JPH02261808A - Preparation of high refractive index resin - Google Patents
Preparation of high refractive index resinInfo
- Publication number
- JPH02261808A JPH02261808A JP8212989A JP8212989A JPH02261808A JP H02261808 A JPH02261808 A JP H02261808A JP 8212989 A JP8212989 A JP 8212989A JP 8212989 A JP8212989 A JP 8212989A JP H02261808 A JPH02261808 A JP H02261808A
- Authority
- JP
- Japan
- Prior art keywords
- formulas
- sulfur
- refractive index
- high refractive
- tables
- 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.)
- Pending
Links
- 229920005989 resin Polymers 0.000 title claims abstract description 28
- 239000011347 resin Substances 0.000 title claims abstract description 28
- 239000000178 monomer Substances 0.000 claims abstract description 20
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 19
- -1 allyl carbonates Chemical class 0.000 claims abstract description 10
- 125000001424 substituent group Chemical group 0.000 claims abstract description 9
- JKJWYKGYGWOAHT-UHFFFAOYSA-N bis(prop-2-enyl) carbonate Chemical compound C=CCOC(=O)OCC=C JKJWYKGYGWOAHT-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000010526 radical polymerization reaction Methods 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 14
- 239000011593 sulfur Substances 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 229910052727 yttrium Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000006839 xylylene group Chemical group 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 abstract description 3
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 10
- 238000006116 polymerization reaction Methods 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical class OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 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 description 4
- 235000019645 odor Nutrition 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical class C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- 239000004641 Diallyl-phthalate Chemical class 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- 239000002390 adhesive tape Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical class C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000005498 polishing Methods 0.000 description 2
- 150000003440 styrenes Chemical class 0.000 description 2
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- RUDUCNPHDIMQCY-UHFFFAOYSA-N [3-(2-sulfanylacetyl)oxy-2,2-bis[(2-sulfanylacetyl)oxymethyl]propyl] 2-sulfanylacetate Chemical compound SCC(=O)OCC(COC(=O)CS)(COC(=O)CS)COC(=O)CS RUDUCNPHDIMQCY-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical class CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 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 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 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
- 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
- C08F18/24—Esters of carbonic or haloformic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野コ
本発明は、高屈折率樹脂である、含硫黄アリルカーボネ
ート樹脂の製造方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a method for producing a sulfur-containing allyl carbonate resin, which is a high refractive index resin.
［従来の技術］
オレフィン系熱硬化性樹脂は一般的に耐熱性・耐薬品性
に優れている。中でも光学用途としてはジエチレングリ
コールビスアリルカーボネートが多く用いられている。[Prior Art] Olefin thermosetting resins generally have excellent heat resistance and chemical resistance. Among them, diethylene glycol bisallyl carbonate is often used for optical purposes.
しかし、ジエチレングリコールビスアリルカーボネート
は低い屈折率が問題となっている。However, diethylene glycol bisallyl carbonate has a problem of low refractive index.
その問題を解決するために、芳香族チオールエステルを
主成分とする樹脂（特開昭６３−３１６７６６号公報）
や脂肪族チオールエステル（特開昭６３−１６２６７１
号公報や特開昭６３−１８８６６０号公報）等のチオー
ル（メタ）アクリレートが提案されている。In order to solve this problem, a resin containing aromatic thiol ester as a main component (Japanese Patent Application Laid-open No. 63-316766)
and aliphatic thiol esters (JP-A-63-162671
Thiol (meth)acrylates such as those disclosed in Japanese Patent Application Laid-open No. 188660/1983 have been proposed.
［本発明が解決しようとする課題］
特開昭６３−３１６７６６号公報の芳香族チオールエス
テルよりなる樹脂や特開昭６３−１６２６７１号公報や
特開昭６３−１８８６６０号公報で提案されている脂肪
族チオールエステルより得られる樹脂は、高屈折率を有
するものの、加水分解を受けやすく、分解により生じた
チオール化合物が強い臭気や毒性を発生するという欠点
があった。また、耐衝撃性が低く、メガネ等の安全性を
必要とするものには不向きである。[Problems to be solved by the present invention] Resins made of aromatic thiol esters disclosed in JP-A-63-316766 and fats proposed in JP-A-63-162,671 and JP-A-63-188,660 Although resins obtained from group thiol esters have a high refractive index, they have the disadvantage that they are susceptible to hydrolysis and the thiol compounds produced by the decomposition generate strong odors and toxicity. In addition, it has low impact resistance, making it unsuitable for items that require safety, such as glasses.
