JPS61195105A - Resin composition of high refractive index - Google Patents

Abstract

PURPOSE:A resin composition that is composed of a copolymer from 2 different kinds of specific monomers, thus being suitably used as optical lenses, because it has high refractive index with reduced color abberatin as well as high light resistance, shock resistance and processability. CONSTITUTION:The objective composition is composed of a copolymer from 10-90pts.wt. of a monomer of formula I (n is 0-2; X is H, methyl, Cl, Br; Y1, Y2 are H, Cl, Br, I) and 10-90pts.wt. of monomers copolymerizable with the above-cited monomer such as a monomer of formula II (Y1, Y2 are H, methyl Cl, Br; Z1-Z4 are H, Cl, Br; n1, n2 are 0-3), preferably giving a homopolymer of more than 1.55 refractive index. EFFECT:The resultant resin composition has more than 35 Abbe number and more than 1.55 refractive index.

Description

DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a novel resin composition, particularly a novel high refractive index resin composition with little chromatic aberration.

[Conventional technology]

Conventionally, various synthetic resins to replace inorganic glass have been studied and proposed. For example, polymers containing diethylene glycol bisallyl carbonate as a main component have been put to practical use as optical lenses.

This polymer has advantages that inorganic glass cannot satisfy, such as light weight, safety, easy processability, and dyeability, and because it is crosslinked, it also has good mechanical properties.

[Problem that the invention seeks to solve]

However, there is a drawback that the refractive index of the polymer is as low as about /, jO. On the other hand, high refractive index resins that have improved this drawback have also been proposed. For example, Japanese Patent Application Publication No. 1986-#; 42/4
Resins containing a large amount of benzene nuclei and halogens, which are found in grade 1, have a high refractive index, and when made into lenses, they can be made thinner than conventional products. However, these resins have extremely low Atsube numbers of 3j or less. When the Abbe number becomes low, the difference in refractive index depending on each wavelength becomes large (high dispersion), which is not preferable in terms of lens design.

Recently, as seen in JP-A-39-790/, resins that have both a high refractive index and a high Atsube number have been developed, but the main component of this resin is a copolymer of monomers with a dicyclopentene skeleton. Many lens materials have insufficient hardness. Further, even after polymerization, double bonds remain within the molecule, and this portion is susceptible to chemical reactions, resulting in coloring, etc.

An object of the present invention is to provide a resin for optical lenses that has optical properties of high refractive index and low dispersion, and has excellent light resistance, impact resistance, cutting/polishing properties, hardness, etc.

[Means for solving problems]

The present inventors completed the present invention as a result of intensive research aimed at improving such defects in conventional resins. That is, the present invention provides a copolymer of one or more first monomers represented by the general formula CI) and one or more comonomers capable of radical copolymerization therewith. It is a resin composition with a high refractive index, which is characterized by having the main component as a main component. Here, the general formula CI) is (ns=o,/or co).

X-H, OH3* 01 or Br Y,, Y2 are each independently, H+ Ol * B
r or l). As the second monomer, the general formula (
Bisphenol derivatives represented by I or styrene derivatives such as styrene, chlorostyrene, dichlorostyrene, bromostyrene, methylstyrene, methoxystyrene, divinylbenzene; phenyl acrylate, chlorophenylacrylate, dichlorophenylacrylate.

Trichlorophenyl acrylate, bromophenyl acrylate, benzyl acrylate, P-chlorobenzyl acrylate, 0-chlorobenzyl acrylate, dichlorobenzyl acrylate.

Esters of acrylic acid such as trichlorobenzyl acrylate, bromobenzyl acrylate, promophenyloxyether acrylate; phenyl methacrylate, chlorophenyl methacrylate.

Dichlorophenyl methacrylate, trichlorophenyl methacrylate, bromophenyl methacrylate, dibromophenyl methacrylate, benzyl methacrylate, P-chlorobenzyl methacrylate, 10-chlorobenzyl methacrylate.

Esters of methacrylic acid such as dichlorobenzyl methacrylate, trichlorobenzyl methacrylate, bromobenzyl methacrylate, bromophenyloxyethyl methacrylate, dibromophenyloxyethyl methacrylate, tribromophenyloxymethacryle-f; allyl cinnamate, diallyl phthalate, diallyl iso-7-thalecite, Allyl compounds such as triallyl cyanurate and triallyl isocyanurate are used.

All of the above-mentioned second monomers have a refractive index of 7.61 or more when made into a polymer alone.

The present invention will be explained in detail below.

At least one first monomer of the present invention and at least one
In a resin composition whose main component is a copolymer with a second monomer of #! If the composition ratio of the 1 monomer is too small, the Abe number of the resin will decrease. Conversely, when the composition ratio of the first monomer is excessive, the refractive index of the resin decreases.

