containing monomer represented by the above formula (8) A monomer mixture consisting of 12.0 parts, 25.3 parts of N, N-dimethylacrylamide (monomer containing an amide group), and 42.7 parts of methyl methacrylate was prepared. To this monomer mixture was added 11.0 parts of erbium acetate tetrahydrate (the content of erbium ion to 100 parts of the monomer mixture was 4.4 parts), and t-butyl vinyloxy neodecanoate (polymerization initiator) 2.0 parts were added to the mixture, and the mixture was sufficiently stirred and mixed to prepare a monomer composition. The monomer composition thus prepared Was poured into a disk molding mold, and casting polymerization was performed under the same conditions as in Example 1 to obtain a transparent disk having a thickness of 2 mm and made of a reference optical material.

Example Example Example Example Example Example Example Example Example Comparative example Reference example

 1 2 3 4 5 6 7 2 2 Specific phosphoric acid group-containing monomer represented by formula (7): S-form 20.0 20.0 33.1 0-13 12.5 21.8 14.7 20.0 20.0 Specific phosphoric acid represented by formula (8) Acid group-containing monomer 12.0 12.0 19.9 0.05 7.5 13.0 8.8 12.0 12.0 Unit

 N, N-Dimethylaminoethyl methyl ester 25.3 47.0 0.1 70.0 30. I

Quantity

 N- (3-dimethylaminopropyl) methacrylamide 30.3

Body

 The triethylamine 20.0

扭 Structure

 N-N-dimethylacrylamide 25.3 Formation ― ― ― ―

 Min Methyl methyl acrylate 42.7 37.7 99.72 10.0 10.0 56.5 68.0 42.7

 Fenokishe Chilume Evening Crate 25.1-Object---

 Erbium acetate tetrahydrate 24.5 24.5 40.0 0.1 18.0 18.0 0.1 IL0

^ Neodymium acid monohydrate 15.0

 Praseodymium acetate dihydrate 7.0

 t--butyl peroxy neodecanoate (polymerization initiator) 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 Content of phosphoric acid group in single S-body mixture (a) [% by mass] 11.52 11.52 19.08 0.0648 7.20 12.50 8.46 11.52 11.52 Percentage of amino in the i-isomer mixture (b) [fi%] 2.25 2.49 4.19 0.00891 6.24 2.68 2.77

 (a) + (b) (quality ¾%) 13.77 14.01 '23 .27 0.07371 13.44 15.18 11.23 11.52 11.52

(b), '(Ca) + (b)) (-) 0.16 0.18 0.18 0.12 0.46 0.18 0.247

Monomer mixture 1 0 0 parts per E r containing ft (Part] 9.84 9.84 16.1 0.04 7.23 7.23 0.04 4.4 Nd 3 * containing 1 [parts per single fi-mixture 1 0 0 parts] 6.37

Monomer mixture] Content of Pr ³ * per 100 parts! : [Part] 2.79

) Solubility evaluation>

 30.0 parts of erbium acetate tetrahydrate was added to each of the monomer mixtures prepared for producing the disks according to Examples 1 and 2 (the content of erbium ion was 100 to 100 parts of the monomer mixture). When the mixture was added and stirred, erbium acetate tetrahydrate was uniformly dissolved, and no microgel was generated in this system. Further, 45.0 parts of erbium acetate tetrahydrate was added to the monomer mixture prepared for producing the disk according to Example 3 (the content of erbium ion was 18.1 parts with respect to 100 parts of the monomer mixture). When the mixture was added and stirred, the erbium acetate tetrahydrate was uniformly dissolved, and no microgel was generated in this system.

<Evaluation of optical materials>

 Using the disks according to Examples 1 to 7, Comparative Example 2 and Reference Example 2 as test pieces, the light absorptance in a specific wavelength range (300 to 800 nm) and the absorption characteristics of light at a wavelength of 520 nm were obtained by the following method. And the water absorption was evaluated. Further, the test piece of Example 6 was evaluated for its antiglare property.

 (Light absorption rate)

 Using a self-recording spectrophotometer “U-4000 (manufactured by Hitachi, Ltd.)”, the spectral transmittance curve of the test piece at a wavelength of 300 to 800 nm was measured.

 [Absorption characteristics of light with wavelength of 520 nm]

 Light of wavelength 520 nm (eg medical laser) Power Eye protection is desired. Therefore, when the light transmittance of the test piece at the wavelength of 520 nm measured as described above was 85% or less, it was determined to be "protective". The usefulness of cutting light having a wavelength of 520 nm is not limited to the above-mentioned medical laser field.

