JP5506812B2 - 放射線硬化性被覆材料 - Google Patents
放射線硬化性被覆材料 Download PDFInfo
- Publication number
- JP5506812B2 JP5506812B2 JP2011535999A JP2011535999A JP5506812B2 JP 5506812 B2 JP5506812 B2 JP 5506812B2 JP 2011535999 A JP2011535999 A JP 2011535999A JP 2011535999 A JP2011535999 A JP 2011535999A JP 5506812 B2 JP5506812 B2 JP 5506812B2
- Authority
- JP
- Japan
- Prior art keywords
- butyl
- alkyl
- ethyl
- methylimidazolium
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
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- 239000000203 mixture Substances 0.000 claims description 29
- 239000003973 paint Substances 0.000 claims description 24
- 150000001450 anions Chemical class 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
- 150000002500 ions Chemical class 0.000 claims description 15
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
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- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 7
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 claims description 5
- 239000003086 colorant Substances 0.000 claims description 5
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- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 claims description 5
- XUAXVBUVQVRIIQ-UHFFFAOYSA-N 1-butyl-2,3-dimethylimidazol-3-ium Chemical compound CCCCN1C=C[N+](C)=C1C XUAXVBUVQVRIIQ-UHFFFAOYSA-N 0.000 claims description 4
- NJMWOUFKYKNWDW-UHFFFAOYSA-N 1-ethyl-3-methylimidazolium Chemical compound CCN1C=C[N+](C)=C1 NJMWOUFKYKNWDW-UHFFFAOYSA-N 0.000 claims description 4
- MCTWTZJPVLRJOU-UHFFFAOYSA-O 1-methylimidazole Chemical compound CN1C=C[NH+]=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-O 0.000 claims description 4
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 4
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- 238000000034 method Methods 0.000 claims description 4
- CHYBTAZWINMGHA-UHFFFAOYSA-N tetraoctylazanium Chemical compound CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC CHYBTAZWINMGHA-UHFFFAOYSA-N 0.000 claims description 4
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 3
- MCMFEZDRQOJKMN-UHFFFAOYSA-O 3-butyl-1h-imidazol-3-ium Chemical compound CCCCN1C=C[NH+]=C1 MCMFEZDRQOJKMN-UHFFFAOYSA-O 0.000 claims description 3
