CN1548988A - Method for producing optical resin material with high-refractivity - Google Patents
Method for producing optical resin material with high-refractivity Download PDFInfo
- Publication number
- CN1548988A CN1548988A CNA031168957A CN03116895A CN1548988A CN 1548988 A CN1548988 A CN 1548988A CN A031168957 A CNA031168957 A CN A031168957A CN 03116895 A CN03116895 A CN 03116895A CN 1548988 A CN1548988 A CN 1548988A
- Authority
- CN
- China
- Prior art keywords
- styrene
- diallyl
- optical resin
- resin material
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000011347 resin Substances 0.000 title claims abstract description 18
- 229920005989 resin Polymers 0.000 title claims abstract description 18
- 230000003287 optical effect Effects 0.000 title claims abstract description 13
- 239000000463 material Substances 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 16
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000012948 isocyanate Substances 0.000 claims abstract description 10
- -1 isocyanate compound Chemical class 0.000 claims abstract description 10
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims abstract description 8
- 235000011187 glycerol Nutrition 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 238000003756 stirring Methods 0.000 claims abstract description 7
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 claims description 15
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 9
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 claims description 5
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 229940124543 ultraviolet light absorber Drugs 0.000 claims description 3
- 239000006097 ultraviolet radiation absorber Substances 0.000 claims description 3
- 229940125773 compound 10 Drugs 0.000 claims description 2
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 abstract 2
- HHQAGBQXOWLTLL-UHFFFAOYSA-N (2-hydroxy-3-phenoxypropyl) prop-2-enoate Chemical compound C=CC(=O)OCC(O)COC1=CC=CC=C1 HHQAGBQXOWLTLL-UHFFFAOYSA-N 0.000 abstract 1
- APPOKADJQUIAHP-GGWOSOGESA-N (2e,4e)-hexa-2,4-diene Chemical group C\C=C\C=C\C APPOKADJQUIAHP-GGWOSOGESA-N 0.000 abstract 1
- PWMWNFMRSKOCEY-UHFFFAOYSA-N 1-Phenyl-1,2-ethanediol Chemical compound OCC(O)C1=CC=CC=C1 PWMWNFMRSKOCEY-UHFFFAOYSA-N 0.000 abstract 1
- OWPUOLBODXJOKH-UHFFFAOYSA-N 2,3-dihydroxypropyl prop-2-enoate Chemical compound OCC(O)COC(=O)C=C OWPUOLBODXJOKH-UHFFFAOYSA-N 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 abstract 1
- 239000006096 absorbing agent Substances 0.000 abstract 1
- ZDNFTNPFYCKVTB-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,4-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=C(C(=O)OCC=C)C=C1 ZDNFTNPFYCKVTB-UHFFFAOYSA-N 0.000 abstract 1
- 239000001055 blue pigment Substances 0.000 abstract 1
- 238000002310 reflectometry Methods 0.000 abstract 1
- 125000005442 diisocyanate group Chemical group 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000977 initiatory effect Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- SHKKTLSDGJRCTR-UHFFFAOYSA-N 1,2-dibromoethylbenzene Chemical compound BrCC(Br)C1=CC=CC=C1 SHKKTLSDGJRCTR-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- QRFALSDGOMLVIR-UHFFFAOYSA-N 1,2,3,4-tetrabromobenzene Chemical compound BrC1=CC=C(Br)C(Br)=C1Br QRFALSDGOMLVIR-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- JWTIVABBBOJWNW-UHFFFAOYSA-N ethene 1,2,3,4-tetrachlorobenzene Chemical compound C=C.ClC1=C(C(=C(C=C1)Cl)Cl)Cl JWTIVABBBOJWNW-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The preparation process of high reflectivity optical resin includes the following steps: mixing 1, 3-di(glyceryl acrylate) glycerin, diallyl terephthalate and dipropenyl styrene glycol bicarbonate via stirring under room temperature; adding a-methyl styrene, styrene and bisphenol A tetrabromide successively; adding 2-hydroxy-3-phenoxy propyl acrylate and isocyanate compound while stirring for 2 hr; and adding ultraviolet absorbing agent in 0.3 % and blue pigment in 0.2-1 ppm. The said preparation process is simple, and has good controllability and repeatability, mild reaction condition, no pollution, low cost and high product surface hardness.
