Optical resin monomer with high refractive index and preparation method thereof

Abstract

The invention provides an optical resin monomer with high refractive index. The monomer has the structural formula shown in the specification, wherein in the structural formula, R is hydrogen, alkyl, alcoxyl, halogen and aryl; Ph is a benzene ring; m and n are integers; m is not less than 1 and not more than 6; and n ranges from 0 to (6-m). A preparation method comprises the following steps: taking the following raw materials: aromatic hydrocarbon, NBS (N-bromosuccinimide), BPO (benzoyl peroxide), thiourea, sodium hydroxide, hydrochloric acid, epichlorohydrin and potassium thiocyanate, wherein the mole ratio of aromatic hydrocarbon to NBS to thiourea to sodium hydroxide to hydrochloric acid to epichlorohydrin to potassium thiocyanate is 1:(3-5):0.1:(3-5):(9-12):(6-10):(3-5):(10-15); step 1. carrying out halogenation; step 2. carrying out halogen methylated thiolation: adopting a thiourea hydrocarbylation hydrolysis method or thiocyanate direct substitution method; 3. carrying out epoxidation: using a universal epichlorohydrin preparation method; and 4. preparing cyclic sulfide products: adopting a universal cyclic sulfide preparation method.

Description

technical field

[0001] The invention relates to a high-refractive-index optical resin monomer and a preparation method thereof. The monomer can be used to prepare high-performance optical resin materials for preparing optical devices such as resin lenses and optical lenses. The outstanding advantage of this monomer is that the optical resin obtained by polymerization of this monomer has a high refractive index and Abbe number. Background technique

[0002] In recent years, the application of optical resins in glasses industry, optical devices and other fields has developed rapidly, and the demand for high-performance optical resin materials has become more and more extensive. For example, the mainstream optical resin in the resin lens market has a refractive index of about 1.5. In order to make the lens ultra-thin and low curvature, the refractive index of the material must be increased.

[0003] The introduction of sulfur is one of the most effective ways to increase the r...

Examples

Embodiment 1

[0083] Example 1: Using NBS as a halogenated reagent to prepare a high refractive index optical resin monomer: (n=0, m=3)

[0084] The steps are as follows: (such as figure 1 shown)

[0085] Raw materials are aromatic hydrocarbons, NBS, BPO, thiourea, sodium hydroxide, hydrochloric acid, epichlorohydrin, potassium thiocyanate; of which aromatic hydrocarbons: NBS: BPO: thiourea: sodium hydroxide: hydrochloric acid: epichlorohydrin: thiocyanate The molar percentage of potassium acid potassium is 1:3~5:0.2~0.4:3~5:9~12:6~10:3~5:10~15;

[0086] Step 1: Synthesis of mesitylene: Add 5g of mesitylene, 25.5g of NBS, and 0.1g of BPO as an initiator in a single-port bottle, and then add CCl 4As a solvent, magnetically stirred, heated to reflux, and reacted for 24h. After the reaction was cooled, a large amount of white solids precipitated out. The solids were removed by filtration, and the solvent was removed by rotary evaporation to obtain a light yellow viscous liquid, which was ...

Embodiment 2

[0093] Example 2: Preparation of high refractive index optical resin monomer by direct halomethylation method: (n=3, m=3)

[0094] The steps are as follows (such as figure 2 ):

[0095] The raw materials are aromatic hydrocarbons, paraformaldehyde, glacial acetic acid, acetic acid solution of hydrogen bromide, thiourea, sodium hydroxide, hydrochloric acid, epichlorohydrin, potassium thiocyanate; among them, aromatic hydrocarbons, paraformaldehyde, glacial acetic acid, hydrogen bromide The molar percentage of acetic acid solution, thiourea, sodium hydroxide, hydrochloric acid, epichlorohydrin and potassium thiocyanate is 1:3~4:15~20:12~20:3~5:9~12:6~ 10: 3-5: 10-15.

[0096] Step 1: Synthesis of 1,3,5-tribromomethyl-2,4,6-trimethylbenzene (A1): Add 12.00 g (0.10 mol) of mesitylene and 10.00 paraformaldehyde in a 250 ml three-necked flask g (0.33 mol), 100 ml of glacial acetic acid, 70 ml of hydrogen bromide in acetic acid solution (31%), react at 120°C for 11 h. During the...

technical field

[0001] The invention relates to a high-refractive-index optical resin monomer and a preparation method thereof. The monomer can be used to prepare high-performance optical resin materials for preparing optical devices such as resin lenses and optical lenses. The outstanding advantage of this monomer is that the optical resin obtained by polymerization of this monomer has a high refractive index and Abbe number. Background technique

[0002] In recent years, the application of optical resins in glasses industry, optical devices and other fields has developed rapidly, and the demand for high-performance optical resin materials has become more and more extensive. For example, the mainstream optical resin in the resin lens market has a refractive index of about 1.5. In order to make the lens ultra-thin and low curvature, the refractive index of the material must be increased.

[0003] The introduction of sulfur is one of the most effective ways to increase the r...

Examples

Embodiment 1

[0083] Example 1: Using NBS as a halogenated reagent to prepare a high refractive index optical resin monomer: (n=0, m=3)

[0084] The steps are as follows: (such as figure 1 shown)

[0085] Raw materials are aromatic hydrocarbons, NBS, BPO, thiourea, sodium hydroxide, hydrochloric acid, epichlorohydrin, potassium thiocyanate; of which aromatic hydrocarbons: NBS: BPO: thiourea: sodium hydroxide: hydrochloric acid: epichlorohydrin: thiocyanate The molar percentage of potassium acid potassium is 1:3~5:0.2~0.4:3~5:9~12:6~10:3~5:10~15;

[0086] Step 1: Synthesis of mesitylene: Add 5g of mesitylene, 25.5g of NBS, and 0.1g of BPO as an initiator in a single-port bottle, and then add CCl 4As a solvent, magnetically stirred, heated to reflux, and reacted for 24h. After the reaction was cooled, a large amount of white solids precipitated out. The solids were removed by filtration, and the solvent was removed by rotary evaporation to obtain a light yellow viscous liquid, which was ...

Embodiment 2

[0093] Example 2: Preparation of high refractive index optical resin monomer by direct halomethylation method: (n=3, m=3)

[0094] The steps are as follows (such as figure 2 ):

[0095] The raw materials are aromatic hydrocarbons, paraformaldehyde, glacial acetic acid, acetic acid solution of hydrogen bromide, thiourea, sodium hydroxide, hydrochloric acid, epichlorohydrin, potassium thiocyanate; among them, aromatic hydrocarbons, paraformaldehyde, glacial acetic acid, hydrogen bromide The molar percentage of acetic acid solution, thiourea, sodium hydroxide, hydrochloric acid, epichlorohydrin and potassium thiocyanate is 1:3~4:15~20:12~20:3~5:9~12:6~ 10: 3-5: 10-15.

[0096] Step 1: Synthesis of 1,3,5-tribromomethyl-2,4,6-trimethylbenzene (A1): Add 12.00 g (0.10 mol) of mesitylene and 10.00 paraformaldehyde in a 250 ml three-necked flask g (0.33 mol), 100 ml of glacial acetic acid, 70 ml of hydrogen bromide in acetic acid solution (31%), react at 120°C for 11 h. During the...

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