JPS6014202A - Plastic lens - Google Patents

Abstract

PURPOSE:To obtain a plastic lens having a high refractive index by using a copolymer which consists essentially of monomers of specific two components and is obtd. in the presence of a radical polymn. initiator. CONSTITUTION:The two components expressed by the formula I (X is halogen except F, (a) is 0-4) and the formula II (R1 is H or an alkyl group, (b) is 0-4, n is 1-4) are used as an essential component and are copolymerized in the presence of a radical polymn. initiator. The copolymer obtd. by incorporating the compd. expressed by the formula I in a 10-90wt% range therein and incorporating the compd. expressed by the foumula II in a 10-50wt% range therein has >=1.57 refractive index. The monomer mixture contg. the above-mentioned radical polymn. initiator is polymerized by using, for example, molds for forming a lens, etc. The polymer obtd. in the above-mentioned way has not only a high refractive index but also excellent mechanical properties, workability, dyeability, formability, chemical resistance, etc. and is usable preferably in the same applications as for inorg. glass, i.e., for a lens of a camera, spectacles, etc. or for a prism, etc.

Description

[Detailed description of the invention]

The present invention relates to a synthetic resin lens that has a relatively high refractive index as a synthetic resin and has excellent optical properties. Conventionally, optical materials made of glass have excellent scratch resistance, but have drawbacks such as being heavy and easily broken. On the other hand, synthetic resin optical materials have the advantages of being light, hard to break, dyeable, and highly fashionable, and polymethyl methacrylate, polydiethylene glycol bisallyl carbonate, and the like are already in use. However, the synthetic resin optical material has a low refractive index of about 1.49, and when molded into a lens, it must be significantly thicker than inorganic glass. Particularly in negative lenses, the edge thickness of the lens becomes significantly thicker, and there is a strong demand for thinner lenses. Furthermore, synthetic resins with a high refractive index, such as polycarbonate and polystyrene, have problems in scratch resistance, chemical resistance, processability, heat resistance, and the like. Various high refractive index synthetic resins have been studied to improve these drawbacks, but they currently have problems with weather resistance, heat resistance, and dyeability, and are not required for synthetic resin lenses. The quality does not fully meet the expected quality. The main object of the present invention is to provide a high refractive index synthetic resin lens that overcomes the drawbacks of synthetic resin lenses described above. Specifically, it is a polymer characterized by containing diallyl orthophthalate, diallyl terephthalate, diallyl isophthalate alone and derivatives thereof as one component, and copolymerizing diacrylate and dimethacrylate having an aromatic ring in the presence of a radical polymerization initiator. be. The polymer not only has a high refractive index but also has good mechanical properties, processability, dyeability, and moldability. It has excellent chemical resistance and can be suitably used for almost the same purposes as inorganic glass, ie, lenses for cameras, glasses, etc., or prisms. The present invention will be explained in detail below. The copolymer of the lens according to the present invention contains 50 to 90% by weight of one or more monomers whose general formula is represented by (1) and one or more monomers whose general formula is represented by (If). It can be obtained by copolymerizing a mixed monomer containing 10 to 50% by weight in the presence of a radical polymerization initiator. [In the formula, X is halogen excluding fluorine, a is o, 1°2.3
or an integer of 4] [In the formula, X is halogen excluding fluorine, b is o, 1°2.3
, 4 or 5, n is an integer of 1 to 4] The halogen in the general formula (1) of diallylphthalate having a nuclear halogen-substituted aromatic ring used in the present invention is not particularly limited to chlorine, bromine, or iodine other than fluorine. Although chlorine and bromine are used, preferably chlorine and bromine are used. 3- The number of halogens contained in the aromatic ring is not particularly limited, and 1 to 4 halogens can be used. Typical compounds that can be suitably used in general formula (1) include tetrachlorodiallyl phthalate, trichlordiallyl phthalate, dichlorodiallyl phthalate, 1
- Chlordialyl phthalate. 2-Chlorodiallyl phthalate, tetrabromo diallyl phthalate, tribromo diallyl phthalate, dibromo allyl phthalate, 1-bromo diallyl phthalate, 2
-Bromodiallyl phthalate, etc. are used. The halogen of the phenoxyethyl acrylate general formula (II) having a nuclear halogen-substituted aromatic ring used in the present invention is not particularly limited and may be chlorine, bromine, or iodine except for fluorine, but chlorine or bromine is preferable. The number of halogens contained in the aromatic ring is not particularly limited, and is 1 to 4.
pieces can be used. Typical compounds that can be suitably used in general formula (II) include phenoxyethyl acrylate, 4-chlorophenoxyethyl acrylate, dichlorophenoxyethyl acrylate, trichlorophenoxyethyl acrylate, pentachlorophenoxyethyl acrylate, and bromphenoxyethyl acrylate. , dibromophenoxyethyl acrylate, tribromophenoxyethyl acrylate, tetrabromophenoxyethyl acrylate, pentabromophenoxyethyl acrylate, and the like. In addition, examples of the polymerization initiator for the monomer include 1゜1-bis(t-butylperoxy)3,3.5-trimethylcyclohexane, 2,2-bis(1-butylperoxy)octane, dicumyl peroxide, α, α′-bis(t
-butylperoxyisopropyl)benzene, 2,5-
Dimethyl 2゜5-di(t-butylperoxy)hexane, benzoyl peroxide, t-butylperoxy(
2-ethylhexanoate), t-butylperoxybenzoate, and the like are suitable. The preferred composition of the metal compound represented by the general formula (1) used in the present invention is 50 to 90% by weight;
) is preferably 10 to 50% by weight. When the composition of the compound of general formula (I) exceeds 90% by weight,
Although performance such as processability, chemical resistance, and heat resistance improves,
Problems with impact resistance and moldability arise. Furthermore, if the composition of the compound of general formula (T) is less than 50% by weight, problems arise such as a decrease in refractive index and deterioration in dyeability. Furthermore, if the composition of the compound represented by the general formula (TI) is less than 10% by weight, problems will arise in impact resistance and moldability, and if it is more than 50% by weight, problems will arise such as a decrease in refractive index and processability. arise. The high refractive index synthetic resin lens of the present invention can be obtained by mixing the compound represented by the general formula (I) and the compound represented by the general formula (n) in the above weight ratio, and then heating or using ultraviolet rays in the presence of a polymerization initiator. It can be obtained by copolymerization using means such as irradiation. The high refractive index synthetic resin optical element of the present invention has a refractive index of 1.5.
7 or more transparent material, dyeable, processable,
It has excellent physical and chemical properties such as chemical resistance, moldability, impact resistance, and heat resistance, and is particularly preferred as a synthetic resin lens for eyeglasses. Next, examples of the present invention will be specifically described. Note that all composition ratios in Examples and Comparative Examples are based on weight. In addition, the test methods for the measured values obtained in Examples and Comparative Examples are shown below. Refractive index: Measured and calculated by the minimum deviation angle method. Chemical resistance: Immersed in isopropyl alcohol and acetone for 24 hours at room temperature, resulting in roughening on two surfaces. Those with no clouding or deformation were considered good. Heat resistance: It was heated at 120° C. for 24 hours, and those with no change in coloring degree or deformation were evaluated as good. Impact resistance: Judgment was made by performing a steel ball drop test on a flat plate with a center thickness of 2w+n according to FDA standards. Dyeability: Lenses after molding were immersed in a dyeing bath, and those whose total light transmittance was reduced to 50% within 20 minutes were evaluated as good.