- KWXICGTUELOLSQ-UHFFFAOYSA-M 4-dodecylbenzenesulfonate Chemical compound CCCCCCCCCCCCC1=CC=C(S([O-])(=O)=O)C=C1 KWXICGTUELOLSQ-UHFFFAOYSA-M 0.000 claims description 3
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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 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
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- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 claims description 3
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 claims description 3
- KCUGPPHNMASOTE-UHFFFAOYSA-N 1,2,3-trimethylimidazol-1-ium Chemical compound CC=1N(C)C=C[N+]=1C KCUGPPHNMASOTE-UHFFFAOYSA-N 0.000 claims description 2
- GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 claims description 2
- NOBVKAMFUBMCCA-UHFFFAOYSA-N 1,3,4,5-tetramethylimidazol-1-ium Chemical compound CC1=C(C)[N+](C)=CN1C NOBVKAMFUBMCCA-UHFFFAOYSA-N 0.000 claims description 2
- CDIWYWUGTVLWJM-UHFFFAOYSA-N 1,3,4-trimethylimidazol-1-ium Chemical compound CC1=C[N+](C)=CN1C CDIWYWUGTVLWJM-UHFFFAOYSA-N 0.000 claims description 2
- NWXVIUBYBJUOAY-UHFFFAOYSA-N 1,3-dibutylimidazol-1-ium Chemical compound CCCCN1C=C[N+](CCCC)=C1 NWXVIUBYBJUOAY-UHFFFAOYSA-N 0.000 claims description 2
- HVVRUQBMAZRKPJ-UHFFFAOYSA-N 1,3-dimethylimidazolium Chemical compound CN1C=C[N+](C)=C1 HVVRUQBMAZRKPJ-UHFFFAOYSA-N 0.000 claims description 2
- HQNBJNDMPLEUDS-UHFFFAOYSA-N 1,5-dimethylimidazole Chemical compound CC1=CN=CN1C HQNBJNDMPLEUDS-UHFFFAOYSA-N 0.000 claims description 2
- BXKLAIZZZVWDLP-UHFFFAOYSA-N 1-butyl-2-ethyl-5-methylimidazole Chemical compound CCCCN1C(C)=CN=C1CC BXKLAIZZZVWDLP-UHFFFAOYSA-N 0.000 claims description 2
- RIDWYWYHKGNNOF-UHFFFAOYSA-N 1-butyl-3,4,5-trimethylimidazol-3-ium Chemical compound CCCCN1C=[N+](C)C(C)=C1C RIDWYWYHKGNNOF-UHFFFAOYSA-N 0.000 claims description 2
- KACBWSJPLBIMGN-UHFFFAOYSA-N 2-ethyl-1,5-dimethylimidazole Chemical compound CCC1=NC=C(C)N1C KACBWSJPLBIMGN-UHFFFAOYSA-N 0.000 claims description 2
- UINDRJHZBAGQFD-UHFFFAOYSA-N 2-ethyl-1-methylimidazole Chemical compound CCC1=NC=CN1C UINDRJHZBAGQFD-UHFFFAOYSA-N 0.000 claims description 2
