JP5509022B2 - 紫外線硬化性液状組成物およびこれを用いた樹脂硬化物 - Google Patents
紫外線硬化性液状組成物およびこれを用いた樹脂硬化物 Download PDFInfo
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- JP5509022B2 JP5509022B2 JP2010227109A JP2010227109A JP5509022B2 JP 5509022 B2 JP5509022 B2 JP 5509022B2 JP 2010227109 A JP2010227109 A JP 2010227109A JP 2010227109 A JP2010227109 A JP 2010227109A JP 5509022 B2 JP5509022 B2 JP 5509022B2
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- acid anhydride
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- XXKOQQBKBHUATC-UHFFFAOYSA-N cyclohexylmethylcyclohexane Chemical group C1CCCCC1CC1CCCCC1 XXKOQQBKBHUATC-UHFFFAOYSA-N 0.000 description 1
- OSIVBHBGRFWHOS-UHFFFAOYSA-N dicarboxycarbamic acid Chemical group OC(=O)N(C(O)=O)C(O)=O OSIVBHBGRFWHOS-UHFFFAOYSA-N 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical group C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- KFEVDPWXEVUUMW-UHFFFAOYSA-N docosanoic acid Natural products CCCCCCCCCCCCCCCCCCCCCC(=O)OCCC1=CC=C(O)C=C1 KFEVDPWXEVUUMW-UHFFFAOYSA-N 0.000 description 1
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 239000007789 gas 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
- 235000019382 gum benzoic Nutrition 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000007542 hardness measurement Methods 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- MEBJLVMIIRFIJS-UHFFFAOYSA-N hexanedioic acid;propane-1,2-diol Chemical compound CC(O)CO.OC(=O)CCCCC(O)=O MEBJLVMIIRFIJS-UHFFFAOYSA-N 0.000 description 1
- 150000002433 hydrophilic molecules Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000001678 irradiating effect Effects 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
- 239000011344 liquid material Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- CAAULPUQFIIOTL-UHFFFAOYSA-N methyl dihydrogen phosphate Chemical compound COP(O)(O)=O CAAULPUQFIIOTL-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- WIBFFTLQMKKBLZ-SEYXRHQNSA-N n-butyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCCC WIBFFTLQMKKBLZ-SEYXRHQNSA-N 0.000 description 1
- CRNNFEKVPRFZKJ-UHFFFAOYSA-N n-fluoren-9-ylidenehydroxylamine Chemical compound C1=CC=C2C(=NO)C3=CC=CC=C3C2=C1 CRNNFEKVPRFZKJ-UHFFFAOYSA-N 0.000 description 1
- CJYCVQJRVSAFKB-UHFFFAOYSA-N octadecane-1,18-diamine Chemical compound NCCCCCCCCCCCCCCCCCCN CJYCVQJRVSAFKB-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000010690 paraffinic oil Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- BPJZKLBPJBMLQG-KWRJMZDGSA-N propanoyl (z,12r)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OC(=O)CC BPJZKLBPJBMLQG-KWRJMZDGSA-N 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-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
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 235000013799 ultramarine blue Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
Landscapes
