JPS6375035A - Photo-curing composition - Google Patents

Photo-curing composition

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Publication number
JPS6375035A
JPS6375035A JP61219226A JP21922686A JPS6375035A JP S6375035 A JPS6375035 A JP S6375035A JP 61219226 A JP61219226 A JP 61219226A JP 21922686 A JP21922686 A JP 21922686A JP S6375035 A JPS6375035 A JP S6375035A
Authority
JP
Japan
Prior art keywords
integer
substituted
atom
parts
polyene
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
Application number
JP61219226A
Other languages
Japanese (ja)
Inventor
Hideki Totani
英樹 戸谷
Eitaro Fukutaka
永太郎 福高
Hiroshi Ogi
扇 寛
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Denka Co Ltd
Original Assignee
Denki Kagaku Kogyo KK
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Denki Kagaku Kogyo KK filed Critical Denki Kagaku Kogyo KK
Priority to JP61219226A priority Critical patent/JPS6375035A/en
Publication of JPS6375035A publication Critical patent/JPS6375035A/en
Pending legal-status Critical Current

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  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)

Abstract

PURPOSE:To provide the titled composition containing a specific polyene, a polythiol and a specific amount of photopolymerization initiator and capable of giving a cured product having excellent weather resistance even under high temperature and humidity condition. CONSTITUTION:The objective composition contains (A) a polyene free from the ester bond expressed by formula I [m is 2-6; R1-R3 are (substituted) alkyl, H, F, Cl, Br, (substituted) aryl or (substituted) alkoxy; Y is -(CH2)n- (n is 0-10), -(OCH2)p- (p is 1-10) or -O-(CH2)q- (q is 1-10); X and Y are atomic groups having m functional groups and may be bonded with each other] (e.g. divinylbenzene), (B) a polythiol of formula II or III (t, w and x are 1-5; A is O or S; R' is polyvalent organic residue; y is 1-2) (e.g. diglycol dimercaptan) and (C) 0.05-5pts.wt. of a photo-polymerization initiator (e.g. benzophenone) based on 100pts.wt. of A+B.

Description

【発明の詳細な説明】 (産業上の利用分野) 本発明は、ポリエンとポリチオールとを含有して放る光
硬化可能な組成物に関する。
DETAILED DESCRIPTION OF THE INVENTION Field of the Invention The present invention relates to a photocurable composition containing and releasing a polyene and a polythiol.

(従来の技術) Iリエンとプリチオールが活性光線の照射により重合体
を形収することはよく知られており(C,S、 Mar
rel et、 al、、 J、 Am、 Chem、
 Soc、 、 70゜993 (1948)〕、ポポ
リンの炭素−炭素不飽和二重結合とポリチオールのメル
カプト基の化学当量全霊えたり、ポリエンとポリチオー
ルの官能基数を変えることによって、エラストマー状か
ら樹脂状まで種々の硬化物が得られる。さらに活性光線
量や光開始剤の量を変えることにより、硬化時間を制御
することも可能である。
(Prior art) It is well known that I-liene and prethiol form polymers by irradiation with actinic rays (C, S, Mar
rel et, al,, J, Am, Chem,
Soc, 70°993 (1948)], by changing the chemical equivalent of the carbon-carbon unsaturated double bond of poporin and the mercapto group of polythiol, and by changing the number of functional groups of polyene and polythiol, it is possible to change from elastomer-like to resin-like. Various cured products can be obtained. Furthermore, it is also possible to control the curing time by changing the amount of actinic light and the amount of photoinitiator.

(発明が解決しようとする問題点) 高分子材料は種々の自然環境下で使用さnるため、その
耐候性が重要となる。劣化の原因としては熱、光、水分
、微生物、汚染大気などが拳げられるが、なかでも自動
酸化反応で劣化が進む熱劣化及び光劣化と並んで問題と
なるのが、水分による劣化である。
(Problems to be Solved by the Invention) Since polymeric materials are used in various natural environments, their weather resistance is important. Causes of deterioration include heat, light, moisture, microorganisms, and contaminated air, but deterioration due to moisture is a problem along with thermal deterioration and photodeterioration, which progress deterioration due to autoxidation reactions. .

