JP2597640B2 - Resin manufacturing method - Google Patents

Description

The present invention relates to a method for producing a resin, and more particularly, to a method for producing a cured resin molded article.

More specifically, when polymerizing a polymerizable liquid material containing a monomer or oligomer containing a bisallyl-based compound and / or a (meth) acrylic compound as an essential component or a mixture thereof, the surface and the inside have the same hardness. The present invention relates to a method for producing a cured resin molded product capable of obtaining a molded product with less distortion.

<Prior art> When polymerizing monomers and oligomers such as diethylene glycol bisallyl carbonate and methyl methacrylate, particularly when polymerizing these using various radical polymerization initiators, these materials may be exposed to oxygen such as air. When it comes in contact with oxygen, radicals required for polymerization are consumed by oxygen, so that a high degree of polymerization cannot be obtained and a sufficient hardness cannot be obtained.

Therefore, when such a product is polymerized, the contact with air or the like is usually interrupted by a mold or the like, so that the polymerization reaction proceeds.

However, due to the shape of the target object and the like, when polymerization must be performed in a state in which a part or the upper part of the mold is open to the air, the contact surface with the air cannot obtain a sufficient degree of polymerization. It becomes a viscous liquid or gel.

Therefore, in such a case, polymerization is performed by covering the surface of the monomer, oligomer or the like that comes into contact with air with an inert gas such as nitrogen or argon.

However, such a polymerization method has a problem that a large amount of energy and time are required for oxygen substitution, and the cost is increased.

On the other hand, a method in which the surface of a monomer or oligomer is blocked by an elastic body or the like to carry out polymerization is also performed. However, this method is difficult to use when the shape of a target resin is complicated, There is a problem that stress of a monomer or the like is applied by an elastic body or the like during polymerization to cause optical distortion in the resin, and that the cost is increased and the productivity is low.

<Problems to be Solved by the Invention> The present invention solves the above-mentioned problems of the prior art and provides a polymer containing a monomer or oligomer containing a bisallylic compound and / or a (meth) acrylic compound as an essential component or a mixture thereof. When a possible liquid material is polymerized in the state of being opened to the atmosphere and a cured resin molded product is obtained, the molded product has the same hardness between the inside and the surface of the resin and has no optical distortion in a simple process. It is an object of the present invention to provide a method for producing a resin which can obtain a resin composition and can also perform molding of a complicated shape.

<Means for Solving the Problems> The present invention provides a polymerizable liquid material containing a monomer or oligomer containing a bisallyl compound and / or a (meth) acrylic compound as an essential component or a mixture [A] thereof. In contact with the polymerizable liquid containing the monomer or oligomer or the mixture [A] thereof, the solubility thereof is low, and the density of the polymerizable liquid containing the monomer or oligomer or the mixture [A] thereof is smaller than that of the polymerizable liquid containing the monomer or oligomer or the mixture [A]. A method for producing a resin, comprising polymerizing a polymerizable liquid containing the monomer or oligomer or a mixture thereof (A) in the presence of a liquid [C] having a small density.

Further, the monomer or oligomer or a mixture thereof [A] is represented by the following formula (a): Wherein R is the residue of a dihydric alcohol, and the value of n or the average value of n is from 1 to 10, preferably from 2 to 10, which is an aliphatic, alicyclic or aromatic dihydric alcohol represented by the formula: It is preferable to include a monomer or oligomer of bis (allyl carbonate) or a mixture thereof.

Further, it is preferable that the liquid material [C] is a low-molecular-weight on-liquid synthetic hydrocarbon polymer, a liquid hydrocarbon mixture, or a mixture thereof.

In the present invention, the monomer or oligomer containing a bisallylic compound as an essential component or a mixture thereof includes a monomer alone, an oligomer alone, a mixture of a monomer and an oligomer, a mixture of two or more monomers, a mixture of two or more oligomers, or Monomer 1 or 2
A mixture of at least one species and one or more oligomers.

In the present invention, the polymer may be a homopolymer or a copolymer.

<Configuration of the Invention> Hereinafter, the present invention will be described in detail.

FIG. 1 shows a preferred embodiment of the resin production method of the present invention.