本発明は、かかる従来技術の欠点を解消しようとするも
のであり、高い屈折率を有し、かつ、耐衝撃性に優れ、
さらに加水分解による臭気を発生しない樹脂を提供する
ことを目的とする。The present invention aims to eliminate the drawbacks of the prior art, and has a high refractive index and excellent impact resistance.
Another object of the present invention is to provide a resin that does not generate odor due to hydrolysis.
［課題を解決するための手段］
上記目的を達成するために本発明は以下の構成よりなる
。[Means for Solving the Problems] In order to achieve the above object, the present invention has the following configuration.
「ラジカル重合により高屈折率樹脂を製造する方法にお
いて、多官能含硫黄アリルカーボネートの少なくとも１
種を必須成分として含む単量体を用いることを特徴とす
る高屈折率樹脂の製造方法。」本発明に用いる多官能含
硫黄アリルカーボネート（以下、重合性単量体１とする
）とは、含硫黄多価アルコールまたは多価メルカプタン
を従来用いられている方法で、アリルカーボネート化す
ることによって得られるものである。"In a method for producing a high refractive index resin by radical polymerization, at least one of the polyfunctional sulfur-containing allyl carbonates
A method for producing a high refractive index resin, characterized by using a monomer containing a species as an essential component. "The polyfunctional sulfur-containing allyl carbonate (hereinafter referred to as polymerizable monomer 1) used in the present invention is obtained by converting a sulfur-containing polyhydric alcohol or polyhydric mercaptan into allyl carbonate by a conventional method. That's what you get.
本発明の重合性単量体１としては、アリルカーボネート
およびアリルチオカーボネートより選ばれる少なくとも
１つの基を有し、かつ、単量体中の重合性官能基が２つ
以上であり、さらに単量体中に必ず硫黄を含有する化合
物であれば特に限定はないが、好ましくは次の一般式（
Ａ）〜（Ｃ）で示される化合物が用いられる。The polymerizable monomer 1 of the present invention has at least one group selected from allyl carbonate and allylthiocarbonate, and has two or more polymerizable functional groups in the monomer, and There is no particular limitation as long as the compound always contains sulfur in its body, but preferably it has the following general formula (
Compounds represented by A) to (C) are used.
（ただし、式（Ａ）、（Ｂ）、（Ｃ）、（Ｄ）および（
Ｅ）中、ｍはＯ〜５、ｎはＯ〜４の整数を示す。ＲＩ
、Ｒ２は、水素、炭素数１〜５のアルキル基、および
含硫黄置換基とから選ばれる。ここで含硫黄置換基とは
、
−８−をα個と、−ＣＨ２−、−ＣＨ−および−Ｃ−か
ら選ばれる少なくとも１つを合計でβ個とからなる置換
基（ただし、−５−Ｓ−を含まず、αは１〜５の整数、
βは１〜１０の整数を示し、α≦βを満たす。）である
。Ｒ３は、フェニレンまたはキシリレンを示す。Ｘは０
またはＳ、Ｙは０またはＳである。（ただし、Ｘ、Ｙと
もにＯである場合を除く。））
一般式（Ａ）〜（Ｃ）で示される化合物中、含硫黄置換
基の具体例としては、以下の置換基が挙げられるが、こ
れらに限定されるものではない。(However, formulas (A), (B), (C), (D) and (
In E), m represents an integer of 0 to 5, and n represents an integer of 0 to 4. R.I.
, R2 are selected from hydrogen, an alkyl group having 1 to 5 carbon atoms, and a sulfur-containing substituent. Here, the sulfur-containing substituent is a substituent consisting of α -8- and a total of β at least one selected from -CH2-, -CH- and -C- (however, -5- Does not include S-, α is an integer from 1 to 5,
β represents an integer from 1 to 10, and satisfies α≦β. ). R3 represents phenylene or xylylene. X is 0
Or S and Y are 0 or S. (However, this excludes the case where both X and Y are O.) In the compounds represented by general formulas (A) to (C), specific examples of the sulfur-containing substituent include the following substituents, It is not limited to these.