- WXMVWUBWIHZLMQ-UHFFFAOYSA-N 3-methyl-1-octylimidazolium Chemical compound CCCCCCCCN1C=C[N+](C)=C1 WXMVWUBWIHZLMQ-UHFFFAOYSA-N 0.000 claims description 2
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- AUHUWFIYJDRPJX-UHFFFAOYSA-N 4-hexylbenzenesulfonic acid Chemical compound CCCCCCC1=CC=C(S(O)(=O)=O)C=C1 AUHUWFIYJDRPJX-UHFFFAOYSA-N 0.000 claims description 2
- MSOTUIWEAQEETA-UHFFFAOYSA-M 4-octylbenzenesulfonate Chemical compound CCCCCCCCC1=CC=C(S([O-])(=O)=O)C=C1 MSOTUIWEAQEETA-UHFFFAOYSA-M 0.000 claims description 2
- QSRFYFHZPSGRQX-UHFFFAOYSA-N benzyl(tributyl)azanium Chemical compound CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 QSRFYFHZPSGRQX-UHFFFAOYSA-N 0.000 claims description 2
- VBQDSLGFSUGBBE-UHFFFAOYSA-N benzyl(triethyl)azanium Chemical compound CC[N+](CC)(CC)CC1=CC=CC=C1 VBQDSLGFSUGBBE-UHFFFAOYSA-N 0.000 claims description 2
- YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical compound C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 claims description 2
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- IJOFIRSIYJDPSC-UHFFFAOYSA-N diethyl-di(propan-2-yl)azanium Chemical compound CC[N+](CC)(C(C)C)C(C)C IJOFIRSIYJDPSC-UHFFFAOYSA-N 0.000 claims description 2
- BBKUZGLUVZZPJQ-UHFFFAOYSA-N ethenylbenzene Chemical compound [CH+]=CC1=CC=CC=C1 BBKUZGLUVZZPJQ-UHFFFAOYSA-N 0.000 claims description 2
- BCUPRSGLHYWGKH-UHFFFAOYSA-N ethyl-methyl-di(propan-2-yl)azanium Chemical compound CC[N+](C)(C(C)C)C(C)C BCUPRSGLHYWGKH-UHFFFAOYSA-N 0.000 claims description 2
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- CLHRGZGPVVFEAO-UHFFFAOYSA-N 1,3-dibutyl-2-methylimidazol-1-ium Chemical compound CCCCN1C=C[N+](CCCC)=C1C CLHRGZGPVVFEAO-UHFFFAOYSA-N 0.000 claims 1
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- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical compound C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 description 1
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- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- BWSZXUOMATYHHI-UHFFFAOYSA-N tert-butyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(C)(C)C BWSZXUOMATYHHI-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 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
