CN105175608B - A kind of high index of refraction lens resin monomer - Google Patents
A kind of high index of refraction lens resin monomer Download PDFInfo
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- CN105175608B CN105175608B CN201510590690.5A CN201510590690A CN105175608B CN 105175608 B CN105175608 B CN 105175608B CN 201510590690 A CN201510590690 A CN 201510590690A CN 105175608 B CN105175608 B CN 105175608B
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Abstract
The invention belongs to optical resin material technical field, more particularly to a kind of high index of refraction lens resin monomer, by weight percentage, the monomer is composed of the following components:Dibenzyl maleate 5~15%, styrene compound 5~15%, the mixture 30~60% of diallyl p phthalate or DAIP or both, containing bromo-ether 30~40%.The preparation method comprises the following steps:The each component is taken in proportion, and mixing and stirring is put into baking oven, then temperature programming is down to room temperature to 120 DEG C, is produced after adding initiator, degassing, injection molding.The high index of refraction lens resin monomer that the present invention is provided, the monomer formed after each component polymerization, with higher refractive index and stronger impact resistance and wearability, its refractive index is up to more than 1.60;The preparation method that the present invention is provided, its technique is simple, the controllability of process and reproducible, and reaction condition is gentle, pollution-free, low cost.
Description
Technical field
The invention belongs to optical resin material technical field, more particularly to a kind of high index of refraction lens resin monomer.
Background technology
In recent years, optical resin lens at home and abroad be a dark horse by glasses in the market, especially high index of refraction optical resin
Eyeglass is deep by amblyopia group more with distinctive advantages such as its quality is light, intensity is high, non-friable, high transmission rate, UV resistance, ultrathin types
The welcome of body.Generally, in eyeglass industry with refractive index reach more than 1.60 for high index of refraction, refractive index reaches more than 1.56
For middle refractive index, refractive index below 1.56 for low-refraction.It is cinnamic acid esters and other groups to have with main component
The refractive index that the chemical monomer of assignment system is made is 1.56 optical resin lens, but its thickness is thicker, and thermal resistance
Property, visible light transmittance rate poor-performing, it is therefore desirable to have make high refractivity resin lens optical resin monomer material.
The content of the invention
An object of the present invention is:There is provided a kind of refractive index height, shock resistance energy in view of the shortcomings of the prior art
The strong high index of refraction lens resin monomer of power.
In order to solve the above technical problems, the technical scheme is that:
A kind of high index of refraction lens resin monomer, by weight percentage, the monomer is composed of the following components:Maleic acid two
Benzyl ester 5~15%, styrene compound 5~15%, diallyl p phthalate or DAIP or
Both mixtures 30~60%, containing bromo-ether 30~40%.
Wherein, the structural formula containing bromo-ether is as follows:
Its chemical name is double (4- (3- allyloxy -2- propoxyls) 3, the 5- dibromo phenyls) propane, English name of 2,2-
Referred to as 2,2-bis (4- (3- (allyloxy) -2-hydroxypropoxy) -3,5-dibromophenyl) propane.
As one kind improvement, by weight percentage, the monomer is composed of the following components:Dibenzyl maleate 7~10%,
Styrene compound 7~10%, the mixture of diallyl p phthalate or DAIP or both
45~50%, containing bromo-ether 35~40%.
As further improving, the styrene compound is styrene or divinylbenzene.
The second object of the present invention is:There is provided a kind of cost relatively low, the simple high index of refraction lens resin monomer of technique
Preparation method.
In order to solve the above technical problems, the technical scheme is that:
A kind of preparation method of high index of refraction lens resin monomer, the preparation method comprises the following steps:Will by right
Ask mixture, Malaysia of the weight described in 1 than taking diallyl p phthalate or DAIP or both
Sour dibenzyl ester, styrene compound and containing bromo-ether, mixing and stirring is put into baking oven, 1 after adding initiator, degassing, injection molding
Rise to be risen in 70 DEG C, insulation 4~10h, 2~5h by 30 DEG C in 30 DEG C, 2~5h by 20 DEG C in~2h and rise to 120 DEG C by 70 DEG C,
It is incubated in 2~6h, 1~5h and is down to room temperature by 120 DEG C, produces.
