CN101107277B - 二甘醇双烯丙基碳酸酯的聚合方法 - Google Patents
二甘醇双烯丙基碳酸酯的聚合方法 Download PDFInfo
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- CN101107277B CN101107277B CN2006800024847A CN200680002484A CN101107277B CN 101107277 B CN101107277 B CN 101107277B CN 2006800024847 A CN2006800024847 A CN 2006800024847A CN 200680002484 A CN200680002484 A CN 200680002484A CN 101107277 B CN101107277 B CN 101107277B
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- Prior art keywords
- glycol bis
- allyl carbonate
- diethylene glycol
- polymerisation
- bis allyl
- 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.)
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- 238000000034 method Methods 0.000 title claims abstract description 19
- SYFOAKAXGNMQAX-UHFFFAOYSA-N bis(prop-2-enyl) carbonate;2-(2-hydroxyethoxy)ethanol Chemical compound OCCOCCO.C=CCOC(=O)OCC=C SYFOAKAXGNMQAX-UHFFFAOYSA-N 0.000 title claims description 15
- 230000005855 radiation Effects 0.000 claims abstract description 10
- 229920003023 plastic Polymers 0.000 claims abstract description 4
- 239000004033 plastic Substances 0.000 claims abstract description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 12
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000000178 monomer Substances 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 4
- JKJWYKGYGWOAHT-UHFFFAOYSA-N bis(prop-2-enyl) carbonate Chemical compound C=CCOC(=O)OCC=C JKJWYKGYGWOAHT-UHFFFAOYSA-N 0.000 abstract 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 2
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000011521 glass Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- NUHSROFQTUXZQQ-UHFFFAOYSA-N isopentenyl diphosphate Chemical compound CC(=C)CCO[P@](O)(=O)OP(O)(O)=O NUHSROFQTUXZQQ-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000005382 thermal cycling Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F18/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid
- C08F18/14—Esters of polycarboxylic acids
- C08F18/16—Esters of polycarboxylic acids with alcohols containing three or more carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F218/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid
- C08F218/14—Esters of polycarboxylic acids
- C08F218/16—Esters of polycarboxylic acids with alcohols containing three or more carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/28—Oxygen or compounds releasing free oxygen
- C08F4/32—Organic compounds
- C08F4/36—Per-compounds with more than one peroxy radical
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
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- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- General Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Casting Or Compression Moulding Of Plastics Or The Like (AREA)
Abstract
二甘醇双烯丙基碳酸酯的聚合方法,该方法可有利地用于生产低折射指数的塑料透镜,该方法包括在作为催化剂的二异丙基过氧化二碳酸酯的存在下对二甘醇双烯丙基碳酸酯进行伽马辐射的步骤。
Description
发明领域
本发明涉二甘醇双烯丙基碳酸酯的聚合方法。该聚合的碳酸酯可用于低折射指数的透镜。
发明背景
塑料眼科透镜根据它们的折射指数分类,且折射指数限定了透镜的度数。
迄今,低折射指数(1.52)的透镜通常由二甘醇双烯丙基碳酸酯的热聚合制成。这个方法在于使二甘醇双烯丙基碳酸酯在热引发剂(通常包含二异丙基过氧化二碳酸酯)存在下进行热聚合。这样的热聚合由不同温度下的热循环组成。
与这个已知方法相关的缺点是高能量消耗和时间耗费。
发明目的
本发明的一个目的是提供改进的二甘醇双烯丙基碳酸酯的聚合方法,该方法可有利地用于低折射指数眼科透镜的生产。
本发明的另一个目的是提供二甘醇双烯丙基碳酸酯的聚合方法,该方法可避免与已知方法相关的高能量消耗。
本发明的又一个目的是提供二甘醇双烯丙基碳酸酯的聚合方法,该方法可有利地用于具有优良光学性能的眼科透镜的生产。
本发明的再一个目的是提供二甘醇双烯丙基碳酸酯的有效的聚合方法。
发明内容
根据本发明,提供了二甘醇双烯丙基碳酸酯的聚合方法,该方法可有利地用于生产低折射指数的塑料透镜,该方法包括对二甘醇双烯丙基碳酸酯在作为催化剂的二异丙基过氧化二碳酸酯存在下进行伽马辐射的步骤。
根据本发明,聚合的方法包括与已知的热聚合方法相区别的伽马辐射步骤。具体而言,本发明使二甘醇双烯丙基碳酸酯在所述的催化剂存在下在75-85KGy的辐射剂量下进行伽马辐射步骤8-10小时。如果剂量增加到高于85KGy,则透镜具有微黄的颜色。然而,如果剂量低于75KGy,聚合是不完全的。
优选地,在所述的聚合步骤中使用1-1.5%的催化剂。
在随后的实施例中,其它的目的和优点将显而易见。
实施例1
取二甘醇双烯丙基碳酸酯(也被称作CR-39)并与1.2%的二异丙基过氧化二碳酸酯(也被称作IPP)相混合。将混合物吸入注射器并注入配有衬垫的玻璃毛坯中。含有聚合混合物的模具暴露在15-85KGy的伽马辐射下。
玻璃毛坯暴露在伽马辐射下变暗(turned dark),得到折射指数为1.52的、透过率高于90%和Barcol硬度为40的无色的、清洁的和透明的透镜。
Claims (3)
1.二甘醇双烯丙基碳酸酯的聚合方法,该方法用于生产折射指数为1.52的塑料透镜,并且该方法包括在作为催化剂的二异丙基过氧化二碳酸酯的存在下对二甘醇双烯丙基碳酸酯单体进行聚合步骤,其特征在于聚合步骤包括伽马辐射步骤,其中辐射剂量是75-85KGy。
2.权利要求1中所述的方法,其中辐射持续进行8-10小时。
3.权利要求1中所述的方法,其中催化剂的存在量为1-1.5%。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IN99DE2005 | 2005-01-17 | ||
IN99/DEL/2005 | 2005-01-17 | ||
PCT/IN2006/000012 WO2006075338A1 (en) | 2005-01-17 | 2006-01-16 | A process for polymerisation of diethylene glycol bis allyl carbonate |
