JP6919255B2 - 活性エネルギー線硬化型組成物 - Google Patents
活性エネルギー線硬化型組成物 Download PDFInfo
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- JP6919255B2 JP6919255B2 JP2017056278A JP2017056278A JP6919255B2 JP 6919255 B2 JP6919255 B2 JP 6919255B2 JP 2017056278 A JP2017056278 A JP 2017056278A JP 2017056278 A JP2017056278 A JP 2017056278A JP 6919255 B2 JP6919255 B2 JP 6919255B2
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- Prior art keywords
- meth
- acrylate
- active energy
- energy ray
- oxidase
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- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer 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
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004634 thermosetting polymer Substances 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- ZUCXUTRTSQLRCV-UHFFFAOYSA-K trisodium;1-amino-4-[3-[[4-chloro-6-(3-sulfonatoanilino)-1,3,5-triazin-2-yl]amino]-2,4,6-trimethyl-5-sulfonatoanilino]-9,10-dioxoanthracene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].CC1=C(S([O-])(=O)=O)C(C)=C(NC=2C=3C(=O)C4=CC=CC=C4C(=O)C=3C(N)=C(C=2)S([O-])(=O)=O)C(C)=C1NC(N=1)=NC(Cl)=NC=1NC1=CC=CC(S([O-])(=O)=O)=C1 ZUCXUTRTSQLRCV-UHFFFAOYSA-K 0.000 description 1
- UJMBCXLDXJUMFB-UHFFFAOYSA-K trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazole-3-carboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-UHFFFAOYSA-K 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Polymerisation Methods In General (AREA)
Description
親水性ラジカル重合性化合物(A)が、下記一般式(1)で表される化合物(a1)、下記一般式(2)で表される化合物(a2)、下記一般式(3)で表される化合物(a3)、下記一般式(4)で表される化合物(a4)、下記一般式(5)で表される化合物(a5)および下記一般式(6)で表される化合物(a6)からなる群より選ばれる一つ以上であることを特徴とする、活性エネルギー線硬化型組成物に関する。
(式中、aは、4〜40の整数を表す。)
