JP6748883B2 - 光遅延硬化性樹脂組成物、接合体および接着方法 - Google Patents
光遅延硬化性樹脂組成物、接合体および接着方法 Download PDFInfo
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- JP6748883B2 JP6748883B2 JP2015076500A JP2015076500A JP6748883B2 JP 6748883 B2 JP6748883 B2 JP 6748883B2 JP 2015076500 A JP2015076500 A JP 2015076500A JP 2015076500 A JP2015076500 A JP 2015076500A JP 6748883 B2 JP6748883 B2 JP 6748883B2
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- YTOVAWUSMUMHIM-UHFFFAOYSA-N iron(2+);5-methylcyclopenta-1,3-diene Chemical compound [Fe+2].C[C-]1C=CC=C1.C[C-]1C=CC=C1 YTOVAWUSMUMHIM-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
- QZUPTXGVPYNUIT-UHFFFAOYSA-N isophthalamide Chemical compound NC(=O)C1=CC=CC(C(N)=O)=C1 QZUPTXGVPYNUIT-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
- 239000010410 layer Substances 0.000 description 1
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- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
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- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
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- 150000004706 metal oxides Chemical class 0.000 description 1
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- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- UICBCXONCUFSOI-UHFFFAOYSA-N n'-phenylacetohydrazide Chemical compound CC(=O)NNC1=CC=CC=C1 UICBCXONCUFSOI-UHFFFAOYSA-N 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
- 229950002083 octabenzone Drugs 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
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 150000001367 organochlorosilanes Chemical class 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 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
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-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
- 230000001681 protective effect Effects 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000012712 reversible addition−fragmentation chain-transfer polymerization Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 238000013112 stability test 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
- 239000010959 steel Substances 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-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
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 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
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 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
- HIZCIEIDIFGZSS-UHFFFAOYSA-L trithiocarbonate Chemical class [S-]C([S-])=S HIZCIEIDIFGZSS-UHFFFAOYSA-L 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
Landscapes
- Polymerisation Methods In General (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
下記の(A)〜(C)成分を含有する光遅延硬化性樹脂組成物。
(A)成分:2官能以上のラジカル重合性官能基を有する化合物
(B)成分:メタロセン化合物
(C)成分:チオカルボニルチオ基含有化合物
<(A)成分>
