JP2007002144A - 紫外線硬化型樹脂組成物並びにその硬化物 - Google Patents
紫外線硬化型樹脂組成物並びにその硬化物 Download PDFInfo
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- JP2007002144A JP2007002144A JP2005185864A JP2005185864A JP2007002144A JP 2007002144 A JP2007002144 A JP 2007002144A JP 2005185864 A JP2005185864 A JP 2005185864A JP 2005185864 A JP2005185864 A JP 2005185864A JP 2007002144 A JP2007002144 A JP 2007002144A
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- resin composition
- curable resin
- ultraviolet curable
- acrylate
- meth
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 48
- 230000003287 optical effect Effects 0.000 claims abstract description 28
- -1 acrylate compound Chemical class 0.000 claims abstract description 26
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- 239000003795 chemical substances by application Substances 0.000 claims abstract description 12
- 238000010521 absorption reaction Methods 0.000 claims abstract description 11
- 239000011253 protective coating Substances 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 15
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 claims description 8
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 4
- 238000005259 measurement Methods 0.000 claims description 3
- 239000003999 initiator Substances 0.000 abstract description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 44
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- 238000003756 stirring Methods 0.000 description 1
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- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Optical Record Carriers And Manufacture Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
Description
(1)下記一般式(1)
で表わされる(メタ)アクリレート化合物(A)、及び光重合開始剤(B)を含有する紫外線硬化型樹脂組成物、
(2)さらに化合物(A)以外のエチレン性不飽和化合物(C)を含有する(1)に記載の紫外線硬化型樹脂組成物、
(3)B型粘度計で測定した25℃の粘度が100〜5000mPa・Sであることを特徴とする(1)又は(2)に記載の紫外線硬化型樹脂組成物、
(4)エチレン性不飽和化合物(C)が分子量400〜10000のウレタンアクリレート及び/又は分子量500〜10000のエポキシアクリレートである(2)乃至(3)のいずれか一項に記載の紫外線硬化型樹脂組成物、
(5)光ディスク用保護コート剤である、(1)乃至(4)に記載の紫外線硬化型樹脂組成物、
(6)(1)乃至(5)のいずれか一項に記載の紫外線硬化型樹脂組成物を硬化して得られる硬化物、
(7)硬化物の吸水率(測定温度25℃)が2.0%以下で、硬化収縮率が6%以下である(6)に記載の紫外線硬化型樹脂組成物の硬化物、
(8)(6)乃至(7)のいずれか一項に記載の紫外線硬化型樹脂組成物の硬化物層を有する光ディスク、
(9)記録光及び/又は再生光が入射する側に当該紫外線硬化型樹脂組成物の硬化物層が構成されている(8)に記載の光ディスク、
に関する。
還流冷却器、攪拌機、温度計、温度調節装置、及び水分離機を備えた反応器に、1−アダマンタンメタノール166.3g(1.0mol)、アクリル酸86.5g(1.2mol)、パラトルエンスルホン酸1.73g、ハイドロキノン0.66g、トルエン88.5g、シクロヘキサン37.9g仕込み、反応温度95〜105℃で生成水を溶媒と共沸留去しながら反応させ、生成水が18.0ml(1.0mol)に達したところで反応の終点とした。反応混合物にトルエン324.5g及びシクロヘキサン139.0gを加え、25重量%苛性ソーダ水溶液で中和した後、15重量%食塩水50gで3回洗浄した。溶媒を減圧留去して淡黄色液状の下記構造式(A−1)を216.2g(収率98.1%)得ることができた。
比 重(25℃) 1.056
粘 度(25℃) 20 mPa・s
屈折率(25℃) 1.501
1H−NMR
1.57−1.80ppm=12H、2.00ppm=3H、3.77ppm=2H、5.83ppm=1H、6.15ppm=1H、6.42ppm=1H
実施例1で得られた生成物に、光開始剤として1−ヒドロキシシクロヘキシルフェニルケトンを0.5重量%加え、ガラス基板上にバーコーターを用いて均一に塗布した後、ベルトコンベア型紫外線照射装置を用いて紫外線を照射し、透明な乾燥した膜状コーティングを得た。この膜状コーティングは下記の性質を有する。
比 重(25℃) 1.127
硬化収縮率(25℃) 6.2%
鉛筆硬度 1H
実施例1で得られた化合物を使用して、以下の実施例3〜5及び比較例1〜2を行った。表1中の部は、重量部である。表1に示した組成からなる紫外線硬化型樹脂組成物を常法により調製した。
実施例3 実施例4 実施例5 比較例1 比較例2
成分(A) (部)
A−1 100 60 70
成分(B) (部)
イルガキュアー184 5 5 5 5
BP−100 5
EPA 3
成分(C) (部)
UX−6101 10 20 20 50
R−604 30 80
PEG−400DA 50
LA 10
粘度 2045 3500 2300 1700 2000
(mPa・S/25℃)
収縮率(%) 4.8 5.3 5.0 7.1 6.7
吸水率(%) 0.3 0.5 0.5 1.0 3.1
透過率(%) 80 80 80 80 80
反り ○ ○ ○ × ×
耐久性 ○ ○ ○ ○ ×
UX−6101:ポリエステル系ウレタンアクリレート(分子量;2700±500)、日本化薬社製
R−604:ヒドロキシピバルアルデヒド変性トリメチロールプロパンジ(メタ)アクリレート、日本化薬社製
PEG−400DA:ポリエチレングリコールジアクリレート、日本化薬社製
LA:ラウリルアクリレート、日本油脂社製
イルガキュアー184:1−ヒドロキシシクロヘキシルフェニルケトン、チバ・スペシャルティーケミカル社製 光重合開始剤
BP−100:ベンゾフェノン、日本化薬社製
EPA:4−ジメチルアミノエチルベンゾエート、日本化薬社製
硬化収縮率=(膜比重−液比重)/膜比重×100 (1)
○・・・ほとんど反りが認められない。
△・・・試験片の片側を指で押さえると、反対側が持ち上がるが2mm以下である。
×・・・試験片の片側を指で押さえると、反対側が5mm以上持ち上がる。
○・・・接着直後から反射膜に変化が見られない。
△・・・反射膜に変色又は、ピンホールが少し見られる。
×・・・反射膜に変色又は、ピンホールが大きく見られる。
Claims (9)
- さらに化合物(A)以外のエチレン性不飽和化合物(C)を含有する請求項1に記載の紫外線硬化型樹脂組成物。
- B型粘度計で測定した25℃の粘度が100〜5000mPa・Sであることを特徴とする請求項1又は請求項2に記載の紫外線硬化型樹脂組成物。
- エチレン性不飽和化合物(C)が分子量400〜10000のウレタンアクリレート及び/又は分子量500〜10000のエポキシアクリレートである請求項2乃至請求項3のいずれか一項に記載の紫外線硬化型樹脂組成物。
- 光ディスク用保護コート剤である、請求項1乃至請求項4に記載の紫外線硬化型樹脂組成物。
- 請求項1乃至請求項5のいずれか一項に記載の紫外線硬化型樹脂組成物を硬化して得られる硬化物。
- 硬化物の吸水率(測定温度25℃)が2.0%以下で、硬化収縮率が6%以下である請求項6に記載の紫外線硬化型樹脂組成物の硬化物。
- 請求項6乃至請求項7のいずれか一項に記載の紫外線硬化型樹脂組成物の硬化物層を有する光ディスク。
- 記録光及び/又は再生光が入射する側に当該紫外線硬化型樹脂組成物の硬化物層が構成されている請求項8に記載の光ディスク。
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