Description
One, technical field:
The present invention relates to a kind of manufacturing process of optical resin material, particularly a kind of preparation method of high index of refraction optical resin material.
Two, background technology:
In recent years, optical resin lens is with its fashionable domestic and international market of special advantage, and the high index of refraction optical resin lens more with its extra-thin fangle, comes out first in the eyeglass industry, the home market of selling well.Yet the resin lens of domestic present production all is a refractive index is 1.499 eyeglass, and still do not have enterprise and produce 1.60 high refractivity resin lens, refractive index is that 1.499 optical resin lens principal ingredient is diallyl two carbonic acid diethyl alcohol esters (being called for short ADC), the lens thickness made from ADC is thicker, and thermal resistance, visible light transmittance rate performance are compared very inferior with high refractivity resin lens.
Three, summary of the invention:
Technical matters to be solved by this invention is: the manufacturing process that the high index of refraction optical resin material of a kind of refractive index between 1.60～1.67 is provided.
The present invention is achieved like this: at ambient temperature, at first 1, after 3-two (acrylic acid glycerine ester group) glycerine and diallyl p phthalate, two compound of diallyl two carbonic acid binaryglycol esters stir, add a-methyl styrene, styrene successively, and tetrabromobisphenol A, continue to add 2-hydroxyl-3-phenoxy group propyl acrylate and isocyanate ester compound while stirring, stirred 2 hours; Add 0.1～0.3% ultraviolet light absorber and the blue toner of 0.2ppm～1ppm again.The weight proportion of described each compound is: isocyanate ester compound 10～12%, diallyl p phthalate 5%, tetrabromobisphenol A 10～15%, 1,3-two (acrylic acid glycerine ester group) glycerine 5%, 2-hydroxyl-3-phenoxy group propyl acrylate 25%, styrene 10～15%, a-methyl styrene 20～30%, diallyl two carbonic acid binaryglycol esters 3%.
Isocyanate ester compound has higher refractive index, halogen atom, the increase of oxygen atom, conjugated system increases in the molecule, the refractive index of the compound that the capital makes improves, the present invention utilizes isocyanates and the hydroxyl compound that contains halogen, compound fragrant hydrocarbon, and other polyol under certain conditions, formulated high dioptrics material, and this material is under the initiating agent effect, after solidifying by the program temperature control, get final product ultrathin high index of refraction optical resin lens, the inventive method synthesis technique is simple, the controllability of process and good reproducibility, the reaction conditions gentleness, pollution-free, cost is low, product surface hardness height.
