CN104945284A - High-Abbe-number ultra-light wear-resistant resin material, lens and preparation methods thereof - Google Patents
High-Abbe-number ultra-light wear-resistant resin material, lens and preparation methods thereof Download PDFInfo
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- CN104945284A CN104945284A CN201510216463.6A CN201510216463A CN104945284A CN 104945284 A CN104945284 A CN 104945284A CN 201510216463 A CN201510216463 A CN 201510216463A CN 104945284 A CN104945284 A CN 104945284A
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Abstract
The invention relates to a high-Abbe-number ultra-light wear-resistant resin material. The material is characterized by comprising polymer resin used for producing an optical material, wherein the polymer resin is a polyurethane-acrylate prepolymer, and obtained by reacting isocyanate with hydroxyl-containing acrylate, with a reaction formula (I) specified in the description. The material disclosed by the invention has the following beneficial effects: the wear resistance, temperature resistance, deformability, Abbe number and thermostability of the resin lens made from the high-Abbe-number ultra-light wear-resistant resin material are effectively improved, the density is reduced, the structure is more flexible, the production method is high in controllability, waste discharge during the preparation process is avoided, and the preparation requirements of lens raw materials with different refractive index levels can be met.
Description
Technical field
The present invention relates to optical material field, be specifically related to the ultralight wear-resistant type resin material of a kind of high Abbe number, eyeglass and preparation method thereof.
Background technology
The chemicals-resistant corrodibility that resin lens has light weight, shock-resistant, transmittance is high, ultraviolet isolating rate is high, higher, do not produce fragment when destroying and the feature such as processing molding method is simple, it has replaced opticglass to be used widely in many fields such as vision correction, building materials and optical lenses.But existing resin lens still exists, and scratch resistance is low, temperature tolerance and the problem such as deformability is higher, Abbe number is on the low side, density is higher, structure design is dumb.Its making method also exists that controllability is poor, waste discharge, cannot meet the preparation requirement of the Raw materials for lenses of different refractivity level.Therefore, need exploitation a kind of low density, high Abbe number and wear-resistant type resin lens material badly, with and preparation method thereof, to solve existing resin lens industry above shortcomings technically.
Summary of the invention
The object of this invention is to provide the ultralight wear-resistant type resin material of a kind of high Abbe number, eyeglass and preparation method thereof, to overcome currently available technology above shortcomings.
The object of the invention is to be achieved through the following technical solutions:
The ultralight wear-resistant type resin material of a kind of high Abbe number, this material comprises the macromolecule resin for making optical material, described macromolecule resin is polyurethane acrylate prepolymer, and it is obtained by the acrylate reactions of isocyanic ester and hydroxyl, and reaction formula I is as follows:
(Ⅰ)
Further, described isocyanic ester is monoisocyanates and/or polyisocyanates, described monoisocyanates comprises benzyl isocyanate ester, one or more in phenyl isocyanate, described polyisocyanates is vulcabond, three or polyisocyanates, described vulcabond comprises hexamethylene diisocyanate, isophorone diisocyanate, m-xylylene diisocyanate, tolylene diisocyanate, hexamethylene diisocyanate, 4, one or more in 4 '-diphenylmethanediisocyanate, described three and polyisocyanates comprise triphenylmethane triisocyanate and/or vulcabond cyclisation product.
Further, the acrylate of described hydroxyl comprises one or more in hydroxyethyl methylacrylate, Rocryl 410, methacrylate, Hydroxyethyl acrylate, Propylene glycol monoacrylate, hy-droxybutyl and long-chain hydroxymethyl acrylate.
Prepare a method for the ultralight wear-resistant type resin material of above-mentioned high Abbe number, comprise the following steps:
Under anhydrous condition, by the acrylate 1160-1450 of hydroxyl gram and isocyanic ester 840-1430 gram, raw material mixes; Add stopper 5.5-7.5 gram, catalyzer 4.0-7.2 gram, under default temperature of reaction, stirring reaction is to the scheduled time, the isocyanate groups of noresidue in reaction system after testing, cooling discharge, obtained polyurethane acrylate prepolymer.