高分子構造中にエステル結合などの加水分解を受けやす
い官能基がろると、多湿下で高分子は除々に加水分解を
受け、化学構造の変化及び物性の低下を起こし劣化する
。上記のポリエン−4リチオールの重合体においても特
公昭47−3269号公報に挙げられているフタル酸ジ
アリル、三β−メルカプトプロピオン酸トリメチロール
プロパンのようなエステル結合を含むポリエン−ポリチ
オールを用いると、多湿下において、軟化や強度の低下
という現象が生起してしまう場合がある。
When a functional group susceptible to hydrolysis, such as an ester bond, is lost in a polymer structure, the polymer gradually undergoes hydrolysis under high humidity, causing a change in the chemical structure and a decrease in physical properties, leading to deterioration. In the above polyene-4 lithiol polymer, when a polyene-polythiol containing an ester bond is used, such as diallyl phthalate and trimethylolpropane tri-β-mercaptopropionate, which are listed in Japanese Patent Publication No. 47-3269, Under high humidity conditions, phenomena such as softening and decrease in strength may occur.

(問題を解決するための手段) 以上の事実を基に、エステル結合をもたないポリエン及
びポリチオールを用いることにょυ、高温多湿下におい
ても加水分解して軟化しない重合物即ち硬化物を与える
光硬化性組成物を発明した。
(Means for solving the problem) Based on the above facts, by using polyenes and polythiols that do not have ester bonds, it is possible to produce a polymer product that does not hydrolyze and soften even under high temperature and high humidity, that is, a cured product. Invented a curable composition.

すなわち本発明の光硬化性組成物は、下記の(t)、(
2)及び(3)の各成分を含有して成り、(1)の成分
と(2)の成分の合計1100重量部に対して、(3)
の成分’kO,05〜5重ts含有することを特徴とす
るものである。
That is, the photocurable composition of the present invention has the following (t), (
It contains each component of (2) and (3), and for a total of 1100 parts by weight of components (1) and (2), (3)
It is characterized by containing the component 'kO, 05 to 5 times ts.

キル基、置換アルキル基、水素原子、フッ素原子、塩素
原子、臭素原子、アリール基、置換アリール基、アルコ
キシ基又!I′iit換アルコキシ基であり、Yは+C
H,−q(nは0又は1〜10の整a) 、JOCHJ
 (pは1〜1゜の整数)又は−o4cn、)  (q
は1〜10の整数)であり、セしてXはYと結合可能で
ろって、m個の官能基全方する原子団である。〕(2)
一般式 %式% で示され、平均分子量が50〜15000の範囲にある
エステル結合をもたないポリチオール(但しtXw、x
は1〜5の整数であり、Aは酸素原子又は硫黄原子であ
り、R′は多価の有機残基であり、セしてyは1〜2の
整数である。) (3)光開始剤 さらに詳しくは、上記の(1)の取分であるポリエンと
しては、ジビニルベンゼン、ジビニルトルエン、トリア
リルシアヌレート、トリアリルイソシアヌレート、テト
ラアリロキシエタンなどが挙げられる。
Kyl group, substituted alkyl group, hydrogen atom, fluorine atom, chlorine atom, bromine atom, aryl group, substituted aryl group, alkoxy group! I'iit-substituted alkoxy group, Y is +C
H, -q (n is 0 or an integer from 1 to 10 a), JOCHJ
(p is an integer from 1 to 1°) or -o4cn, ) (q
is an integer from 1 to 10), and X is an atomic group capable of bonding with Y and having all m functional groups. ](2)
A polythiol having no ester bond and having an average molecular weight in the range of 50 to 15,000 (however, tXw, x
is an integer of 1 to 5, A is an oxygen atom or a sulfur atom, R' is a polyvalent organic residue, and y is an integer of 1 to 2. (3) Photoinitiator More specifically, examples of the polyenes mentioned in (1) above include divinylbenzene, divinyltoluene, triallyl cyanurate, triallyl isocyanurate, and tetraallyloxyethane.

