JPS629545B2 - - Google Patents
Info
- Publication number
- JPS629545B2 JPS629545B2 JP2025078A JP2025078A JPS629545B2 JP S629545 B2 JPS629545 B2 JP S629545B2 JP 2025078 A JP2025078 A JP 2025078A JP 2025078 A JP2025078 A JP 2025078A JP S629545 B2 JPS629545 B2 JP S629545B2
- Authority
- JP
- Japan
- Prior art keywords
- optical glass
- polyene
- polythiol
- adhesives
- consisting essentially
- 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.)
- Expired
Links
- 239000005304 optical glass Substances 0.000 claims description 14
- 150000004291 polyenes Chemical class 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- 229920006295 polythiol Polymers 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000000853 adhesive Substances 0.000 description 11
- 230000001070 adhesive effect Effects 0.000 description 11
- 238000000034 method Methods 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 244000283070 Abies balsamea Species 0.000 description 2
- 235000007173 Abies balsamea Nutrition 0.000 description 2
- 239000004858 Canada balsam Substances 0.000 description 2
- 239000012790 adhesive layer Substances 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920001225 polyester resin Polymers 0.000 description 2
- 239000004645 polyester resin Substances 0.000 description 2
- 238000011179 visual inspection Methods 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- LPUUPYOHXHWKAR-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol 3,3,3-tris(sulfanyl)propanoic acid Chemical compound SC(CC(=O)O)(S)S.C(O)C(CC)(CO)CO LPUUPYOHXHWKAR-UHFFFAOYSA-N 0.000 description 1
- VSZSIEBALNXIFG-UHFFFAOYSA-N 2-hydroxyethyl 2,2-bis(sulfanyl)acetate Chemical compound OCCOC(=O)C(S)S VSZSIEBALNXIFG-UHFFFAOYSA-N 0.000 description 1
- 229920001651 Cyanoacrylate Polymers 0.000 description 1
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 description 1
- 239000004830 Super Glue Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 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 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- -1 diallyl diphenyl phthalate Chemical compound 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 230000013011 mating Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
Landscapes
- Joining Of Glass To Other Materials (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Laminated Bodies (AREA)
Description
本発明は光学ガラスの接着法に関する。特にポ
リエンおよびポリチオールより本質的に成る光硬
化性組成物を用いることを特徴とする光学ガラス
の接着法に関するものである。ここで言う“ポ
リ”とは二官能性以上の多官能性を示す。また本
発明は光学ガラス／光学ガラスの接着に限定され
るものではなく、光学ガラスと他の物質、例え
ば、金属、プラスチツク、木材などの接着にも応
用でき、更には光学用プラスチツクのような活性
光線透過性の物質の接着にも応用できる。
光学ガラス用の接着剤として求められる一般的
な条件を挙げれば、次の通りである。
(1) 無色透明で可視部にはとくに吸収・散乱がな
い。
(2) 螢光性をもたない。
(3) 屈折率が光学ガラスに近似している。
(4) 接着力が強く、経年変化がない。
(5) 熱、低温、振動、油および溶剤によつて影響
されない。
(6) 硬化時の接着層体積変化、あるいは化学反応
により被着体面を犯さない。
(7) 作業性がよい。
従来より、光学ガラスの接着剤としては、カナ
ダバルサム、エポキシ樹脂、ポリビニルブチラー
ル、ポリエステル樹脂、シアノアクレート系樹脂
などが用いられてきたが、それらには各々、作業
上、性能上に欠点があつた。
即ち、カナダバルサム、ポリビニルブチラール
などは熱可塑性接着剤である為、使用温度に制限
があり、また加熱にともなう接着層の収縮ヒズミ
を是正する為に、工程が長時間を要するなどの欠
点がある。エポキシ樹脂は一般にアミン系硬化剤
と計量混合して使用され、作業性がよくないなど
の欠点がある。ポリエステル樹脂は重合時の収縮
が大きいことと、高温多湿の条件では水分の影響
を受けて、周辺から剥離してくる。また、最近使
用され始めたシアノ・アクリレート系接着剤は広
い面積に適さないなどの欠点がある。
ポリエンおよびポリチオールの混合物が、光増
感剤の存在下あるいは非存在下において、紫外線
照射により重合硬化することは公知であるが
〓〓〓〓〓
