TW202112747A - 胺甲醯肟化合物以及含有該化合物之聚合起始劑及聚合性組合物 - Google Patents
胺甲醯肟化合物以及含有該化合物之聚合起始劑及聚合性組合物 Download PDFInfo
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- TW202112747A TW202112747A TW109119445A TW109119445A TW202112747A TW 202112747 A TW202112747 A TW 202112747A TW 109119445 A TW109119445 A TW 109119445A TW 109119445 A TW109119445 A TW 109119445A TW 202112747 A TW202112747 A TW 202112747A
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- 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
- 125000003944 tolyl group Chemical group 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
本發明係關於一種胺甲醯肟化合物。
一般而言,感光性樹脂組合物等聚合性組合物係於感光性樹脂等聚合性化合物中添加光聚合起始劑而成者,可藉由照射能量線(光)進行聚合硬化或顯影,因此可用於光硬化性油墨、感光性印刷版、各種光阻劑、光硬化性接著劑等。
光聚合起始劑根據藉由照射能量線(光)而產生之活性種之差異而被分成光自由基產生劑、光產酸劑、光產鹼劑。光自由基產生劑具有硬化速度較快、硬化後不會殘存活性種等優點,但另一方面,存在如下缺點:由於會因氧氣而產生硬化阻礙,故而於薄膜之硬化中必須設置阻隔氧氣之層等。光產酸劑具有不會因氧氣而受到阻礙之優點,但另一方面,存在如下缺點:因活性種之酸殘存而腐蝕金屬基板或使硬化後之樹脂改性等。光產鹼劑由於不易產生上述由氧氣導致之硬化阻礙及由殘存活性種導致之腐蝕等問題而受到關注,但總體而言,存在與光產酸劑相比為低感度(低硬化性)之問題。光產鹼劑例如記載於專利文獻1及2中。
先前技術文獻
專利文獻
專利文獻1:US9594302
專利文獻2:日本專利特開2013-163670號公報
然而,先前之光產鹼劑之產鹼效率較低,硬化感度並不充分。
因此,本發明之課題在於提供一種具有較高之光產鹼效率之化合物。
本發明者進行努力研究,發現特定結構之化合物具有較高之光產鹼效率而作為聚合起始劑有用。
即,本發明係一種胺甲醯肟化合物,其以下述通式(I)表示。
[化1]
(式中,R1
表示氫原子、鹵素原子、硝基、氰基、碳原子數1~20之烴基或烴基中之亞甲基被取代為選自下述<群A>中之二價基而成之碳原子數1~20之基,
R2
表示氫原子、碳原子數1~20之烴基或烴基中之亞甲基被取代為選自下述<群A>中之二價基而成之碳原子數1~20之基,
R3
、R4
、R5
、R6
、R7
、R8
及R9
分別獨立地表示氫原子、鹵素原子、氰基、硝基、-OR10
、-COOR10
、-CO-R10
、-SR10
、碳原子數1~20之烴基或碳原子數2~20之含雜環之基,
R10
表示氫原子、碳原子數1~20之烴基、碳原子數2~20之含雜環之基或烴基中之亞甲基被取代為選自下述<群A>中之二價基而成之碳原子數1~20之基,於分子中存在複數個R10
之情形時,其等可相同,亦可不同,
X1
表示-NR21
R22
或下述通式(a)或者下述通式(b)所表示之基,
R21
及R22
分別獨立地表示氫原子、碳原子數1~20之烴基或烴基中之亞甲基被取代為選自下述<群A>中之二價基而成之碳原子數1~20之基,
R1
、R2
、R3
、R4
、R5
、R6
、R7
、R8
、R9
、R10
、R21
及R22
亦可為烴基中之氫原子之1個或2個以上被取代為鹵素原子、氰基、硝基、羥基、-OR11
、-COOR11
、-CO-R11
或-SR11
而成之碳原子數1~20之基,
R11
表示氫原子、碳原子數1~20之烴基、烴基中之亞甲基被取代為選自下述<群A>中之二價基而成之碳原子數1~20之基或烴基中之氫原子之1個或2個以上被取代為鹵素原子、氰基、硝基或羥基而成之碳原子數1~20之基,於分子中存在複數個R11
之情形時,其等可相同,亦可不同,
<群A>為-O-、-CO-、-COO-、-NR12
-、-NR12
CO-及-S-,
R12
表示氫原子或碳原子數1~20之烴基,於分子中存在複數個R12
之情形時,其等可相同,亦可不同,
R3
與R4
、R6
與R7
、R7
與R8
及R8
與R9
可分別獨立地相互連結而形成包含氫原子及碳原子之碳原子數3~10之環,
R3
與R4
、R6
與R7
、R7
與R8
及R8
與R9
中之至少1組相互連結而形成苯環,
R21
與R22
可相互連結而形成包含氫原子、氮原子及碳原子之碳原子數2~10之環或包含氫原子、氧原子、氮原子及碳原子之碳原子數2~10之環,
n表示0或1)
[化2]
(式中,R31
、R32
、R33
、R34
、R35
、R36
、R37
、R38
、R39
及R40
分別獨立地表示氫原子、碳原子數1~20之烴基或烴基中之亞甲基被取代為選自下述<群B>中之二價基而成之碳原子數1~20之基,
R31
、R32
、R33
、R34
、R35
、R36
、R37
、R38
、R39
及R40
亦可為烴基中之氫原子之1個或2個以上被取代為鹵素原子、氰基、硝基、羥基、-OR41
、-COOR41
、-CO-R41
或-SR41
而成之碳原子數1~20之基,
R41
表示氫原子或碳原子數1~20之烴基,於基中存在複數個R41
之情形時,其等可相同,亦可不同,
<群B>為-O-、-CO-、-COO-、-NR42
-、-NR42
CO-及-S-,
R42
表示氫原子或碳原子數1~20之烴基,於基中存在複數個R42
之情形時,其等可相同,亦可不同,
R31
與R32
、R33
與R34
、R35
與R36
、R37
與R38
、及R39
與R40
可分別獨立地相互連結而形成包含氫原子、氮原子及碳原子之碳原子數2~10之環或包含氫原子、氧原子、氮原子及碳原子之碳原子數2~10之環,
*表示鍵結鍵)
以下,對本發明詳細地進行說明。
本發明之胺甲醯肟化合物係上述通式(I)所表示者。上述通式(I)所表示之胺甲醯肟化合物中存在因肟之雙鍵而產生之幾何異構物,但不對該等進行區別。
即,於本說明書中,上述通式(I)所表示之胺甲醯肟化合物、以及下述作為該化合物之較佳形態之化合物及例示化合物表示異構物之混合物或其中任一者,並不限定於所示結構之異構物。
以下,將上述通式(I)所表示之胺甲醯肟化合物亦簡稱為「通式(I)所表示之化合物」或「本發明之化合物」。
作為上述通式(I)、上述通式(a)及上述通式(b)中之鹵素原子,可列舉:氟原子、氯原子、溴原子、碘原子。
作為上述通式(I)、上述通式(a)及上述通式(b)中之碳原子數1~20之烴基,可列舉:碳原子數1~20之脂肪族烴基及碳原子數6~20之芳香族烴基。
