CN105175608A - High-refractivity lens resin monomer - Google Patents
High-refractivity lens resin monomer Download PDFInfo
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- CN105175608A CN105175608A CN201510590690.5A CN201510590690A CN105175608A CN 105175608 A CN105175608 A CN 105175608A CN 201510590690 A CN201510590690 A CN 201510590690A CN 105175608 A CN105175608 A CN 105175608A
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- resin monomer
- lens resin
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Abstract
The invention belongs to the technical field of optical resin materials, and particularly relates to a high-refractivity lens resin monomer which is composed of the following components in percentage by weight: 5-15% of dibenzyl maleate, 5-15% of styrene compound, 30-60% of diallyl terephthalate, diallyl isophthalate or mixture thereof and 30-40% of bromo ether. The preparation method comprises the following steps: proportionally taking the components, uniformly mixing, adding an initiator, degassing, injecting into a mold, putting in a drying oven, carrying out programmed heating to 120 DEG C, and cooling to room temperature. The high-refractivity lens resin monomer formed by component polymerization has the advantages of higher refractivity, higher impact resistance and higher wear resistance; and the refractivity can reach 1.60 or above. The preparation method provided by the invention has the advantages of simple technique, high process controllability and repetitiveness, mild reaction conditions, no pollution and low cost.
Description
Technical field
The invention belongs to optical resin material technical field, particularly relate to a kind of high refractive index lens resin monomer.
Background technology
In recent years, optical resin lens is at home and abroad a dark horse in glasses market, the distinctive advantages such as especially high refractive index optical resin lens is lighter with its quality, intensity is high, non-friable, high transmission rate, UV resistance, ultrathin type, the dark welcome by amblyopia colony.Usually, in eyeglass industry with specific refractory power reach more than 1.60 for high refractive index, specific refractory power reach more than 1.56 for middle specific refractory power, specific refractory power is low-refraction below 1.56.To have with main component be the specific refractory power that the formulated chemical monomer of bezene acrylic acid class and other component is made is the optical resin lens of 1.56, but its thickness is thicker, and thermal resistance, visible light transmittance rate poor-performing, therefore need the optical resin monomer material making high refractivity resin lens.
Summary of the invention
An object of the present invention is: the deficiency existed for prior art, provides that a kind of specific refractory power is high, the high refractive index lens resin monomer of strong shock resistance.
For solving the problems of the technologies described above, technical scheme of the present invention is:
A kind of high refractive index lens resin monomer, by weight percentage, described monomer is composed of the following components: dibenzyl maleate 5 ~ 15%, styrene compound 5 ~ 15%, diallyl p phthalate or diallyl isophthalate or both mixtures 30 ~ 60%, containing bromo-ether 30 ~ 40%.
Wherein, the structural formula containing bromo-ether is as follows:
Its chemical name is 2, two (the 4-(3-allyloxy-2-propoxyl) 3 of 2-, 5-dibromo phenyl) propane, English name is 2,2-bis (4-(3-(allyloxy)-2-hydroxypropoxy)-3,5-dibromophenyl) propane.
Improve as one, by weight percentage, described monomer is composed of the following components: dibenzyl maleate 7 ~ 10%, styrene compound 7 ~ 10%, diallyl p phthalate or diallyl isophthalate or both mixtures 45 ~ 50%, containing bromo-ether 35 ~ 40%.
As improving further, described styrene compound is vinylbenzene or Vinylstyrene.
Two of object of the present invention is: provide a kind of cost lower, the preparation method of technique simple high refractive index lens resin monomer.
For solving the problems of the technologies described above, technical scheme of the present invention is:
A kind of preparation method of high refractive index lens resin monomer, described preparation method comprises the following steps: get diallyl p phthalate or diallyl isophthalate or both mixtures by weight ratio according to claim 1, dibenzyl maleate, styrene compound and containing bromo-ether, mixing and stirring, add initiator, degassed, baking oven is put into after injection molding, 30 DEG C are risen to by 20 DEG C in 1 ~ 2h, 70 DEG C are risen to by 30 DEG C in 2 ~ 5h, insulation 4 ~ 10h, 120 DEG C are risen to by 70 DEG C in 2 ~ 5h, insulation 2 ~ 6h, room temperature is down to by 120 DEG C in 1 ~ 5h, obtain.
Preferably, described initiator is Diisopropyl azodicarboxylate or 2,2'-Azobis(2,4-dimethylvaleronitrile).
