JP5070903B2 - 水溶性光開始剤、及びそれを用いた光重合/架橋性組成物 - Google Patents
水溶性光開始剤、及びそれを用いた光重合/架橋性組成物 Download PDFInfo
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- JP5070903B2 JP5070903B2 JP2007087237A JP2007087237A JP5070903B2 JP 5070903 B2 JP5070903 B2 JP 5070903B2 JP 2007087237 A JP2007087237 A JP 2007087237A JP 2007087237 A JP2007087237 A JP 2007087237A JP 5070903 B2 JP5070903 B2 JP 5070903B2
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- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 1
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- XUDUTRMKKYUAKI-UHFFFAOYSA-N 3-[1-(1-phenylethyl)piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound C1CC(N2C(NC3=CC=CC=C32)=O)CCN1C(C)C1=CC=CC=C1 XUDUTRMKKYUAKI-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
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- 231100000039 Ames test Toxicity 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
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- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
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- OFSAUHSCHWRZKM-UHFFFAOYSA-N Padimate A Chemical compound CC(C)CCOC(=O)C1=CC=C(N(C)C)C=C1 OFSAUHSCHWRZKM-UHFFFAOYSA-N 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920000562 Poly(ethylene adipate) Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
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- 239000002253 acid Substances 0.000 description 1
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- 150000003926 acrylamides Chemical class 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
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- 125000003158 alcohol group Chemical group 0.000 description 1
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- 125000000129 anionic group Chemical group 0.000 description 1
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- NJVHCUNZAMFQNA-UHFFFAOYSA-N azane;n-hydroxy-n-phenylnitrous amide Chemical compound N.O=NN(O)C1=CC=CC=C1 NJVHCUNZAMFQNA-UHFFFAOYSA-N 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
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- 230000031709 bromination Effects 0.000 description 1
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- PTIXVVCRANICNC-UHFFFAOYSA-N butane-1,1-diol;hexanedioic acid Chemical compound CCCC(O)O.OC(=O)CCCCC(O)=O PTIXVVCRANICNC-UHFFFAOYSA-N 0.000 description 1
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- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
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- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical group C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- 238000007269 dehydrobromination reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- FZWBABZIGXEXES-UHFFFAOYSA-N ethane-1,2-diol;hexanedioic acid Chemical compound OCCO.OC(=O)CCCCC(O)=O FZWBABZIGXEXES-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
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- 235000011187 glycerol Nutrition 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- QYZOHCUQJUKDLD-UHFFFAOYSA-N hexane-1,1-diol;phthalic acid Chemical compound CCCCCC(O)O.OC(=O)C1=CC=CC=C1C(O)=O QYZOHCUQJUKDLD-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 125000003010 ionic group Chemical group 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical group OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- BZCKRPHEZOHHBK-UHFFFAOYSA-N methyl 2-phenoxyacetate Chemical compound COC(=O)COC1=CC=CC=C1 BZCKRPHEZOHHBK-UHFFFAOYSA-N 0.000 description 1