Further, described stopper comprises inorganic stopper and organic stopper, and described inorganic stopper comprises cuprous chloride, iron(ic) chloride; Described organic stopper comprise in benzoquinones class, nitrobenzene, phenols, sulphur class one or more.
Further, described organic stopper is phenolic inhibitor.
Further, described catalyzer comprises tertiary amines, metal alkyl compound class or the combination of the two, and described metal alkyl compound class is tin type organic, comprises one or more in dibutyl tin laurate, stannous octoate.
Further, range of reaction temperature is 0-120 DEG C.
Further, described range of reaction temperature is 40-80 DEG C.
Further, described reaction time range is 4-12 hour.
Further, described reaction time range is 5-8 hour.
The ultralight wear-resistant type resin lens of a kind of high Abbe number, this eyeglass is made up of the ultralight wear-resistant type resin material of above-mentioned high Abbe number.
Prepare the method for the ultralight wear-resistant type resin lens of above-mentioned high Abbe number, comprise the following steps:
Under room temperature, isolated air conditions, by polyurethane acrylate prepolymer 1000 grams, UV light absorber 2.5-4.5 gram, anti-aging agent 1.0-2.5 gram, releasing agent 0.3-0.6 gram, blue 1.2-1.7 gram of dyestuff, the red 1.0-1.4 of dyestuff gram, initiator 2,2'-Azobis(2,4-dimethylvaleronitrile) 0.5-0.6 gram adds in mixing kettle, stirring at normal temperature is dissolved to all auxiliary agents, obtain lilac clear solution, after micropore filter paper filtering, liquid starting material mixture is poured in lens mold, carry out one-step solidification, obtain eyeglass, eyeglass through cleaning, after coating process process, test performance.
Further, during preparation high refractive index eyeglass, 1.0-1.5 gram of powdery sodium hypophosphite is added according to the actual requirements.
Further, described UV light absorber comprises UV-329, UV-234, one or more in SLF-1130.
Further, described anti-aging agent comprises one or more in SLF-1076, SLF-2246.
Further, described releasing agent comprises butyl phosphate.
Beneficial effect of the present invention is: adopt the resin lens that the ultralight wear-resistant type resin material of high Abbe number is made, its wear resistance, temperature tolerance, deformability, Abbe number, thermostability effectively improve, density reduces, structure is more flexible, its making method controllability is strong, no waste discharge in preparation process, can meet the preparation requirement of the Raw materials for lenses of different refractivity level.
Embodiment
Be clearly and completely described to the technical scheme in the embodiment of the present invention below, obviously, described embodiment is only the present invention's part embodiment, instead of whole embodiments.Based on the embodiment in the present invention, the every other embodiment that those of ordinary skill in the art obtain, all belongs to the scope of protection of the invention.
Embodiment one
The preparation of polyurethane acrylate prepolymer:
Under room temperature and nitrogen protection; hydroxyethyl methylacrylate (HEMA) 1300 grams is added successively in the four-hole bottle that stirring arm, thermometer and prolong are housed; p methoxy phenol 3.5 grams; add hexamethylene diisocyanate (HDI) 841g under stirring, stirring at room temperature obtains transparent homogeneous mixed solution for 0.5 hour.In mixed solution, drip 20 grams of hydroxyethyl methylacrylate solution containing 4.2 grams of dibutyl tin laurates, during dropping, temperature controls to be no more than 30 DEG C.Stirring 0.5 hour is continued at this temperature after being added dropwise to complete.Then temperature is risen to 75 DEG C of reactions 5 hours.Monitoring system isocyanate content, adds 3.0 grams of stopper p methoxy phenols, cools to room temperature, after filtration discharging, obtain raw material polyurethane acrylate prepolymer after qualified.