Ｓ−Ｃｈ、−３ＣＨ２ＣＨ＋ 、−３ＣＨ２ＣＨ２５Ｈ
１−３ＣＬ ＣＨ２５ＣＨ２Ｃｈ、Ｃｌｌ３
Ｓ−ＣＬ−Ｃ−Ｃ１ｈ、 −８−ＣＨ２−ＣＩ（−３Ｃ
Ｉ（ＩＳＣＨｓ ＳＣＨ＋
重合性単量体１としては、さらに具体的には、下記化合
物があげられるが特にこれらに限定されるものではない
。S-Ch, -3CH2CH+, -3CH2CH25H
1-3CL CH25CH2Ch, Cll3 S-CL-C-C1h, -8-CH2-CI(-3C
I(ISCHs SCH+ More specifically, the polymerizable monomer 1 includes the following compounds, but is not particularly limited to these.
ＣＨ３
ＳＣＨ３３ＣＨ３
本発明の高屈折率樹脂は、重合性単量体１の少なくとも
１種を必須成分として含む単量体１００重量部に対して
、過酸化物系あるいはアゾ系の開始剤を、０．０１〜５
重量部加えた後、加熱あるいは光照射することによって
重合し、透明性に優れた樹脂を製造することができる。CH3 SCH33CH3 The high refractive index resin of the present invention contains 0.00 parts by weight of a peroxide-based or azo-based initiator based on 100 parts by weight of a monomer containing at least one kind of polymerizable monomer 1 as an essential component. 01-5
After adding part by weight, it is polymerized by heating or irradiation with light, and a resin with excellent transparency can be produced.
この時、単量体としては、重合性単量体１と、これ以外
の単量体とを共重合させたものを用いることができる。At this time, as the monomer, a copolymer of Polymerizable Monomer 1 and other monomers can be used.
この場合、得られる樹脂の特性上、本発明の重合性単量
体１を全単量体に対して２０重量％以上加えることが好
ましい。In this case, in view of the properties of the resulting resin, it is preferable to add 20% by weight or more of the polymerizable monomer 1 of the present invention based on the total monomers.
加える単量体としては、オレフィン系化合物であれば特
に限定はせず、好ましくはアリル系化合物、（メタ）ア
クリル系化合物やスチレン系化合物、アクリロニトリル
、Ｎ−フェニルマレイミド等があげられる。具体的には
、メチル（メタ）アクリレート、エチル（メタ）アクリ
レート、プロピル（メタ）アクリレート、ベンジル（メ
タ）アクリレート、フェニル（メタ）アクリレート、ベ
ンジル（メタ）アクリレート、シクロヘキシル（メタ）
アクリレート、シクロへキシルメチレン（メタ）アクリ
レート、スチレン、ビニルナフタレン、ハロゲン置換ス
チレン、α−メチルスチレン、ジビニルベンゼン、ジア
リルフタレート、エチレングリコールジ（メタ）アクリ
レート、ジエｆ１ノングリコールビスアリルカーボネー
ト、ジアリルフタレート等である。The monomer to be added is not particularly limited as long as it is an olefin compound, and preferably includes allyl compounds, (meth)acrylic compounds, styrene compounds, acrylonitrile, N-phenylmaleimide, and the like. Specifically, methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, benzyl (meth)acrylate, phenyl (meth)acrylate, benzyl (meth)acrylate, and cyclohexyl (meth)acrylate.
Acrylate, cyclohexylmethylene (meth)acrylate, styrene, vinylnaphthalene, halogen-substituted styrene, α-methylstyrene, divinylbenzene, diallyl phthalate, ethylene glycol di(meth)acrylate, dief1 non-glycol bisallyl carbonate, diallyl phthalate, etc. It is.
また、共重合成分として、多価メルカプタン化合物を加
えることによって、加工性に優れた樹脂を得ることがで
きる。Furthermore, by adding a polyvalent mercaptan compound as a copolymerization component, a resin with excellent processability can be obtained.
多価メルカプタン化合物としては、ペンタエリスリトー
ルテトラキスチオグリコレート、トリスメルカプトプロ
ピルイソシアヌレート等がある。Examples of polyvalent mercaptan compounds include pentaerythritol tetrakisthioglycolate and trismercaptopropyl isocyanurate.
本発明の重合性単量体１より高屈折率樹脂を製造する方
法としては、従来公知のラジカル重合法であれば、特に
限定されることはないが、好ましくは注型重合法によっ
て成形できる。この場合の成形方法の好ましい一例とし
ては、本発明の重合性単量体１を、あるいは前述の共重
合成分のうち少なくとも１成分と本発明の重合性単量体
１とを混合した液体を重合開始剤とともに、ガラスある
いは金属製のモールドと粘着テープあるいは塩ビ製のガ
スケットよりなる型に注入し、３０〜１５０℃で０．１
〜４０時間加熱、あるいは、紫外線を照射することによ
って成形できる。The method for producing a high refractive index resin from the polymerizable monomer 1 of the present invention is not particularly limited as long as it is a conventionally known radical polymerization method, but preferably it can be molded by a cast polymerization method. A preferred example of the molding method in this case is to polymerize a liquid obtained by mixing the polymerizable monomer 1 of the present invention or at least one component of the copolymerization components described above with the polymerizable monomer 1 of the present invention. It is injected together with an initiator into a mold consisting of a glass or metal mold and an adhesive tape or a PVC gasket, and is heated to 0.1 at 30 to 150°C.