Five, embodiment:
Stir at ambient temperature, at first 5% 1,3-two (acrylic acid glycerine ester group) glycerine and 5% diallyl p phthalate, after two compound of diallyl two carbonic acid binaryglycol esters of 3% are even, add 20～30% a-methyl styrene successively, 10～15% styrene and 10～15% tetrabromobisphenol A, because tetrabromobisphenol A is separated than indissoluble, under agitation, continue the 2-hydroxyl-3-phenoxy group propyl acrylate of adding 25% and 10～12% isocyanate ester compound, stirred 2 hours, as standard recipe, the blue toner that has added commercially available 0.3% ultraviolet light absorber and commercially available 0.2ppm～1ppm in mix monomer gets a pale blue transparency liquid, refractive index is 1.56, viscosity is 7mpa.s, moisture content 170ppm.Isocyanate ester compound can be to diisocyanate cpd, also can be a diisocyanate cpd or adjacent diisocyanate cpd, and its chemical structural formula is:
R can be chlorine, bromine, methyl, ethyl etc., 0～3 is the number of CH2NCO, n is the number of R, inferior Xylene Diisocyanate for example, inferior Xylene Diisocyanate etc. between the 4-bromine, tetrabromobisphenol A can be tetrabromobisphenol A two (3-hydroxypropyl) ether, perhaps tetrabromobisphenol A dihydroxy methyl ether etc., and its chemical structural formula is:
Distyryl compound can be styrene, tetrachlorobenzene ethene, tetrabromo-benzene ethene, Dowspray 9 etc., and its chemical structural formula is:
X＝Cl、Brm＝0～4
The embodiment one of concrete prescription:
Between eylylene diisocyanate 10%, diallyl p phthalate 5%, tetrabromobisphenol A two (2-hydroxyethyl) ether 12%, 1,3-two (acrylic acid glycerine ester group) glycerine 5%, 2-hydroxyl-3-phenoxy group olefin(e) acid propyl ester 25%, styrene 13%, a-methyl styrene 27%, diallyl two carbonic acid binaryglycol esters 3%, the monomer proterties that is made into is: proportion is that 1.07 refractive indexes are 1.563, viscosity is 70mpa.s, moisture content 170ppm, curing molding behind the initiating agent of adding 0.5～1%, become ultrathin high refractivity resin lens, its refractive index is 1.595, and Ah's multiple is 32.
The embodiment two of concrete prescription:
Between inferior dimethyl benzene group diisocyanate 10%, diallyl p phthalate 5%, tetrabromobisphenol A two (2-hydroxyethyl) ether 15%, 1,3-two (acrylic acid glycerine ester group) glycerine 5%, 2-hydroxyl-3-phenoxy group acrylate 25%, Dowspray 9 15%, a-methyl styrene 22%, diallyl two carbonic acid binaryglycol esters 3%, monomer proterties proportion is: 1.08, refractive index is 1.567, and viscosity is 72mpa.s, and moisture content is 165ppm, curing molding behind the initiating agent of adding 0.5～1%, become ultra-thin high refractivity resin lens, its refractive index is 1.602, and Ah's multiple is 33.
Claims (3)
1, the preparation method of high index of refraction optical resin material, it is characterized in that: at ambient temperature, at first 1, after 3-two (acrylic acid glycerine ester group) glycerine and diallyl p phthalate, two compound of diallyl two carbonic acid binaryglycol esters stir, add a-methyl styrene, styrene and tetrabromobisphenol A successively, continue to add 2-hydroxyl-3-phenoxy group propyl acrylate and isocyanate ester compound while stirring, stirred 2 hours; Add the ultraviolet light absorber of weight ratio 0.1～0.2% and the blue toner of 0.2ppm～1ppm again.
2, the preparation method of high index of refraction optical resin material according to claim 1, it is characterized in that: the weight proportion of described each compound is: isocyanate ester compound 10～12%, diallyl p phthalate 5%, tetrabromobisphenol A 10～15%, 1,3-two (acrylic acid glycerine ester group) glycerine 5%, 2-hydroxyl-3-phenoxy group propyl acrylate 25%, styrene 10～15%, a-methyl styrene 20～30%, diallyl two carbonic acid binaryglycol esters 3%.