Improve as one, the described bromo-ether that contains synthesizes according to the following steps: get reactant tetrabromo-bisphenol and glycidyl allyl ether, add organic solvent, then mixing and stirring, the weight of described organic solvent is 30 ~ 60% of described reactant gross weight, add catalyzer again, the weight of described catalyzer is 0.3 ~ 3% of described reactant gross weight, stir at 30 ~ 80 DEG C, react 5 ~ 15h, after reaction terminates, underpressure distillation, except desolventizing, by distilled water washing, separatory, underpressure distillation purified product, to obtain final product.
Building-up process containing bromo-ether is as follows:
Improve as one, the mol ratio of described tetrabromo-bisphenol and described glycidyl allyl ether is 1:1 ~ 2.
Preferably, described organic solvent is methyl alcohol, ethanol or Virahol.
Preferably, described catalyzer is triethylamine, tripropyl amine, tri-n-butylamine, N, N-dimethyl benzylamine or N, N-diethyl benzylamine.
Owing to have employed technique scheme, the invention has the beneficial effects as follows:
High refractive index lens resin monomer provided by the invention, introduce in component containing bromo-ether, effectively improve the specific refractory power of monomer, the dibenzyl maleate introduced in component, styrene compound and dially phthalate compounds, the monomer formed after each component polymerization, have higher specific refractory power and stronger shock resistance and wear resistance, its specific refractory power can reach more than 1.60.Preparation method provided by the invention, its technique is simple, the controllability of process and reproducible, and reaction conditions is gentle, and pollution-free, cost is low, and obtained product specific refractory power is high, and shock resistance is good.
Embodiment
In order to make object of the present invention, technical scheme and advantage clearly understand, below in conjunction with embodiment, the present invention is further elaborated.Should be appreciated that specific embodiment described herein only in order to explain the present invention, be not intended to limit the present invention.
Embodiment one
A kind of high refractive index lens resin monomer, by weight percentage, described monomer is composed of the following components: dibenzyl maleate 5%, styrene compound 15%, diallyl p phthalate compounds 50%, containing bromo-ether 30%; Wherein, styrene compound is vinylbenzene.
Embodiment two
A kind of high refractive index lens resin monomer, by weight percentage, described monomer is composed of the following components: dibenzyl maleate 10%, styrene compound 10%, diallyl isophthalate compounds 40%, containing bromo-ether 40%; Wherein, styrene compound is Vinylstyrene.
Embodiment three
A kind of high refractive index lens resin monomer, by weight percentage, described monomer is composed of the following components: dibenzyl maleate 15%, styrene compound 5%, the mixture 45% of diallyl p phthalate and diallyl isophthalate, containing bromo-ether 35%; Wherein, styrene compound is vinylbenzene, and in described mixture, diallyl p phthalate and diallyl isophthalate mix in any proportion.
Embodiment four
A kind of high refractive index lens resin monomer, by weight percentage, described monomer is composed of the following components: dibenzyl maleate 15%, styrene compound 15%, diallyl isophthalate compounds 30%, containing bromo-ether 40%; Wherein, styrene compound is vinylbenzene.
Embodiment five
A kind of high refractive index lens resin monomer, by weight percentage, described monomer is composed of the following components: dibenzyl maleate 7%, styrene compound 13%, diallyl p phthalate 60%, containing bromo-ether 30%; Wherein, styrene compound is Vinylstyrene.
Embodiment six
A kind of high refractive index lens resin monomer, by weight percentage, described monomer is composed of the following components: dibenzyl maleate 13%, styrene compound 7%, diallyl p phthalate 30%, containing bromo-ether 40%; Wherein, styrene compound is vinylbenzene.
Embodiment seven
A preparation method for high refractive index lens resin monomer, described preparation method comprises the following steps:
(1) containing the synthesis of bromo-ether: get reactant tetrabromo-bisphenol 271.9g and glycidyl allyl ether 85.6g, join and be equipped with in the four-hole bottle of stirring rake, add organic solvent methyl alcohol, then mixing and stirring, the weight of organic solvent is 30% of reactant gross weight, add catalyst of triethylamine again, the weight of catalyzer is 0.3% of reactant gross weight, stir at 30 DEG C, react 5h, after reaction terminates, underpressure distillation, except desolventizing, by distilled water washing, separatory, underpressure distillation purified product, to obtain final product;
(2) preparation of lens resin monomer: get dibenzyl maleate, vinylbenzene, diallyl p phthalate by the weight ratio described in embodiment one and contain bromo-ether, mixing and stirring, adds initiator Diisopropyl azodicarboxylate, degassed, baking oven is put into after injection molding, rise to 30 DEG C by 20 DEG C in 1 ~ 2h, in 2 ~ 5h, rise to 70 DEG C by 30 DEG C, insulation 4 ~ 10h, 120 DEG C are risen to by 70 DEG C in 2 ~ 5h, be down to room temperature by 120 DEG C in insulation 2 ~ 6h, 1 ~ 5h, obtain final product.