〔Organic Reaction Vol.13.165−376（1963）〕、
積層光学ガラスの製造に応用された実例および公
知文献はない。
本発明者は種々の接着剤を検討した結果、特定
のポリエンとポリチオールより本質的に成る光硬
化性組成物を用い活性光線の照射により硬化接着
することにより、光学ガラスの接着における作業
性および物性が大幅に改善されることを見い出
し、本発明に至つた。すなわち、光学ガラスの接
着において、特定のポポリエンとポリチオールよ
り本質的に成る光硬化性組成物を用い、活性光線
の照射により硬化接着すると、前記の光学ガラス
用接着剤として要求される諸条件を満足するだけ
でなく、泡出し時の加熱および接着剤の混合の必
要がなく、更にセツテイングまでの時間が自由に
調整できるなど作業性においても大幅に改善され
る。また、通常の不飽和二重結合性物質を主体と
したラジカル重合方式の光硬化性接着剤は、空気
の存在下において硬化不良を起こしたり、はみ出
し部分の洗浄などが必要であつたが、特定のポリ
エンとポリチオールより本質的になる光硬化性接
着剤を用いることにより、これらの点も改善され
る。
本発明の積層光学ガラスの製造法で用いる光硬
化性組成物は、ポリエンとポリチオールより本質
的になるが、ポリエンとしてはアリル基を１分子
中に２個以上もつ化合物を用いる。このポリエン
の例としてはジアリルテレフタレート、ジアリル
ジフエニルフタレート及びトリアリルフオスフエ
ート等が挙げられる。ポリチオールは特に限定せ
ずに使用可能であるが、例えば上記ポリエンと反
応するトリメチロールプロパントリスメルカプト
プロピオネート、エチレングリコールジメルカプ
トアセテート、ジブチルメチレンビスチオグリコ
レート及びジペンタエリスリトールヘキサチオプ
ロピオネート等が好ましい。
以下に実施例を示すが、本発明はこれらによつ
て限定されるものではない。
実施例 １
第１表No.１に示した組成物を、直径５cmの合わ
せレンズ間に注加し、光軸合わせ後、400W紫外
線ランプを30cmの距離より５分間照射し、接着し
た。この合わせレンズは、外観検査、光軸試験、
耐熱・耐寒試験、振動試験にパスした。
実施例 ２
第１表No.２に示した組成物を用いて、実施例１
と同様に合わせレンズを製造した。この合わせレ
ンズは、外観検査、光軸試験、耐熱・耐寒試験に
パスした。
The present invention relates to a method for bonding optical glass. In particular, the present invention relates to a method for adhering optical glass, which is characterized by using a photocurable composition consisting essentially of polyene and polythiol. The term "poly" used herein indicates polyfunctionality greater than bifunctionality. Furthermore, the present invention is not limited to adhesion of optical glass/optical glass, but can also be applied to adhesion of optical glass and other substances such as metal, plastic, wood, etc. It can also be applied to adhesion of light-transparent substances. The general conditions required for adhesives for optical glass are as follows. (1) Colorless and transparent with no absorption or scattering in the visible region. (2) Not fluorescent. (3) The refractive index is similar to that of optical glass. (4) Strong adhesive strength and no deterioration over time. (5) Unaffected by heat, low temperature, vibration, oil and solvents. (6) No damage to the adherend surface due to changes in adhesive layer volume or chemical reactions during curing. (7) Good workability. Conventionally, Canada balsam, epoxy resin, polyvinyl butyral, polyester resin, cyanoacrylate resin, etc. have been used as adhesives for optical glass, but each of them has drawbacks in terms of workability and performance. Ta. In other words, Canada balsam, polyvinyl butyral, etc. are thermoplastic adhesives, so there are restrictions on the temperature at which they can be used, and they also have drawbacks such as requiring a long process to correct the shrinkage distortion of the adhesive layer due to heating. . Epoxy resins are generally mixed with amine hardeners and have disadvantages such as poor workability. Polyester resin has a large shrinkage during polymerization and is susceptible to moisture under high temperature and humidity conditions, causing it to peel off from the surrounding area. Additionally, cyanoacrylate adhesives that have recently come into use have drawbacks such as being unsuitable for large areas. It is known that mixtures of polyenes and polythiols are polymerized and cured by UV irradiation in the presence or absence of photosensitizers.