- 239000013008 thixotropic agent Substances 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 239000001003 triarylmethane dye Substances 0.000 description 1
- DWWMSEANWMWMCB-UHFFFAOYSA-N tribromomethylsulfonylbenzene Chemical compound BrC(Br)(Br)S(=O)(=O)C1=CC=CC=C1 DWWMSEANWMWMCB-UHFFFAOYSA-N 0.000 description 1
- VZUBRRXYUOJBRS-UHFFFAOYSA-N trichloromethylsulfonylbenzene Chemical compound ClC(Cl)(Cl)S(=O)(=O)C1=CC=CC=C1 VZUBRRXYUOJBRS-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- XKGLSKVNOSHTAD-UHFFFAOYSA-N valerophenone Chemical compound CCCCC(=O)C1=CC=CC=C1 XKGLSKVNOSHTAD-UHFFFAOYSA-N 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
- OIHZGFWAMWHYPA-UHFFFAOYSA-N xanthylium Chemical compound C1=CC=CC2=CC3=CC=CC=C3[O+]=C21 OIHZGFWAMWHYPA-UHFFFAOYSA-N 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
- 239000008096 xylene Substances 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
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Description
本発明は、新規の光開始剤を有する放射線硬化性被覆材料及びその使用に関する。
及び対イオンとして式(II)
と式(III)
R1、R5、R6、R7及びR8は、そのつど互いに無関係に、水素、C1〜C18−アルキル又はC1〜C18−アルキルオキシ、
R1は、付加的にハロゲン、有利には臭素、
R2、R3及びR4は、そのつど互いに無関係に、C1〜C18−アルキル、
R9及びR10は、そのつど互いに無関係に、場合によりアリール、アルキル、アリールオキシ、アルキルオキシ、ヘテロ原子及び/又は複素環によって置換されたC1〜C18−アルキル、C6〜C12−アリール又はC5〜C12−シクロアルキル、
R11は、C5〜C18−アルキル、及び
R12は、C1〜C18−アルキル
を意味してよい。式中での定義は、以下の通りである:
場合によりアリール、アルキル、アリールオキシ、アルキルオキシ、ヘテロ原子及び/又は複素環により置換されたC1〜C18−アルキルは、例えば、メチル、エチル、プロピル、イソプロピル、n−ブチル、s−ブチル、t−ブチル、ペンチル、ヘキシル、ヘプチル、オクチル、2−エチルヘキシル、2,4,4−トリメチルペンチル、デシル、ドデシル、テトラデシル、ヘプタデシル、オクタデシル、1,1−ジメチルプロピル、1,1−ジメチルブチル、1,1,3,3−テトラメチルブチル、ベンジル、1−フェニルエチル、2−フェニルエチル、α,α−ジメチルベンジル、ベンズヒドリル、p−トリルメチル、1−(p−ブチルフェニル)−エチル、p−クロロベンジル、2,4−ジクロロベンジル、p−メトキシベンジル、m−エトキシベンジル、2−シアノエチル、2−シアノプロピル、2−メトキシカルボニルエチル、2−エトキシカルボニルエチル、2−ブトキシカルボニルプロピル、1,2−ジ−(メトキシカルボニル)−エチル、2−メトキシエチル、2−エトキシエチル、2−ブトキシエチル、ジエトキシメチル、ジエトキシエチル、1,3−ジオキソラン−2−イル、1,3−ジオキサン−2−イル、2−メチル−1,3−ジオキソラン−2−イル、4−メチル−1,3−ジオキソラン−2−イル、2−イソプロポキシエチル、2−ブトキシプロピル、2−オクチルオキシエチル、クロロメチル、2−クロロエチル、トリクロロメチル、トリフルオロメチル、1,1−ジメチル−2−クロロエチル、2−メトキシイソプロピル、2−エトキシエチル、ブチルチオメチル、2−ドデシルチオエチル、2−フェニルチオエチル、2,2,2−トリフルオロエチル、2−ヒドロキシエチル、2−ヒドロキシプロピル、3−ヒドロキシプロピル、4−ヒドロキブチル、6−ヒドロキシヘキシル、2−アミノエチル、2−アミノプロピル、3−アミノプロピル、4−アミノブチル、6−アミノヘキシル、2−メチルアミノエチル、2−メチルアミノプロピル、3−メチルアミノプロピル、4−メチルアミノブチル、6−メチルアミノヘキシル、2−ジメチルアミノエチル、2−ジメチルアミノプロピル、3−ジメチルアミノプロピル、4−ジメチルアミノブチル、6−ジメチルアミノヘキシル、2−ヒドロキシ−2,2−ジメチルエチル、2−フェノキシエチル、2−フェノキシプロピル、3−フェノキシプロピル、4−フェノキシブチル、6−フェノキシヘキシル、2−メトキシエチル、2−メトキシプロピル、3−メトキシプロピル、4−メトキシブチル、6−メトキシヘキシル、2−エトキシエチル、2−エトキシプロピル、3−エトキシプロピル、4−エトキシブチル又は6−エトキシヘキシルであり、