Therefore, the resin composition of the present invention contains 10 to 90% of the first monomer.
It is obtained by copolymerizing a monomer mixture containing 70 to 90 weight %, preferably 30 to 10 weight % of Sλ monomer.

In addition, the resin composition of the present invention may contain an ultraviolet absorber of 0.03 to improve its weather resistance and light resistance, if necessary.
It is preferable to contain up to 3.0 parts by weight. Ultraviolet II
If the concentration of the s-absorbent is less than 0.0j% by weight, there will be little effect on improving weather resistance and light resistance, and 3.
If the amount exceeds 0% by weight, yellow coloring becomes noticeable and the commercial value tends to decrease.

As the ultraviolet absorber used in the present invention, a wide range of UV absorbers can be used, such as benzotriazole type, benzophenone type, salicylic acid type, cyanoacrylate type, hindered amine type as ultraviolet stabilizer, N1 complex #i type, benzoate type, etc.

The method of polymerizing the composition of the present invention is not particularly limited, and any known polymerization method can be employed. For example, between the molds held by an elastomer gasket or spacer, the The composition can be produced by adding a polymerization initiator to the second monomer and the ultraviolet ls absorber and heating the mixture, but the composition can also be produced by photopolymerization or radiation polymerization. Furthermore, by selecting the type and amount of the polymerization initiator, it is possible to manufacture by a reaction injection molding method (RIM), and the method is not limited to the casting method. Examples of the above polymerization initiator include benzoyl peroxide diisopropylberoxydicarbonate, lauroyl peroxide, organic peroxides, and azo compounds such as azobisisobutyronitrile, etc. from 0.03~! , used by mixing zero weight.

The type and concentration of the polymerization initiator to be used are determined in 1. It is determined by considering the composition, reactivity, reaction rate control, etc. of the second monomer mixture.

〔Effect of the invention〕

The resin composition of the present invention as described above has an excellent Atsube number, such as at least 3j, and a high refractive index, e.g., at least 31, as compared to conventionally proposed high refractive index resins. It has optical properties.

Furthermore, it has excellent light resistance, dyeability, and processability, and can be used for various optical lenses and optical elements such as cameras and eyeglasses.

〔Example〕

Examples of the present invention are shown below. The test method for each characteristic was performed as follows.

Lightfastness Near Needmeter After a long period of time, yellowness was measured using a color difference meter, and judgment was made based on the difference from the initial yellowness. The difference is j
, those below O were marked ○, and those above were marked ×.

Examples are given in general formula (1), n-0r X-H, Y, -Y
2■H dicyclopentanyl acrylate 3j% by weight, varabromophenyl methacrylate 33% by weight,
Bisphenol A dimethacrylate 30% by weight, azobisisobutyronitrile o,! % by weight and co(co-hydroxy-3'j/-ditertiary-
butylphenyl)-yo-chlorobenzotriazole1.
A mixed solution containing 0% by weight was poured into a glass mold and polymerized in hot air. Polymerization conditions are 50℃
After heating at 60°C for 7 hours and 5 hours at 60°C, the temperature was raised to 90°C over 1 hour and held at 90°C for 1 hour. The lens was taken out from the glass mold and aired at 110° C. for 2 hours. The obtained lens had a refractive index of i, stt, and an Atsube number of 31.0, and showed excellent results in terms of light resistance, impact resistance, hardness, machinability, and dyeability, making it an excellent lens material. It had certain characteristics.

Examples 2 to 3 Polymerization was carried out in exactly the same manner as in Example 1 to obtain lenses of various compositions. The results are shown in Table/.

Comparative Examples 7 to 3 Table 1 shows the properties of lenses cast and polymerized in the same manner as in Example 1.

(Note) Monomer abbreviation DCPA Nidicyclopentanyl acrylate P
-Brf'hM included; bara bromophenyl methacrylateBPMA: bisphenol A dimethacrylate N0pol -MA: Nopol methacrylic acid ester P-(JBzMA: parachlorobenzyl methacrylate c14npv =2,2-bis(II-methacryloxy-j,j -dichlorophenyl)propane

Claims (3)

[Claims] (1) First monomer 10 to 9 represented by general formula [I]
0 parts by weight and a second monomer radically copolymerizable with this 10
High refractive index resin composition consisting of a copolymer polymerized with ~90 parts by weight as the main component ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼ [I] (n = 0, 1, or 2. X = H, CH_3, Cl or Br. Y_1 and Y_2 each independently represent H, Cl,
Br or I) (2) The refractive index of the homopolymer of the second monomer is 1.55.
The high refractive index resin composition according to claim 1, which is the above. (3) The high refractive index resin composition according to claim 2, wherein the second monomer is represented by general formula [II]. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [II] (Y_1 and Y_2 are each independently H, CH_3
, Cl or BrZ_1 to Z_4 are each independently H
, Cl or Brn_1 and n_2 are each independently 0, 1, 2, or 3)