[Organic Reaction Vol.13.165−376 (1963)],
There are no examples or known documents that apply this method to the production of laminated optical glass. As a result of studying various adhesives, the present inventor discovered that the workability and physical properties of optical glass bonding could be improved by using a photocurable composition consisting essentially of a specific polyene and polythiol and curing the adhesive by irradiation with actinic rays. The inventors have discovered that this can be significantly improved, leading to the present invention. That is, when adhering optical glass, if a photocurable composition consisting essentially of a specific polyene and polythiol is used and the adhesive is cured by irradiation with actinic rays, it satisfies the conditions required for an adhesive for optical glass. In addition, there is no need for heating or mixing of adhesives during foaming, and the time until setting can be adjusted freely, greatly improving workability. In addition, conventional photocurable adhesives using a radical polymerization method based on unsaturated double-bond substances tend to fail to cure in the presence of air and require cleaning of protruding parts. These points are also improved by using a photocurable adhesive consisting essentially of polyene and polythiol. The photocurable composition used in the method for producing laminated optical glass of the present invention essentially consists of polyene and polythiol, and as the polyene, a compound having two or more allyl groups in one molecule is used. Examples of the polyene include diallyl terephthalate, diallyl diphenyl phthalate, triallylphosphate, and the like. Polythiols can be used without particular limitation, but examples include trimethylolpropane trismercaptopropionate, ethylene glycol dimercaptoacetate, dibutylmethylene bisthioglycolate, and dipentaerythritol hexathiopropionate, which react with the above polyenes. is preferred. Examples are shown below, but the present invention is not limited thereto. Example 1 The composition shown in Table 1 No. 1 was poured between mating lenses having a diameter of 5 cm, and after aligning the optical axes, a 400 W ultraviolet lamp was irradiated from a distance of 30 cm for 5 minutes to bond them together. This combination lens can be used for visual inspection, optical axis test,
It passed the heat resistance test, cold resistance test, and vibration test. Example 2 Using the composition shown in Table 1 No. 2, Example 1
A combined lens was manufactured in the same manner. This combined lens passed visual inspection, optical axis test, and heat and cold resistance tests.
【表】
〓〓〓〓〓
[Table] 〓〓〓〓〓
Claims (1)
上もつ化合物とポリチオールより本質的になる光
硬化性組成物を用い、活性光線の照射により硬化
接着することを特徴とする積層光学ガラスの製造
法。1. A method for producing laminated optical glass, which comprises using a photocurable composition consisting essentially of a compound having two or more allyl groups in one molecule as a polyene and polythiol, and curing and adhering the composition by irradiation with actinic light.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2025078A JPS54112918A (en) | 1978-02-23 | 1978-02-23 | Preparation of laminated optical glass |
| US06/008,105 US4272586A (en) | 1978-02-23 | 1979-01-31 | Laminated glass product |
| DE2907176A DE2907176C2 (en) | 1978-02-23 | 1979-02-23 | Laminated glass product |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2025078A JPS54112918A (en) | 1978-02-23 | 1978-02-23 | Preparation of laminated optical glass |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS54112918A JPS54112918A (en) | 1979-09-04 |
| JPS629545B2 true JPS629545B2 (en) | 1987-02-28 |
Family
ID=12021943
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2025078A Granted JPS54112918A (en) | 1978-02-23 | 1978-02-23 | Preparation of laminated optical glass |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS54112918A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63100045A (en) * | 1986-05-02 | 1988-05-02 | Mitsubishi Rayon Co Ltd | Adhesive for glass |
-
1978
- 1978-02-23 JP JP2025078A patent/JPS54112918A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS54112918A (en) | 1979-09-04 |
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