The method for producing a resin according to the present invention is capable of polymerizing a monomer or oligomer containing a bisallyl compound and / or a (meth) acrylic compound as an essential component or a mixture [A] thereof (hereinafter, referred to as [A]). This is a method for polymerizing a liquid material, as shown in FIG. 1, which is in contact with the polymerizable liquid material containing [A] and has low solubility with the polymerizable liquid material containing [A]. And [A]
Is polymerized in the presence of a liquid material [C] having a density smaller than the density of the polymerizable liquid material containing

[A] polymerized by the polymerization method (curing method) of the present invention
Is a monomer or oligomer containing a bisallyl compound and / or a (meth) acrylic compound as an essential component, or a mixture thereof.

The bisallyl compound used in [A] is not particularly limited as long as it is a bisallyl compound.
Examples thereof include a copolymerization composition [I] of a nucleus-halogen-substituted benzenedicarboxylic acid with dialylene glycol diallyl carbonate described in JP-A-59-45312, and a halogen-substituted benzenedicarboxylic acid described in JP-A-59-8709. One or more esters of substituted benzenedicarboxylic acids (for example, bisallyl 2,4-dichloroterephthalate) and monofunctionality containing a radical polymerizable aromatic ring having a refractive index of 1.55 or more as a homopolymer. A copolymerizable composition [II] with one or more monomers (eg, phenyl methacrylate, etc.), a specific bisallyl carbonate or bis-β-methylallyl carbonate [for example, as described in JP-A-59-8710; , 4-bis (hydroxyethoxy) benzenebisallylcarbonate, etc.] and a radical polymerizable as a homopolymer having a refractive index of 1.55 or more. Monofunctional monomer ring-containing (e.g. phenyl methacrylate) copolymer composition of one or more [III], described in JP-A 59-96109, monool (e.g. 4-
A monomer obtained by reacting benzyl-phenol) with an unsaturated carboxylic acid (chloride) [e.g., acrylic acid (chlorad)]; And allyl esters of chlorobenzoic acid (e.g., diallyl 2,3-dichlorobenzoate) and difunctional monomers (e.g., tetraethylamine) described in JP-A-59-96113. Copolymer (V) with bromophthalic acid (diallyl ester of bromophthalic acid), copolymerizable composition [VI] described in JP-A-59-184210, diethylene glycol bisalcarbonate [VI]
I], and general formula (Wherein R is a residue of a dihydric alcohol, and the value of n or the average value of n is from 1 to 10, preferably from 2 to 10.) A composition [VIII] containing a monomer or oligomer of an alcohol bis (allyl carbonate) or a mixture (a) thereof is mentioned. In the case of this [VIII], the component (a) is preferably a molar ratio of diallyl carbonate to a dihydric alcohol of 4: 1 or less, more preferably a molar ratio of 2: 1.
It is good to be a reaction product in the above. As the dihydric alcohol, preferably, ethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,6-hexanediol, diethylene glycol, polyethylene glycol, dipropylene glycol, propylene glycol,
Neopentyl glycol, trimethylpentanediol, cyclohexanedimethanol, bis (hydroxymethyl) tricyclodecane, 2,7-norbornanediol, α, α'-xylenediol, 1,4-bis (hydroxyethoxybenzene) and 2,2 It is preferred to use one or more of -bis [4- (hydroxyethoxy) phenyl] propane.

In the present invention, such a bisallyl compound is more preferably a bis (allyl carbonate) liquid composition [VIII '] containing the following components (a'), (b) and (c). And JP-A-59-1402
The description of JP-A No. 14 is hereby incorporated by reference.

The component (a ') has the general formula: Wherein R is a residue of a dihydric alcohol, and the value of n or the average value of n is 2 to 10. Bis of an aliphatic, alicyclic or aromatic dihydric alcohol represented by the formula ( 10 to 90% by weight of an oligomer or a mixture of oligomers (allicarbonate), wherein the bis (allyl carbonate) monomer of a dihydric alcohol optionally contained in the oligomer in the above formula is 50% by weight or less, Component (b) has the general formula Wherein R ′ is a residue of a dihydric or trihydric alcohol, and n ′ is 2 or 3. Bis or aliphatic dihydric or aromatic dihydric alcohol or trihydric alcohol represented by Tri (allyl carbonate) monomer or mixture (30% by weight of bis (allyl carbonate oligomer or poly (allyl carbonate) of a di- or trihydric alcohol optionally contained in the monomer or mixture)
Below), general formula Wherein R ″ is a residue of a dicarboxylic acid or a tricarboxylic acid, and n ″ is 2 or 3. Allyl esters of an aliphatic or aromatic dicarboxylic acid or a tricarboxylic acid, and triallyl and isocyanurate cyanurates. Compounds 0 to 90 selected from triallylic acid
Component (c) comprises 0 to 30% by weight of an acrylic monomer or a vinyl monomer, and the sum of the compounds (b) and (c) is greater than 0.