It can be molded by heating for ~40 hours or by irradiating with ultraviolet rays.
本発明の含硫黄アリルカーボネートを用いて高屈折で耐
衝撃性・透明性に優れた樹脂を製造することができる。Using the sulfur-containing allyl carbonate of the present invention, a resin with high refraction and excellent impact resistance and transparency can be produced.
［実施例］ 以下実施例により、本発明を具体的に説明する。[Example] The present invention will be specifically described below with reference to Examples.
実施例１
下記式（Ｆ）の化合物７０重量部にジエチレングリコー
ルビスアリルカーボネート２７重量部とジイソプロピル
パーオキシジカーボネート３重量部を加えた溶液をガラ
スモールドと粘着テープよりなるモールド型に注入し、
４０℃で３時間、６０℃で５時間、９０°Ｃで１０時間
かけて重合し樹脂を製造した。Example 1 A solution prepared by adding 27 parts by weight of diethylene glycol bisallyl carbonate and 3 parts by weight of diisopropyl peroxydicarbonate to 70 parts by weight of the compound of the following formula (F) was injected into a mold made of a glass mold and adhesive tape.
Polymerization was performed at 40°C for 3 hours, at 60°C for 5 hours, and at 90°C for 10 hours to produce a resin.
実施例２
式（Ｆ）の化合物を下記式（Ｇ）の化合物に変えた以外
は実施例１と同様にして重合し樹脂を製造した。Example 2 A resin was produced by polymerization in the same manner as in Example 1, except that the compound of formula (F) was changed to the compound of formula (G) below.
実施例３
式（Ｆ）の化合物を下記式（Ｈ）の化合物に変えた以外
は実施例１と同様にして重合し樹脂を製造した。Example 3 A resin was produced by polymerization in the same manner as in Example 1, except that the compound of formula (F) was replaced with the compound of formula (H) below.
実施例４
式（Ｆ）の化合物を下記式（Ｉ）の化合物に変えた以外
は実施例１と同様にして重合し樹脂を製造した。Example 4 A resin was produced by polymerization in the same manner as in Example 1, except that the compound of formula (F) was replaced with the compound of formula (I) below.
比較例１
式（Ｆ）の化合物を下記式（Ｊ）の化合物に変えた以外
は実施例１と同様にして重合し樹脂を製造した。Comparative Example 1 A resin was produced by polymerization in the same manner as in Example 1, except that the compound of formula (F) was replaced with the compound of formula (J) below.
比較例２
式（Ｆ）の化合物を下記式（Ｋ）の化合物に変えた以外
は実施例１と同様にして重合し樹脂を製造した。Comparative Example 2 A resin was produced by polymerization in the same manner as in Example 1, except that the compound of formula (F) was replaced with the compound of formula (K) below.
以外のものを○とした。Items other than those were marked as ○.
加工時の臭気は研磨機を用いて研磨し、臭気のしないも
のを○、それ以外のものを×とした。The odor during processing was removed by polishing using a polishing machine, and those with no odor were rated as ○, and the others were rated as ×.
屈折率およびアツベ数は、プルフリッヒ屈折計を用いて
測定した。The refractive index and Atsube number were measured using a Pulfrich refractometer.
実施例１〜２及び比較例１．２に示した樹脂の性質を表
１に示した。Table 1 shows the properties of the resins shown in Examples 1-2 and Comparative Example 1.2.
耐光性はカラーコンピューターとフェードメーターを用
いて測定した。Light fastness was measured using a color computer and a fade meter.
耐衝撃性については、厚さ２ｍｍの樹脂に１６゜３ｇの
鉄球を１２７ｃｍの高さより落下し、破損したものを×
、クラックに入ったものを△、それ表１
に、透明性、耐光性にも優れるため、塗料や電子部品・
光学用途等幅広い分野に利用できる。Regarding impact resistance, a 16° 3g iron ball was dropped onto a 2mm thick resin from a height of 127cm, and the damaged one was
, Those with cracks are marked as △.