(式中、R3〜R5は、それぞれ独立に、水素原子またはメチル基を表す。式中、b、cおよびdは、それぞれ独立に、2〜40の整数を表す。)
(式中、R6〜R8は、それぞれ独立に、水素原子またはメチル基を表す。式中、e、fおよびgは、それぞれ独立に、2〜40の整数を表す。)
(式中、R9〜R12は、それぞれ独立に、水素原子またはメチル基を表す。式中、h、i、jおよびkは、それぞれ独立に、2〜40の整数を表す。)
(式中、R13〜R16は、それぞれ独立に、水素原子またはメチル基を表す。式中、l、m、nおよびoは、それぞれ独立に、2〜40の整数を表す。)
メチル(メタ)アクリレート、エチル(メタ)アクリレート、プロピル(メタ)アクリレート、イソプロピル(メタ)アクリレート、ブチル(メタ)アクリレート、イソアミル(メタ)アクリレート、ヘキシル(メタ)アクリレート、2−エチルヘキシル(メタ)アクリレート、オクチル(メタ)アクリレート、デシル(メタ)アクリレート、ラウリル(メタ)アクリレート、ステアリル(メタ)アクリレート、イソボルニル(メタ)アクリレート、シクロヘキシル(メタ)アクリレート、ジシクロペンテニル(メタ)アクリレート、ジシクロペンテニルオキシエチル(メタ)アクリレート、ベンジル(メタ)アクリレート。
2−ヒドロキシエチル(メタ)アクリレート、2−ヒドロキシプロピル(メタ)アクリレート、2−ヒドロキシ−3−クロロプロピル(メタ)アクリレート、2−ヒドロキシ−3−フェノキシプロピル(メタ)アクリレート、2−ヒドロキシ−3−アリルオキシプロピル(メタ)アクリレート、(メタ)アクリル酸−2−ヒドロキシ−3−アリルオキシプロピル、2−(メタ)アクリロイルオキシエチル−2−ヒドロキシプロピルフタレート。
2,2,2−トリフルオロエチル(メタ)アクリレート、2,2,3,3−テトラフルオロプロピル(メタ)アクリレート、1H−ヘキサフルオロイソプロピル(メタ)アクリレート、1H,1H,5H−オクタフルオロペンチル(メタ)アクリレート、1H,1H,2H,2H−ヘプタデカフルオロデシル(メタ)アクリレート、2,6−ジブロモ−4−ブチルフェニル(メタ)アクリレート、2,4,6−トリブロモフェノキシエチル(メタ)アクリレート、2,4,6−トリブロモフェノール3EO(エチレンオキサイド)付加(メタ)アクリレート。
2−メトキシエチル(メタ)アクリレート、1,3−ブチレングリコールメチルエーテル(メタ)アクリレート、ブトキシエチル(メタ)アクリレート、メトキシトリエチレングリコール(メタ)アクリレート、メトキシポリエチレングリコール#400(メタ)アクリレート、メトキシジプロピレングリコール(メタ)アクリレート、メトキシトリプロピレングリコール(メタ)アクリレート、メトキシポリプロピレングリコール(メタ)アクリレート、エトキシジエチレングリコール(メタ)アクリレート、エチルカルビトール(メタ)アクリレート、2−エチルヘキシルカルビトール(メタ)アクリレート、テトラヒドロフルフリル(メタ)アクリレート、フェノキシエチル(メタ)アクリレート、フェノキシジエチレングリコール(メタ)アクリレート、フェノキシポリエチレングリコール(メタ)アクリレート、クレジルポリエチレングリコール(メタ)アクリレート、(メタ)アクリル酸−2−(ビニロキシエトキシ)エチル、p−ノニルフェノキシエチル(メタ)アクリレート、p−ノニルフェノキシポリエチレングリコール(メタ)アクリレート、グリシジル(メタ)アクリレート。
β−カルボキシエチル(メタ)アクリレート、コハク酸モノアクリロイルオキシエチルエステル、ω−カルボキシポリカプロラクトンモノ(メタ)アクリレート、2−(メタ)アクリロイルオキシエチルハイドロゲンフタレート、2−(メタ)アクリロイルオキシプロピルハイドロゲンフタレート、2−(メタ)アクリロイルオキシプロピルヘキサヒドロハイドロゲンフタレート、2−(メタ)アクリロイルオキシプロピルテトラヒドロハイドロゲンフタレート。