作為上述碳原子數1~20之脂肪族烴基,例如可列舉:甲基、乙基、丙基、異丙基、丁基、異丁基、第二丁基、第三丁基、戊基、異戊基、第三戊基、己基、庚基、辛基、異辛基、2-乙基己基、第三辛基、壬基、異壬基、癸基、異癸基、十一烷基、十二烷基、十四烷基、十六烷基、十八烷基、二十烷基等烷基;環戊基、環己基等環烷基;及環己基甲基等環烷基烷基、以及作為將該等基之碳-碳單鍵取代為碳-碳雙鍵或碳-碳三鍵而成之結構之不飽和脂肪族烴基等。
作為上述碳原子數6~20之芳香族烴基,例如可列舉:苯基、甲苯基、二甲苯基、2,4,6-三甲苯基、苄基、萘基、菲基、芘基及聯苯基等。
作為R1
~R10
、R21
及R22
所表示之烴基中之氫原子之1個或2個以上被取代為鹵素原子、氰基、硝基、羥基、-OR11
、-COOR11
、-CO-R11
或-SR11
而成之碳原子數1~20之基,可列舉為上述碳原子數1~20之烴基中之氫原子之1個或2個以上被取代為鹵素原子、氰基、硝基、羥基、-OR11
、-COOR11
、-CO-R11
或-SR11
而成之結構且整體之碳原子數為1~20之基。又,作為R11
所表示之烴基中之氫原子之1個或2個以上被取代為鹵素原子、氰基、硝基、羥基而成之碳原子數1~20之基,可列舉為上述碳原子數1~20之烴基中之氫原子之1個或2個以上被取代為鹵素原子、氰基、硝基、羥基而成之結構且整體之碳原子數為1~20之基。
作為R1
~R11
、R21
及R22
所表示之烴基中之亞甲基被取代為選自上述<群A>中之二價基而成之碳原子數1~20之基,可列舉為上述碳原子數1~20之烴基中之亞甲基之1個或2個以上被取代為-O-、-CO-、-COO-、-NR12
-、-NR12
CO-或-S-而成之結構且整體之碳原子數為1~20之基。
作為R31
~R40
所表示之烴基中之氫原子之1個或2個以上被取代為鹵素原子、氰基、硝基、羥基、-OR41
、-COOR41
、-CO-R41
或-SR41
而成之碳原子數1~20之基,可列舉為上述碳原子數1~20之烴基中之氫原子之1個或2個以上被取代為鹵素原子、氰基、硝基、羥基、-OR41
、-COOR41
、-CO-R41
或-SR41
而成之結構且整體之碳原子數為1~20之基。
作為R31
~R40
所表示之烴基中之亞甲基被取代為選自上述<群B>中之二價基而成之碳原子數1~20之基,可列舉為上述碳原子數1~20之烴基中之亞甲基之1個或2個以上被取代為-O-、-CO-、-COO-、-NR42
-、-NR42
CO-或-S-而成之結構且整體之碳原子數為1~20之基。
作為上述通式(I)中之碳原子數2~20之含雜環之基,例如可列舉:四氫呋喃基、二氧戊環基、四氫哌喃基、嗎啉基、呋喃基、噻吩基、甲基噻吩基、己基噻吩基、苯并噻吩基、吡咯基、吡咯啶基、咪唑基、咪唑啉基、咪唑啶基、吡唑啉基、吡唑啶基、哌啶基及哌嗪基等雜環基、以及含有該等基之基等。
又,碳原子數2~20之含雜環之基可具有鹵素原子、氰基、硝基、羥基、-OR50
、-COOR50
、-CO-R50
或-SR50
等取代基,亦可包含-O-、-CO-、-COO-、-NR51
-、-NR51
CO-或-S-等結構。
此處,R50
及R51
分別獨立地表示氫原子或碳原子數1~20之烴基。R50
及R51
所表示之碳原子數1~20之烴基係與上述通式(I)、上述通式(a)及上述通式(b)中之碳原子數1~20之烴基相同。
作為上述通式(I)中之R3
與R4
、R6
與R7
、R7
與R8
及R8
與R9
相互連結而形成之包含氫原子及碳原子之碳原子數3~10之環,可列舉:苯環、環己烯環、環己烷環、環戊二烯環、環戊烷環等。又,該等環亦可具有取代基,作為該情形時之取代基,可列舉上述碳原子數2~20之含雜環之基可具有之取代基。
作為上述通式(I)、上述通式(a)及上述通式(b)中之R21
與R22
、R31
與R32
、R33
與R34
、R35
與R36
、R37
與R38
、及R39
與R40
相互連結而形成之包含氫原子、氮原子及碳原子之碳原子數2~10之環,作為包括所鍵結之氮原子在內之環,可列舉:吡咯環、吡咯啶環、咪唑環、咪唑啶環、咪唑啉環、吡唑環、吡唑啶環、哌啶環、哌𠯤環等。該等環亦可具有取代基,作為該情形時之取代基,可列舉上述碳原子數2~20之含雜環之基可具有之取代基。
作為上述通式(I)、上述通式(a)及上述通式(b)中之R21
與R22
、R31
與R32
、R33
與R34
、R35
與R36
、R37
與R38
、及R39
與R40
相互連結而形成之包含氫原子、氧原子、氮原子及碳原子之碳原子數2~10之環,作為包括所鍵結之氮原子在內之環,可列舉:嗎啉環、㗁唑環、㗁唑啉環、㗁二唑環等。該等環亦可具有取代基,作為該情形時之取代基,可列舉上述碳原子數2~20之含雜環之基可具有之取代基。
通式(I)中之R1
為碳原子數6~20之芳香族烴基之胺甲醯肟化合物由於所獲得之聚合性組合物會於低曝光量下進行硬化,故而較佳,尤佳為通式(I)中之R1
為含有苯環之碳原子數6~20之芳香族烴基之胺甲醯肟化合物。又,上述R1
為碳原子數1~20之脂肪族烴基之情況亦由於所獲得之聚合性組合物會於低曝光量下進行硬化,故而較佳。
於本發明中,就對溶劑之溶解性優異之方面而言,較佳為通式(I)中之R2
為碳原子數1~10之脂肪族烴基之胺甲醯肟化合物,尤佳為通式(I)中之R2
為碳原子數1~10之具有支鏈之烷基。
上述通式(I)中之R3
與R4
或R8
與R9
相互連結而形成苯環之胺甲醯肟化合物由於所獲得之聚合性組合物會於低曝光量下進行硬化,故而較佳。
通式(I)中之X1
為-NR21
R22
且R21
與R22
相互連結而形成包含氫原子、氮原子及碳原子之碳原子數2~10之環或包含氫原子、氧原子、氮原子及碳原子之碳原子數2~10之環之胺甲醯肟化合物由於產鹼效率較高,故而較佳,更佳為形成包含氫原子、氮原子及碳原子之碳原子數2~6之環或包含氫原子、氧原子、氮原子及碳原子之碳原子數2~6之環。
尤佳為R21
與R22
相互連結而形成包含氫原子、氮原子及碳原子之碳原子數2~6之環,進而較佳為形成哌啶環或吡咯啶環。
又,於通式(I)中之X1
為-NR21
R22
之胺甲醯肟化合物中,R21
為氫原子且R22
為碳原子數6~20之芳香族烴基、以及R21
及R22
均為碳原子數1~20之脂肪族烴基亦由於產鹼效率較高,故而較佳。
R3
、R4
、R5
、R6
、R7
、R8
及R9
中之一個以上為-CO-R10
且R10
為碳原子數6~20之芳香族烴基之胺甲醯肟化合物由於所獲得之聚合性組合物會於低曝光量下進行硬化,故而較佳,尤佳為R7
為-CO-R10
且R10
為含有苯環之碳原子數6~20之芳香族烴基之胺甲醯肟化合物。
上述通式(I)中之n為0之胺甲醯肟化合物由於對熱之穩定性較高,故而較佳。
上述通式(I)中之n為1之胺甲醯肟化合物由於所獲得之聚合性組合物會於低曝光量下進行硬化,故而較佳。
於本發明中,最佳為如下胺甲醯肟化合物,即通式(I)中之R1
為碳原子數6~20之芳香族烴基,R2
為碳原子數1~10之具有支鏈之烷基,R8
與R9
相互連結而形成苯環,X1
為-NR21
R22
且R21
與R22
相互連結而形成包含氫原子、氮原子及碳原子之碳原子數2~10之環,R7
為-CO-R10
,R10
為碳原子數6~20之芳香族烴基,n為0。
作為上述通式(I)所表示之胺甲醯肟化合物之具體例,可列舉以下化學式(1)~(52)所表示之化合物。但是,本發明並不受以下化合物任何限制。
上述通式(I)所表示之本發明之胺甲醯肟化合物之製造方法並無特別限定,例如於R8
與R9