 [Anti-glare properties (Example 6)]

 In the same manner as above, the light transmittance of the test piece at a wavelength of 560 to 610 nm was measured, and this light transmittance was measured as a glass anti-glare lens “NEO” (HOYA) at a wavelength of 560 to 610 nm. If the light transmittance is smaller than (the light absorption is large)

It was evaluated as having "anti-glare properties". (Water absorption)

 Specimen mass W. After the test piece is immersed in water at 23 ° C for 20 hours, the water adhering to the surface of the test piece is wiped off, and the mass W, (g) of the test piece is measured. The water absorption was calculated by the following equation.

 Table 2 shows the above results.

Water absorption (%) = {(Wi — W.) / W. } 1 o 0

(Table 2)

The invention's effect

 The optical material of the present invention has a resin component (acrylic resin) capable of dispersing rare earth metal ions at a high ratio.

Therefore, according to the present invention, regardless of the type of the rare earth metal, a resin optical material containing the rare earth metal ion in a high ratio and in a uniformly dispersed state is provided. Can be offered.

 The optical material of the present invention can absorb light in a specific wavelength range with high efficiency and can emit light in a specific wavelength range with high efficiency, and is excellent in optical functions.

 ADVANTAGE OF THE INVENTION According to the manufacturing method of this invention, regardless of the kind of rare earth metal, the said rare earth metal ion can be dispersed and contained in the acrylic resin in a high ratio, vigorously and in a uniform state. Excellent optical materials can be advantageously produced.