N,N−ジメチルアミノエチル(メタ)アクリレート、N,N−ジメチルアミノプロピル(メタ)アクリレート、モルホリノエチル(メタ)アクリレート、トリメチルシロキシエチル(メタ)アクリレート、ジフェニル−2−(メタ)アクリロイルオキシエチルホスフェート、2−(メタ)アクリロイルオキシエチルアシッドホスフェート、カプロラクトン変性−2−(メタ)アクリロイルオキシエチルアシッドホスフェート、2−ヒドロキシ−1−(メタ)アクリロキシ−3−メタクリロキシプロパン。
1,4−ブタンジオールジ(メタ)アクリレート、1,6−ヘキサンジオールジ(メタ)アクリレート、エチレングリコールジ(メタ)アクリレート、ジエチレングリコールジ(メタ)アクリレート、トリエチレングリコールジ(メタ)アクリレート、テトラエチレングリコールジ(メタ)アクリレート、ジプロピレングリコールジ(メタ)アクリレート、トリプロピレングリコールジ(メタ)アクリレート、テトラプロピレングリコールジ(メタ)アクリレート、ポリプロピレングリコール#400ジ(メタ)アクリレート、ポリプロピレングリコール#700ジ(メタ)アクリレート、ネオペンチルグリコールジ(メタ)アクリレート、ネオペンチルグリコールPO(プロピレンオキサイド)変性ジ(メタ)アクリレート、ヒドロキシピバリン酸ネオペンチルグリコールエステルジ(メタ)アクリレート、ヒドロキシピバリン酸ネオペンチルグリコールエステルのカプロラクトン付加物ジ(メタ)アクリレート、1,6−ヘキサンジオールビス(2−ヒドロキシ−3−(メタ)アクリロイルオキシプロピル)エーテル、ビス(4−(メタ)アクリロキシポリエトキシフェニル)プロパン、1,9−ノナンジオールジ(メタ)アクリレート、ペンタエリスリトールジ(メタ)アクリレート、ペンタエリスリトールジ(メタ)アクリレートモノステアレート、ペンタエリスリトールジ(メタ)アクリレートモノベンゾエート、ビスフェノールAジ(メタ)アクリレート、EO変性ビスフェノールAジ(メタ)アクリレート、PO変性ビスフェノールAジ(メタ)アクリレート、水素化ビスフェノールAジ(メタ)アクリレート、EO変性水素化ビスフェノールAジ(メタ)アクリレート、PO変性水素化ビスフェノールAジ(メタ)アクリレート、ビスフェノールFジ(メタ)アクリレート、EO変性ビスフェノールFジ(メタ)アクリレート、PO変性ビスフェノールFジ(メタ)アクリレート、EO変性テトラブロモビスフェノールAジ(メタ)アクリレート、トリシクロデカンジメチロールジ(メタ)アクリレート、イソシアヌル酸EO変性ジ(メタ)アクリレート、2−ヒドロキシ−1,3−ジ(メタ)アクリロキシプロパン。
(メタ)アクリル酸−2−ビニロキシエチル、(メタ)アクリル酸−3−ビニロキシプロピル、(メタ)アクリル酸−1−メチル−2−ビニロキシエチル、(メタ)アクリル酸−2−ビニロキシプロピル、(メタ)アクリル酸−4−ビニロキシブチル、(メタ)アクリル酸−1−メチル−3−ビニロキシプロピル、(メタ)アクリル酸−1−ビニロキシメチルプロピル、(メタ)アクリル酸−2−メチル−3−ビニロキシプロピル、(メタ)アクリル酸−3−メチル−3−ビニロキシプロピル、(メタ)アクリル酸−1,1−ジメチル−2−ビニロキシエチル、(メタ)アクリル酸−3−ビニロキシブチル、(メタ)アクリル酸−1−メチル−2−ビニロキシプロピル、(メタ)アクリル酸−2−ビニロキシブチル、(メタ)アクリル酸−4−ビニロキシシクロヘキシル、(メタ)アクリル酸−5−ビニロキシペンチル、(メタ)アクリル酸−6−ビニロキシヘキシル、(メタ)アクリル酸−4−ビニロキシメチルシクロヘキシルメチル、(メタ)アクリル酸−3−ビニロキシメチルシクロヘキシルメチル、(メタ)アクリル酸−2−ビニロキシメチルシクロヘキシルメチル、(メタ)アクリル酸−p−ビニロキシメチルフェニルメチル、(メタ)アクリル酸−m−ビニロキシメチルフェニルメチル、(メタ)アクリル酸−o−ビニロキシメチルフェニルメチル、(メタ)アクリル酸−2−(ビニロキシイソプロポキシ)エチル、(メタ)アクリル酸−2−(ビニロキシエトキシ)プロピル、(メタ)アクリル酸−2−(ビニロキシエトキシ)イソプロピル、(メタ)アクリル酸−2−(ビニロキシイソプロポキシ)プロピル、(メタ)アクリル酸−2−(ビニロキシイソプロポキシ)イソプロピル、(メタ)アクリル酸−2−(ビニロキシエトキシエトキシ)エチル、(メタ)アクリル酸−2−(ビニロキシエトキシイソプロポキシ)エチル、(メタ)アクリル酸−2−(ビニロキシイソプロポキシエトキシ)エチル、(メタ)アクリル酸−2−(ビニロキシイソプロポキシイソプロポキシ)エチル。