ま九、(2)の成分であるポリチオールとしては、ジグ
リコールジメルカプタン、トリグリコールゾメルカブタ
ン、テトラグリコールジメルカプタン、チオジグリコー
ルゾメルヵブタン、テトラグリコールジメルカプタン、
チオテトラグリコールジメルカプタン及びダイヤモンド
ジャムロック社よりDION3−800LCの商品名で
市販されているポリチオールなどが挙げられるが、これ
らの多価チオールに限定されるものではない。特に好ま
しいものは、25℃における粘度が10〜10.0OO
CpSのものである。
Nine, the polythiol that is the component (2) includes diglycol dimercaptan, triglycol somercaptan, tetraglycol dimercaptan, thiodiglycol somercaptan, tetraglycol dimercaptan,
Examples include thiotetraglycol dimercaptan and polythiol commercially available from Diamond Jamrock Co. under the trade name DION3-800LC, but are not limited to these polyvalent thiols. Particularly preferable ones have a viscosity of 10 to 10.0OO at 25°C.
It is from CpS.

(3)の取分である光開始剤としては、ベンゾフェノン
、p−メトキシベンゾフェノン、4.4−ビスジメチル
アミノベンゾフェノン、キサントン、チオキサントン、
クロロチオキサントン、m−クロルアセトン、プロピオ
フェノン、アンスラΦノン、ベンゾインメチルエーテル
、ベンゾインエチルエーテル、ベンゾインイソプロピル
エーテル、ベンゾインブチルエーテル、ベンジル、ベン
ジルジメチルケタール、アセトフェノン、2.2−ジェ
トキシアセトフェノン、2−ヒドロキシ2.2−1’メ
チルアセトフエノンなどが挙げられるが、これらに限定
されるものではない。
(3) Photoinitiators include benzophenone, p-methoxybenzophenone, 4,4-bisdimethylaminobenzophenone, xanthone, thioxanthone,
Chlorothioxanthone, m-chloroacetone, propiophenone, anthranonone, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin butyl ether, benzyl, benzyl dimethyl ketal, acetophenone, 2.2-jethoxyacetophenone, 2-hydroxy Examples include, but are not limited to, 2.2-1' methylacetophenone.

本発明の組成物の各成分の好ましい割合は、ポリエン2
5〜75重量部、Iリテオール25〜75重量部、ポリ
エンとポリチオールの合計量100重量部に対して、光
開始剤0.05〜5重量部である。
The preferred ratio of each component of the composition of the present invention is polyene 2
5 to 75 parts by weight, 25 to 75 parts by weight of I-Liteol, and 0.05 to 5 parts by weight of photoinitiator per 100 parts by weight of the total amount of polyene and polythiol.

本発明の組成物は前記(1)、(2)及び(3)の取分
を必須成分として含み、必要に応じてこれに酸化防止剤
、キレート化剤、硬化促進剤、染料、顔料、充填剤、チ
クソトロピー賦与剤、帯電防止剤、可塑剤、界面活性剤
、シランカップリング剤、粘度調節剤、粘着剤などの添
加剤を加えることができる。
The composition of the present invention contains the above (1), (2), and (3) as essential components, and optionally includes antioxidants, chelating agents, hardening accelerators, dyes, pigments, and fillers. Additives such as a thixotropy agent, an antistatic agent, a plasticizer, a surfactant, a silane coupling agent, a viscosity modifier, and an adhesive can be added.

本発明の組成物は、活性光線、例えば紫外線の照射によ
って容易に硬化される。硬化物は高温多湿下でも安定で
あシ、この条件下で長期間放置しても軟化することがな
い。
The composition of the present invention is easily cured by irradiation with actinic light, such as ultraviolet light. The cured product is stable even under high temperature and high humidity conditions, and will not soften even if left for a long time under these conditions.