Embodiment eight
A preparation method for high refractive index lens resin monomer, described preparation method comprises the following steps:
(1) containing the synthesis of bromo-ether: get reactant tetrabromo-bisphenol 271.9g and glycidyl allyl ether 114.0g, join and be equipped with in the four-hole bottle of stirring rake, add organic solvent ethanol, then mixing and stirring, the weight of organic solvent is 60% of reactant gross weight, add catalyzer tripropyl amine again, the weight of catalyzer is 3% of reactant gross weight, stir at 80 DEG C, react 15h, after reaction terminates, underpressure distillation, except desolventizing, by distilled water washing, separatory, underpressure distillation purified product, to obtain final product;
(2) preparation of lens resin monomer: get dibenzyl maleate, Vinylstyrene, diallyl isophthalate by the weight ratio described in embodiment two and contain bromo-ether, mixing and stirring, adds initiator 2,2'-Azobis(2,4-dimethylvaleronitrile), degassed, baking oven is put into after injection molding, rise to 30 DEG C by 20 DEG C in 1 ~ 2h, in 2 ~ 5h, rise to 70 DEG C by 30 DEG C, insulation 4 ~ 10h, 120 DEG C are risen to by 70 DEG C in 2 ~ 5h, be down to room temperature by 120 DEG C in insulation 2 ~ 6h, 1 ~ 5h, obtain final product.
Embodiment nine
A preparation method for high refractive index lens resin monomer, described preparation method comprises the following steps:
(1) containing the synthesis of bromo-ether: get reactant tetrabromo-bisphenol 271.9g and glycidyl allyl ether 52.6g, join and be equipped with in the four-hole bottle of stirring rake, then organic solvent Virahol is added, mixing and stirring, the weight of organic solvent is 40% of reactant gross weight, add catalyzer tri-n-butylamine again, the weight of catalyzer is 1% of reactant gross weight, stir at 50 DEG C, react 7h, after reaction terminates, underpressure distillation, except desolventizing, by distilled water washing, separatory, underpressure distillation purified product, to obtain final product;
(2) preparation of lens resin monomer: get dibenzyl maleate, vinylbenzene, diallyl p phthalate and diallyl isophthalate by the weight ratio described in embodiment three and contain bromo-ether, mixing and stirring, adds initiator 2,2'-Azobis(2,4-dimethylvaleronitrile), degassed, baking oven is put into after injection molding, rise to 30 DEG C by 20 DEG C in 1 ~ 2h, in 2 ~ 5h, rise to 70 DEG C by 30 DEG C, insulation 4 ~ 10h, 120 DEG C are risen to by 70 DEG C in 2 ~ 5h, be down to room temperature by 120 DEG C in insulation 2 ~ 6h, 1 ~ 5h, obtain final product.
Embodiment ten
A preparation method for high refractive index lens resin monomer, described preparation method comprises the following steps:
(1) containing the synthesis of bromo-ether: get reactant tetrabromo-bisphenol 271.9g and glycidyl allyl ether 87.9g, join and be equipped with in the four-hole bottle of stirring rake, then organic solvent methyl alcohol is added, mixing and stirring, the weight of organic solvent is 50% of reactant gross weight, add catalyst n again, N-dimethyl benzylamine, the weight of catalyzer is 2% of reactant gross weight, stir at 60 DEG C, react 8h, after reaction terminates, underpressure distillation is except desolventizing, by distilled water washing, separatory, underpressure distillation purified product, to obtain final product;
(2) preparation of lens resin monomer: get dibenzyl maleate, vinylbenzene, diallyl isophthalate by the weight ratio described in embodiment four and contain bromo-ether, mixing and stirring, adds initiator Diisopropyl azodicarboxylate, degassed, baking oven is put into after injection molding, rise to 30 DEG C by 20 DEG C in 1 ~ 2h, in 2 ~ 5h, rise to 70 DEG C by 30 DEG C, insulation 4 ~ 10h, 120 DEG C are risen to by 70 DEG C in 2 ~ 5h, be down to room temperature by 120 DEG C in insulation 2 ~ 6h, 1 ~ 5h, obtain final product.