相互連結而形成苯環且X1
為-NR21
R22
、n=0之情形時,可依據下述反應式1並藉由以下方法來製造。
即,藉由使公知之酮化合物與鹽酸羥胺於吡啶等鹼之存在下進行反應而獲得肟化合物。繼而,使氯甲酸4-硝基苯酯與肟化合物反應,繼而使胺反應,藉此獲得本發明之胺甲醯肟化合物。
上述反應式1表示X1
為-NR21
R22
之情形,但藉由變更所使用之胺,亦可製造X1
為上述通式(a)或上述通式(b)所表示之基之化合物。
肟化合物亦可利用日本專利第4223071號公報所記載之方法來製造。
本發明之胺甲醯肟化合物由於藉由紫外線等光照射或加熱而有效率地產生鹼及自由基,故而作為潛在性產鹼劑及聚合起始劑有用,尤其是作為聚合起始劑有用。
所謂本發明之潛在性產鹼劑,意指含有如下化合物之組成物,該化合物具有藉由照射紫外線等光而高效率地產生鹼之功能,作為該組成物之用途,可列舉pH值調整劑、利用鹼之觸媒等。
又,本發明之胺甲醯肟化合物由於在上述聚合起始劑之中,藉由光照射所帶來之鹼及自由基之產生效率較高,故而作為光產鹼劑及光自由基聚合起始劑有用,且由於產鹼效率非常高,故而尤其是作為光產鹼劑有用。
本發明之聚合起始劑含有至少1種上述通式(I)所表示之胺甲醯肟化合物。作為可與上述通式(I)所表示之胺甲醯肟化合物併用之聚合起始劑,並無特別限制,可列舉先前已知之光產鹼劑及光自由基聚合起始劑。
關於上述聚合起始劑中之上述通式(I)所表示之化合物之含量,就所獲得之聚合性組合物會於低曝光量下進行硬化之方面而言,較佳為1~100質量%,更佳為50~100質量%。
本發明之聚合性組合物含有具有至少1種上述通式(I)所表示之胺甲醯肟化合物之聚合起始劑(A)、及聚合性化合物(B)。
關於聚合起始劑(A)之含量,就所獲得之聚合性組合物會於低曝光量下進行硬化之方面而言,相對於聚合性化合物(B)100質量份較佳為1~20質量份,更佳為1~10質量份。藉由使聚合起始劑(A)之含量為1質量份以上,容易防止由硬化感度不足所導致之硬化不良,故而較佳,藉由設為20質量份以下,可抑制光照射時或加熱時之揮發物,故而較佳。
作為本發明中所使用之聚合性化合物(B),可列舉:具有陰離子聚合性官能基之化合物、藉由鹼作為觸媒發揮作用之反應或鹼所加成之反應而硬化之化合物、及自由基聚合性化合物,就所獲得之聚合性組合物會於低曝光量下進行硬化之方面而言,較佳為藉由照射紫外線等能量線而進行聚合並硬化之感光性樹脂或硬化溫度低溫化之硬化樹脂。所謂上述陰離子聚合性官能基,意指可藉由利用紫外線等活性能量線而自光產鹼劑產生之鹼進行聚合之官能基,例如可列舉:環氧基、環硫化物基、環狀單體(σ-戊內酯、ε-己內醯胺)、丙二酸酯等。作為鹼作為觸媒發揮作用之反應或鹼所加成之反應,可列舉:藉由異氰酸酯與醇所進行之胺基甲酸酯鍵形成反應、含有環氧樹脂與羥基之化合物之加成反應、含有環氧樹脂與羧酸基之化合物之加成反應、環氧樹脂與硫醇化合物之加成反應、(甲基)丙烯酸基之麥可加成反應、聚醯胺酸之脫水縮合反應、烷氧基矽烷之水解/縮聚反應等。
作為具有陰離子聚合性官能基之化合物,例如可列舉:環氧樹脂、氧雜環丁烷樹脂、環硫樹脂、環狀醯胺(內醯胺系化合物)、環狀酯(內酯系化合物)、環狀碳酸酯系化合物、丙二酸酯等。作為藉由鹼作為觸媒發揮作用之反應或鹼所加成之反應而硬化之化合物,例如可列舉:聚醯胺樹脂(藉由脫水環化進行之聚醯亞胺化反應)、環氧基・羥基系(開環加成反應)、環氧基・羧酸系(開環加成反應)、環氧基・硫醇系(開環加成反應)、環氧基・酸酐系(開環縮聚)、氰酸酯(三𠯤環化反應)、氰酸酯・環氧系(環化反應)、氰酸酯・馬來醯亞胺系(交聯共聚)、氧雜環丁烷・羥基系(開環加成反應)、氧雜環丁烷・羧酸系(開環加成反應)、氧雜環丁烷・硫醇系(開環加成反應)、氧雜環丁烷・酸酐系(開環縮聚)、環硫化物・羥基系(開環加成反應)、環硫化物・羧酸系(開環加成反應)、環硫化物・硫醇系(開環加成反應)、環硫化物・酸酐系(開環縮聚)、丙烯酸・硫醇系(麥可加成反應)、甲基丙烯酸・硫醇系(麥可加成反應)、丙烯酸・胺系(麥可加成反應)、甲基丙烯酸・胺系(麥可加成反應)、羧酸・羥基系(聚酯化反應)、羧酸・胺系(聚醯胺化反應)、異氰酸酯・羥基系(聚胺基甲酸酯化反應)、異氰酸酯・硫醇系(多硫胺基甲酸酯化反應)、烷氧基矽烷系(水解・縮聚)等。作為藉由自由基進行聚合之化合物,可列舉乙烯性不飽和化合物。就反應性較高之方面而言,較佳為使用進行自由基聚合之化合物。該等樹脂可單獨使用,亦可將2種以上併用。作為較佳組合,就反應快速進行或接著性良好之方面而言,可列舉環氧樹脂與酚樹脂之組合,就低溫硬化性優異之方面而言,可列舉環氧樹脂與硫醇化合物之組合,就反應性較高之方面而言,可列舉乙烯性不飽和化合物與硫醇化合物之組合。
上述環氧樹脂只要具有環氧基即可,但本發明之胺甲醯肟化合物除外。作為環氧樹脂,例如可列舉:對苯二酚、間苯二酚、鄰苯二酚、間苯三酚等單核多酚化合物之聚縮水甘油醚化合物;二羥基萘、聯苯酚、亞甲基雙酚(雙酚F)、亞甲基雙(鄰甲酚)、亞乙基雙酚、亞異丙基雙酚(雙酚A)、4,4'-二羥基二苯甲酮、亞異丙基雙(鄰甲酚)、四溴雙酚A、1,3-雙(4-羥基異丙苯基苯)、1,4-雙(4-羥基異丙苯基苯)、1,1,3-三(4-羥基苯基)丁烷、1,1,2,2-四(4-羥基苯基)乙烷、硫代雙酚、磺基雙酚、氧基雙酚、酚系酚醛清漆、鄰甲酚酚醛清漆、乙基酚系酚醛清漆、丁基酚系酚醛清漆、辛基酚系酚醛清漆、間苯二酚酚醛清漆、萜酚等多核多酚化合物之聚縮水甘油醚化合物;乙二醇、丙二醇、丁二醇、己二醇、聚二醇、硫代雙乙醇、甘油、三羥甲基丙烷、季戊四醇、山梨糖醇、雙酚A-環氧乙烷加成物等多元醇類之聚縮水甘油醚;順丁烯二酸、反丁烯二酸、伊康酸、琥珀酸、戊二酸、辛二酸、己二酸、壬二酸、癸二酸、二聚酸、三聚物酸、鄰苯二甲酸、間苯二甲酸、對苯二甲酸、偏苯三甲酸、均苯三酸、均苯四甲酸、四氫鄰苯二甲酸、六氫鄰苯二甲酸、內亞甲基四氫鄰苯二甲酸等脂肪族、芳香族或脂環族多元酸之縮水甘油酯類、及甲基丙烯酸縮水甘油酯之均聚物或共聚物;N,N-二縮水甘油基苯胺、雙(4-(N-甲基-N-縮水甘油基胺基)苯基)甲烷、二縮水甘油基鄰甲苯胺等具有縮水甘油基胺基之環氧化合物;乙烯基環己烯二環氧化物、二環戊二烯二環氧化物、3,4-環氧環己基甲基-3,4-環氧環己烷羧酸酯、3,4-環氧-6-甲基環己基甲基-6-甲基環己烷羧酸酯、己二酸雙(3,4-環氧-6-甲基環己基甲基)酯等環狀烯烴化合物之環氧化物;環氧化聚丁二烯、環氧化丙烯腈-丁二烯共聚物、環氧化苯乙烯-丁二烯共聚物等環氧化共軛二烯聚合物、三縮水甘油基異氰尿酸酯等雜環化合物。又,該等環氧樹脂亦可為藉由封端異氰酸酯之預聚物進行內部交聯而成者或利用多元活性氫化合物(多酚、聚胺、含羰基之化合物、聚磷酸酯等)進行高分子量化而成者。
上述環氧樹脂之中,就所獲得之聚合性組合物之硬化性優異之方面而言,較佳為具有縮水甘油基者,更佳為具有2官能以上之縮水甘油基者。
上述酚樹脂只要具有酚性羥基即可,但上述胺甲醯肟化合物及環氧樹脂除外。作為酚樹脂,就所獲得之聚合性組合物之硬化性優異之方面而言,較佳為1分子中具有2個以上羥基之酚樹脂,通常可使用公知者。作為酚樹脂,例如可列舉:雙酚A型酚樹脂、雙酚E型酚樹脂、雙酚F型酚樹脂、雙酚S型酚樹脂、酚系酚醛清漆型樹脂、雙酚A酚醛清漆型酚樹脂、縮水甘油酯型酚樹脂、芳烷基酚醛清漆型酚樹脂、聯苯基芳烷基型酚樹脂、甲酚酚醛清漆型酚樹脂、多官能酚樹脂、萘酚樹脂、萘酚酚醛清漆樹脂、多官能萘酚樹脂、蒽型酚樹脂、萘骨架改性酚醛清漆型酚樹脂、苯酚芳烷基型酚樹脂、萘酚芳烷基型酚樹脂、二環戊二烯型酚樹脂、聯苯型酚樹脂、脂環式酚樹脂、多元醇型酚樹脂、含磷之酚樹脂、含聚合性不飽和烴基之酚樹脂及含羥基之聚矽氧樹脂類,並無特別限制。該等酚樹脂可單獨使用1種或將2種以上組合使用。
