JPWO2016072142A1 - 光硬化性樹脂組成物およびその硬化物、ならびに硬化物の製造方法 - Google Patents
光硬化性樹脂組成物およびその硬化物、ならびに硬化物の製造方法 Download PDFInfo
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- JPWO2016072142A1 JPWO2016072142A1 JP2016557480A JP2016557480A JPWO2016072142A1 JP WO2016072142 A1 JPWO2016072142 A1 JP WO2016072142A1 JP 2016557480 A JP2016557480 A JP 2016557480A JP 2016557480 A JP2016557480 A JP 2016557480A JP WO2016072142 A1 JPWO2016072142 A1 JP WO2016072142A1
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- photocurable resin
- acrylate
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- 239000011521 glass Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 125000006203 morpholinoethyl group Chemical group [H]C([H])(*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 description 1
- ZIOFXYGGAJKWHX-UHFFFAOYSA-N n,2,4-trimethylaniline Chemical compound CNC1=CC=C(C)C=C1C ZIOFXYGGAJKWHX-UHFFFAOYSA-N 0.000 description 1
- GUAWMXYQZKVRCW-UHFFFAOYSA-N n,2-dimethylaniline Chemical compound CNC1=CC=CC=C1C GUAWMXYQZKVRCW-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000001367 organochlorosilanes Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- FILUFGAZMJGNEN-UHFFFAOYSA-N pent-1-en-3-yne Chemical group CC#CC=C FILUFGAZMJGNEN-UHFFFAOYSA-N 0.000 description 1
- LGOPTUPXVVNJFH-UHFFFAOYSA-N pentadecanethioic s-acid Chemical compound CCCCCCCCCCCCCCC(O)=S LGOPTUPXVVNJFH-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- LVEOKSIILWWVEO-UHFFFAOYSA-N tetradecyl 3-(3-oxo-3-tetradecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCC LVEOKSIILWWVEO-UHFFFAOYSA-N 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 150000003712 vitamin E derivatives Chemical class 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
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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1811—C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (meth)acrylate
-
- 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
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- 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
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- 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
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- 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
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/12—Esters of monohydric alcohols or phenols