3, the preparation method of high index of refraction optical resin material according to claim 1 and 2 is characterized in that: the chemical structural formula of described isocyanate ester compound is:
The chemical structural formula of described tetrabromobisphenol A is:
Described cinnamic chemical structural formula is:
X＝Cl、Br m＝0～4
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB031168957A CN1325943C (en) | 2003-05-14 | 2003-05-14 | Method for producing optical resin material with high-refractivity |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB031168957A CN1325943C (en) | 2003-05-14 | 2003-05-14 | Method for producing optical resin material with high-refractivity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1548988A true CN1548988A (en) | 2004-11-24 |
| CN1325943C CN1325943C (en) | 2007-07-11 |
Family
ID=34320521
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB031168957A Expired - Lifetime CN1325943C (en) | 2003-05-14 | 2003-05-14 | Method for producing optical resin material with high-refractivity |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1325943C (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101665552B (en) * | 2008-09-03 | 2012-10-31 | 浙江海洋学院 | Optical resin monomer material |
| CN103676203A (en) * | 2013-12-05 | 2014-03-26 | 上海伟星光学有限公司 | Dark brown resin lens with visible-light color-changing performance and manufacture method thereof |
| CN106273570A (en) * | 2016-08-30 | 2017-01-04 | 东兴华鸿光学科技有限公司 | The production technology of resin lens |
| 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 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU573471B2 (en) * | 1986-03-01 | 1988-06-09 | Mitsui Chemicals, Inc. | Polythiocarbamate lense material |
| US4946923A (en) * | 1988-02-18 | 1990-08-07 | Mitsui Toatsu Chemicals, Inc. | S-alkyl thiocarbamate base resin, plastic lens comprising the resin, and process for making the lens |
| CA1316315C (en) * | 1988-02-22 | 1993-04-20 | Nobuyuki Kajimoto | Highly-refractive plastic lens and process for making the lens |
| EP0351073B1 (en) * | 1988-07-14 | 1994-09-21 | MITSUI TOATSU CHEMICALS, Inc. | Lens comprising a resin having a large refractive index and process for preparing the lens |
| US5306799A (en) * | 1992-08-26 | 1994-04-26 | Mitsui Toatsu Chemicals, Inc. | High refractive index plastic lens and composition therefor |
-
2003
- 2003-05-14 CN CNB031168957A patent/CN1325943C/en not_active Expired - Lifetime
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101665552B (en) * | 2008-09-03 | 2012-10-31 | 浙江海洋学院 | Optical resin monomer material |
| CN103676203A (en) * | 2013-12-05 | 2014-03-26 | 上海伟星光学有限公司 | Dark brown resin lens with visible-light color-changing performance and manufacture method thereof |
| CN103676203B (en) * | 2013-12-05 | 2014-11-12 | 上海伟星光学有限公司 | Dark brown resin lens with visible-light color-changing performance and manufacture method thereof |
| CN106273570A (en) * | 2016-08-30 | 2017-01-04 | 东兴华鸿光学科技有限公司 | The production technology of resin lens |
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1325943C (en) | 2007-07-11 |
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Owner name: SHANGHAI CONANT OPTICAL CO., LTD. Free format text: FORMER NAME OR ADDRESS: SHANGHAI KANIGHT OPTICAL CO., LTD. |
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Address after: Shanghai City, Pudong New Area Sichuan Road No. 555 Patentee after: SHANGHAI CONANT OPTICS Co.,Ltd. Address before: No. 400, Huaxia three road, Shanghai, Pudong Patentee before: SHANGHAI CONANT OPTICAL Co.,Ltd. |
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Denomination of invention: Method for producing optical resin material with high-refractivity Effective date of registration: 20141115 Granted publication date: 20070711 Pledgee: Bank of China Limited by Share Ltd. Shanghai Development Zone Pudong branch Pledgor: SHANGHAI CONANT OPTICS Co.,Ltd. Registration number: 2014310000078 |
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Address after: 201299 Shanghai city Pudong New Area Sichuan Road No. 555 Patentee after: Shanghai Conant's Smart Meter Technology Group Co. Address before: 201200 Shanghai city Pudong New Area Sichuan Road No. 555 Patentee before: SHANGHAI CONANT OPTICS Co.,Ltd. |
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Effective date of registration: 20171106 Address after: 201299 Shanghai city Pudong New Area Sichuan Road 555, No. 585 building 1-15 Patentee after: SHANGHAI CONANT OPTICAL Co.,Ltd. Address before: 201299 Shanghai city Pudong New Area Sichuan Road No. 555 Patentee before: Shanghai Conant's Smart Meter Technology Group Co. |
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