上述硫醇化合物只要具有硫醇基即可,但上述胺甲醯肟化合物、環氧樹脂及酚樹脂除外。硫醇化合物之中,就所獲得之聚合性組合物之硬化性優異之方面而言,較佳為1分子中具有2個以上硫醇基者。
作為硫醇化合物之較佳具體例,為雙(2-巰基乙基)硫醚、2,5-二巰基甲基-1,4-二噻烷、1,3-雙(巰基甲基)苯、1,4-雙(巰基甲基)苯、4-巰基甲基-1,8-二巰基-3,6-二噻辛烷、4,8-二巰基甲基-1,11-二巰基-3,6,9-三噻十一烷、4,7-二巰基甲基-1,11-二巰基-3,6,9-三噻十一烷、5,7-二巰基甲基-1,11-二巰基-3,6,9-三噻十一烷、1,2,6,7-四巰基-4-噻庚烷、季戊四醇、1,1,3,3-四(巰基甲基硫基)丙烷、季戊四醇四巰基丙酸酯、季戊四醇四巰基乙醇酸酯、三羥甲基丙烷巰基乙醇酸酯、及三羥甲基丙烷三巰基丙酸酯,更佳為列舉:1,2,6,7-四巰基-4-噻庚烷、季戊四醇、雙(2-巰基乙基)硫醚、2,5-雙(2-巰基甲基)-1,4-二噻烷、4-巰基甲基-1,8-二巰基-3,6-二噻辛烷、1,3-雙(巰基甲基)苯、季戊四醇四巰基丙酸酯、及季戊四醇四巰基乙醇酸酯。
尤佳之化合物為1,2,6,7-四巰基-4-噻庚烷、季戊四醇、雙(2-巰基乙基)硫醚、2,5-二巰基甲基-1,4-二噻烷、及4-巰基甲基-1,8-二巰基-3,6-二噻辛烷。
硫醇化合物可單獨使用1種或將2種以上組合使用。
作為上述聚醯胺樹脂,可列舉以作為酸二酐之伸乙基四羧酸二酐、1,2,3,4-苯四羧酸二酐、1,2,3,4-環己烷四羧酸二酐、2,2',3,3'-二苯甲酮四羧酸二酐、2,2,3,3-聯苯基四羧酸酐、1,4,5,8-萘四羧酸二酐等作為原料且以作為二胺之(鄰、間或者對)苯二胺、(3,3'-或者4,4'-)二胺基二苯醚、二胺基二苯甲酮、(3,3'-或者4,4'-)二胺基二苯甲烷等作為原料之樹脂。
作為上述聚胺基甲酸酯樹脂,可列舉以甲苯二異氰酸酯、六亞甲基二異氰酸酯、二苯甲烷二異氰酸酯、異佛酮二異氰酸酯等多官能異氰酸酯與聚醚多元醇、聚酯聚醇、聚碳酸酯多元醇等多元醇(多官能醇)作為原料之樹脂等。
又,作為上述尼龍樹脂,可列舉以ε-己內醯胺、十二內醯胺等環狀單體作為原料之樹脂等。
又,作為上述聚酯樹脂,可列舉以δ-戊內酯、β-丙內酯等環狀單體作為原料之樹脂等。
上述乙烯性不飽和化合物只要具有乙烯性不飽和鍵即可,但上述胺甲醯肟化合物、環氧樹脂、酚樹脂及硫醇化合物除外。作為乙烯性不飽和化合物,例如可列舉:乙烯、丙烯、丁烯、異丁烯、氯乙烯、偏二氯乙烯、偏二氟乙烯、四氟乙烯等不飽和脂肪族烴;(甲基)丙烯酸、α-氯丙烯酸、伊康酸、順丁烯二酸、檸康酸、反丁烯二酸、雙環庚烯二甲酸、丁烯酸、異丁烯酸、乙酸乙烯酯、乙酸烯丙酯、桂皮酸、山梨酸、中康酸、琥珀酸單[2-(甲基)丙烯醯氧基乙基]酯、鄰苯二甲酸單[2-(甲基)丙烯醯氧基乙基]酯、ω-羧基聚己內酯單(甲基)丙烯酸酯等兩末端具有羧基及羥基之聚合物之單(甲基)丙烯酸酯;(甲基)丙烯酸羥乙酯・順丁烯二酸酯、(甲基)丙烯酸羥丙酯・順丁烯二酸酯、二環戊二烯・順丁烯二酸酯或具有1個羧基及2個以上(甲基)丙烯醯基之多官能(甲基)丙烯酸酯等不飽和多元酸;(甲基)丙烯酸2-羥基乙酯、(甲基)丙烯酸2-羥基丙酯、(甲基)丙烯酸縮水甘油酯、(甲基)丙烯酸甲酯、(甲基)丙烯酸丁酯、(甲基)丙烯酸異丁酯、(甲基)丙烯酸第三丁酯、(甲基)丙烯酸環己酯、(甲基)丙烯酸正辛酯、(甲基)丙烯酸異辛酯、(甲基)丙烯酸異壬酯、(甲基)丙烯酸硬脂酯、(甲基)丙烯酸月桂酯、(甲基)丙烯酸甲氧基乙酯、(甲基)丙烯酸二甲基胺基甲酯、(甲基)丙烯酸二甲基胺基乙酯、(甲基)丙烯酸胺基丙酯、(甲基)丙烯酸二甲基胺基丙酯、(甲基)丙烯酸乙氧基乙酯、(甲基)丙烯酸聚(乙氧基)乙酯、(甲基)丙烯酸丁氧基乙氧基乙酯、(甲基)丙烯酸乙酯己酯、(甲基)丙烯酸苯氧基乙酯、(甲基)丙烯酸四氫呋喃酯、(甲基)丙烯酸乙烯酯、(甲基)丙烯酸烯丙酯、(甲基)丙烯酸苄酯、乙二醇二(甲基)丙烯酸酯、二乙二醇二(甲基)丙烯酸酯、三乙二醇二(甲基)丙烯酸酯、聚乙二醇二(甲基)丙烯酸酯、丙二醇二(甲基)丙烯酸酯、1,4-丁二醇二(甲基)丙烯酸酯、1,6-己二醇二(甲基)丙烯酸酯、三羥甲基乙烷三(甲基)丙烯酸酯、三羥甲基丙烷三(甲基)丙烯酸酯、二季戊四醇六(甲基)丙烯酸酯、二季戊四醇五(甲基)丙烯酸酯、季戊四醇四(甲基)丙烯酸酯、季戊四醇三(甲基)丙烯酸酯、三環癸烷二羥甲基二(甲基)丙烯酸酯、異氰尿酸三[(甲基)丙烯醯基乙基]酯、聚酯(甲基)丙烯酸酯低聚物等不飽和一元酸及多元醇或多酚之酯;(甲基)丙烯酸鋅、(甲基)丙烯酸鎂等不飽和多元酸之金屬鹽;順丁烯二酸酐、伊康酸酐、檸康酸酐、甲基四氫鄰苯二甲酸酐、四氫鄰苯二甲酸酐、三烷基四氫鄰苯二甲酸酐、5-(2,5-二側氧四氫呋喃基)-3-甲基-3-環己烯-1,2-二羧酸酐、三烷基四氫鄰苯二甲酸酐-順丁烯二酸酐加成物、十二烯基琥珀酸酐、甲基雙環庚烯二甲酸酐等不飽和多元酸之酸酐;(甲基)丙烯醯胺、亞甲基雙-(甲基)丙烯醯胺、二伸乙基三胺三(甲基)丙烯醯胺、苯二甲基雙(甲基)丙烯醯胺、α-氯丙烯醯胺、N-2-羥基乙基(甲基)丙烯醯胺等不飽和一元酸及多元胺之醯胺;丙烯醛等不飽和醛;(甲基)丙烯腈、α-氯丙烯腈、二氰亞乙烯、氰化烯丙基等不飽和腈;苯乙烯、4-甲基苯乙烯、4-乙基苯乙烯、4-甲氧基苯乙烯、4-羥基苯乙烯、4-氯苯乙烯、二乙烯苯、乙烯基甲苯、乙烯基苯甲酸、乙烯基苯酚、乙烯基磺酸、4-乙烯基苯磺酸、乙烯基苄基甲醚、乙烯基苄基縮水甘油醚等不飽和芳香族化合物;甲基乙烯基酮等不飽和酮;乙烯胺、烯丙胺、N-乙烯基吡咯啶酮、乙烯基哌啶等不飽和胺化合物;烯丙醇、巴豆醇等乙烯醇;乙烯基甲醚、乙烯基***、正丁基乙烯醚、異丁基乙烯醚、烯丙基縮水甘油醚等乙烯醚;順丁烯二醯亞胺、N-苯基順丁烯二醯亞胺、N-環己基順丁烯二醯亞胺等不飽和醯亞胺類;茚、1-甲基茚等茚類;1,3-丁二烯、異戊二烯、氯丁二烯等脂肪族共軛二烯類;聚苯乙烯、聚(甲基)丙烯酸甲酯、聚-(甲基)丙烯酸正丁酯、聚矽氧烷等於聚合物分子鏈之末端具有單(甲基)丙烯醯基之巨單體類;氯乙烯、偏二氯乙烯、丁二酸二乙烯酯、鄰苯二甲酸二烯丙酯、磷酸三烯丙酯、異氰尿酸三烯丙酯、乙烯基硫醚、乙烯基咪唑、乙烯基㗁唑啉、乙烯基咔唑、乙烯基吡咯啶酮、乙烯基吡啶、含羥基之乙烯基單體及聚異氰酸酯化合物之胺基甲酸乙烯酯化合物、含羥基之乙烯基單體及聚環氧化合物之乙烯基環氧化合物。
乙烯性不飽和化合物可單獨使用或將2種以上混合使用。
作為上述乙烯性不飽和化合物,亦可使用市售品,例如可列舉:Kayarad DPHA、DPEA-12、PEG400DA、THE-330、RP-1040、NPGDA、PET30、R-684(以上由日本化藥製造);ARONIX M-215、M-350(以上由東亞合成製造);NK ESTER A-DPH、A-TMPT、A-DCP、A-HD-N、TMPT、DCP、NPG及HD-N(以上由新中村化學工業製造);SPC-1000、SPC-3000(以上由昭和電工製造)等。