グリセリンPO変性トリ(メタ)アクリレート、トリメチロールプロパントリ(メタ)アクリレート、トリメチロールプロパンPO変性トリ(メタ)アクリレート、イソシアヌル酸EO変性トリ(メタ)アクリレート、イソシアヌル酸EO変性ε−カプロラクトン変性トリ(メタ)アクリレート、1,3,5−トリ(メタ)アクリロイルヘキサヒドロ−s−トリアジン、ペンタエリスリトールトリ(メタ)アクリレート、ジペンタエリスリトールトリ(メタ)アクリレートトリプロピオネート。
ペンタエリスリトールテトラ(メタ)アクリレート、ジペンタエリスリトールテトラ(メタ)アクリレート、ジペンタエリスリトールペンタ(メタ)アクリレートモノプロピオネート、ジペンタエリスリトールヘキサ(メタ)アクリレート、テトラメチロールメタンテトラ(メタ)アクリレート、オリゴエステルテトラ(メタ)アクリレート、トリス(アクリロイルオキシ)ホスフェート。
<合成例1>親水性ラジカル重合性化合物(A):化合物(A−9)
攪拌装置を備えた容量2Lのオートクレーブ内に、グリセリン92g(1.0mol)、蒸留水36g、水酸化カリウム0.3gを仕込み、90℃まで昇温、攪拌し、スラリー状の液体とした。次いで130℃に加熱し、エチレンオキサイド1365g(31mol)を徐々にオートクレーブ内に導入し反応させた。エチレンオキサイドの導入とともに、オートクレーブ内温度は上昇した。随時冷却を加え、反応温度は140℃以下に保つようにした。反応後、140℃にて水銀柱10mmHg以下にて減圧することで、過剰のエチレンオキサイド、副生するエチレングリコールの重合体を除去した。その後、酢酸にて中和を行い、pH6〜7に調整した。
続いて、得られたグリセリン30molエチレンオキサイド付加化合物141g(0.1mol)、アクリル酸230g(3.2mol)、パラトルエンスルホン酸16g、トルエン500g、ハイドロキノン1gをガラス製四つ口フラスコに仕込み、空気を吹き込みながら加熱反応を行った。反応で生じた水はトルエンと共沸することで系外に随時除去した。反応温度は100〜110℃を保つように調節した。反応後、アルカリ水洗、水洗を行い、上層のトルエン層を分離し、トルエンを減圧留去し、化合物(A−9)で表される、グリセリン30molエチレンオキサイド付加アクリレートを352g(収率86%)得た。
攪拌装置を備えた容量2Lのオートクレーブ内に、トリメチロールプロパン137g(1.0mol)、蒸留水36g、水酸化カリウム0.3gを仕込み、90℃まで昇温、攪拌し、スラリー状の液体とした。次いで130℃に加熱し、エチレンオキサイド1365g(31mol)を徐々にオートクレーブ内に導入し反応させた。エチレンオキサイドの導入とともに、オートクレーブ内温度は上昇した。随時冷却を加え、反応温度は140℃以下に保つようにした。反応後、140℃にて水銀柱10mmHg以下にて減圧することで、過剰のエチレンオキサイド、副生するエチレングリコールの重合体を除去した。その後、酢酸にて中和を行い、pH6〜7に調整した。
続いて、得られたトリメチロールプロパン30molエチレンオキサイド付加化合物146g(0.1mol)、アクリル酸230g(3.2mol)、パラトルエンスルホン酸16g、トルエン500g、ハイドロキノン1gをガラス製四つ口フラスコに仕込み、空気を吹き込みながら加熱反応を行った。反応で生じた水はトルエンと共沸することで系外に随時除去した。反応温度は100〜110℃を保つように調節した。反応後、アルカリ水洗、水洗を行い、上層のトルエン層を分離し、トルエンを減圧留去し、化合物(A−19)で表される、トリメチロールプロパン30molエチレンオキサイド付加アクリレートを303g(収率84%)得た。