It is preferred that, the initiator is azodiisobutyronitrile or ABVN.
It is described to be synthesized according to the following steps containing bromo-ether as one kind improvement:Take reactant tetrabromobisphenol A and allyl glycidyl sweet
Oily ether, adds organic solvent, then mixing and stirring, the weight of the organic solvent for the reactant gross weight 30~
60%, catalyst is added, the weight of the catalyst is the 0.3~3% of the reactant gross weight, is stirred at 30~80 DEG C
Mix, react 5~15h, after reaction terminates, vacuum distillation removes solvent, washed with distilled water, divide liquid, vacuum distillation purified product,
Produce.
Building-up process containing bromo-ether is as follows:
As one kind improvement, the tetrabromobisphenol A is 1 with the mol ratio of the allyl glycidyl ether:1~2.
It is preferred that, the organic solvent is methanol, ethanol or isopropanol.
It is preferred that, the catalyst is triethylamine, tripropyl amine (TPA), tri-n-butylamine, N, N- dimethyl benzylamines or N, N- diethyl
Benzylamine.
By adopting the above-described technical solution, the beneficial effects of the invention are as follows:
Introduced in the high index of refraction lens resin monomer that the present invention is provided, component and contain bromo-ether, be effectively improved monomer
Dibenzyl maleate, styrene compound and the dially phthalate class compound introduced in refractive index, component, each group
The monomer that segregation is formed after closing, with higher refractive index and stronger impact resistance and wearability, its refractive index is up to 1.60
More than.The preparation method that the present invention is provided, its technique is simple, the controllability of process and reproducible, and reaction condition is gentle, no dirt
Dye, low cost, obtained product refractive index is high, and shock resistance is good.
Embodiment
In order to make the purpose , technical scheme and advantage of the present invention be clearer, with reference to embodiments, to the present invention
It is further elaborated.It should be appreciated that the specific embodiments described herein are merely illustrative of the present invention, it is not used to
Limit the present invention.
Embodiment one
A kind of high index of refraction lens resin monomer, by weight percentage, the monomer is composed of the following components:Maleic acid two
Benzyl ester 5%, styrene compound 15%, diallyl p phthalate class compound 50%, containing bromo-ether 30%;Wherein, benzene
Ethylene compounds are styrene.
Embodiment two
A kind of high index of refraction lens resin monomer, by weight percentage, the monomer is composed of the following components:Maleic acid two
Benzyl ester 10%, styrene compound 10%, DAIP class compound 40%, containing bromo-ether 40%;Wherein, benzene
Ethylene compounds are divinylbenzene.
Embodiment three
A kind of high index of refraction lens resin monomer, by weight percentage, the monomer is composed of the following components:Maleic acid two
The mixture of benzyl ester 15%, styrene compound 5%, diallyl p phthalate and DAIP
45%, containing bromo-ether 35%;Wherein, styrene compound is styrene, in the mixture diallyl p phthalate and
DAIP is mixed in any proportion.
Example IV
A kind of high index of refraction lens resin monomer, by weight percentage, the monomer is composed of the following components:Maleic acid two
Benzyl ester 15%, styrene compound 15%, DAIP class compound 30%, containing bromo-ether 40%;Wherein, benzene
Ethylene compounds are styrene.
Embodiment five
A kind of high index of refraction lens resin monomer, by weight percentage, the monomer is composed of the following components:Maleic acid two
Benzyl ester 7%, styrene compound 13%, diallyl p phthalate 60%, containing bromo-ether 30%;Wherein, phenylethylene
Compound is divinylbenzene.
Embodiment six
A kind of high index of refraction lens resin monomer, by weight percentage, the monomer is composed of the following components:Maleic acid two
Benzyl ester 13%, styrene compound 7%, diallyl p phthalate 30%, containing bromo-ether 40%;Wherein, phenylethylene
Compound is styrene.