It can be used in a wide range of fields such as optical applications.
さらに、現在、工業的に大量に生産されているジエチレ
ングリコールビスアリルカーボネートとほぼ同じ条件で
重合・成型できるため、現状の設備および生産技術を利
用できるという利点がある。Furthermore, since it can be polymerized and molded under almost the same conditions as diethylene glycol bisallyl carbonate, which is currently produced in large quantities industrially, it has the advantage of being able to use current equipment and production technology.
Claims (2)
において、多官能含硫黄アリルカーボネートの少なくと
も１種を必須成分として含む単量体を用いることを特徴
とする高屈折率樹脂の製造方法。(1) A method for producing a high refractive index resin by radical polymerization, which is characterized in that a monomer containing at least one polyfunctional sulfur-containing allyl carbonate as an essential component is used.
（Ａ）、（Ｂ）または（Ｃ）で示される多官能含硫黄ア
リルカーボネートから選ばれる少なくとも１種を用いた
ものであることを特徴とする請求項（１）記載の高屈折
率樹脂の製造方法。 ▲数式、化学式、表等があります▼（Ａ） ▲数式、化学式、表等があります▼（Ｂ） ▲数式、化学式、表等があります▼（Ｃ） ▲数式、化学式、表等があります▼（Ｄ） ▲数式、化学式、表等があります▼（Ｅ） （ただし、式（Ａ）、（Ｂ）、（Ｃ）、（Ｄ）および（
Ｅ）中、ｍは０〜５、ｎは０〜４の整数を示す。Ｒ＿１
、Ｒ＿２は、水素、炭素数１〜５のアルキル基、および
含硫黄置換基から選ばれる。ここで含硫黄置換基とは、 −Ｓ−をα個と、−ＣＨ＿２−、▲数式、化学式、表等
があります▼および▲数式、化学式、表等があります▼
から選ばれる少なくとも１つを合計でβ個とからなる置
換基（ただし、−Ｓ−Ｓ−を含まず、αは１〜５の整数
、βは１〜１０の整数を示し、α≦βを満たす。）であ
る。Ｒ＿３は、フェニレンまたはキシリレンを示す。Ｘ
はＯまたはＳ、ＹはＯまたはＳである。（ただし、Ｘ、
ＹともにＯである場合を除く。）(2) The polyfunctional sulfur-containing allyl carbonate is characterized by using at least one selected from polyfunctional sulfur-containing allyl carbonates represented by the following general formula (A), (B), or (C). The method for producing a high refractive index resin according to claim (1). ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (A) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (B) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (C) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ ( D) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(E) (However, formulas (A), (B), (C), (D) and (
In E), m represents an integer of 0 to 5, and n represents an integer of 0 to 4. R_1
, R_2 is selected from hydrogen, an alkyl group having 1 to 5 carbon atoms, and a sulfur-containing substituent. Here, the sulfur-containing substituents include α -S-, -CH_2-, ▲Mathematical formulas, chemical formulas, tables, etc.▼ and ▲Mathematical formulas, chemical formulas, tables, etc.▼
A substituent consisting of a total of β at least one selected from ). R_3 represents phenylene or xylylene. X
is O or S, and Y is O or S. (However, X,
Except when both Y and O are O. )
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8212989A JPH02261808A (en) | 1989-03-31 | 1989-03-31 | Preparation of high refractive index resin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8212989A JPH02261808A (en) | 1989-03-31 | 1989-03-31 | Preparation of high refractive index resin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02261808A true JPH02261808A (en) | 1990-10-24 |
Family
ID=13765805
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8212989A Pending JPH02261808A (en) | 1989-03-31 | 1989-03-31 | Preparation of high refractive index resin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02261808A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014030711A1 (en) | 2012-08-24 | 2014-02-27 | 大日本印刷株式会社 | Photosensitive composition for volume hologram recording, photosensitive substrate for volume hologram recording, and volume hologram-recorded object |
-
1989
- 1989-03-31 JP JP8212989A patent/JPH02261808A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014030711A1 (en) | 2012-08-24 | 2014-02-27 | 大日本印刷株式会社 | Photosensitive composition for volume hologram recording, photosensitive substrate for volume hologram recording, and volume hologram-recorded object |
| US9709952B2 (en) | 2012-08-24 | 2017-07-18 | Dai Nippon Printing Co., Ltd. | Photosensitive composition for volume hologram recording, photosensitive substrate for volume hologram recording, and volume hologram recorded medium |
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