The preparation of low refractive index resin eyeglass:
Get this prepolymer 1000 grams in mixing kettle, add 2.5 grams of UV light absorber UV-329,1.0 grams of anti-aging agent SLF-1076,0.5 gram of releasing agent butyl phosphate, 1.3 grams of dyestuff orchids, 1.0 grams of dyestuffs are red, 0.5 gram of initiator 2,2'-Azobis(2,4-dimethylvaleronitrile).Stirring at room temperature 2 hours under nitrogen protection, dissolves to all auxiliary agents, obtains the clear solution of lilac.Temperature in mixing process can not more than 25 DEG C.After micropore filter paper filtering, liquid starting material mixture is poured in lens mold, carries out one-step solidification, obtain eyeglass.Eyeglass is after cleaning, coating process process, and test specific refractory power is 1.526, and Abbe number ≮ 40, can float on saturated brine, pass through boiling test.
Embodiment two
The preparation of polyurethane acrylate prepolymer:
Under room temperature and nitrogen protection; hy-droxybutyl 1441.7 grams is added successively in the four-hole bottle that stirring arm, thermometer and prolong are housed; p methoxy phenol 4.2 grams, add different Buddhist diisocyanates 1112g under stirring, stirring at room temperature obtains transparent homogeneous mixed solution for 0.5 hour.In mixed solution, drip 20 grams of hy-droxybutyl solution containing 5.6 grams of dibutyl tin laurates, during dropping, temperature controls to be no more than 30 DEG C.Stirring 0.5 hour is continued at this temperature after being added dropwise to complete.Then temperature is risen to 65 DEG C of reactions 6 hours.Monitoring system isocyanate content, adds 3.0 grams of stopper p methoxy phenols, cools to room temperature, after filtration discharging, obtain raw material polyurethane acrylate prepolymer after qualified.
The preparation of low refractive index resin eyeglass:
Get this prepolymer 1000 grams in mixing kettle, add 2.5 grams of UV light absorber UV-329,1.0 grams of anti-aging agent SLF-1076,0.5 gram of releasing agent butyl phosphate, 1.2 grams of dyestuff orchids, 1.0 grams of dyestuffs are red, 0.5 gram of initiator 2,2'-Azobis(2,4-dimethylvaleronitrile).Stirring at room temperature 2 hours under nitrogen protection, dissolves to all auxiliary agents, obtains the clear solution of lilac.Temperature in mixing process can not more than 25 DEG C.After micropore filter paper filtering, liquid starting material mixture is poured in lens mold, carries out one-step solidification, obtain eyeglass.Eyeglass is after cleaning, coating process process, and testing lens specific refractory power is 1.536, and Abbe number ≮ 42 can float on saturated brine, pass through boiling test.
Embodiment three
The preparation of polyurethane acrylate prepolymer:
Under room temperature and nitrogen protection; Hydroxyethyl acrylate 1161 grams is added successively in the four-hole bottle that stirring arm, thermometer and prolong are housed; p methoxy phenol 3.8 grams; two (cyclohexyl isocyanate) 1162g of isopropylidene is added under stirring; benzyl isocyanate ester 266 grams, stirring at room temperature obtains transparent homogeneous mixed solution for 0.5 hour.In mixed solution, drip 20 grams of Hydroxyethyl acrylate solution containing 7.1 grams of dibutyl tin laurates, during dropping, temperature controls to be no more than 30 DEG C.Stirring 0.5 hour is continued at this temperature after being added dropwise to complete.Then temperature is risen to 75 DEG C of reactions 7 hours.Monitoring system isocyanate content, adds 2.0 grams of stopper p methoxy phenols, cools to room temperature, after filtration discharging, obtain raw material polyurethane acrylate prepolymer after qualified.
The preparation of middle refractive index resin eyeglass:
Get this prepolymer 1000 grams in mixing kettle, add 2.5 grams of UV light absorber UV-234,1.0 grams of anti-aging agent SLF-2246,0.6 gram of releasing agent butyl phosphate, 1.5 grams of dyestuff orchids, 1.2 grams of dyestuffs are red, 0.5 gram of initiator 2,2'-Azobis(2,4-dimethylvaleronitrile).Stirring at room temperature 2 hours under nitrogen protection, dissolves to all auxiliary agents, obtains the clear solution of lilac.Temperature in mixing process can not more than 25 DEG C.After micropore filter paper filtering, liquid starting material mixture is poured in lens mold, carries out one-step solidification, obtain eyeglass.Eyeglass is after cleaning, coating process process, and test specific refractory power is 1.554, and Abbe number ≮ 38, can float on saturated brine, pass through boiling test.