- C08F20/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F20/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
-
- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/067—Polyurethanes; Polyureas
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/18—Amines; Quaternary ammonium compounds with aromatically bound amino groups
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- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
- C08F220/343—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate in the form of urethane links
- C08F220/346—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate in the form of urethane links and further oxygen
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- Chemical & Material Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polymerisation Methods In General (AREA)
- Paints Or Removers (AREA)
- Sealing Material Composition (AREA)
Abstract
Description
(A)成分:ロイコ染料、
(B)成分:光酸発生剤、
(C)成分:ラジカル重合性化合物、
(D)成分:熱分解温度が200℃以上であるα−ヒドロキシアセトフェノン系ラジカル開始剤。
(A)成分:ロイコ染料、
(B)成分:光酸発生剤、
(C)成分:ラジカル重合性化合物、
(D)成分:熱分解温度が200℃以上であるα−ヒドロキシアセトフェノン系ラジカル開始剤。
本発明の(A)成分であるロイコ染料とは、酸との接触により発色する化合物であり、硬化物に隠蔽性を与える成分である。また、ロイコ染料は、種類によって黒色、青色、緑色、赤色などの発色させることができるが、隠蔽性が優れるという観点から、黒色の発色が得られるロイコ染料が好ましい。
本発明の(B)成分である光酸発生剤とは、活性エネルギー線の照射によりルイス酸やブレンステッド酸などの酸を発生する化合物である。また、(B)成分により発生した酸によりロイコ染料を発色させることが可能となる。また、隠蔽性および光硬化性を両立できるという観点で、365nm以上の波長領域に吸収を持つ光酸発生剤であることが好ましい。また、(B)成分としては、オニウム塩系光酸発生剤、非イオン性光酸発生剤に大別される。これらの中でもオニウム塩系光酸発生剤を用いることが好ましい。
本発明の(C)成分であるラジカル重合性化合物とは、接着剤及び塗料等に通常使用されているエチレン性不飽和基を有する化合物を使用することができ、具体的には(メタ)アクリロイル基含有化合物等が挙げられる。前記(C)成分としては、例えば、単官能性、二官能性、三官能性および多官能性の(メタ)アクリロイル基含有モノマー、(メタ)アクリロイル基含有オリゴマー等を使用することができる。これらは単独で若しくは二種以上の混合物として用いることができる。
本発明に用いられる(D)成分は、熱分解温度が200℃以上であるα−ヒドロキシアセトフェノン系ラジカル開始剤である。(D)成分は、熱分解温度が200℃以上であるα−ヒドロキシアセトフェノン系ラジカル開始剤であれば、特に限定されるものではない。多数ある光ラジカル開始剤の中でも、(D)成分を選択し、本発明に係るその他必須成分と組み合わせることにより、紫外線による黒色硬化物の退色を抑制するという顕著な効果が得られる。なお、本発明において熱分解温度とは、TGA法で10℃/分の昇温速度で、窒素雰囲気下で5%重量減少する温度を意味する。前記(D)成分は、光硬化性の観点から、熱分解温度が350℃以下であることが好ましい。紫外線による黒色硬化物の退色抑止効果および光硬化性の観点から、熱分解温度が200〜300℃であることが好ましく、200〜250℃であることがより好ましい。
各成分を表1に示す質量部で採取し、常温にてプラネタリーミキサーで60分混合し、光硬化性樹脂組成物を調整し、各種物性に関して次のようにして測定した。尚詳細な調整量は表1に従い、数値は全て質量部で表記した。
a1:3−ジブチルアミノ−6−メチル−7−アニリノフルオラン(ODB−2、山本化成株式会社製)
a2:3−ジエチルアミノ−6−メチル−7−アニリノフルオラン(ODB、山本化成株式会社製)
<(B)成分>
b1:トリアリ−ルスルホニウム−ヘキサフルオロホスフェート塩(CPI−100P、サンアプロ株式会社製)
<(C)成分>
c1:ウレタン(メタ)アクリレート(UV−3000B、日本合成化学工業株式会社製)
c2:イソボルニルアクリレート(ライトアクリレート(登録商標)IBX−A、共栄社化学株式会社製)