Embodiment seven
A kind of preparation method of high index of refraction lens resin monomer, the preparation method comprises the following steps:
(1) synthesis containing bromo-ether:Reactant tetrabromobisphenol A 271.9g and allyl glycidyl ether 85.6g are taken, is added
To being equipped with the four-hole bottle of agitating paddle, organic solvent methanol is added, then mixing and stirring, the weight of organic solvent is reaction
The 30% of thing gross weight, adds catalyst of triethylamine, the weight of catalyst is the 0.3% of reactant gross weight, at 30 DEG C
Stirring, reaction 5h, after reaction terminates, vacuum distillation removes solvent, is washed with distilled water, divides liquid, vacuum distillation purified product, i.e.,
;
(2) preparation of lens resin monomer:Weight ratio as described in embodiment one takes dibenzyl maleate, styrene, right
Dially phthalate and containing bromo-ether, mixing and stirring is put into after adding initiator azodiisobutyronitrile, degassing, injection molding
Rise to be risen in 70 DEG C, insulation 4~10h, 2~5h by 30 DEG C in 30 DEG C, 2~5h by 20 DEG C in baking oven, 1~2h and is risen to by 70 DEG C
120 DEG C, it is incubated in 2~6h, 1~5h and is down to room temperature by 120 DEG C, produce.
Embodiment eight
A kind of preparation method of high index of refraction lens resin monomer, the preparation method comprises the following steps:
(1) synthesis containing bromo-ether:Reactant tetrabromobisphenol A 271.9g and allyl glycidyl ether 114.0g are taken, is added
To being equipped with the four-hole bottle of agitating paddle, organic solvent ethanol is added, then mixing and stirring, the weight of organic solvent is reaction
The 60% of thing gross weight, adds catalyst tripropyl amine (TPA), and the weight of catalyst is the 3% of reactant gross weight, is stirred at 80 DEG C
Mix, react 15h, after reaction terminates, vacuum distillation removes solvent, washed with distilled water, divide liquid, vacuum distillation purified product, i.e.,
;
(2) preparation of lens resin monomer:Weight ratio as described in embodiment two takes dibenzyl maleate, divinyl
Benzene, DAIP and containing bromo-ether, mixing and stirring is added after initiator ABVN, degassing, injection molding
It is put into baking oven, 1~2h and rises to 30 DEG C by 20 DEG C, 2~5h is interior rises to 70 DEG C by 30 DEG C, is incubated in 4~10h, 2~5h by 70 DEG C
120 DEG C are risen to, is incubated in 2~6h, 1~5h and is down to room temperature by 120 DEG C, produce.
Embodiment nine
A kind of preparation method of high index of refraction lens resin monomer, the preparation method comprises the following steps:
(1) synthesis containing bromo-ether:Reactant tetrabromobisphenol A 271.9g and allyl glycidyl ether 52.6g are taken, is added to
It is equipped with the four-hole bottle of agitating paddle, then adds organic solvent isopropanol, mixing and stirring, the weight of organic solvent is to react
The 40% of thing gross weight, adds catalyst tri-n-butylamine, the weight of catalyst is the 1% of reactant gross weight, at 50 DEG C
Stirring, reaction 7h, after reaction terminates, vacuum distillation removes solvent, is washed with distilled water, divides liquid, vacuum distillation purified product, i.e.,
;
(2) preparation of lens resin monomer:Weight ratio as described in embodiment three takes dibenzyl maleate, styrene, right
Dially phthalate is with DAIP and containing bromo-ether, and mixing and stirring adds initiator azo two different
Heptonitrile, degassing is put into after injection molding in baking oven, 1~2h to be risen in 30 DEG C, 2~5h by 20 DEG C and rises to 70 DEG C by 30 DEG C, and insulation 4~
120 DEG C are risen to by 70 DEG C in 10h, 2~5h, is incubated in 2~6h, 1~5h and is down to room temperature by 120 DEG C, produce.