場合によりアリール、アルキル、アリールオキシ、アルキルオキシ、ヘテロ原子及び/又は複素環によって置換されたC5〜C18−アルキルは、例えば、ペンチル、ヘキシル、ヘプチル、オクチル、2−エチルヘキシル、2,4,4−トリメチルペンチル、デシル、ドデシル、テトラデシル、ヘプタデシル、オクタデシル、1,1−ジメチルプロピル、1,1−ジメチルブチル、1,1,3,3−テトラメチルブチルであり、
場合によりアリール、アルキル、アリールオキシ、アルキルオキシ、ヘテロ原子及び/又は複素環によって置換されたC6〜C12−アリールは、例えば、フェニル、トリル、キシリル、α−ナフチル、β−ナフチル、4−ジフェニリル、クロロフェニル、ジクロロフェニル、トリクロロフェニル、ジフルオロフェニル、メチルフェニル、ジメチルフェニル、トリメチルフェニル、エチルフェニル、ジエチルフェニル、イソプロピルフェニル、t−ブチルフェニル、ドデシルフェニル、メトキシフェニル、ジメトキシフェニル、エトキシフェニル、ヘキシルオキシフェニル、メチルナフチル、イソプロピルナフチル、クロロナフチル、エトキシナフチル、2,6−ジメチルフェニル、2,4,6−トリメチルフェニル、2,6−ジメトキシフェニル、2,6−ジクロロフェニル、4−ブロモフェニル、2−又は4−ニトロフェニル、2,4−又は2,6−ジニトロフェニル、4−ジメチルアミノフェニル、4−アセチルフェニル、メトキシエチルフェニル又はエトキシメチルフェニルであり、
場合によりアリール、アルキル、アリールオキシ、ヘテロ原子及び/又は複素環によって置換されたC5〜C12−シクロアルキルは、例えば、シクロペンチル、シクロヘキシル、シクロオクチル、シクロドデシル、メチルシクロペンチル、ジメチルシクロペンチル、メチルシクロヘキシル、ジメチルシクロヘキシル、ジエチルシクロヘキシル、ブチルシクロヘキシル、メトキシシクロヘキシル、ジメトキシシクロヘキシル、ジエトキシシクロヘキシル、ブチルチオシクロヘキシル、クロロシクロヘキシル、ジクロロシクロヘキシル、ジクロロシクロペンチル並びに飽和又は不飽和の二環系、例えば、ノルボルニル又はノルボルネニルである。
xは、1又は2、
Katは、カチオン、
z1、z2、z3及びz4は、互いに無関係に、そのつど0又は1を意味し、
その際、z1+z2+z3+z4の合計は、0、1、2又は3、有利には0、1又は2、特に有利には0又は1であり、極めて有利には0であり、
Y1、Y2、Y3及びY4は、互いに無関係に、そのつどO、S又はNR17、
R13、R14、R15及びR16は、そのつど互いに無関係に、C1〜C18−アルキル、場合により1個以上の酸素原子及び/又は硫黄原子及び/又は1個以上の置換された又は置換されていないイミノ基によって中断されたC2〜C18−アルキル、C6−C12−アリール、C5〜C12−シクロアルキル又は五員又は六員の、酸素原子、窒素原子及び/又は硫黄原子を有する複素環を意味し、その際、上述の基は、そのつどアリール、アルキル、アリールオキシ、アルキルオキシ、ヘテロ原子及び/又は複素環によって置換されていてよく、かつ
R17は、水素、C1〜C18−アルキル又はC6〜C12−アリールを意味する]の共開始剤(B)との混合物において使用され、但し、基R13〜R16の少なくとも1個は、C1〜C18−アルキル基であり、かつ基R13〜R16の少なくとも1個は、C6〜C12−アリール基であり、その際、上述の基は、そのつどアリール、アルキル、アリールオキシ、アルキルオキシ、ヘテロ原子及び/又は複素環によって置換されていてよい。
本発明による混合物は、
− 上で示される式An-Cya+の少なくとも1つの成分(A)
及び
− 対イオン1/x Katx+を有する、有利には式(IV)の少なくとも1つの成分(B)
を含有する。
R18及びR19は、そのつど場合により置換されたアリール基を意味し、かつ
R20は、場合により置換されたアルキル基、場合により置換されたアルケニル基、場合により置換された脂環式基、場合により置換されたアリール基又は場合により置換されたアラルキル基を意味し、かつAnA-は、アニオンを意味する]の塩である。
R21−I+−R22 AnB-
[式中、
R21及びR22は、場合により置換されたアリール基を意味し、かつAnB-は、アニオンを意味する]の塩である。
R25は、場合により置換されたアリールを意味し、かつ