(実施例) 以下に本発明の実施例を示す。部は全て重量によって表
わす。
(Example) Examples of the present invention are shown below. All parts are expressed by weight.

実施例1 (1)トリアリルイソシアヌード   55部(2)ジ
グリコールジメルカプタン  45部(3)ベンジルジ
メチルケタール   0.5部上記化合物金均−に混合
後、25φX5(m)のポリエチレン製カップ内に充填
し、400Wの紫外線ラング下30!の距離で30分間
照射した。得られた硬化物を温度70℃、湿度80%の
条件下に40日間放置し、硬化直後の硬度と比較した。
Example 1 (1) Triallylisocyanide 55 parts (2) Diglycol dimercaptan 45 parts (3) Benzyl dimethyl ketal 0.5 part After mixing the above compounds evenly, the mixture was placed in a 25φ x 5 (m) polyethylene cup. Filled with 400W ultraviolet rays for 30 minutes! It was irradiated for 30 minutes at a distance of The obtained cured product was left for 40 days at a temperature of 70° C. and a humidity of 80%, and the hardness was compared with the hardness immediately after curing.

結果を表1に示す。The results are shown in Table 1.

実施例2 (1)トリアリルイソシアヌード     47部(2
)トリグリコールジメルカプタン  53部(3)ベン
ジルジメチルケタール    0.5部上記化会物を均
一に混合後、実施例1と同様の操作を行い、硬化の変化
を測定し友。結果を表1に示す。
Example 2 (1) Triallylisocyanudo 47 parts (2
) Triglycol dimercaptan 53 parts (3) Benzyl dimethyl ketal 0.5 part After uniformly mixing the above compounds, the same operation as in Example 1 was performed and the change in curing was measured. The results are shown in Table 1.

比較例1 (1)トリアリルイソシアヌレート     41部(
2)トリメチロールプロパントリス→チオグリコレート
)59部(3)ベンジルジメチルケタール      
0.5部上記化合物金均−に混合後、冥施例1と同様の
操作を行い、硬度の変化を測定し之。結果を表1に示す
Comparative Example 1 (1) 41 parts of triallyl isocyanurate (
2) Trimethylolpropane tris → thioglycolate) 59 parts (3) Benzyl dimethyl ketal
After mixing 0.5 parts of the above compound with gold, the same operation as in Example 1 was carried out, and the change in hardness was measured. The results are shown in Table 1.

表1 硬化物の硬度変化 実施例3 実施例2の混せ物(試料A)を用い、これを平型に流し
込み、400Wの紫外線ランプ下30cWLの距離で3
0分間照射してシートを作成した。このシートを用いて
JIS規格に7113の2弓形ダンベル試料を作成した
。得られた硬化物(ダンベル試料)を温度70℃、湿度
80%の条件下に20日間放置し次後、引張り試験を行
い、強度保持率〔(放置後の強度/硬化直後の強度)X
100(%)〕を求めた。また、比較サンプルとして(
1)トリアリルイソシアヌレ−)32m、(2))リス
−2−とドロキシエチルイソシアヌレート−トリス−β
−メルカデトデロビオネート68部及び(3)ベンジル
ジメチルケタール0.5部から取るダンベル(試料B)
を作成し、試験に供し念。結果を表2に示す。
Table 1 Change in hardness of cured product Example 3 Using the mixture of Example 2 (sample A), pour it into a flat mold and place it under a 400W ultraviolet lamp at a distance of 30cWL for 30 minutes.
A sheet was created by irradiating for 0 minutes. Using this sheet, a JIS standard 7113 two-bow dumbbell sample was prepared. The obtained cured product (dumbbell sample) was left for 20 days at a temperature of 70°C and a humidity of 80%, and then a tensile test was conducted to determine the strength retention rate [(strength after standing/strength immediately after curing)
100 (%)] was calculated. Also, as a comparison sample (
1) triallylisocyanurate) 32m, (2)) lis-2- and droxyethyl isocyanurate-tris-β
- Dumbbell (sample B) taken from 68 parts of mercadetodelobionate and (3) 0.5 parts of benzyl dimethyl ketal
I created it and submitted it for testing. The results are shown in Table 2.