Embodiment four
The preparation of polyurethane acrylate prepolymer:
Under room temperature and nitrogen protection; Rocryl 410 1442 grams is added successively in the four-hole bottle that stirring arm, thermometer and prolong are housed; p methoxy phenol 4.2 grams; stir lower m-xylylene diisocyanate 847g; benzyl isocyanate ester 133 grams, stirring at room temperature obtains transparent homogeneous mixed solution for 0.5 hour.In mixed solution, drip 20 grams of hydroxyethyl methylacrylate solution containing 5.4 grams of dibutyl tin laurates, during dropping, temperature controls to be no more than 30 DEG C.Stirring 0.5 hour is continued at this temperature after being added dropwise to complete.Then temperature is risen to 75 DEG C of reactions 6 hours.Monitoring system isocyanate content, adds 3.0 grams of stopper p methoxy phenols, cools to room temperature, after filtration discharging, obtain raw material polyurethane acrylate prepolymer after qualified.
The preparation of middle refractive index resin eyeglass:
Get this prepolymer 1000 grams in mixing kettle, add 2.5 grams of UV light absorber UV-234,1.0 grams of anti-aging agent SLF-2246,0.4 gram of releasing agent butyl phosphate, 1.3 grams of dyestuff orchids, 1.0 grams of dyestuffs are red, 0.6 gram of initiator 2,2'-Azobis(2,4-dimethylvaleronitrile).Stirring at room temperature 2 hours under nitrogen protection, dissolves to all auxiliary agents, obtains clear solution azury.Temperature in mixing process can not more than 25 DEG C.After micropore filter paper filtering, liquid starting material mixture is poured in lens mold, carries out one-step solidification, obtain eyeglass.Eyeglass is after cleaning, coating process process, and test specific refractory power is 1.565, and Abbe number ≮ 36, can float on saturated brine, pass through boiling test.
Embodiment five
The preparation of polyurethane acrylate prepolymer:
Under room temperature and nitrogen protection; hydroxyethyl methylacrylate 1301 grams is added successively in the four-hole bottle that stirring arm, thermometer and prolong are housed; p methoxy phenol 3.5 grams, adds tolylene diisocyanate 871g under stirring, stirring at room temperature obtains transparent homogeneous mixed solution for 0.5 hour.In mixed solution, drip 20 grams of hydroxyethyl methylacrylate solution containing 4.4 grams of dibutyl tin laurates, during dropping, temperature controls to be no more than 30 DEG C.Stirring 0.5 hour is continued at this temperature after being added dropwise to complete.Then temperature is risen to 70 DEG C of reactions 8 hours.Monitoring system isocyanate content, adds 3.0 grams of stopper p methoxy phenols, cools to room temperature, after filtration discharging, obtain raw material polyurethane acrylate prepolymer after qualified.
The preparation of high refractivity resin lens: get this prepolymer 1000 grams in mixing kettle, add 2.5 grams of UV light absorber UV-234,1.0 grams of UV light absorber SLF-1130,1.0 grams of anti-aging agent SLF-2246,1.0 grams of powdery sodium hypophosphites, 0.3 gram of releasing agent butyl phosphate, 1.7 grams of dyestuff orchids, 1.4 grams of dyestuffs are red, 0.5 gram of initiator 2,2'-Azobis(2,4-dimethylvaleronitrile).Stirring at room temperature 2 hours under nitrogen protection, dissolves to all auxiliary agents, obtains the clear solution of purple.Temperature in mixing process can not more than 25 DEG C.After micropore filter paper filtering, liquid starting material mixture is poured in lens mold, carries out one-step solidification, obtain eyeglass.Eyeglass is after cleaning, coating process process, and test specific refractory power is 1.607, and Abbe number ≮ 32, can float on saturated brine, pass through boiling test.