聚合性組合物(B)之含量只要為適合其使用目的之量即可,為了防止硬化不良,較佳為以於聚合性組合物中之固形物成分(溶劑以外之總成分)中成為50質量份以上之方式含有,更佳為60質量份以上,尤佳為70質量份以上。
本發明之聚合性組合物可使用無機化合物、色料、潛在性環氧硬化劑、鏈轉移劑、增感劑、溶劑等添加劑作為任意成分。
作為上述無機化合物,例如可列舉:氧化鎳、氧化鐵、氧化銥、氧化鈦、氧化鋅、氧化鎂、氧化鈣、氧化鉀、二氧化矽、氧化鋁等金屬氧化物;層狀黏土礦物、米洛麗藍、碳酸鈣、碳酸鎂、鈷系、錳系、玻璃粉末(尤其是玻璃漿料)、雲母、滑石、高嶺土、亞鐵氰化物、各種金屬硫酸鹽、硫化物、硒化物、矽酸鋁、矽酸鈣、氫氧化鋁、鉑、金、銀、銅等。該等無機化合物例如可用作填充劑、抗反射劑、導電材、穩定劑、阻燃劑、機械強度改善劑、特殊波長吸收劑、發墨劑等。
作為上述色料,可列舉:顏料、染料、天然色素等。該等色料可單獨使用或將2種以上混合使用。
作為上述顏料,例如可使用:亞硝基化合物;硝基化合物;偶氮化合物;二偶氮化合物;𠮿化合物;喹啉化合物;蒽醌化合物;香豆素化合物;酞菁化合物;異吲哚啉酮化合物;異吲哚啉化合物;喹吖啶酮化合物;蒽締蒽酮化合物;芘酮化合物;苝化合物;吡咯并吡咯二酮化合物;硫靛化合物;二㗁𠯤化合物;三苯甲烷化合物;喹酞酮化合物;萘四羧酸;偶氮染料、花青染料之金屬錯合物化合物;色澱顏料;藉由爐排法、導槽法或熱分析法所獲得之碳黑或乙炔黑、科琴黑或燈黑等碳黑;利用環氧樹脂對上述碳黑進行調整或被覆而成者、預先於溶劑中利用樹脂對上述碳黑進行分散處理而使之吸附20~200 mg/g之樹脂而成者、對上述碳黑進行酸性或鹼性表面處理而成者、平均粒徑為8 nm以上且DBP(Dibutyl Phthalate,鄰苯二甲酸二丁酯)吸油量為90 ml/100 g以下之碳黑、表面積每100 m2
根據950℃下之揮發成分中之CO及CO2
算出之總氧氣量為9 mg以上之碳黑;石墨、石墨化碳黑、活性碳、碳纖維、奈米碳管、螺旋碳纖維、碳奈米角、碳氣凝膠、富勒烯;苯胺黑、顏料黑7、鈦黑;氧化鉻綠、米洛麗藍、鈷綠、鈷青、錳系、亞鐵氰化物、磷酸鹽群青、鐵藍、群青、天藍、濃綠色、翡翠綠、硫酸鉛、黃丹、鋅黃、鐵丹(紅色氧化鐵(III))、鎘紅、合成鐵黑、棕土等有機或無機顏料。該等顏料可單獨使用或將複數種混合使用。
作為上述顏料,亦可使用市售之顏料,例如可列舉:顏料紅1、2、3、9、10、14、17、22、23、31、38、41、48、49、88、90、97、112、119、122、123、144、149、166、168、169、170、171、177、179、180、184、185、192、200、202、209、215、216、217、220、223、224、226、227、228、240、254;顏料橙13、31、34、36、38、43、46、48、49、51、52、55、59、60、61、62、64、65、71;顏料黃1、3、12、13、14、16、17、20、24、55、60、73、81、83、86、93、95、97、98、100、109、110、113、114、117、120、125、126、127、129、137、138、139、147、148、150、151、152、153、154、166、168、175、180、185;顏料綠7、10、36;顏料藍15、15:1、15:2、15:3、15:4、15:5、15:6、22、24、56、60、61、62、64;顏料紫1、19、23、27、29、30、32、37、40、50等。
作為上述染料,可列舉:偶氮染料、蒽醌染料、靛屬染料、三芳基甲烷染料、𠮿染料、茜素染料、吖啶染料、茋染料、噻唑染料、萘酚染料、喹啉染料、硝基染料、吲達胺染料、㗁𠯤染料、酞菁染料、花青染料等染料等;該等亦可混合複數種使用。
作為上述潛在性環氧硬化劑,例如可列舉:雙氰胺、改性聚胺、醯肼類、4,4'-二胺基二苯基碸、三氟化硼胺錯鹽、咪唑類、胍胺類、咪唑類、脲類及三聚氰胺等。
作為上述鏈轉移劑或增感劑,通常可使用含硫原子之化合物。例如可列舉:硫代乙醇酸、硫代蘋果酸、硫代水楊酸、2-巰基丙酸、3-巰基丙酸、3-巰基丁酸、N-(2-巰基丙醯基)甘胺酸、2-巰基菸鹼酸、3-[N-(2-巰基乙基)胺甲醯基]丙酸、3-[N-(2-巰基乙基)胺基]丙酸、N-(3-巰基丙醯基)丙胺酸、2-巰基乙磺酸、3-巰基丙磺酸、4-巰基丁磺酸、十二烷基(4-甲基硫基)苯醚、2-巰基乙醇、3-巰基-1,2-丙二醇、1-巰基-2-丙醇、3-巰基-2-丁醇、巰基苯酚、2-巰基乙基胺、2-巰基咪唑、2-巰基苯并咪唑、2-巰基-3-羥基吡啶、2-巰基苯并噻唑、巰基乙酸、三羥甲基丙烷三(3-巰基丙酸酯)、季戊四醇四(3-巰基丙酸酯)等巰基化合物、使該巰基化合物氧化所獲得之二硫醚化合物、碘乙酸、碘丙酸、2-碘乙醇、2-碘乙磺酸、3-碘丙磺酸等碘化烷基化合物、三羥甲基丙烷三(3-巰基異丁酸酯)、丁二醇雙(3-巰基異丁酸酯)、己二硫醇、癸二硫醇、1,4-二甲基巰基苯、丁二醇雙巰基丙酸酯、丁二醇雙巰基乙醇酸酯、乙二醇雙巰基乙醇酸酯、三羥甲基丙烷三巰基乙醇酸酯、丁二醇雙巰基丙酸酯、三羥甲基丙烷三巰基丙酸酯、三羥甲基丙烷三巰基乙醇酸酯、季戊四醇四巰基丙酸酯、季戊四醇四巰基乙醇酸酯、三羥基乙基三巰基丙酸酯、二乙基9-氧硫𠮿、二異丙基9-氧硫𠮿、下述化合物No.C1、三巰基丙酸三(2-羥基乙基)異氰尿酸酯等脂肪族多官能硫醇化合物、昭和電工公司製造之Karenz MT BD1、PE1、NR1等。
作為上述溶劑,通常可使用:可使上述各成分(聚合起始劑(A)及聚合性化合物(B)等)溶解或分散之溶劑、例如甲基乙基酮、甲基戊基酮、二乙基酮、丙酮、甲基異丙基酮、甲基異丁基酮、環己酮、2-庚酮等酮類;***、二㗁烷、四氫呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷、二丙二醇二甲醚等醚系溶劑;乙酸甲酯、乙酸乙酯、乙酸-正丙酯、乙酸異丙酯、乙酸正丁酯、乙酸環己酯、乳酸乙酯、琥珀酸二甲酯、TEXANOL等酯系溶劑;γ-己內酯、δ-己內酯、γ-丁內酯等內酯系溶劑;乙二醇單甲醚、乙二醇單***等溶纖素系溶劑;甲醇、乙醇、異或正丙醇、異或正丁醇、戊醇等醇系溶劑;乙二醇單甲基乙酸酯、乙二醇單乙基乙酸酯、丙二醇-1-單甲醚-2-乙酸酯、二丙二醇單甲醚乙酸酯、乙酸3-甲氧基丁酯、丙酸乙氧基乙酯等醚酯系溶劑;苯、甲苯、二甲苯等BTX系溶劑;己烷、庚烷、辛烷、環己烷等脂肪族烴系溶劑;松節油、D-檸檬烯、蒎烯等萜烯系烴油;礦油精、Swazol#310(科斯莫松山石油(股))、Solvesso#100(Exxon Chemical(股))等烷烴系溶劑;四氯化碳、氯仿、三氯乙烯、二氯甲烷、1,2-二氯乙烷等鹵化脂肪族烴系溶劑;氯苯等鹵化芳香族烴系溶劑;卡必醇系溶劑;苯胺;三乙胺;吡啶;乙酸;乙腈;二硫化碳;N,N-二甲基甲醯胺;N,N-二甲基乙醯胺;N-甲基吡咯啶酮;二甲基亞碸;水等;該等溶劑可使用1種或以2種以上之混合溶劑之形式來使用。
該等之中,就鹼性顯影性、製圖性、製膜性、溶解性之方面而言,可較佳地使用酮類或醚酯系溶劑、尤其是丙二醇-1-單甲醚-2-乙酸酯(以下,亦稱為「PGMEA」)或環己酮。
於本發明之聚合性組合物中,溶劑之含量並無特別限制,只要為使各成分均勻地分散或溶解且使本發明之聚合性組合物呈適合各用途之液狀或糊狀之量即可,通常於本發明之聚合性組合物中之固形物成分(溶劑以外之總成分)之量成為10~90質量%之範圍內含有溶劑能夠獲得均勻之硬化物,故而較佳。