Component (a ') is preferably the product of a reaction of diallyl carbonate with a dihydric alcohol at a molar ratio of 4: 1 or less, preferably at a ratio of 2: 1, wherein the dihydric alcohol is ethylene glycol, 1,3-propane. Diol, 1,4-butanediol, 1,6-hexanediol, diethylene glycol, polyethylene glycol, dipropylene glycol, propylene glycol, neopentyl glycol,
Trimethylpentanediol, cyclohexanedimethanol, bis (hydroxymethyl) tricyclodecane, 2,
7-norbornanediol, α, α'-xylenediol, 1,4-bis (hydroxyethoxybenzene), and 2,2-bis [4- (hydroxyethoxy) phenyl]
It is preferably selected from among propane.

Component (b) is preferably the product of the reaction of diallyl carbonate with a dihydric or trihydric alcohol in a molar ratio of at least 6: 1, preferably 12: 1, wherein the dihydric or trihydric alcohol is ethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,6-hexanediol, diethylene glycol, polyethylene glycol, dipropylene glycol, propylene glycol, neopentyl glycol, trimethylpentanediol, cyclohexanedimethanol, bis (hydroxymethyl) Tricyclodecane, 2,7-norbornanediol, α, α'-
One or two of xylene diol, 1,4-bis (hydroxyethoxybenzene), 2,2-bis [4- (hydroxyethoxy) phenyl] propane, trimethylolpropane and tri (hydroxyethyl) isocyanurate
Preferably, it is at least one species.

Further, the component (b) may be diallyl phthalate, diallyl succinate, diallyl adipate, diallyl chlorendate, diallyl glycolate, diallyl naphthalenedicarboxylate, and triallyl melidate.

Component (c) includes vinyl acetate, vinyl benzoate, methyl methacrylate, phenyl methacrylate, methyl acrylate, methyl maleate, maleic anhydride,
And one or more of vinylidene chloride.

Examples of such a polymerizable liquid containing [A] include:
Preferably, bisethylene compounds such as diethylene glycol bisallyl carbonate, 1,4 bis (hydroxyethoxy) benzenebisallyl carbonate, bisallyl 2,4-dichloroterephthalate, and vinyl monomers having an aromatic ring such as phenyl methacrylate and benzyl methacrylate. Can be exemplified.

The (meth) acrylic compound used in [A] is not particularly limited, but mono (meth) acrylate and di (meth) acrylate represented by the following structural formulas are preferably used. (Meth) acrylates are preferred.

_{CH 2 = CH-CO- (OCH} 2 -CH 2) n -OCH 3 n = 3~9 _{CH 2 = CH-COOCH 2 CH} 2 OCOCH 2 CH 2 -COOH CH 2 = CHCO- (OCH 2 CH 2) 2 -O- (CH 2) 3 -CH 3 _{CH 2 = CH-CO-O} (CH 2 -CH 2 O) n CO-CH = CH 2 n = 4~14 CH 2 = CH-COO- (CH 2) 6 OOC-CH = CH 2 Such a polymerizable liquid containing [A] may contain various polymerization initiators.

In the present invention, when polymerizing a polymerizable liquid material containing [A], the polymerization initiator used is not particularly limited as long as it does not adversely affect the transparency, color, and other properties of the resin to be formed. Instead, any initiator such as a photopolymerization initiator, a thermal polymerization initiator, or a combined photo- and heat-polymerization initiator may be used.

Examples of the photopolymerization initiator include an electron beam, a radiation polymerization initiator, and the like, in addition to the photopolymerization initiator.

As the photopolymerization initiator, for example, 2-hydroxy-2-
Methyl-1-phenyl-propan-1-one is mentioned.

As a thermal polymerization initiator, diisopropyl peroxydicarbonate, disecondary butyl peroxydicarbonate, dicyclohexylperoxydicarbonate,
Peroxydicarbonates such as tert-butyl perbenzoate, benzoyl peroxide, acetyl peroxide,
Organic peroxides such as t-butyl hydroperoxide, cumene hydroperoxide, di-t-butyl peroxide, t-butyl peroxybenzoate, lauroyl peroxide, diisopropylperoxydicarbonate, methyl ethyl ketone peroxide, diacyl peroxides, and inorganic peroxides. Oxides and radical initiators such as azobisisobutyronitrile and azobismethylisovaleronitrile are mentioned.