Embodiment six
The preparation of polyurethane acrylate prepolymer:
Under room temperature and nitrogen protection; Hydroxyethyl acrylate 1161 grams is added successively in the four-hole bottle that stirring arm, thermometer and prolong are housed; p methoxy phenol 3.5 grams; 4 are added under stirring; 4 '-diphenylmethanediisocyanate 876g; benzyl isocyanate ester 400 grams, stirring at room temperature obtains transparent homogeneous mixed solution for 0.5 hour.In mixed solution, drip 20 grams of Hydroxyethyl acrylate solution containing 6.4 grams of stannous octoates, during dropping, temperature controls to be no more than 30 DEG C.Stirring 0.5 hour is continued at this temperature after being added dropwise to complete.Then temperature is risen to 80 DEG C of reactions 5 hours.Monitoring system isocyanate content, adds 3.3 grams of stopper p methoxy phenols, cools to room temperature, after filtration discharging, obtain raw material polyurethane acrylate prepolymer after qualified.
The preparation of high refractivity resin lens:
Get this prepolymer 1000 grams in mixing kettle, add 2.5 grams of UV light absorber UV-234,2.0 grams of UV light absorber SLF-1130,2.5 grams of anti-aging agent SLF-2246,1.5 grams of powdery sodium hypophosphites, 0.6 gram of releasing agent butyl phosphate, 1.5 grams of dyestuff orchids, 1.2 grams of dyestuffs are red, 0.5 gram of initiator 2,2'-Azobis(2,4-dimethylvaleronitrile).Stirring at room temperature 2 hours under nitrogen protection, dissolves to all auxiliary agents, obtains the clear solution of lilac.Temperature in mixing process can not more than 25 DEG C.After micropore filter paper filtering, liquid starting material mixture is poured in lens mold, carries out one-step solidification, obtain eyeglass.Eyeglass is after cleaning, coating process process, and test specific refractory power is 1.617, and Abbe number ≮ 38, can float on saturated brine, pass through boiling test.
The present invention is not limited to above-mentioned preferred forms; anyone can draw other various forms of products under enlightenment of the present invention; no matter but any change is done in its shape or structure; every have identical with the application or akin technical scheme, all drops within protection scope of the present invention.
Claims (10)
1. the ultralight wear-resistant type resin material of high Abbe number, it is characterized in that, this material comprises the macromolecule resin for making optical material, described macromolecule resin is polyurethane acrylate prepolymer, it is obtained by the acrylate reactions of isocyanic ester and hydroxyl, and reaction formula I is as follows:
(Ⅰ)。
2. the ultralight wear-resistant type resin material of high Abbe number according to claim 1, it is characterized in that, described isocyanic ester is monoisocyanates and/or polyisocyanates, described monoisocyanates comprises benzyl isocyanate ester, one or more in phenyl isocyanate, described polyisocyanates is vulcabond, three or polyisocyanates, described vulcabond comprises hexamethylene diisocyanate, isophorone diisocyanate, m-xylylene diisocyanate, tolylene diisocyanate, hexamethylene diisocyanate, 4, one or more in 4 '-diphenylmethanediisocyanate, described three and polyisocyanates comprise triphenylmethane triisocyanate and/or vulcabond cyclisation product.
3. the ultralight wear-resistant type resin material of high Abbe number according to claim 2, it is characterized in that, the acrylate of described hydroxyl comprise in hydroxyethyl methylacrylate, Rocryl 410, methacrylate, Hydroxyethyl acrylate, Propylene glycol monoacrylate, hy-droxybutyl and long-chain hydroxymethyl acrylate one or more.
4. prepare the method for the ultralight wear-resistant type resin material of high Abbe number described in claim 1-3 any one, it is characterized in that, comprise the following steps:
Under anhydrous condition, by the acrylate 1160-1450 of hydroxyl gram and isocyanic ester 840-1430, raw material mixes; Add stopper 5.5-7.5 gram, catalyzer 4.0-7.2 gram, under default temperature of reaction, stirring reaction is to the scheduled time, the isocyanate groups of noresidue in reaction system after testing, cooling discharge, obtained polyurethane acrylate prepolymer.
5. the preparation method of the ultralight wear-resistant type resin material of high Abbe number according to claim 4, is characterized in that, described stopper comprises inorganic stopper and organic stopper, and described inorganic stopper comprises cuprous chloride, iron(ic) chloride; Described organic stopper comprise in benzoquinones class, nitrobenzene, phenols, sulphur class one or more.