攪拌装置を備えた容量2Lのオートクレーブ内に、ジトリメチロールプロパン256g(1.0mol)、蒸留水36g、水酸化カリウム0.3gを仕込み、110℃まで昇温、攪拌し、スラリー状の液体とした。次いで130℃に加熱し、エチレンオキサイド1585g(36mol)を徐々にオートクレーブ内に導入し反応させた。エチレンオキサイドの導入とともに、オートクレーブ内温度は上昇した。随時冷却を加え、反応温度は140℃以下に保つようにした。反応後、140℃にて水銀柱10mmHg以下にて減圧することで、過剰のエチレンオキサイド、副生するエチレングリコールの重合体を除去した。その後、酢酸にて中和を行い、pH6〜7に調整した。
続いて、得られたジトリメチロールプロパン35molエチレンオキサイド付加化合物180g(0.1mol)、アクリル酸273g(3.8mol)、パラトルエンスルホン酸16g、トルエン500g、ハイドロキノン1gをガラス製四つ口フラスコに仕込み、空気を吹き込みながら加熱反応を行った。反応で生じた水はトルエンと共沸することで系外に随時除去した。反応温度は100〜110℃を保つように調節した。反応後、アルカリ水洗、水洗を行い、上層のトルエン層を分離し、トルエンを減圧留去し、化合物(A−9)で表される、ジトリメチロールプロパン35molエチレンオキサイド付加アクリレート367g(収率85%)を得た。
表2記載の配合にて活性エネルギー線硬化型組成物を得た。得られた重合性組成物を用いて、以下の方法で硬化性、硬化物の硬度、硬化物の外観の評価を実施した。結果を表2に示す。
調製した活性エネルギー線硬化型組成物を、マイクロメーター調節式アプリケーターを用いて、ポリエチレンテレフタレート(PET)基材上に、ウェット膜厚が1000μmとなるように塗布し、塗布膜を作製した。活性エネルギー線として高圧UVランプUSH−500SC(ウシオ電機)を用いて、30mW/cm2の照射強度(254nm換算)で1秒間紫外線照射を行った。照射後の硬化物の表面を綿布で擦って、皮膜に傷がつかなくなるまで紫外線照射を繰り返し、硬化性の判定を実施した。紫外線照射の時間が短いほど硬化性が良いと判断した。判断基準は下記の通りである。
◎ :1〜15秒。特に良好。
○ :16秒〜60秒。良好。
△ :61秒以上。やや不良。
× :紫外線照射前に硬化してしまうため、実用に適さない。特に不良。
調製した活性エネルギー線硬化型組成物を、マイクロメーター調節式アプリケーターを用いて、ポリエチレンテレフタレート(PET)基材上に、ウェット膜厚が1000μmとなるように塗布し、塗布膜を作製した。活性エネルギー線として高圧UVランプUSH−500SC(ウシオ電機)を用いて、50mW/cm2の照射強度(365nm換算)で紫外線照射を30秒間行った。綿棒を用いて、硬化物を0.1kgf(0.98N)の荷重で5秒間押し込んだ際と、押し込んだ後の硬化物の様子を観察し、硬化物の硬度の判定を実施した。判断基準は下記の通りである。
◎ :押し込み時、押し込み後共に凹みなし。特に良好。
○ :押し込み時に凹み発生、押し込み後は凹みなし。やや良好。
× :押し込み時にひび割れ発生、または、硬化物が崩壊。不良。
硬化物の硬度評価試験に使用した硬化物を目視で観察し、硬化物の外観の判定を実施した。判断基準は下記の通りである。
◎ :無色透明。良好。
× :白濁、または、黄色着色。不良。
<低分子化合物の残留率評価試験>