Embodiment 11
A preparation method for high refractive index lens resin monomer, described preparation method comprises the following steps:
(1) containing the synthesis of bromo-ether: get reactant tetrabromo-bisphenol 271.9g and glycidyl allyl ether 102.8g, join and be equipped with in the four-hole bottle of stirring rake, then organic solvent isopropylcarbinol is added, mixing and stirring, the weight of organic solvent is 30% of reactant gross weight, add catalyst n again, N-diethyl benzylamine, the weight of catalyzer is 0.5% of reactant gross weight, stir at 60 DEG C, react 5h, after reaction terminates, underpressure distillation is except desolventizing, by distilled water washing, separatory, underpressure distillation purified product, to obtain final product;
(2) preparation of lens resin monomer: get dibenzyl maleate, Vinylstyrene, diallyl p phthalate by the weight ratio described in embodiment five and contain bromo-ether, mixing and stirring, adds initiator Diisopropyl azodicarboxylate, degassed, baking oven is put into after injection molding, rise to 30 DEG C by 20 DEG C in 1 ~ 2h, in 2 ~ 5h, rise to 70 DEG C by 30 DEG C, insulation 4 ~ 10h, 120 DEG C are risen to by 70 DEG C in 2 ~ 5h, be down to room temperature by 120 DEG C in insulation 2 ~ 6h, 1 ~ 5h, obtain final product.
Embodiment 12
A preparation method for high refractive index lens resin monomer, described preparation method comprises the following steps:
(1) containing the synthesis of bromo-ether: get reactant tetrabromo-bisphenol 271.9g and glycidyl allyl ether 68.5g, join and be equipped with in the four-hole bottle of stirring rake, then organic solvent isopropylcarbinol is added, mixing and stirring, the weight of organic solvent is 360% of reactant gross weight, add catalyst of triethylamine again, the weight of catalyzer is 3% of reactant gross weight, stir at 70 DEG C, react 12h, after reaction terminates, underpressure distillation, except desolventizing, by distilled water washing, separatory, underpressure distillation purified product, to obtain final product;
(2) preparation of lens resin monomer: get dibenzyl maleate, vinylbenzene, diallyl p phthalate by the weight ratio described in embodiment six and contain bromo-ether, mixing and stirring, adds initiator Diisopropyl azodicarboxylate, degassed, baking oven is put into after injection molding, rise to 30 DEG C by 20 DEG C in 1 ~ 2h, in 2 ~ 5h, rise to 70 DEG C by 30 DEG C, insulation 4 ~ 10h, 120 DEG C are risen to by 70 DEG C in 2 ~ 5h, be down to room temperature by 120 DEG C in insulation 2 ~ 6h, 1 ~ 5h, obtain final product.
The foregoing is only preferred embodiment of the present invention, not in order to limit the present invention, all any amendments done within the spirit and principles in the present invention, equivalent replacement and improvement etc., all should be included within protection scope of the present invention.
Claims (9)
1. a high refractive index lens resin monomer, it is characterized in that, by weight percentage, described monomer is composed of the following components: dibenzyl maleate 5 ~ 15%, styrene compound 5 ~ 15%, diallyl p phthalate or diallyl isophthalate or both mixtures 30 ~ 60%, containing bromo-ether 30 ~ 40%.
2. high refractive index lens resin monomer as claimed in claim 1, it is characterized in that, by weight percentage, described monomer is composed of the following components: dibenzyl maleate 7 ~ 10%, styrene compound 7 ~ 10%, diallyl p phthalate or diallyl isophthalate or both mixtures 45 ~ 50%, containing bromo-ether 35 ~ 40%.
3. high refractive index lens resin monomer as claimed in claim 1 or 2, it is characterized in that, described styrene compound is vinylbenzene or Vinylstyrene.
4. the preparation method of a high refractive index lens resin monomer, it is characterized in that, described preparation method comprises the following steps: get diallyl p phthalate or diallyl isophthalate or both mixtures by weight ratio according to claim 1, dibenzyl maleate, styrene compound and containing bromo-ether, mixing and stirring, add initiator, degassed, baking oven is put into after injection molding, 30 DEG C are risen to by 20 DEG C in 1 ~ 2h, 70 DEG C are risen to by 30 DEG C in 2 ~ 5h, insulation 4 ~ 10h, 120 DEG C are risen to by 70 DEG C in 2 ~ 5h, insulation 2 ~ 6h, room temperature is down to by 120 DEG C in 1 ~ 5h, obtain.