6. the preparation method of the ultralight wear-resistant type resin material of high Abbe number according to claim 5, it is characterized in that, described catalyzer comprises tertiary amines, metal alkyl compound class or the combination of the two, described metal alkyl compound class is tin type organic, comprises one or more in dibutyl tin laurate, stannous octoate.
7. the preparation method of the ultralight wear-resistant type resin material of high Abbe number according to claim 6, is characterized in that, range of reaction temperature is 0-120 DEG C.
8. the preparation method of the ultralight wear-resistant type resin material of high Abbe number according to claim 7, is characterized in that, described reaction time range is 4-12 hour.
9. the ultralight wear-resistant type resin lens of high Abbe number according to claim 8, is characterized in that, this resin lens adopts the ultralight wear-resistant type resin material of high Abbe number in claim 1-3 described in any one to make.
10. prepare the method for the ultralight wear-resistant type resin lens of high Abbe number according to claim 9, it is characterized in that, comprise the following steps:
Under room temperature, isolated air conditions, by polyurethane acrylate prepolymer 1000 grams, UV light absorber 2.5-4.5 gram, anti-aging agent 1.0-2.5 gram, releasing agent 0.3-0.6 gram, blue 1.2-1.7 gram of dyestuff, the red 1.0-1.4 of dyestuff gram, initiator 2,2'-Azobis(2,4-dimethylvaleronitrile) 0.5-0.6 gram adds in mixing kettle, stirring at normal temperature is dissolved to all auxiliary agents, obtain lilac clear solution, after micropore filter paper filtering, liquid starting material mixture is poured in lens mold, carry out one-step solidification, obtain eyeglass, eyeglass through cleaning, after coating process process, test performance.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107703565A (en) * | 2017-08-04 | 2018-02-16 | 江苏明月光电科技有限公司 | A kind of anti-high-energy gold-tinted resin lens and its production method |
| CN110028649A (en) * | 2019-05-07 | 2019-07-19 | 河南达人视界眼镜有限公司 | One kind having the impact-resistant light-duty eyeglass of the anti-blue light of high light transmission |
| CN112596270A (en) * | 2020-12-02 | 2021-04-02 | 明月镜片股份有限公司 | Novel infrared-proof lens |
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| CN1234408A (en) * | 1999-05-14 | 1999-11-10 | 上海交通大学 | Transparent polymer material and preparation method thereof |
| CN101614831A (en) * | 2009-08-11 | 2009-12-30 | 杭州新顺化工有限公司 | High refractivity resin lens and preparation method thereof |
| CN102405241A (en) * | 2008-10-09 | 2012-04-04 | 赛普敦牙科部门 | Carbamate-methacrylate monomers and their use in dental applications |
| CN103224458A (en) * | 2013-04-16 | 2013-07-31 | 沈阳化工大学 | Preparation method of HMA-HDI-HMA diacrylate macromonomer |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1234408A (en) * | 1999-05-14 | 1999-11-10 | 上海交通大学 | Transparent polymer material and preparation method thereof |
| CN102405241A (en) * | 2008-10-09 | 2012-04-04 | 赛普敦牙科部门 | Carbamate-methacrylate monomers and their use in dental applications |
| CN101614831A (en) * | 2009-08-11 | 2009-12-30 | 杭州新顺化工有限公司 | High refractivity resin lens and preparation method thereof |
| CN103224458A (en) * | 2013-04-16 | 2013-07-31 | 沈阳化工大学 | Preparation method of HMA-HDI-HMA diacrylate macromonomer |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107703565A (en) * | 2017-08-04 | 2018-02-16 | 江苏明月光电科技有限公司 | A kind of anti-high-energy gold-tinted resin lens and its production method |
| CN110028649A (en) * | 2019-05-07 | 2019-07-19 | 河南达人视界眼镜有限公司 | One kind having the impact-resistant light-duty eyeglass of the anti-blue light of high light transmission |
| CN112596270A (en) * | 2020-12-02 | 2021-04-02 | 明月镜片股份有限公司 | Novel infrared-proof lens |
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Application publication date: 20150930 |