本発明の(A)成分であるラジカル重合性官能基を2以上有する化合物とは、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、例えば(メタ)アクリロイル基含有化合物等が挙げられる。(A)成分としては、例えば、二官能性、三官能性及び多官能性のモノマー、オリゴマー等を使用することができる。(A)成分としては、好ましくは、アルキレンオキサイド構造または脂環構造を有し、且つラジカル重合性官能基を2以上の有する化合物である。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。
本発明の(B)成分であるメタロセン化合物の具体例としては、遷移金属が鉄であるフェロセン化合物、オスミウムであるオスモセン化合物、ルテニウムであるルテノセン化合物、チタンであるチタノセン化合物、コバルトであるコバルセン化合物、ニッケルであるニッケルセン化合物などが挙げられる。これらの中でも、光活性が高いことから、フェロセン化合物またはチタノセン化合物が好ましい。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。
本発明の(C)成分であるチオカルボニルチオ基含有化合物は、−S−C(=S)−基を有する化合物である。また、(C)成分は、リビングラジカル重合の1種であるRAFT重合(Reveresible Addition−Fragmen Transfer Polymerization)に用いられるRAFT剤として知られているものであるが、これに限定されない。(C)成分を本発明のその他成分と組み合わせることにより、光遅延硬化性と貯蔵安定性の優れた光遅延硬化性樹脂組成物が得られる。
本発明に対し、本発明の目的を損なわない範囲で、単官能のラジカル重合性官能基を有する化合物、増感剤、重合促進剤、スチレン系共重合体等の各種エラストマー、充填材、保存安定剤、酸化防止剤、光安定剤、接着助剤、可塑剤、顔料、難燃剤、及び界面活性剤等の添加剤を使用することができる。
(実施例1)
本発明の(A)成分としてトリシクロデカンジメタノールジメタクリレート(DCP、新中村化学社製)100質量部と、(B)成分としてチタノセンジクロリド(試薬)0.1質量部と、(C)成分として化学式4で表されるチオカルボニルチオ基含有トリチオカルボナート化合物(製品名723274 、アルドリッチ社製)0.1質量部を添加し、遮光下で常温にてプラネタリーミキサーで60分混合し、光遅延硬化性樹脂組成物である実施例1を得た。
実施例1において、トリシクロデカンジメタノールジメタクリレートの代わりに、(A)成分に該当するノナエチレングリコールジメタクリレート(製品名ライトエステル9EG、共栄社化学工業株式会社製)を用いた以外は、実施例1と同様にして調製し、実施例2を得た。
実施例1において、チタノセンジクロライド0.1質量部を0.5質量部に変更した以外は実施例1と同様にして調製し、実施例4を得た。
実施例1において、トリシクロデカンジメタノールジメタクリレートの代わりに、(A)成分に該当しないイソボルニルアクリレートにした以外は、実施例1と同様にして調製し、比較例1を得た。
実施例1において、チタノセンジクロライドを除いた以外は、実施例1と同様にして調製し、比較例2を得た。
実施例1において、チタノセンジクロライドの代わりに(B)成分に該当しない2−ヒドロキシ−2−メチル−1−フェニル−プロパン−1−オン(ダロキュア1173、BASF社製)にした以外は、実施例1と同様にして調製し、比較例3を得た。
実施例1において、化学式4で表されるチオカルボニルチオ基含有トリチオカルボナート化合物を除いた以外は、実施例1と同様にして調製し、比較例4を得た。
比較例4において、チタノセンジクロライドの代わりに(B)成分に該当するフェロセン(試薬)にした以外は、比較例4と同様にして調製し、比較例5を得た。
各種特性に関して次のようにして測定した。
10mm×10mmのガラス板に各組成物を100μmの厚みになるように塗布する。次に、紫外線照射機を用いて0.2J/cm2の積算光量の光を照射した。その後、25℃環境下で、試験片表面のべたつきがなくなるまでの時間を評価し、その結果を表1に示す。なお、べたつきがなくなったかどうかの判断は、ポリテトラフルオロエチレンの棒による接触試験で判断した。
なお、表中の「即硬化」とは、光照射直後に硬化しており、光遅延硬化性が確認できなかったものである。「未硬化」とは照射後60分経過後も硬化していなかったものである。
各組成物を25℃の環境下で遮光容器中に60日間密閉保存し、下記基準に基づき評価し、その結果を表1に示す。
評価基準
○:組成物の流動性が確認できた。
×:組成物がゲル化して流動しなくなっていた。
Claims (6)
- 下記の(A)〜(C)成分を含有する光遅延硬化性樹脂組成物。
(A)成分:(メタ)アクリロイル基を2以上有する化合物
(B)成分:メタロセン化合物
(C)成分:下記の式(1)〜(15)のいずれかで表される、RAFT剤として用いられるトリチオカルボナート化合物
- 前記(A)成分が、アルキレンオキサイド構造または脂環構造を有する化合物であることを特徴とする請求項1に記載の光遅延硬化性樹脂組成物。
- 更に、単官能性(メタ)アクリレート化合物を含むことを特徴とする請求項1または2のいずれか1項に記載の光遅延硬化性樹脂組成物。
- 前記(A)成分100質量部に対して、前記(B)成分が0.001〜5質量部であり、前記(C)成分が0.001〜5質量部であることを特徴とする請求項1〜3のいずれか1項に記載の光遅延硬化性樹脂組成物。
- 請求項1〜4のいずれか1項に記載の光遅延硬化性樹脂組成物を用いて光透過性に劣る被着体同士を接着してなる接合体。
- 請求項1〜4のいずれか1項に記載の光遅延硬化性樹脂組成物を用いて光透過性に劣る被着体同士を接合する接着方法であって、
前記被着体の少なくとも一方に塗布した前記光遅延硬化性樹脂組成物に、活性エネルギー線を照射し、接合するか、あるいは、
塗布する前に活性エネルギー線を照射した前記光遅延硬化性樹脂組成物を、前記被着体の少なくとも一方に塗布し、接合する、
接着方法。
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JP5579217B2 (ja) * | 2012-03-27 | 2014-08-27 | 富士フイルム株式会社 | 平版印刷版原版 |
CN103540241A (zh) * | 2013-10-18 | 2014-01-29 | 安徽蓝柯复合材料有限公司 | 一种紫外光固化底漆木器涂料及其制备方法 |
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