又,本發明之聚合性組合物亦可藉由使用有機聚合物來改善硬化物之特性。作為該有機聚合物,例如可列舉:聚苯乙烯、聚甲基丙烯酸甲酯、甲基丙烯酸甲酯-丙烯酸乙酯共聚物、聚(甲基)丙烯酸、苯乙烯-(甲基)丙烯酸共聚物、(甲基)丙烯酸-甲基丙烯酸甲酯共聚物、乙烯-氯乙烯共聚物、乙烯-乙烯基共聚物、聚氯乙烯樹脂、ABS(Acrylonitrile Butadiene Styrene,丙烯腈-丁二烯-苯乙烯)樹脂、尼龍6、尼龍66、尼龍12、胺基甲酸酯樹脂、聚碳酸酯聚乙烯醇縮丁醛、纖維素酯、聚丙烯醯胺、飽和聚酯、酚樹脂、苯氧基樹脂等。
於使用上述有機聚合物之情形時,就所獲得之聚合性組合物之硬化性優異之方面而言,其含量相對於聚合性化合物(B)100質量份,較佳為10~500質量份。
本發明之聚合性組合物可進而併用界面活性劑、矽烷偶合劑、三聚氰胺化合物等。
作為上述界面活性劑,可使用:全氟烷基磷酸酯、全氟烷基羧酸鹽等氟系界面活性劑;高級脂肪酸鹼鹽、烷基磺酸鹽、烷基硫酸鹽等陰離子系界面活性劑;高級胺鹵酸鹽、四級銨鹽等陽離子系界面活性劑;聚乙二醇烷基醚、聚乙二醇脂肪酸酯、山梨糖醇酐脂肪酸酯、單甘油脂肪酸酯等非離子界面活性劑;兩性界面活性劑;聚矽氧系界面活性劑等界面活性劑;該等亦可組合使用。
作為上述矽烷偶合劑,例如可使用信越化學公司製造之矽烷偶合劑,其中可較佳地使用KBE-9007、KBM-502、KBE-403等具有異氰酸基、甲基丙烯醯基或環氧基之矽烷偶合劑。
作為上述三聚氰胺化合物,可列舉(聚)羥甲基三聚氰胺、(聚)羥甲基甘脲、(聚)羥甲基苯胍𠯤、(聚)羥甲基脲等氮化合物中之活性羥甲基(CH2
OH基)之全部或一部分(至少2個)經烷基醚化而成之化合物等。
此處,作為構成烷基醚之烷基,可列舉:甲基、乙基或丁基;相互可相同亦可不同。又,未經烷基醚化之羥甲基可於一分子中自我縮合,亦可於兩分子間縮合,結果形成低聚物成分。
具體而言,可使用六甲氧基甲基三聚氰胺、六丁氧基甲基三聚氰胺、四甲氧基甲基甘脲、四丁氧基甲基甘脲等。
該等之中,就對溶劑之溶解性、不易自聚合性組合物析出結晶之方面而言,較佳為六甲氧基甲基三聚氰胺、六丁氧基甲基三聚氰胺等經烷基醚化之三聚氰胺。
於本發明之聚合性組合物中,聚合起始劑(A)及聚合性化合物(B)以外之任意成分(其中,無機化合物、色料、及溶劑除外)之含量視其使用目的來適當選擇,並無特別限制,就所獲得之聚合性組合物之硬化性優異之方面而言,較佳為相對於聚合性化合物(B)100質量份設為合計50質量份以下。
本發明之聚合性組合物可照射能量線而製成硬化物。該硬化物形成為與用途對應之適當形狀。例如於形成膜狀硬化物之情形時,本發明之聚合性組合物可利用旋轉塗佈機、輥式塗佈機、棒式塗佈機、模嘴塗佈機、簾幕式塗佈機、各種印刷、浸漬等公知之機構應用於鈉玻璃、石英玻璃、半導體基板、金屬、紙、塑膠等支持基體上。又,亦可暫時於膜等支持基體上實施後轉印至其他支持基體上,其應用方法並無限制。
作為使本發明之聚合性組合物硬化時可使用之能量線之光源,可利用自超高壓水銀燈、高壓水銀燈、中壓水銀燈、低壓水銀燈、水銀蒸氣弧燈、氙弧燈、碳弧燈、金屬鹵化物燈、螢光燈、鎢燈、準分子燈、殺菌燈、發光二極體、CRT光源等獲得之具有2000埃~7000埃之波長之電磁波能量或電子束、X射線、放射線等高能量線,就所獲得之聚合性組合物之硬化性優異之方面而言,較佳為可使用發出波長300~450 nm之光之超高壓水銀燈、水銀蒸氣弧燈、碳弧燈、氙弧燈等。
進而,藉由使曝光光源使用雷射光,不使用遮罩而根據電腦等數位資訊直接形成圖像之雷射直接描繪法不僅會提高生產性,亦會提高解像性或位置精度等,故而有用,作為該雷射光,可較佳地使用340~430 nm之波長之光,亦可使用準分子雷射、氮雷射、氬離子雷射、氦鎘雷射、氦氖雷射、氪離子雷射、各種半導體雷射及YAG(Yttrium Aluminum Garnet,釔-鋁-石榴石)雷射等發出可見至紅外區域之光者。於使用該等雷射光之情形時,就所獲得之聚合性組合物之硬化性優異之方面而言,較佳為添加於可見至紅外之相關區域進行吸收之增感色素。
又,於本發明之聚合性組合物之硬化時,通常必須於上述能量線之照射後進行加熱,就硬化率之方面而言,較佳為40~150℃左右之加熱。
本發明之聚合性組合物可使用於如下等各種用途:光硬化性塗料或清漆;光硬化性接著劑;金屬用塗佈劑;印刷基板;彩色電視、PC(Personal Computer,個人電腦)監視器、便攜型資訊終端、數位相機等彩色顯示之液晶顯示元件中之彩色濾光片;CCD(CCD,電荷耦合元件)影像感測器之彩色濾光片;電漿顯示面板用之電極材料;粉末塗佈;印刷油墨;印刷版;接著劑;牙科用組合物;凝膠塗層;電子工程用之光阻劑;電鍍抗蝕劑;蝕刻抗蝕劑;乾膜;焊料抗蝕劑;用以製造各種顯示用途用之彩色濾光片或者用以於電漿顯示面板、電發光顯示裝置、及LCD(Liquid Crystal Display,液晶顯示裝置)之製造步驟中形成其等構造之抗蝕劑;用以封入電氣及電子零件之組合物;阻焊劑;磁記錄材料;微小機械零件;光波導;光開關;鍍覆用遮罩;蝕刻遮罩;彩色試驗系統;玻璃纖維電纜塗層;網版印刷用模板;用以藉由立體光刻製造三維物體之材料;全像術記錄用材料;圖像記錄材料;微細電子電路;脫色材料;用於圖像記錄材料之脫色材料;使用微膠囊之圖像記錄材料用之脫色材料;印刷配線板用光阻材料;UV(ultraviolet,紫外線)及可見光雷射直接圖像系統用之光阻劑材料;印刷電路基板之逐次積層中之介電體層形成所使用之光阻劑材料或保護膜,其用途並無特別限制。
本發明之聚合性組合物亦可用於形成液晶顯示面板用間隔件及用於形成垂直配向型液晶顯示元件用突起。尤其是作為用以同時形成垂直配向型液晶顯示元件用之突起與間隔件之感光性樹脂組合物有用。
上述液晶顯示面板用間隔件係藉由如下步驟而較佳地形成:(1)於基板上形成本發明之聚合性組合物之塗膜之步驟;(2)隔著具有特定圖案形狀之遮罩對該塗膜照射能量線(光)之步驟;(3)曝光後之烘烤步驟;(4)使曝光後之覆膜顯影之步驟;及(5)對顯影後之該覆膜進行加熱之步驟。
添加有色料之本發明之聚合性組合物可較佳地用作構成彩色濾光片中之RGB(Red-Green-Blue,紅-綠-藍)等各像素之抗蝕劑或形成各像素之間隔壁之黑矩陣用抗蝕劑。進而,於添加撥墨劑之黑矩陣用抗蝕劑之情形時,可較佳地用於分佈角為50°以上之噴墨方式彩色濾光片用間隔壁。作為該撥墨劑,可較佳地使用氟系界面活性劑及含有氟系界面活性劑之組合物。
於用於上述噴墨方式彩色濾光片用間隔壁之情形時,藉由如下方法來製造光學元件:於被轉印體上劃分由本發明之聚合性組合物形成之間隔壁,藉由噴墨法對經劃分之被轉印體上之凹部賦予液滴而形成圖像區域。此時,較佳為上述液滴含有著色劑而使上述圖像區域著色,於該情形時,藉由上述製造方法所製作之光學元件於基板上至少具有包含複數個著色區域之像素群及將該像素群之各著色區域隔開之間隔壁。
本發明之聚合性組合物亦可用作保護膜或絕緣膜用組合物。於該情形時,可含有紫外線吸收劑、烷基化改性三聚氰胺及/或丙烯酸改性三聚氰胺、分子中含有醇性羥基之1或2官能之(甲基)丙烯酸酯單體及/或矽溶膠。
上述絕緣膜可用於在能夠剝離之支持基材上設置有絕緣樹脂層之積層體中之該絕緣樹脂層,該積層體係藉由鹼性水溶液能夠顯影者,絕緣樹脂層之膜厚較佳為10~100 μm。