表2 硬化物の引張り強度 (発明の効果) 以上の様に、本発明の光硬化性組成物よシ得られる硬化
物は、高温多湿下においても優れた耐候性を示し、この
ような条件下での使用も可能である。
Table 2 Tensile strength of cured product (effects of the invention) As described above, the cured product obtained from the photocurable composition of the present invention exhibits excellent weather resistance even under high temperature and high humidity conditions. It can also be used in

特許出願人  電気化学工業株式会社 手続補正書 昭和62年8月19日Patent applicant: Denki Kagaku Kogyo Co., Ltd. Procedural amendment August 19, 1986

Claims (1)

【特許請求の範囲】 下記の(1)、(2)及び(3)の各成分を含有して成
り、(1)と(2)の成分の合計量100重量部に対し
(3)の成分を0.05〜5重量部含有することを特徴
とする光硬化性組成物。 (1)一般式 ▲数式、化学式、表等があります▼ で示されるエステル結合をもたないポリエン〔但し、m
は2〜6の整数であり、R_1、R_2及びR_3はア
ルキル基、置換アルキル基、水素原子、フッ素原子、塩
素原子、臭素原子、アリール基、置換アリール基、アル
コキシ基又は置換アルコキシ基であり、Yは−(CH_
2)−_n(nは0又は1〜10の整数)、−(OCH
_2)−_p(Pは1〜10の整数)又は−O−(CH
_2)−_q(qは1〜10の整数)であり、そしてX
はYと結合可能であって、m個の官能基を有する原子団
である。〕 (2)一般式 HS−(C_tH_2_t−A)−_wC_xH_2_
x−SH 又は ▲数式、化学式、表等があります▼ で示され、平均分子量が50〜15000の範囲にある
エステル結合をもたないポリチオール(但し、t、w、
xは1〜5の整数であり、Aは酸素原子又は硫黄原子で
あり、R′は多価の有機残基であり、そしてyは1〜2
の整数である。) (3)光開始剤
[Scope of Claims] Contains each of the following components (1), (2), and (3), where component (3) is contained per 100 parts by weight of the total amount of components (1) and (2). A photocurable composition containing 0.05 to 5 parts by weight of. (1) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ Polyene that does not have an ester bond [However, m
is an integer from 2 to 6, R_1, R_2 and R_3 are an alkyl group, a substituted alkyl group, a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an aryl group, a substituted aryl group, an alkoxy group or a substituted alkoxy group, Y is -(CH_
2) -_n (n is 0 or an integer from 1 to 10), -(OCH
_2) -_p (P is an integer of 1 to 10) or -O-(CH
_2)-_q (q is an integer from 1 to 10), and
is an atomic group capable of bonding with Y and having m functional groups. ] (2) General formula HS-(C_tH_2_t-A)-_wC_xH_2_
x-SH or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, and the average molecular weight is in the range of 50 to 15,000.
x is an integer from 1 to 5, A is an oxygen atom or a sulfur atom, R' is a polyvalent organic residue, and y is an integer from 1 to 2.
is an integer. ) (3) Photoinitiator
JP61219226A 1986-09-19 1986-09-19 Photo-curing composition Pending JPS6375035A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP61219226A JPS6375035A (en) 1986-09-19 1986-09-19 Photo-curing composition

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP61219226A JPS6375035A (en) 1986-09-19 1986-09-19 Photo-curing composition

Publications (1)

Publication Number Publication Date
JPS6375035A true JPS6375035A (en) 1988-04-05

Family

ID=16732176

Family Applications (1)