[Examples 1 to 3 and Comparative Example 1] Tetrachloro diallyl phthalate and phenoxyethyl acrylate were mixed in the composition shown in Table 1, 2% by weight of benzoyl peroxide was added as a radical polymerization initiator, and the mixture was thoroughly stirred. . This mixed monomer was poured into a casting mold consisting of two glass molds and a polyethylene gasket, and heated to 30°C for 24 hours.
The temperature was raised to ~80°C to conduct polymerization. After polymerization,
The polymer was removed from the cast mold and its various properties were investigated. The results are shown in Examples 1 to 3 in Table 1. This is shown in Comparative Example 1. Comparative Examples 2 and 31 Comparative Examples 1 to 3 were carried out in the same manner as in Examples 1 to 3, except that styrene was used instead of tetrachlorodiallyl phthalate, and the results are shown in Table 1. [Execution @ 4, 51 The procedure was carried out in the same manner as in Examples 1 to 3, except that tetrabrom diallyl phthalate was used instead of tetrachloro diallyl phthalate in Examples 1 to 3. The results are shown in the table below.
Shown in 1. 8- The abbreviations in the following table represent the compounds shown below. C14DAP: Tetrachloro diallyl phthalate PhE
A: Phenoxyethyl acrylate St: Styrene Br4DAP: Tetrabrom diallyl phthalate. O indicates excellent, Δ indicates slightly inferior, and × indicates inferior.

Claims (1)

[Claims] 1. A synthetic resin characterized in that the main component is a two-component copolymer of general formula (1) and general formula (II), which is copolymerized in the presence of a radical polymerization initiator. lens. [In the formula, X is halogen excluding fluorine, a is 0.1°2.3
or an integer of 4] [In the formula or halogen excluding fluorine, b is 0.1°2.3
, 4 or an integer of demand, n is an integer from 1 to 4]2 General formula (1)
The synthetic resin lens according to claim 1, which contains 50 to 90% by weight of general formula (II) and 10 to 50% by weight of general formula (II) and has a refractive index of 1.57 or more.