本發明之聚合性組合物可藉由含有無機化合物而用作感光性漿料組合物。該感光性漿料組合物可用於形成電漿顯示器面板之間隔壁圖案、介電體圖案、電極圖案及黑矩陣圖案等焙燒物圖案。
[實施例]
以下,列舉實施例及比較例對本發明進一步詳細地進行說明,但本發明並不限定於該等實施例等。
[實施例1]
依據以下所示之方案合成化合物1。
向100 ml四口燒瓶中添加肟體1 1.0 eq.、二氯甲烷(理論產量之600重量%)、三乙胺3.0 eq.,於冰浴上以5℃進行攪拌。向其中滴加添加使氯甲酸4-硝基苯酯1.1 eq.溶解於二氯甲烷中而成者。滴加結束後,於冰浴上冷卻至0℃,滴加添加哌啶1.1 eq.。將混合液於室溫下攪拌1.5小時,於減壓下將溶劑蒸餾去除。使濃縮後之殘渣溶解於乙酸乙酯中,利用1質量%NaOH水溶液洗淨2次後,進而藉由離子交換水洗淨3次。藉由硫酸鎂使有機層乾燥、濃縮。藉由矽膠管柱層析法(溶離劑=乙酸乙酯:己烷=1:4→1:3)對有機層進行精製,以產率41%獲得了作為淡褐色粉狀化合物之目標物。將1
H-NMR(Nuclear Magnetic Resonance,核磁共振)測定結果示於表1。
[表1]
化學位移/ppm(多重性、質子數) | |
化合物1 (CDCl3 、400 MHz) | 9.51 (d, 1H), 8.63 (d, 1H), 8.48 (s, 1H), 8.37 (s, 1H), 7.6 - 7.8 (m, 2H), 7.4 - 7.5 (m, 2H), 7.3 - 7.4 (m, 1H), 7.2 - 7.3 (m, 1H), 7.1 - 7.2 (m, 1H), 6.99 (d, 1H), 6.94 (s, 2H), 4.71 (m, 2H), 4.28 (m, 2H), 3.3 - 3.5 (m, 2H), 2.9 - 3.1 (m, 2H), 2.38 (s, 3H), 2.19 (s, 6H), 1.1 - 1.7 (m, 15H), 0.87 (t, 3H), 0.80 (t, 3H) |
[實施例2及比較例1]聚合性組合物之製備
進行表2所記載之調配,獲得聚合性組合物1及比較聚合性組合物1。再者,表中之調配數值表示質量份。
又,表中之各成分之符號表示下述成分。
A-1:化合物1
A'-2:比較化合物1
B-1:EPPN-201(酚系酚醛清漆型環氧樹脂、環氧當量193 g/ eq.、日本化藥公司製造)
B-2:H-3M(酚樹脂、羥基當量105~109 g/ eq.、明和化成公司製造)
C-1:FZ-2122(聚醚改性聚矽氧烷、東麗道康寧公司製造、1重量%PGMEA溶液)
D-1:環戊酮(溶劑)
[表2]
實施例2 | 比較例1 | |
聚合性組合物 | 聚合性組合物1 | 比較聚合性組合物1 |
A-1 | 1.5 | - |
A'-2 | - | 1.5 |
B-1 | 23.6 | 23.6 |
B-2 | 14.8 | 14.8 |
C-1 | 7.3 | 7.3 |
D-1 | 52.8 | 52.8 |
合計 | 100 | 100 |
[評價例1以及比較評價例1]
針對聚合性組合物1及比較聚合性組合物1之硬化物,按下述順序確認有無殘膜。將結果示於表4。
使用旋轉塗佈機將聚合性組合物1及比較聚合性組合物1分別塗佈(500 rpm×2秒→1000 rpm×10秒→斜度×0.5秒、塗佈量約2 mL)於玻璃基材(10 cm×10 cm),於烘箱中進行預烘烤(90℃×90秒)而製膜。
針對各膜,遮蔽具有透過率連續變化之灰階之階段式曝光表(33段型、OD值0~3、表3),使用UV-LED(365 nm)照射特定量之紫外線光(照度20 mW/cm2
、曝光時間150秒、累計曝光量3000 mJ/cm2
)。
曝光後,於烘箱中進行後烘烤(100℃×20分鐘),並進行顯影(PGMEA、30秒)及沖洗(異丙醇、10秒)。
針對所獲得之硬化膜樣品,藉由目視確認剩餘階數。所謂剩餘階數,意指硬化膜殘存之最大階數。根據剩餘階數並根據表3來確定透過率,藉由使用下述式算出換算感度。
換算感度(mJ/cm2
)=累計曝光量(3000 mJ/cm2
)×透過率(%)
將剩餘階數與換算感度示於表4。
[表3]
階數 | OD值 | 透過率(%) |
0 | 0 | 100.000 |
1 | 0.06 | 87.096 |
2 | 0.15 | 70.795 |
3 | 0.24 | 57.544 |
4 | 0.35 | 44.668 |
5 | 0.44 | 36.308 |
6 | 0.54 | 28.840 |
7 | 0.64 | 22.909 |
8 | 0.74 | 18.197 |
9 | 0.84 | 14.454 |
10 | 0.94 | 11.482 |
11 | 1.05 | 8.913 |
12 | 1.15 | 7.079 |
13 | 1.25 | 5.623 |
14 | 1.35 | 4.467 |
15 | 1.44 | 3.631 |
16 | 1.54 | 2.884 |
17 | 1.64 | 2.291 |
18 | 1.74 | 1.820 |
19 | 1.84 | 1.445 |
20 | 1.94 | 1.148 |
21 | 2.04 | 0.912 |
22 | 2.14 | 0.724 |
23 | 2.24 | 0.575 |
24 | 2.34 | 0.457 |
25 | 2.44 | 0.363 |
26 | 2.54 | 0.288 |
27 | 2.65 | 0.224 |
28 | 2.75 | 0.178 |
29 | 2.84 | 0.145 |
30 | 2.93 | 0.117 |
31 | 2.95 | 0.112 |
32 | 2.97 | 0.107 |
33 | 3.00 | 0.100 |
[表4]
聚合性組合物1 | 比較聚合性組合物1 | |
剩餘階數(階) | 2 | 0 |
換算感度(mJ/cm2 ) | 2124 | >3000 |
根據上述表4之結果,含有本發明之胺甲醯肟化合物之聚合性組合物與比較聚合性組合物相比,剩餘階數較多(硬化性較高),因此光產鹼效率較高,於低曝光量下能夠硬化且對於UV-LED光源呈高感度。因此,明確本發明之化合物作為聚合起始劑優異。
[實施例3]
依據以下所示之方案合成化合物2。
(肟體2之合成)
向燒瓶中添加8-(3-環戊基丙基)-11-(2-乙基己基)-11H-苯并[a]咔唑1.0 eq.,使之溶解於二甲基甲醯胺(理論產量之500重量%)中。向溶液中添加氯化羥基銨2.2 eq.及吡啶2.2 eq.。將反應混合物於60℃下加熱攪拌9小時後,添加離子交換水,利用氯仿進行萃取。利用離子交換水將有機層洗淨2次,藉由硫酸鎂進行乾燥、濃縮。藉由矽膠管柱層析法(溶離劑=己烷:乙酸乙酯=94:6)對殘渣進行精製,以產率28%獲得了作為白色粉狀化合物之目標物。
(化合物2之合成)
向燒瓶中添加肟體2 1.0 eq.、氯仿(理論產量之500重量%)、三乙胺2.0 eq.,於冰浴上以5℃下進行攪拌。向其中滴加添加使氯甲酸4-硝基苯酯1.1 eq.溶解於氯仿(理論產量之500重量%)中而成者。滴加結束後於室溫下攪拌1小時。再次於冰浴上冷卻至5℃後,滴加添加苯胺1.1 eq.。於室溫下攪拌2小時後,利用1質量%氫氧化鈉水溶液洗淨3次,利用離子交換水洗淨3次,藉由硫酸鎂使有機層乾燥、濃縮。藉由矽膠管柱層析法(溶離劑=己烷:乙酸乙酯=94:6)對殘渣進行精製,以產率35%獲得了作為黃色不定形固體化合物之目標物。將所獲得之化合物之1