As the polymerization initiator combined with light and heat, for example, the following formula, The compound of.

The amount of the polymerization initiator used is 0.1 to 10% by weight, preferably 1 to 6% by weight, based on the polymerizable liquid containing [A].

Further, other monomers and other fillers can be added to the polymerizable liquid material containing the polymerizable liquid material containing [A] to such an extent that the physical properties of the produced polymer are not impaired.

For example, an unsaturated carboxylic acid such as maleic anhydride or a silane coupling agent such as vinyltriethoxysilane in a proportion of up to 10% by weight can be added.

The density of the polymerizable liquid containing [A] is not particularly limited, but is usually about 0.9 to 1.2 g / m ² .

In addition, as such a polymerizable liquid material containing [A], a prepolymer obtained by pre-polymerizing the above-mentioned material using a polymerization initiator or the like to a level that maintains fluidity is also preferably used.

In the polymerization method of the present invention, as shown in FIG. 1, the solubility of the polymerizable liquid material containing [A] on the polymerizable liquid material containing [A] is low. And the presence of a liquid [C] having a density smaller than the density of the polymerizable liquid containing [A] to polymerize the polymerizable liquid containing [A], preferably in the presence of a polymerization initiator. I do.

The liquid material [C] is not particularly limited as long as it has low solubility with the polymerizable liquid material containing [A] and has a density smaller than the density of the polymerizable liquid material containing [A]. Absent.

In this case, the solubility in the polymerizable liquid material [C] containing [A] must be small enough not to adversely affect the transparency, weather resistance, surface properties, surface hardness, etc. of the resin to be formed. For example, when expressed in terms of solubility, it is usually 5% or less, preferably 2% or less.

When the solubility is such, a preferable result is obtained in that the same hardness (degree of polymerization) is obtained between the surface and the inner surface of the obtained resin.

The density of the liquid material [C] is not particularly limited, but is usually 1 or less, preferably about 0.8 to 0.95.

Such a liquid material [C] is preferably a low-molecular-weight liquid synthetic hydrocarbon polymer, a liquid hydrocarbon mixture, or a mixture thereof.

Examples of the synthetic hydrocarbon polymer include poly (α-olefin) oils such as polydecene-1, alkyl aromatic oils such as alkylbenzene, polybutene oil (liquid polybutene), polyhexene, 2,4-dicyclohexyl-2-methylpentane oil, and the like. And an ethylene / α-olefin random copolymer oil such as an ethylene-propylene landane copolymer oil.

Among them, the molecular weight is 500 or more, preferably 1000 to 1
0000 is preferred.

Furthermore, the number average quantity (n) is 500-5000, especially 1500
Ethylene, α-olefin random copolymer oils of up to 3000 are also preferred.

Further, it is composed of 30 to 70 mol% of an ethylene component unit and 30 to 70 mol% of an α-olefin component unit, has a number average molecular weight (n) in a range of 1,000 to 5,000, and has a Q value (weight average molecular weight / number average molecular weight). Is particularly preferably a liquid low-molecular-weight ethylene / α-olefin copolymer having a molecular weight of 3 or less. When a liquid polyolefin or the like is used for the liquid material [C], the liquid material itself exerts a releasing effect, so that the release is extremely easy. After polymerization, the liquid polyolefin can be easily removed with an organic solvent such as hexane, kerosene, and trichlene.

Water is also suitably used as the liquid material [C].
Water is suitable for polymerizing at a relatively low temperature because of its high vapor pressure.

Further, the polymerization may be carried out by covering the surface of the liquid material [C] in an inert gas atmosphere having an oxygen concentration of 1% or less. In such a case, a resin having a high surface hardness can be obtained. obtain.

In the polymerization method of the present invention, the polymerizable liquid containing [A] is in contact with the polymerizable liquid containing [A], and has low solubility with the polymerizable liquid containing [A]. This is a polymerization method in which a liquid substance [C] having a density smaller than the density of the liquid substance is present to perform polymerization.

Although any method may be used as a method for causing the liquid material [C] to be in contact with the polymerizable liquid material containing [A], the following method is preferable.