Application Number Title Priority Date Filing Date
JP61219226A Pending JPS6375035A (en) 1986-09-19 1986-09-19 Photo-curing composition

Country Status (1)

Country Link
JP (1) JPS6375035A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998038146A2 (en) * 1997-02-14 1998-09-03 Sola International Holdings Ltd. Cross-linkable polymeric composition
WO1998058294A1 (en) * 1997-06-19 1998-12-23 Macdermid Acumen, Inc. Photocurable composition based on acid functional, primary resinous mercaptans
WO1998058295A1 (en) * 1997-06-19 1998-12-23 Macdermid Acumen, Inc. A PHOTORESIST DEVELOPABLE IN AQUEOUS BASE MADE FROM AN ACID FUNCTIONAL β-HYDROXY THIOL RESIN AND AN UNSATURATED RESIN
US6479622B1 (en) 1999-05-10 2002-11-12 3M Innovative Properties Company Compositions for making ene-thiol elastomers

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS54142299A (en) * 1978-04-28 1979-11-06 Denki Kagaku Kogyo Kk Photo-setting composition
JPS5665025A (en) * 1979-11-02 1981-06-02 Asahi Denka Kogyo Kk Curable resin composition
JPS5665023A (en) * 1979-10-31 1981-06-02 Asahi Denka Kogyo Kk Curable resin composition
JPS5760382A (en) * 1980-09-29 1982-04-12 Canon Kk Character processor
JPS6198734A (en) * 1984-10-19 1986-05-17 Showa Denko Kk Curable composition

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS54142299A (en) * 1978-04-28 1979-11-06 Denki Kagaku Kogyo Kk Photo-setting composition
JPS5665023A (en) * 1979-10-31 1981-06-02 Asahi Denka Kogyo Kk Curable resin composition
JPS5665025A (en) * 1979-11-02 1981-06-02 Asahi Denka Kogyo Kk Curable resin composition
JPS5760382A (en) * 1980-09-29 1982-04-12 Canon Kk Character processor
JPS6198734A (en) * 1984-10-19 1986-05-17 Showa Denko Kk Curable composition

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998038146A2 (en) * 1997-02-14 1998-09-03 Sola International Holdings Ltd. Cross-linkable polymeric composition
WO1998038146A3 (en) * 1997-02-14 2000-04-06 Sola Int Holdings Cross-linkable polymeric composition
US6391983B1 (en) 1997-02-14 2002-05-21 Sola International Holdings, Ltd. Casting composition of aromatic polyvinyl monomer, polythiol and epoxy strain reducer
WO1998058294A1 (en) * 1997-06-19 1998-12-23 Macdermid Acumen, Inc. Photocurable composition based on acid functional, primary resinous mercaptans
WO1998058295A1 (en) * 1997-06-19 1998-12-23 Macdermid Acumen, Inc. A PHOTORESIST DEVELOPABLE IN AQUEOUS BASE MADE FROM AN ACID FUNCTIONAL β-HYDROXY THIOL RESIN AND AN UNSATURATED RESIN
US6479622B1 (en) 1999-05-10 2002-11-12 3M Innovative Properties Company Compositions for making ene-thiol elastomers
JP2002544306A (en) * 1999-05-10 2002-12-24 スリーエム イノベイティブ プロパティズ カンパニー Compositions for making en-thiol elastomers
US6605687B1 (en) 1999-05-10 2003-08-12 3M Innovative Properties Company Compositions for making ene-thiol elastomers
US6605689B1 (en) 1999-05-10 2003-08-12 3M Innovative Properties Company Compositions for making ene-thiol elastomers
US6605690B1 (en) 1999-05-10 2003-08-12 3M Innovative Properties Company Compositions for making ene-thiol elastomers
US6605691B1 (en) 1999-05-10 2003-08-12 3M Innovative Properties Company Compositions for making ene-thiol elastomers
US6605692B1 (en) 1999-05-10 2003-08-12 3M Innovative Properties Company Compositions for making ene-thiol elastomers

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