- 229940086559 methyl benzoin Drugs 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- FVXBCDWMKCEPCL-UHFFFAOYSA-N nonane-1,1-diol Chemical compound CCCCCCCCC(O)O FVXBCDWMKCEPCL-UHFFFAOYSA-N 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- QUANRIQJNFHVEU-UHFFFAOYSA-N oxirane;propane-1,2,3-triol Chemical compound C1CO1.OCC(O)CO QUANRIQJNFHVEU-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 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
- FJWSMXKFXFFEPV-UHFFFAOYSA-N prop-2-enamide;hydrochloride Chemical class Cl.NC(=O)C=C FJWSMXKFXFFEPV-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
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- 238000000926 separation method Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 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
- 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
Landscapes
- Inks, Pencil-Leads, Or Crayons (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
- Polymerisation Methods In General (AREA)
Description
2.前記一般式(1)に前記−X−Y基を有する水溶性光開始剤が下記一般式(A)、(B)、(C)から選ばれることを特徴とする前記1に記載の水溶性光開始剤。
3.前記Xが酸素原子であることを特徴とする前記1または2に記載の水溶性光開始剤。
エチレン性不飽和基を有する化合物とは、化合物中に1個以上のエチレン性不飽和基を持つ化合物。具体的にはスチレン基、アクリル基、メタクリル基、アリル基、クロトン酸基、マレイン酸基、イタコン酸基を少なくとも1つ以上分子中に有する化合物をいう。好ましくはアクリル基、メタクリル基を1つ以上分子中に有する化合物である。
本発明においては、本発明に係る光開始剤の他に必要に応じて他の光開始剤や光増感剤を添加してもよい。
2)チオキサントン、2,4−ジエチルチオキサントン、イソプロピルチオキサントン、クロロチオキサントン、イソプロポキシクロロチオキサントン等のチオキサントン類、及びそれらの塩
3)エチルアントラキノン、ベンズアントラキノン、アミノアントラキノン、クロロアントラキノン等のアントラキノン類
4)アセトフェノン類
5)ベンゾインメチルエーテル等のベンゾインエーテル類
6)2,4,6−トリハロメチルトリアジン類。
8)ベンジルジメチルケタール、2−ベンジル−2−ジメチルアミノ−1−(4−モルホリノフェニル)ブタン−1−オン、2−メチル−1−[4−(メチルチオ)フェニル]−2−モルホリノ−1−プロパノン、2−ヒドロキシ−2−メチル−1−フェニル−プロパン−1−オン、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、フェナントレンキノン、9,10−フェナンスレンキノン、メチルベンゾイン、エチルベンゾイン等のベンゾイン類。
10)ビスアシルフォスフィンオキサイド、ビスフェニルフォスフィンオキサイド、ビス(2,4,6−トリメチルベンゾイル)−フェニルフォスフィンオキサイド
11)4−(2−ヒドロキシエトキシ)フェニル−(2−ヒドロキシ−2−プロピル)ケトン、及びこれらのエチレンオキシド付加物。
本発明の水溶性光開始剤を得るためには、水溶性光開始剤の前駆体であるベンジル誘導体からケタール化を行い、必要に応じて加水分解等を行うことで目的物を得ることができる。
塩化アルミニウム11.7g(84mmol)をジクロロメタン33mlに加え、氷冷する。フェノキシ酢酸メチル(化合物A)6.6g(40mmol)を内温15℃以下で滴下し、次いでオキザリルクロリド2.8g(22mmol)をゆっくり滴下する。盛んに塩化水素ガスが発生する。塩化水素ガスの発生の終了後、反応液を氷水100g中に投入し、酢酸エチル30mlを加え攪拌すると結晶が析出してくる。この結晶を濾過洗浄して、化合物B、2.5gを白色結晶として得る。
化合物B、23.9g(62mmol)、オルトギ酸トリメチル65.6g(620mmol)、メタノール19.8g(618mmol)、トルエン360mlの混合物を還流する。この液にトリフルオロメタンスルホン酸を2.8g(18.6mmol)を滴下して加え、還流を5時間続ける。酢酸エチルと炭酸水素ナトリウム水溶液をかき混ぜた液中に、反応液を投入し、酢酸エチル相を分離エバポレートする。カラムで分離精製して、化合物Cを白色結晶として18.8g得る。
化合物C、16.7g、メタノール130ml、水酸化ナトリウムの30質量%水溶液10mlを加え、還流を2時間行う。黄色物質が析出してくるので、濾過して取り除いた後、溶媒等を留去する。得られた透明オイルにエタノールを加え、結晶化させる。濾過、乾燥して、例示化合物1を15.1g得る。
グリシジルメタクリレート56g、p−ヒドロキシベンズアルデヒド48g、ピリジン2g、及びN−ニトロソ−フェニルヒドロキシアミンアンモニウム塩1gを反応容器に入れ、80度の湯浴中で8時間攪拌した。
(ブラック顔料分散液の調製)
以下の各添加剤を混合し、0.5mmのジルコニアビーズを体積率で50%充填したサンドグラインダーを用いて分散し、イオン交換水で希釈してブラック顔料の含有量が10%のブラック顔料分散液を調製した。このブラック顔料分散液に含まれるブラック顔料粒子の平均粒径は154nmであった。なお、粒径測定はマルバーン製ゼータサイザ1000HSにより行った。
高分子分散剤(スチレン/アクリル酸/ブチルアクリレート共重合体、Tg65℃、数平均分子量7000) 4部
グリセリン 18部
イオン交換水 残り
〔ブラック印刷インク1の調製〕
ブラック顔料分散液 30部
A400(新中村化学製) 20部
TO−1343(東亞合成製、アクリロイル基を2個以上有する水溶性ポリエステル系アクリルオリゴマー) 5部
ジョンクリル537J(ジョンソンポリマー製、固形分46%) 8部
水溶性光開始剤(1) 2部
ジエチレングリコール 20部
水 残り
以下、水溶性光開始剤を表1に記した化合物に変えて、ブラック印刷インク2〜16を調製した。
(365nmLEDでの硬化性)
アート紙上に得られたインクをワイヤーバーでWet膜厚10μmで塗布し、λ365nmのLEDランプ(日亜化学工業製)で115mJ/cm2の照度で照射し、照射後の状態を目視で観察した。
△:一部に流動性がある
×:流動性がある。
アート紙上に得られたインクをワイヤーバーでWet膜厚50μmで塗布し、高圧水銀灯で(ウシオ電機製)で96mJ/cm2の照度で照射し、照射後の状態を目視で観察した。
△:一部に流動性がある
×:流動性がある。
インク20mlを50mlビーカーに入れ、上部50cmより100Wに蛍光灯を24時間照射し、保存性の評価を行った。
△:表面の一部がゲル化している
×:不溶物がある。
表2中の各顔料分散液は下記のように調製した。
ブラック顔料分散液(濃度15%):実施例1参照
マゼンタ顔料分散液(濃度15%):実施例1のブラック顔料分散液の調製において、カーボンブラックに代えて、C.I.Pigment Red122を使用した以外は同様にして、マゼンタ顔料分散液を調製した。
UA−W2A:新中村化学製、水溶性ウレタンアクリレートオリゴマー
アクリル基含有ポリビニルアルコール(重合度500、変性率3%、濃度10%)
DEG:ジエチレングリコール
EG:エチレングリコール
オルフィンE1010:日信化学製。
高圧水銀灯を搭載したUVインクジェットプリンターで、アート紙上に15g/m2の付量になるようにベタ画像を作成した。
Claims (4)
- 前記Xが酸素原子であることを特徴とする請求項1または2に記載の水溶性光開始剤。
- 少なくとも、水、エチレン性不飽和基を有する化合物と請求項1〜3のいずれか1項に記載の水溶性開始剤を含有することを特徴とする光重合/架橋性組成物。
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