- Processes Of Treating Macromolecular Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
<化合物A(式5)の合成>
冷却還流管と温度計を付した100ml三口フラスコに乾燥トルエン50mlを入れ、さらに2−ニトロベンジルアルコール2.8g(18.3mmol)とジラウリン酸ジブチルすずを1滴入れて、常温下で攪拌子で攪拌して溶解させた。攪拌を続けながら、そこにヘキサメチレンジイソシアネート1.05g(6.25mmol)を5分かけて滴下した。その後70℃まで加温し、3時間その温度で攪拌を続けて反応させた。反応終了後、室温まで冷却し、析出物を吸引濾過により採取した。濾過採取物は再び、10mlのトルエンから再結晶して乾燥し、白色粉末の目的物である化合物A(式5)を2.8g得た。(収率94%)
ヘキサメチレンジイソシアネートに代えて、1,3−ビス(イソシアナトメチル)シクロヘキサン1.21g(6.22mmol)を用いたこと以外、化合物Aと同様にして合成した。(収率89%)
ヘキサメチレンジイソシアネートに代えて、ジシクロヘキシルメタン−4,4’−ジイソシアナート1.64g(6.25mmol)を用いたこと以外、化合物Aと同様にして合成した。(収率85%)
ヘキサメチレンジイソシアネートに代えて、4,4’−ジイソシアン酸メチレンジフェニル1.56g(6.23mmol)を用いたこと以外、化合物Aと同様にして合成した。(収率81%)
冷却還流管と温度計を付した100ml三口フラスコに乾燥トルエン50mlを入れ、さらに2−ニトロベンジルアルコール2.8g(18.3mmol)とジラウリン酸ジブチルすずを1滴入れて、常温下で攪拌子で攪拌して溶解させた。攪拌を続けながら、そこに下記の式(11)に示す構造を有するデスモジュールN3600(住化バイエルウレタン社製)3.16g(6.25mmol)を5分かけて滴下した。その後70℃まで加温し、3時間その温度で攪拌を続けて反応させた。反応終了後、室温まで冷却すると、反応液は2層に分離するので、上層をデカンテーションにて除き、さらにトルエン50mlを加え、室温にてデカント洗浄を行った。その後、エバポレータにて乾燥し、淡褐色オイルの化合物Fを3.8g得た。(収率75%)
・酸無水物変性ポリブタジエン[日本シーマ社製、「コルノバMAH−1」]
・酸無水物変性ポリイソプレン[アルドリッチ社製、「Polyisoprene−graft−maleic anhydride」]
・ポリイソプレン[アルドリッチ社製、「Polyisoprene cis」]
・末端ヒドロキシポリブタジエン[アルドリッチ社製、「Polybutadiene hydroxyl terminated」]
・シリコーン硬化樹脂「東レダウコーニング社製、「SE9120」]
・グリシジルビスフェノールA:[東京化成製、2,2−Bis(4−glycidyloxyphenyl)propane」]
表1に記載の配合割合(質量部)となるように液状高分子と光発生型の潜在性アミン硬化剤とを攪拌機を用いて混合し、分散させることにより、紫外線硬化性液状組成物を調製した。
市販のアクリル系UV硬化剤(東亜合成社製、「UV−3300」)を用いた。
実施例の紫外線硬化性液状組成物あるいは比較例のアクリル系UV硬化剤を、縦50mm×横50mm×厚さ1mmの型に流し込み、上面の半分(縦25mm×横50mm)をアルミ板で遮光し、UVランプ(SEN特殊光源社製100mW/cm2)で30秒間紫外線照射を行った。その後、10分間室温下で放置した後、アルミ遮光板を取り除き、上面における紫外線照射面と遮光面の境界から遮光面(非照射部)方向に広がり進んだ硬化部の距離をノギスで計測した。なお、硬化しているか否かは、指触により判断した。この結果を表1に示した。
表2に記載の配合割合(質量部)となるように液状高分子と光発生型の潜在性アミン硬化剤とを攪拌機を用いて混合し、分散させることにより、紫外線硬化性液状組成物を調製した。
表2に記載の配合割合(質量部)となるように液状高分子と光発生型の潜在性アミン硬化剤あるいはエチレンジアミドとを攪拌機を用いて混合し、分散させることにより、液状組成物を調製した。
調製した組成物をアルミホイルで遮光したサンプル瓶に入れ、40℃恒温槽中で7日間放置し、その外観変化を目視により確認することで、組成物の保存安定性を評価した。この際、外観において、変色、固化が見られなかったものを「○」、固化が見られたものを「△」、変色が見られたものを「×」とした。
調製した組成物を、縦50mm×横50mm×厚さ1mmの型に流し込み、UVランプ(SEN特殊光源社製100mW/cm2)で30秒間紫外線照射を行った。この際、硬化せずに型から取り出せなかったものは硬化不良「×」とした。硬化したものについては、型から取り出し、硬度を測定した。硬度測定は、水平な金属板上に配置した硬化物に対し、JIS K 6253に準拠してタイプA硬度計を用いて、10Nの荷重がかかるまで1mm/minの速さで押し付け、荷重が10Nに達した時点での硬度計の目盛りを読みこんだ。測定された硬度の値から、硬化物がゴム弾性を有するか否かを判断した。一般には、タイプA硬度が50以下の場合、ゴム弾性を有するとされている。
上記硬化性試験において硬化することが分かっている組成物について、縦100mm×横50mm×厚さ1mmの型に流し込み、UVランプ(SEN特殊光源社製100mW/cm2)で30秒間紫外線照射を行った。その後、型から取り出し、硬化物を縦100mm×横5mm×厚さ1mmの帯状に裁断して、試験片を作製した。作製した試験片を用いて、引張試験機(島津製作所製)で破断伸び(%)を測定し、100%以上の破断伸びを示したものを柔軟性が十分と判断した。
Claims (4)
- 酸無水物基を有する液状高分子と、
ポリアミン化合物のアミノ基がアミン保護基により保護されてなり、紫外線により前記アミン保護基が脱離して前記ポリアミン化合物が発生する光発生型の潜在性アミン硬化剤と、を含有し、
前記酸無水物基を有する液状高分子の主鎖は、ジエン系液状ゴムであることを特徴とする紫外線硬化性液状組成物。 - 前記ジエン系液状ゴムは、ポリブタジエン、ポリクロロプレン、ポリイソプレン、ポリアクリロニトリル−ブタジエン、ポリ1,3−ペンタジエンから選択された1種または2種以上のゴムであることを特徴とする請求項1または2に記載の紫外線硬化性液状組成物。
- 請求項1から3のいずれか1項に記載の紫外線硬化性液状組成物が硬化されてなることを特徴とする樹脂硬化物。
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