c3:アクリロイルモルホリン(ACMO(登録商標)、KJケミカルズ株式会社製)
<(D)成分>
d1:1−[4−(2−ヒドロキシエトキシ)−フェニル]−2−ヒドロキシ−2−メチル−1−プロパン−1−オン、熱分解温度が204℃(IRGACURE(登録商標) 2959、BASF社製)
ここで、熱分解温度とは、TGA法で10℃/分の昇温速度で、窒素雰囲気下で5%重量減少する温度であり、以下も同様である。
<(D)成分の比較成分>
d’1:2−ヒドロキシ−2−メチル−1−フェニル−プロパン−1−オン、熱分解温度が101℃(DAROCUR(登録商標) 1173、BASF社製)
d’2:1−ヒドロキシ−シクロヘキシル−フェニル−ケトン、熱分解温度が155℃(IRGACURE(登録商標) 184、BASF社製)
d’3:2,2−ジメトキシ−1,2−ジフェニルエタン−1−オン、熱分解温度が170℃(DAROCUR(登録商標) 651、BASF社製)
d’4:2−ベンジル−2−ジメチルアミノ−1−(4−モルフォリノフェニル)−ブタノン−1、熱分解温度が248℃(DAROCUR(登録商標) 369、BASF社製)
d’5:ベンゾフェノン(BASF社製)
表1の実施例、比較例において使用した試験方法は下記の通りである。
各硬化性樹脂組成物を深さ150μmの型に流し込み、厚みが150μmになるように表面が平滑な試験片を作成した。次いで、LED照射機(波長365nm)を用いて100mW/cm2×120秒の条件で紫外線照射し、硬化物を得た。その硬化物の外観を目視で確認し、その結果を表1にまとめた。
各硬化性樹脂組成物を用いて、硬化物の外観確認における試験片の作製と同様に、厚みが150μmになるように表面が平滑な試験片を作製した。次いで、LED照射機(波長365nm)を用いて100mW/cm2×120秒の条件で紫外線照射し硬化物を得た。直径3mmの黒点を記した紙の上に、得られた硬化物を置き、黒点を目視で確認し、下記の基準に基づき評価した。
○:黒点の輪郭が不明瞭であり、隠蔽性が確認できた場合
×:黒点の輪郭がはっきりと、確認された場合。
各硬化性樹脂組成物を用いて、硬化物の外観確認における試験片の作製と同様に、厚みが150μmになるように表面が平滑な試験片を作製した。次いで、120kJ/m2(100mW/cm2×120秒)の紫外線を照射し、硬化物を得た。
〇:「照射前の硬化物」と「照射後の硬化物」とを比較して、退色は確認されなかった場合
×:「照射前の硬化物」と「照射後の硬化物」とを比較して、明らかに退色が確認された場合。
実施例1、2および4ならびに比較例1の各硬化性樹脂組成物を用いて、硬化物の外観確認における試験片の作製と同様に、厚みが150μmになるよう表面が平滑な試験片を作製した。次いで、120kJ/m2(100mW/cm2×120秒)の紫外線を照射し、硬化物を得た。次に、紫外線による硬化物の退色を確認するため、その硬化物に対して、1800kJ/m2(100mW/cm2×1800秒)の紫外線を照射した。この照射後の硬化物の透過率を分光光度計UV−2450(株式会社島津製作所製)にて測定した。
Claims (8)
- 下記の(A)〜(D)成分を含有する光硬化性樹脂組成物;
(A)成分:ロイコ染料、
(B)成分:光酸発生剤、
(C)成分:ラジカル重合性化合物、
(D)成分:熱分解温度が200℃以上であるα−ヒドロキシアセトフェノン系ラジカル開始剤。 - 前記(C)成分100質量部に対して、前記(D)成分が0.01〜15質量部を含有することを特徴とする、請求項1に記載の光硬化性樹脂組成物。
- 前記(D)成分が、1−[4−(2−ヒドロキシエトキシ)−フェニル]−2−ヒドロキシ−2−メチル−1−プロパン−1−オンまたは2−ヒドロキシ−1−{4−[4−(2−ヒドロキシ−2−メチル−プロピオニル)−ベンジル]フェニル}−2−メチル−プロパン−1−オンであることを特徴とする、請求項1または2に記載の光硬化性樹脂組成物。
- 前記(C)成分が、(メタ)アクリロイル基含有オリゴマーと(メタ)アクリロイル基含有モノマーとを含むことを特徴とする、請求項1〜3のいずれか1項に記載の光硬化性樹脂組成物。
- 硬化物が黒色であることを特徴とする、請求項1〜4のいずれか1項に記載の光硬化性樹脂組成物。
- 被覆材、注型用樹脂、シール剤、ポッティング剤、接着剤またはコーティング材用途であることを特徴とする、請求項1〜5のいずれか1項に記載の光硬化性樹脂組成物。
- 請求項1〜6のいずれか1項に記載の光硬化性樹脂組成物の硬化物。
- 光硬化性樹脂組成物に光を照射して硬化する硬化工程を含む、請求項7に記載の硬化物の製造方法。
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US11339241B2 (en) | 2016-12-15 | 2022-05-24 | Clariant International Ltd. | Water-soluble and/or water-swellable hybrid polymer |
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CN107935720A (zh) * | 2017-12-13 | 2018-04-20 | 烟台燕晟信息技术有限公司 | 一种互穿网络包膜染色肥料的制备方法 |
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