A polymerizable liquid containing the above-mentioned [A] containing a polymerization initiator is injected into a mold 10 having an open top. And
On the upper interface (surface) of the polymerizable liquid material containing [A],
Further, a liquid material [C] is injected, and the contact between the polymerizable liquid material including [A] and air (oxygen) is cut off.

The polymerizable liquid containing [A] is polymerized in the state of the system comprising two layers of the polymerizable liquid containing [A]-[C] as shown in FIG. I do.

As for the order of adding each liquid, it is preferable to inject the liquids in order of increasing density as described above. However, paying attention to suspension between the liquids, the liquid [C] is first injected into the mold 10,
A liquid material [C] may be formed on the polymerizable liquid material layer containing [A] by injecting the polymerizable liquid material containing [A].

As the mold 10 used in the polymerization method of the present invention, any of commonly used molds such as glass, polyvinyl chloride, polyethylene resin, polypropylene resin, and poly-4-methyl-1-pentene resin can be used.

Further, the shape of the mold 10 may be appropriately selected according to the shape of the object to be formed.

The polymerization can be carried out under various conditions depending on the composition of the polymerizable liquid material containing [A] and the polymerization initiator contained.

In the thermal polymerization, although it depends on the shape and size, for example, 30 to 150 ° C., preferably 40 to 120 ° C., 0.5
It is good to heat for up to 72 hours, preferably 1 to 4 hours. In photopolymerization, for example, under a high pressure mercury lamp of 60 W / cm to 150 W / cm,
The polymerization is preferably carried out for 2 to 2 hours, preferably 3 to 30 minutes, at 40 to 120 ° C, preferably 60 to 100 ° C.

The cured resin molded product obtained by the polymerization method of the present invention,
Since there is substantially no difference in hardness between the surface and the inside, and there is no optical distortion inside, it can be widely used for optical lenses, transparent plates, rod-shaped transparent bodies and the like.

<Example> Hereinafter, the present invention will be described specifically with reference to examples.

(Example 1) Into a beaker having an inner diameter of 5 cm, 25.8 g of the following as a polymerizable liquid material containing [A] was injected.

Polymerizable liquid material containing [A] -1: diallyl carbonate and diethylene glycol were mixed at a molar ratio of 2: 1 in the presence of sodium ethoxide.
Prepared under the conditions described in JP-A-133246 (30% by weight is diethylene glycol bisallyl carbonate, 70% by weight is oligocarbonate, n = 3 to 10)
Tris (allyl carbonate) of tris (hydroxyethyl) isocyanurate prepared by reacting diallyl carbonate with tris (hydroxyethyl) isocyanurate at a molar ratio of 12: 1 12.4% by weight of diethylene glycol bisallyl carbonate … 2
7.5% by weight Vinyl acetate 5% by weight Diisopropyl peroxydicarbonate 2.5% by weight On top of the polymerizable liquid 1 containing [A], ethylene propylene having a density of 0.846 is added as liquid [C]. The polymer (Mn 2500, Q value 2.0) was injected to a layer thickness of 1 cm.

The beaker containing the two layers thus obtained is placed in an air oven, and the temperature is increased stepwise from 40 ° C. to 85 ° C. over 5 hours to polymerize the polymerizable liquid material-1 containing [A]. Was terminated.

The surface of the obtained resin has a pencil hardness of 3H and a density of 1.331.
Was sufficiently cured.

Further, when observed with a polariscope, the optical distortion was extremely small. Further surface roughness meter (Mitoyo Seisakusho) measuring length was measured surface roughness at 0.75 mm, R _a 0.002
μm and _Rmax 0.03 μm, and the surface smoothness was also good.

(Example 2) A polymerizable liquid material containing [A] in the same manner as in Example 1 except that the layer thickness of the liquid material [C] of Example 1 was changed to 0.2 cm.
The polymerization of 1 was terminated.

The surface of the obtained resin has a pencil hardness of 3H and a density of 1.330.
Was sufficiently cured.

Further, when observed with a polariscope, the optical distortion was extremely small. Furthermore, when the surface roughness was measured with a surface roughness meter (manufactured by Mitoyo Seisakusho), the measurement length was 0.75 mm, and _Ra 0.003
μm, _Rmax 0.05 μm, and the surface smoothness was also good.

Example 3 The following polymerizable liquid containing [A] was poured into a beaker having an inner diameter of 5 cm to a layer thickness of 0.8 cm.