5. the preparation method of high refractive index lens resin monomer as claimed in claim 4, it is characterized in that, described initiator is Diisopropyl azodicarboxylate or 2,2'-Azobis(2,4-dimethylvaleronitrile).
6. the preparation method of high refractive index lens resin monomer as claimed in claim 4, it is characterized in that, the described bromo-ether that contains synthesizes according to the following steps: get reactant tetrabromo-bisphenol and glycidyl allyl ether, mixing and stirring, add organic solvent, then mixing and stirring, the weight of described organic solvent is 30 ~ 60% of described reactant gross weight, add catalyzer again, the weight of described catalyzer is 0.3 ~ 3% of described reactant gross weight, stir at 30 ~ 80 DEG C, reaction 5 ~ 15h, after reaction terminates, underpressure distillation is except desolventizing, wash with distilled water, separatory, underpressure distillation purified product, obtain.
7. the preparation method of high refractive index lens resin monomer as claimed in claim 6, it is characterized in that, the mol ratio of described tetrabromo-bisphenol and described glycidyl allyl ether is 1:1 ~ 2.
8. the preparation method of high refractive index lens resin monomer as claimed in claim 6, it is characterized in that, described organic solvent is methyl alcohol, ethanol or Virahol.
9. the preparation method of high refractive index lens resin monomer as claimed in claim 6, it is characterized in that, described catalyzer is triethylamine, tripropyl amine, tri-n-butylamine, N, N-dimethyl benzylamine or N, N-diethyl benzylamine.
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| CN201510590690.5A CN105175608B (en) | 2015-09-16 | 2015-09-16 | A kind of high index of refraction lens resin monomer |
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| CN201510590690.5A CN105175608B (en) | 2015-09-16 | 2015-09-16 | A kind of high index of refraction lens resin monomer |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109627399A (en) * | 2018-12-13 | 2019-04-16 | 山东鲁源化工科技有限公司 | A kind of high refractive index optical resin monomer and preparation method thereof |
| CN109627386A (en) * | 2018-12-12 | 2019-04-16 | 潍坊科技学院 | A kind of resin monomer composition |
| CN113248646A (en) * | 2021-04-30 | 2021-08-13 | 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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| US4522993A (en) * | 1982-07-08 | 1985-06-11 | Mitsui Toatsu Chemicals, Incorporated | Resin for high-refractivity lenses and lenses made of same resin |
| US4644025A (en) * | 1984-06-20 | 1987-02-17 | Kureha Kagaku Kogyo Kabushiki Kaisha | Lens materials of high refractive indexes |
| US4855374A (en) * | 1985-12-11 | 1989-08-08 | Nippon Oil And Fats Co., Ltd. | Optical resin from diallyl esters |
| CN1324892A (en) * | 2000-04-19 | 2001-12-05 | 株式会社昌佑 | Monomer composition for optical lens |
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2015
- 2015-09-16 CN CN201510590690.5A patent/CN105175608B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4522993A (en) * | 1982-07-08 | 1985-06-11 | Mitsui Toatsu Chemicals, Incorporated | Resin for high-refractivity lenses and lenses made of same resin |
| US4644025A (en) * | 1984-06-20 | 1987-02-17 | Kureha Kagaku Kogyo Kabushiki Kaisha | Lens materials of high refractive indexes |
| US4855374A (en) * | 1985-12-11 | 1989-08-08 | Nippon Oil And Fats Co., Ltd. | Optical resin from diallyl esters |
| CN1324892A (en) * | 2000-04-19 | 2001-12-05 | 株式会社昌佑 | Monomer composition for optical lens |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109627386A (en) * | 2018-12-12 | 2019-04-16 | 潍坊科技学院 | A kind of resin monomer composition |
| CN109627386B (en) * | 2018-12-12 | 2022-01-28 | 潍坊科技学院 | Resin monomer composition |
| CN109627399A (en) * | 2018-12-13 | 2019-04-16 | 山东鲁源化工科技有限公司 | A kind of high refractive index optical resin monomer and preparation method thereof |
| 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 |
| CN113248646A (en) * | 2021-04-30 | 2021-08-13 | 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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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. |