Embodiment ten
A kind of preparation method of high index of refraction lens resin monomer, the preparation method comprises the following steps:
(1) synthesis containing bromo-ether:Reactant tetrabromobisphenol A 271.9g and allyl glycidyl ether 87.9g are taken, is added to
It is equipped with the four-hole bottle of agitating paddle, then addition organic solvent methanol, mixing and stirring, the weight of organic solvent is reactant
The 50% of gross weight, adds catalyst n, N- dimethyl benzylamines, the weight of catalyst is the 2% of reactant gross weight, in 60
Stirred at DEG C, react 8h, after reaction terminates, vacuum distillation removes solvent, washed with distilled water, divide liquid, vacuum distillation purification production
Thing, is produced;
(2) preparation of lens resin monomer:Weight ratio as described in example IV take dibenzyl maleate, styrene,
Dially phthalate and containing bromo-ether, mixing and stirring is put into after adding initiator azodiisobutyronitrile, degassing, injection molding
Rise to be risen in 70 DEG C, insulation 4~10h, 2~5h by 30 DEG C in 30 DEG C, 2~5h by 20 DEG C in baking oven, 1~2h and is risen to by 70 DEG C
120 DEG C, it is incubated in 2~6h, 1~5h and is down to room temperature by 120 DEG C, produce.
Embodiment 11
A kind of preparation method of high index of refraction lens resin monomer, the preparation method comprises the following steps:
(1) synthesis containing bromo-ether:Reactant tetrabromobisphenol A 271.9g and allyl glycidyl ether 102.8g are taken, is added
To being equipped with the four-hole bottle of agitating paddle, then add organic solvent isobutanol, mixing and stirring, the weight of organic solvent is anti-
The 30% of thing gross weight is answered, catalyst n is added, N- diethyl benzylamines, the weight of catalyst is reactant gross weight
0.5%, in being stirred at 60 DEG C, reacting 5h, after reaction terminates, vacuum distillation removes solvent, is washed with distilled water, divides liquid, decompression
Distilation product, is produced;
(2) preparation of lens resin monomer:Weight ratio as described in embodiment five takes dibenzyl maleate, divinyl
Benzene, diallyl p phthalate and containing bromo-ether, mixing and stirring is added after initiator azodiisobutyronitrile, degassing, injection molding
It is put into baking oven, 1~2h and rises to 30 DEG C by 20 DEG C, 2~5h is interior rises to 70 DEG C by 30 DEG C, is incubated in 4~10h, 2~5h by 70 DEG C
120 DEG C are risen to, is incubated in 2~6h, 1~5h and is down to room temperature by 120 DEG C, produce.
Embodiment 12
A kind of preparation method of high index of refraction lens resin monomer, the preparation method comprises the following steps:
(1) synthesis containing bromo-ether:Reactant tetrabromobisphenol A 271.9g and allyl glycidyl ether 68.5g are taken, is added to
It is equipped with the four-hole bottle of agitating paddle, then adds organic solvent isobutanol, mixing and stirring, the weight of organic solvent is to react
The 360% of thing gross weight, adds catalyst of triethylamine, and the weight of catalyst is the 3% of reactant gross weight, is stirred at 70 DEG C
Mix, react 12h, after reaction terminates, vacuum distillation removes solvent, washed with distilled water, divide liquid, vacuum distillation purified product, i.e.,
;
(2) preparation of lens resin monomer:Weight ratio as described in embodiment six takes dibenzyl maleate, styrene, right
Dially phthalate and containing bromo-ether, mixing and stirring is put into after adding initiator azodiisobutyronitrile, degassing, injection molding
Rise to be risen in 70 DEG C, insulation 4~10h, 2~5h by 30 DEG C in 30 DEG C, 2~5h by 20 DEG C in baking oven, 1~2h and is risen to by 70 DEG C
120 DEG C, it is incubated in 2~6h, 1~5h and is down to room temperature by 120 DEG C, produce.
Presently preferred embodiments of the present invention is the foregoing is only, is not intended to limit the invention, all essences in the present invention
Any modification, equivalent and improvement made within refreshing and principle etc., should be included within the scope of the present invention.
Claims (9)
1. a kind of high index of refraction lens resin monomer, it is characterised in that by weight percentage, the monomer is by following components group
Into:Dibenzyl maleate 5~15%, styrene compound 5~15%, diallyl p phthalate or M-phthalic acid two
The mixture 30~60% of allyl ester or both, containing bromo-ether 30~40%;Wherein, the structural formula containing bromo-ether is as follows:
2. high index of refraction lens resin monomer as claimed in claim 1, it is characterised in that by weight percentage, the monomer
It is composed of the following components:Dibenzyl maleate 7~10%, styrene compound 7~10%, diallyl p phthalate or
The mixture 45~50% of DAIP or both, containing bromo-ether 35~40%.