Publications (2)
Publication Number | Publication Date |
---|---|
CN101107277A CN101107277A (zh) | 2008-01-16 |
CN101107277B true CN101107277B (zh) | 2011-06-08 |
Family
ID=36677389
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN2006800024847A Expired - Fee Related CN101107277B (zh) | 2005-01-17 | 2006-01-16 | 二甘醇双烯丙基碳酸酯的聚合方法 |
Country Status (5)
Country | Link |
---|---|
US (1) | US7923484B2 (zh) |
CN (1) | CN101107277B (zh) |
CH (1) | CH698556B1 (zh) |
GB (1) | GB2436768B (zh) |
WO (1) | WO2006075338A1 (zh) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
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US11944574B2 (en) | 2019-04-05 | 2024-04-02 | Amo Groningen B.V. | Systems and methods for multiple layer intraocular lens and using refractive index writing |
US11564839B2 (en) | 2019-04-05 | 2023-01-31 | Amo Groningen B.V. | Systems and methods for vergence matching of an intraocular lens with refractive index writing |
US11529230B2 (en) | 2019-04-05 | 2022-12-20 | Amo Groningen B.V. | Systems and methods for correcting power of an intraocular lens using refractive index writing |
US11583389B2 (en) | 2019-04-05 | 2023-02-21 | Amo Groningen B.V. | Systems and methods for correcting photic phenomenon from an intraocular lens and using refractive index writing |
US11678975B2 (en) | 2019-04-05 | 2023-06-20 | Amo Groningen B.V. | Systems and methods for treating ocular disease with an intraocular lens and refractive index writing |
US11583388B2 (en) | 2019-04-05 | 2023-02-21 | Amo Groningen B.V. | Systems and methods for spectacle independence using refractive index writing with an intraocular lens |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5237032A (en) * | 1992-09-30 | 1993-08-17 | Istituto Guido Donegani S.P.A. | Microwave processing of carbonate monomers |
CN1211594A (zh) * | 1997-09-17 | 1999-03-24 | 保谷株式会社 | 用于塑料透镜的铸塑材料和生产塑料透镜的方法 |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
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JPS5845445B2 (ja) * | 1975-03-26 | 1983-10-11 | 日本原子力研究所 | 透明プラスチック成形体の製法 |
JPS5357847A (en) * | 1976-11-05 | 1978-05-25 | Seiko Epson Corp | Lens |
JPS57158239A (en) * | 1981-03-26 | 1982-09-30 | Toray Ind Inc | Surface treatment of polymer article |
JPS58130450A (ja) * | 1982-01-28 | 1983-08-03 | Seiko Epson Corp | デイスク材料 |
JPS58167124A (ja) * | 1982-03-29 | 1983-10-03 | Nippon Oil & Fats Co Ltd | プラスチツクレンズの製造法 |
JPS5945312A (ja) * | 1982-09-08 | 1984-03-14 | Mitsui Toatsu Chem Inc | 染色性に優れる高屈折率レンズ用樹脂 |
JPS60159013A (ja) * | 1984-01-31 | 1985-08-20 | Asahi Glass Co Ltd | 硬質プラスチツクレンズの製造方法 |
IT1191615B (it) * | 1985-05-15 | 1988-03-23 | Enichem Sintesi | Procedimento per la preparazione di sostituti di vetri ottici e composizione liquida polimerizzabile adatta allo scopo |
JPH0445134A (ja) * | 1990-06-12 | 1992-02-14 | Mitsubishi Rayon Co Ltd | 表面変性ジエチレングリコールビスアリルカーボネート成型物及びその製法 |
US5715829A (en) * | 1995-11-29 | 1998-02-10 | Hewlett-Packard Company | Method and apparatus for detecting heartbeats in an ECG waveform using an activity function and on-time search |
-
2006
- 2006-01-16 US US11/886,387 patent/US7923484B2/en not_active Expired - Fee Related
- 2006-01-16 CN CN2006800024847A patent/CN101107277B/zh not_active Expired - Fee Related
- 2006-01-16 CH CH01395/07A patent/CH698556B1/de not_active IP Right Cessation
- 2006-01-16 GB GB0713904A patent/GB2436768B/en not_active Expired - Fee Related
- 2006-01-16 WO PCT/IN2006/000012 patent/WO2006075338A1/en not_active Application Discontinuation
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5237032A (en) * | 1992-09-30 | 1993-08-17 | Istituto Guido Donegani S.P.A. | Microwave processing of carbonate monomers |
CN1211594A (zh) * | 1997-09-17 | 1999-03-24 | 保谷株式会社 | 用于塑料透镜的铸塑材料和生产塑料透镜的方法 |
Also Published As
Publication number | Publication date |
---|---|
CN101107277A (zh) | 2008-01-16 |
US7923484B2 (en) | 2011-04-12 |
GB0713904D0 (en) | 2007-08-29 |
WO2006075338A1 (en) | 2006-07-20 |
US20080182916A1 (en) | 2008-07-31 |
GB2436768A (en) | 2007-10-03 |
WO2006075338B1 (en) | 2006-11-02 |
CH698556B1 (de) | 2009-08-31 |
GB2436768B (en) | 2009-10-14 |
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