H-NMR測定結果示於表5。
[實施例4]
依據以下所示之方案合成化合物3。
(肟體3之合成)
向燒瓶中添加1-(11-(2-乙基己基)-11H-苯并[a]咔唑-8-基)辛烷-1-酮1.0 eq.,使之溶解於二甲基甲醯胺(理論產量之400重量%)中。向其中添加4M・HCl-乙酸乙酯1.1 eq.及亞硝酸異丁酯1.1 eq.,並於45℃下攪拌1小時。向反應液中添加氯仿,利用離子交換水洗淨4次,藉由硫酸鎂使有機層乾燥後進行濃縮。藉由矽膠管柱層析法(溶離劑=己烷:乙酸乙酯=91:9)對殘渣進行精製,以產率18%獲得了作為白色粉狀化合物之目標物。
(化合物3之合成)
將實施例3之肟體2變更為肟體3,除此以外,以相同順序進行至水洗後之濃縮。藉由矽膠管柱層析法(溶離劑=己烷:乙酸乙酯=95:5)對殘渣進行精製,以產率27%獲得了作為黃色不定形固體化合物之化合物2。將所獲得之化合物之1
H-NMR測定結果示於表5。
[表5]
[產業上之可利用性]
化學位移/ppm(多重性、質子數) | |
化合物2 (CDCl3 、400 MHz) | 8.62 - 8.50 (m, 2H), 8.45 (s, 1H), 8.22 (d, 1H), 8.06 (d, 1H), 7.85 (d, 1H), 7.73 (d, 1H), 7.66 - 7.50 (m, 5H), 7.37 (t, 2H), 7.13 (t, 1H), 4.71 (t, 2H), 3.16 - 3.08 (m, 2H), 2.37 - 2.20 (m, 1H), 2.04 - 1.13 (m, 19H), 0.90 (t, 3H), 0.83 (t, 3H) |
化合物3 (CDCl3 、400 MHz) | 9.07 (d, 1H), 8.50 (d, 1H), 8.36 (dd, 1H), 8.25 (d, 1H), 8.03 (dd, 1H), 7.72 (d, 1H), 7.65 - 7.50 (m, 3H), 4.77 - 4.59 (m, 2H), 3.45 - 3.25 (m, 4H), 2.83 (t, 2H), 2.33 - 2.20 (m, 1H), 1.73 - 1.15 (m, 24H), 1.05 - 0.78 (m, 15H) |
本發明之胺甲醯肟化合物具有較高之光產鹼效率,於用作聚合起始劑之情形時,可較先前之光產鹼劑更有效率地產生鹼,因此即便於低曝光量下亦可使聚合性化合物硬化。尤其是於用於含有環氧樹脂或酚樹脂之硬化性樹脂組合物之情形時顯示出較高之硬化性。
Claims (10)
- 一種胺甲醯肟化合物,其以下述通式(I)表示, [化1] (式中,R1 表示氫原子、鹵素原子、硝基、氰基、碳原子數1~20之烴基或烴基中之亞甲基被取代為選自下述<群A>中之二價基而成之碳原子數1~20之基, R2 表示氫原子、碳原子數1~20之烴基或烴基中之亞甲基被取代為選自下述<群A>中之二價基而成之碳原子數1~20之基, R3 、R4 、R5 、R6 、R7 、R8 及R9 分別獨立地表示氫原子、鹵素原子、氰基、硝基、-OR10 、-COOR10 、-CO-R10 、-SR10 、碳原子數1~20之烴基或碳原子數2~20之含雜環之基, R10 表示氫原子、碳原子數1~20之烴基、碳原子數2~20之含雜環之基或烴基中之亞甲基被取代為選自下述<群A>中之二價基而成之碳原子數1~20之基,於分子中存在複數個R10 之情形時,其等可相同,亦可不同, X1 表示-NR21 R22 或下述通式(a)或者下述通式(b)所表示之基, R21 及R22 分別獨立地表示氫原子、碳原子數1~20之烴基或烴基中之亞甲基被取代為選自下述<群A>中之二價基而成之碳原子數1~20之基, R1 、R2 、R3 、R4 、R5 、R6 、R7 、R8 、R9 、R10 、R21 及R22 亦可為烴基中之氫原子之1個或2個以上被取代為鹵素原子、氰基、硝基、羥基、-OR11 、-COOR11 、-CO-R11 或-SR11 而成之碳原子數1~20之基, R11 表示氫原子、碳原子數1~20之烴基、烴基中之亞甲基被取代為選自下述<群A>中之二價基而成之碳原子數1~20之基或烴基中之氫原子之1個或2個以上被取代為鹵素原子、氰基、硝基或羥基而成之碳原子數1~20之基,於分子中存在複數個R11 之情形時,其等可相同,亦可不同, <群A>為-O-、-CO-、-COO-、-NR12 -、-NR12 CO-及-S-, R12 表示氫原子或碳原子數1~20之烴基,於分子中存在複數個R12 之情形時,其等可相同,亦可不同, R3 與R4 、R6 與R7 、R7 與R8 及R8 與R9 可分別獨立地相互連結而形成包含氫原子及碳原子之碳原子數3~10之環, R3 與R4 、R6 與R7 、R7 與R8 及R8 與R9 中之至少1組相互連結而形成苯環, R21 與R22 可相互連結而形成包含氫原子、氮原子及碳原子之碳原子數2~10之環或包含氫原子、氧原子、氮原子及碳原子之碳原子數2~10之環, n表示0或1) [化2] (式中,R31 、R32 、R33 、R34 、R35 、R36 、R37 、R38 、R39 及R40 分別獨立地表示氫原子、碳原子數1~20之烴基或烴基中之亞甲基被取代為選自下述<群B>中之二價基而成之碳原子數1~20之基, R31 、R32 、R33 、R34 、R35 、R36 、R37 、R38 、R39 及R40 亦可為烴基中之氫原子之1個或2個以上被取代為鹵素原子、氰基、硝基、羥基、-OR41 、-COOR41 、-CO-R41 或-SR41 而成之碳原子數1~20之基, R41 表示氫原子或碳原子數1~20之烴基,於基中存在複數個R41 之情形時,其等可相同,亦可不同, <群B>為-O-、-CO-、-COO-、-NR42 -、-NR42 CO-及-S-, R42 表示氫原子或碳原子數1~20之烴基,於基中存在複數個R42 之情形時,其等可相同,亦可不同, R31 與R32 、R33 與R34 、R35 與R36 、R37 與R38 、及R39 與R40 可分別獨立地相互連結而形成包含氫原子、氮原子及碳原子之碳原子數2~10之環或包含氫原子、氧原子、氮原子及碳原子之碳原子數2~10之環, *表示鍵結鍵)。
- 如請求項1之胺甲醯肟化合物,其中通式(I)中之R3 與R4 或R8 與R9 相互連結而形成苯環。
- 如請求項1之胺甲醯肟化合物,其中通式(I)中之X1 為-NR21 R22 。
- 如請求項1之胺甲醯肟化合物,其中通式(I)中之R2 為碳原子數1~10之脂肪族烴基。
- 一種潛在性產鹼劑,其含有如請求項1至4中任一項之胺甲醯肟化合物。
- 一種聚合起始劑,其含有如請求項1至4中任一項之胺甲醯肟化合物。
- 一種聚合性組合物,其含有如請求項1至4中任一項之胺甲醯肟化合物及聚合性化合物。
- 如請求項7之聚合性組合物,其中上述聚合性化合物為環氧樹脂或者乙烯性不飽和化合物、或包含環氧樹脂與酚樹脂之混合物、包含環氧樹脂與硫醇化合物之混合物、或者包含乙烯性不飽和化合物與硫醇化合物之混合物。
- 一種硬化物,其係如請求項7之聚合性組合物之硬化物。
- 一種硬化物之製造方法,其具有對如請求項7之聚合性組合物照射能量線之步驟。
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