Polymerizable liquid substance containing [A] -2 Prepared by reacting diallyl carbonate and diethylene glycol at a molar ratio of 2: 1 in the presence of sodium ethoxyside under the conditions described in JP-A-56-133246. (30 wt% is diethylene glycol, bisallyl carbonate, 70 wt% is oligocarbonate, n = 3-7)
58% by weight of tris (hydroxyethyl) isocyanurate prepared by reacting diallyl carbonate with tris (hydroxyethyl) isocyanurate at a molar ratio of 12: 1 13% by weight of diethylene glycol bisallyl Carbonate ... 29
2.7% by weight Diisopropyl peroxydicarbonate Further, as a liquid material [C], an ethylene propylene copolymer having a density of 0.846 (M2500, Q value 2.0) was used.
Injected to 0.5 cm.

The beaker containing the two layers thus obtained is put into an air oven, and the temperature is gradually increased from 40 ° C. to 85 ° C. over 5 hours to polymerize the polymerizable liquid material-2 containing [A]. Finished.

The surface of the obtained resin was sufficiently cured with a pencil hardness of 3H and a density of 1.340.

Further, when observed with a polariscope, the optical distortion was extremely small. In addition the surface roughness meter (Mitoyo Seisakusho) measuring length was measured surface roughness at 12.5mm, R _a 0.03μ
m and _{Rmax were} 0.3 μm, and the surface smoothness was also good.

(Example 4) Into a 50 ml beaker having an inner diameter of 5 cm, the following as a polymerizable liquid containing [A] was injected to a layer thickness of 0.8 cm.

Polymerizable liquid material containing [A] -3 Viscosity 14 cps / 25 ° C, saponification value 340, brominated 93
Monomer: 99.5 benzoyl peroxide: 0.5% by weight The density of the monomer was 1.08 g / cm ³ .

The beaker containing the three layers thus obtained was placed in an air oven and heated at 88 ° C. for 6 hours and at 100 ° C. for 2 hours.

The resulting resin had a pencil hardness of 3H on both the upper and lower surfaces and a density of 1.2250.

Further, when observed with a polariscope, the optical distortion was extremely small. Furthermore, the surface smoothness was also good.

 From the above results, the effect of the present invention is clear.

<Effect of the Invention> According to the method for producing a resin of the present invention, a monomer or oligomer containing a bisallyl-based compound and / or a (meth) acrylic compound as an essential component or a mixture thereof is used by using a mold partially open. In obtaining a resin molded product which has been polymerized and cured by a simple process, a molded product having a high surface hardness can be obtained in a simple process at a low cost.

In addition, since the surface of the above-mentioned monomer or oligomer or a mixture thereof and the air (oxygen) air are shielded by a predetermined liquid, molding of a complicated shape can be easily performed. Can be reliably shielded from the air by following the contraction of the volume.

Further, since no stress is applied to the monomer or oligomer during the polymerization from an elastic body such as a mold, a molded product without distortion can be obtained.

[Brief description of the drawings]

FIG. 1 is a schematic view showing one embodiment of the polymerization method of the present invention. EXPLANATION OF SYMBOLS 10 …… MOLD

Claims (3)

(57) [Claims] 1. A monomer or oligomer containing a bisallyl compound and / or a (meth) acrylic compound as an essential component or a polymerizable liquid material containing a mixture [A] thereof in contact with said monomer or oligomer or A liquid [C] which has low solubility with the polymerizable liquid containing the mixture [A] and has a density smaller than the density of the polymerizable liquid containing the monomer or oligomer or the mixture [A] thereof ], And polymerizing a polymerizable liquid containing the monomer or oligomer or a mixture [A] thereof. 2. A method according to claim 1, wherein said monomer or oligomer or a mixture thereof [A] is represented by the following formula (a): Wherein R is the residue of a dihydric alcohol, and the value of n or the average value of n is from 1 to 10, preferably from 2 to 10, which is an aliphatic, alicyclic or aromatic dihydric alcohol represented by the formula: The method for producing a resin according to claim 1, which comprises a bis (allyl carbonate) monomer or oligomer or a mixture thereof. 3. The method for producing a resin according to claim 1, wherein the liquid [C] is a low-molecular-weight liquid synthetic hydrocarbon polymer, a liquid hydrocarbon mixture, or a mixture thereof.