Claims

The scope of the claims  [1] The acrylic resin contains a phosphate group derived from a phosphate group-containing monomer, a substituted or unsubstituted amino group, and a metal ion component containing a rare earth metal ion. Optical material. [2] An acrylic resin containing a phosphate group-containing monomer represented by the following formula (1) and an acrylic resin obtained by copolymerizing a monomer copolymerizable therewith. The optical material according to claim 1. Equation (1): P 0 (OH ) n R '-n Wherein, R ¹¹ is, HC - C (X) C 00 (R 12 - 0) m one (X represents a hydrogen atom or a methyl group, R ¹² represents a hydrocarbon group having 1 to 18 carbon atoms, and m is an integer of 1 to 5.)  n is 1 or 2. ] [3] A phosphoric acid group-containing monomer represented by the following formula (1), an amino group-containing monomer represented by the following formula (2), and a monomer which can be copolymerized with these, if necessary. 2. The optical material according to claim 1, wherein the optical material contains an ataryl resin obtained by copolymerizing a polymer. Formula (1): P 0 (OH) „R ' [In the formula, R ¹ _{'is, H 2 C = C (X} ) COO (R 12 - 0) m one (X represents a hydrogen atom or a methyl group, R ¹² represents a hydrocarbon group having 1 to 18 carbon atoms, and m is an integer of 1 to 5). n is 1 or 2. ] Formula (2): R ¹ -N-R ²³  I R ²² Wherein R ²¹ , R ²² and R ²³ are each  Hydrogen atom, alkyl group having 1 to 6 carbon atoms, phenyl group, H ₂ C = C (X) COOR ^24- (X represents a hydrogen atom or a methyl group, and R ²⁴ represents a hydrocarbon group having 1 to 18 carbon atoms.) _{H 2 C = C (X)} CONHR 25 - (X represents a hydrogen atom or a methyl group, and R ²⁵ represents a hydrocarbon group having 1 to 18 carbon atoms.)  These may be the same or different, but of these At least one is H ₂ C = C (X) C 00 R ²⁴ — or H ₂ C = C (X) A group represented by CONHR ²⁵ —. ] [4] The optical material according to claim 1, wherein the optical material contains an amino group-containing compound represented by the following formula (3). Equation ^{(3): R 3 '-} N - R 33 R ³² (In the formula, R ³ ′, R ³ ^ and R ³³ each represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a phenyl group, which may be the same or different.) [5] The optical material according to claim 1, wherein the optical material contains an amino group-containing compound represented by the following formula (4). Equation (4): — N-— N—  I I (Wherein, R ", R ⁴ R ⁴³ and each represent a hydrogen atom, an alkyl group or a phenyl group, which may be the same or different  Represents an alkylene group. ) [6] The total mass of the acrylic resin and the amino group-containing compound is “R”, the mass of the phosphate group is “A”, the mass of the substituted or unsubstituted amino group is “B”, and the mass of the metal ion component is “ The optical material according to any one of claims 1 to 5, wherein when "M" is satisfied, the following conditions (a) to (c) are satisfied.  [B] [(A + B) ZR] 'The straight line of 100 must be 0.05 to 50.  [Mouth] [BZ (A + B)],: The value of 100 must be 10 to 70.  [C] The value of (M / R) X 100 is 0.005 to 43.  [7] The total mass of the acrylic resin and the amino group-containing compound is “R”, the mass of the phosphate group is “A”, the mass of the substituted or unsubstituted amino group is “B”, and the mass of the metal ion component is “ The optical material according to any one of claims 1 to 5, wherein when "M" is satisfied, the following conditions (a) to (c) are satisfied.  [B] [(A + B) ZR]: The direct value of 100 must be 0:! ~ 40.  [Mouth] [B / (A + B)] input 100 value should be 12-60.  [C] The value of (M / R) X 100 is 0.01 to 35.  [8] The acryl resin according to any one of claims 1 to 5, wherein at least one rare earth metal ion selected from the group consisting of praseodymium ions, neodymium ions and erbium ions is contained in the acryl resin. An optical material according to item 1. [9] Step of polymerizing a monomer composition containing a phosphate group-containing monomer represented by the following formula (1) and an amino group-containing monomer represented by the following formula (2) A method for producing an optical material, comprising: Equation (1): P 0 (〇H) _n R _3- „ [Wherein R ¹ ′ is H ₂ C = C (X) COO (R ^{1 S} —〇) _m ― (X represents a hydrogen atom or a methyl group, R ¹² represents a hydrocarbon group having 1 to 18 carbon atoms, and m is an integer of 1 to 5.)  n is 1 or 2. ] Equation ^{(2): R 21 - N} - R 23 [Wherein 1 ^ ', R ²² and R ²³ are respectively  Hydrogen atom, alkyl group having 1 to 6 carbon atoms, funinyl group, H ₂ C = C (X) C OO R ^- (X represents a hydrogen atom or a methyl group, and R ²⁴ represents a hydrocarbon group having 1 to 18 carbon atoms.) H ₂ C = C (X) C〇NHR ²⁵ (X represents a hydrogen atom or a methyl group, and R ²⁵ represents a hydrocarbon group having 1 to 18 carbon atoms.)  These are the same or different forces, of which At least one is H ₂ C = C (X) COOR ²⁴ — or H ₂ C—C (X) C is a group represented by ONHR ²⁵ —. ] [10] A monomer containing a phosphate group-containing monomer represented by the following formula (1), a monomer copolymerizable therewith, and an amino group-containing compound represented by the following formula (3): A method for producing an optical material, comprising a step of polymerizing a monomer composition. Formula (1): P 0 (OH) _n R Wherein, R ^M _{is, H 2 C = C (X} ) C OO (R 12 - 0) m - (X represents a hydrogen atom or a methyl group, R ¹² represents a hydrocarbon group having 1 to 18 carbon atoms, and m is an integer of 1 to 5).  n is 1 or 2. ] Formula (3): R ^3, -NR ³³  I R ³² (In the formula, R ³ ′, R ³² and R ³ each represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a phenyl group, which may be the same or different.) [11] A monomer containing a phosphate group-containing monomer represented by the following formula (1), a monomer copolymerizable therewith, and an amino group-containing compound represented by the following formula (4): A method for producing an optical material, comprising a step of polymerizing a monomer composition. Formula (1): P 0 (OH) _n R [Wherein R ¹ ′ is H ₂ C—C (X) C OO (R ¹² — 0) _m (X represents a hydrogen atom or a methyl group, R ′ ² represents a hydrocarbon group having 1 to 18 carbon atoms, and m is an integer of 1 to 5.) η is 1 or 2. ] Equation ^{(4): R 4 '-} N - R 4 5 - N- IT ² R ^{4 3} (Wherein, R ", RR ^{4 3} and each represents a hydrogen atom, an alkyl group or full We two group, they may be different even shall apply the same _c  Represents an alkylene group. ) [12] The method for producing an optical material according to any one of claims 9 to 11, wherein the monomer mixture is polymerized in the presence of a rare earth metal ion. Method.  [13] A wavelength conversion material comprising the optical material according to any one of claims 1 to 5. [14] A fluorescent light-emitting material comprising the optical material according to any one of claims 1 to 5. [15] An optical isolator comprising the optical material according to any one of claims 1 to 5.  [16] An optical amplifier comprising the optical material according to any one of claims 1 to 5. [17] A color image comprising the optical material according to any one of claims 1 to 5. [18] A color image comprising the optical material according to any one of claims 1 to 5. [19] Anti-glare glasses made of the optical material according to any one of claims 1 to 5. [20] A lighting fixture comprising the optical material according to any one of claims 1 to 5.