3. high index of refraction lens resin monomer as claimed in claim 1 or 2, it is characterised in that the styrene compound
It is styrene or divinylbenzene.
4. a kind of preparation method of high index of refraction lens resin, it is characterised in that the preparation method comprises the following steps:By power
Profit require weight described in 1 than take diallyl p phthalate or DAIP or both mixture,
Dibenzyl maleate, styrene compound and containing bromo-ether, mixing and stirring is put into baking after adding initiator, degassing, injection molding
Rise to be risen in 70 DEG C, insulation 4~10h, 2~5h by 30 DEG C in 30 DEG C, 2~5h by 20 DEG C in case, 1~2h and is risen to by 70 DEG C
120 DEG C, it is incubated in 2~6h, 1~5h and is down to room temperature by 120 DEG C, produce.
5. the preparation method of high index of refraction lens resin as claimed in claim 4, it is characterised in that the initiator is azo
Bis-isobutyronitrile or ABVN.
6. the preparation method of high index of refraction lens resin as claimed in claim 4, it is characterised in that described to press following containing bromo-ether
Step is synthesized:Reactant tetrabromobisphenol A and allyl glycidyl ether are taken, mixing and stirring adds organic solvent, then mixed
Conjunction stirs, and the weight of the organic solvent is the 30~60% of the reactant gross weight, adds catalyst, described to urge
The weight of agent is the 0.3~3% of the reactant gross weight, and in being stirred at 30~80 DEG C, reacting 5~15h, reaction terminates
Afterwards, vacuum distillation removes solvent, is washed with distilled water, divides liquid, vacuum distillation purified product, produced.
7. the preparation method of high index of refraction lens resin as claimed in claim 6, it is characterised in that the tetrabromobisphenol A with
The mol ratio of the allyl glycidyl ether is 1:1~2.
8. the preparation method of high index of refraction lens resin as claimed in claim 6, it is characterised in that the organic solvent is first
Alcohol, ethanol or isopropanol.
9. the preparation method of high index of refraction lens resin as claimed in claim 6, it is characterised in that the catalyst is three second
Amine, tripropyl amine (TPA), tri-n-butylamine, N, N- dimethyl benzylamines or N, N- diethyl benzylamine.
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CN109627386B (en) * | 2018-12-12 | 2022-01-28 | 潍坊科技学院 | Resin monomer composition |
CN109627399B (en) * | 2018-12-13 | 2022-03-25 | 山东鲁源化工科技有限公司 | High-refractive-index optical resin monomer and preparation method thereof |
CN113248646B (en) * | 2021-04-30 | 2023-03-31 | 江苏可奥熙光学材料科技有限公司 | Medium-refractive index m-benzene resin monomer and preparation method thereof |
CN114921081A (en) * | 2022-06-13 | 2022-08-19 | 江苏全真光学科技股份有限公司 | Photo-curing resin lens monomer and preparation method thereof |
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JPS598709A (en) * | 1982-07-08 | 1984-01-18 | Mitsui Toatsu Chem Inc | Resin for lens having high refractive index |
JPS617314A (en) * | 1984-06-20 | 1986-01-14 | Kureha Chem Ind Co Ltd | Lens material having high refractive index |
DE3582176D1 (en) * | 1985-12-11 | 1991-04-18 | Nippon Oils & Fats Co Ltd | OPTICAL RESINS AND METHOD FOR THE PRODUCTION THEREOF. |
CN1157440C (en) * | 2000-04-19 | 2004-07-14 | 株式会社昌佑 | Monomer composition for optical lens |
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Address after: 262725 Luyuan Road, Hou Town Industrial Park, Shouguang City, Weifang City, Shandong Province Co-patentee after: Weifang University of Science & Technology Patentee after: Shandong Luyuan Chemical Technology Co., Ltd. Address before: 262725 Luyuan Road, Hou Town Industrial Park, Shouguang City, Weifang City, Shandong Province Co-patentee before: Weifang University of Science & Technology Patentee before: Shouguang Luyuan Salt Chemical Co., Ltd. |