調製した活性エネルギー線硬化型組成物を、調製した活性エネルギー線硬化型組成物を、マイクロメーター調節式アプリケーターを用いて、ポリエチレンテレフタレート(PET)基材上に、ウェット膜厚が1000μmとなるように塗布し、塗布膜を作製した。活性エネルギー線として高圧UVランプUSH−500SC(ウシオ電機)を用いて、50mW/cm2の照射強度(365nm換算)で紫外線照射を30秒間行い、硬化物を得た。得られた硬化物(10cm×10cm)を、基材ごと1cm四方に切断し、密閉した容器に入ったメチルエチルケトン100mlに3日間60℃で浸漬することにより、硬化膜中の低分子化残留成分の残留率を抽出した。2日後、攪拌して均一化させたメチルエチルケトンを容器内から取り出し、抽出した成分をHPLC(島津製作所製)にて同定した。検出された化合物の検量線を作製して各化合物を定量することにより、硬化膜中の低分子化合物の残留率を算出した。なお、低分子化合物とは、分子量1000未満の化合物のことを示し、親水性ラジカル重合性化合物(A)、オキシダーゼ基質(C)、光重合開始剤(D)が含まれる。低分子化合物の残留率が少ないほど優れていると判断した。判断基準は下記の通りである。
硬化膜質量は、以下のように算出した。
硬化膜質量=紫外線照射後の硬化物(硬化膜+基材)質量−紫外線照射前の基材質量
硬化膜中に残留する未反応の光重合開始剤の残留率は、以下のように算出した。
光重合開始剤の残留率=抽出された光重合開始剤総量(g)/硬化膜質量(g)
○ :低分子化合物残留率は0.5%未満。特に良好。
△ :低分子化合物残留率は0.5%〜1%未満。やや良好。
× :低分子化合物残留率は1%以上、実用には適さない。不良。
PEGDMA:ポリエチレングリコール(分子量400)ジメタクリレート;NKエステル9G(新中村工業株式会社社製);
PET−3A:ペンタエリスリトールトリアクリレート;ライトアクリレートPE−3A(協栄社化学株式会社社製)
GOx:グルコースオキシダーゼ 活性190U/mg(和光純薬工業株式会社社製)
GaOx:ガラクトースオキシダーゼ(和光純薬工業株式会社社製)
ChOx:コリンオキシダーゼ(和光純薬工業株式会社社製)
Gl:β−D−グルコース(東京化成工業株式会社社製)
Ga:D−ガラクトース(東京化成工業株式会社社製)
Ch:コリン(東京化成工業株式会社社製)
水:脱イオン水
FeSO4:硫化鉄(シグマアルドリッチ社製)
NaTS:トルエンスルフォン酸ナトリウム(シグマアルドリッチ社製)
AA:アスコルビン酸(シグマアルドリッチ社製)
Irg.184:1−ヒドロキシ−シクロヘキシル−フェニル−ケトン(BASF社製)
Claims (4)
- 親水性ラジカル重合性化合物(A)と、オキシダーゼ酵素(B)と、オキシダーゼ基質(C)と、水とを含んでなり、光重合開始剤(D)および還元剤を含まないことを特徴とする、活性エネルギー線硬化型組成物であって、
親水性ラジカル重合性化合物(A)が、下記一般式(1)で表される化合物(a1)、下記一般式(2)で表される化合物(a2)、下記一般式(3)で表される化合物(a3)、下記一般式(4)で表される化合物(a4)、下記一般式(5)で表される化合物(a5)および下記一般式(6)で表される化合物(a6)からなる群より選ばれる一つ以上であることを特徴とする、活性エネルギー線硬化型組成物。
i、jおよびkは、それぞれ独立に、2〜40の整数を表す。)
- オキシダーゼ酵素(B)がグルコースオキシダーゼであり、オキシダーゼ基質(C)がグルコースであることを特徴とする、請求項1記載の活性エネルギー線硬化型組成物。
- 親水性ラジカル重合性化合物(A)の100質量部に対して、オキシダーゼ酵素(B)を0.01質量部から0.1質量部の範囲で含んでなり、オキシダーゼ基質(C)を0.17質量部から1.7質量部を含んでなり、水を10質量部以下を含んでなることを特徴とする、請求項1または2記載の活性エネルギー線硬化型組成物。
- 請求項1〜3いずれか記載の活性エネルギー線硬化型組成物の硬化物。
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