R26は、有利には式R25−(CO)−の、場合により置換されたアルキル基、場合により置換されたアリール基又は場合により置換されたベンゾイル基を意味する]のペルオキシドである。
R27、R28、R29、R30又はR31は、そのつど互いに無関係に、水素原子、ハロゲン原子、シアノ基、場合により置換されたアルキル基、場合により置換されたアルコキシ基又は場合により置換されたアリール基を意味し、R32は、場合により置換されたアルキル基を意味し、かつAnC-は、アニオンを意味する]のN−オキシドである。
R33、R34及びR35は、そのつど互いに無関係に、トリハロゲンメチル基、場合により置換されたアルキル基、場合により置換されたアルケニル基又は場合により置換されたアリール基を意味する]のハロゲンメチルトリアジンであり、但し、少なくとも1個の基は、トリハロゲンメチル基である。
− 上で示される式An-Cya+の少なくとも1つの成分(A)、
− 対イオン1/x Katx+を有する、有利には式(IV)の少なくとも1つの成分(B)、及び
− 場合により少なくとも1つの溶媒(C)
から成る。
− 上で示される式An-Cya+の少なくとも1つの成分(A)、
− 対イオン1/x Katx+を有する、有利には式(IV)の少なくとも1つの成分(B)、
− 場合により少なくとも1つの溶媒(C)、
− 少なくとも1つの結合剤(D)、
− 場合により少なくとも1つの反応性希釈剤(E)、
− 場合により少なくとも1つのUV光開始剤(F)、
− 場合により少なくとも1つの着色剤(G)及び
− 場合によりさらなる一般的な塗料添加剤(H)
を含有する。
ベンゾフェノン類は、例えばベンゾフェノン、4−アミノベンゾフェノン、4,4'−ビス(ジメチルアミノ)ベンゾフェノン、4−フェニルベンゾフェノン、4−クロロベンゾフェノン、ミヒラーケトン、o−メトキシベンゾフェノン、2,4,6−トリメチルベンゾフェノン、4−メチルベンゾフェノン、2,4−ジメチルベンゾフェノン、4−イソプロピルベンゾフェノン、2−クロロベンゾフェノン、2,2'−ジクロロベンゾフェノン、4−メトキシベンゾフェノン、4−プロポキシベンゾフェノン又は4−ブトキシベンゾフェノンであり、α−ヒドロキシ−アルキル−アリール−ケトンは、例えば1−ベンゾイルシクロヘキサン−1−オール(1−ヒドロキシ−シクロヘキシル−フェニルケトン)、2−ヒドロキシ−2,2−ジメチルアセトフェノン(2−ヒドロキシ−2−メチル−1−フェニル−プロパン−1−オン)、1−ヒドロキシアセトフェノン、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−オン又は2−ヒドロキシ−2−メチル−1−(4−イソプロペン−2−イル−フェニル)−プロパン−1−オンを重合導入して含有するポリマーであり、
キサントン類及びチオキサントン類は、例えば、10−チオキサンテノン、チオキサンテン−9−オン、キサンテン−9−オン、2,4−ジメチルチオキサントン、2,4−ジエチルチオキサントン、2,4−ジイソプロピルチオキサントン、2,4−ジクロロチオキサントン又はクロロキサンテノンであり、
アントラキノン類は、例えば、β−メチルアントラキノン、t−ブチルアントラキノン、アントラキノンカルボン酸エステル、ベンズ[デ]アントラセン−7−オン、ベンズ[ア]アントラセン−7,12−ジオン、12−ジオン、2−メチルアントラキノン、2−エチルアントラキノン、2−t−ブチルアントラキノン、1−クロロアントラキノン又は2−アミルアントラキノンであり、
アセトフェノン類は、例えば、アセトフェノン、アセトナフトキノン、バレロフェノン、ヘキサノフェノン、α−フェニルブチロフェノン、p−モルホリノプロピオフェノン、ジベンゾスベロン、4−モルホリノベンゾフェノン、p−ジアセチルベンゼン、4'−メトキシアセトフェノン、α−テトラロン、9−アセチルフェナントレン、2−アセチルフェナントレン、3−アセチルフェナントレン、3−アセチルインドール、9−フルオレノン、1−インダノン、1,3,4−トリアセチルベンゼン、1−アセトナフトン、2−アセトナフトン、2,2−ジメトキシ−2−フェニルアセトフェノン、2,2−ジエトキシ−2−フェニルアセトフェノン、1,1−ジクロロアセトフェノン、1−ヒドロキシアセトフェノン、2,2−ジエトキシアセトフェノン、2−メチル−1−[4−(メチルチオ)−フェニル]−2−モルホリノプロパン−1−オン、2,2−ジメトキシ−1,2−ジフェニルエタン−2−オン又は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−オンであり、
ベンゾイン類及びベンゾインエーテル類は、例えば、4−モルホリノデオキシベンゾイン、ベンゾイン、ベンゾインイソブチルエーテル、ベンゾインテトラヒドロピラニルエーテル、ベンゾインメチルエーテル、ベンゾインエチルエーテル、ベンゾインブチルエーテル、ベンゾインイソプロピルエーテル又は7−H−ベンゾインメチルエーテルであり、又は
ケタール類は、例えば、アセトフェノンジメチルケタール、2,2−ジエトキシアセトフェノン、又はベンジルケタール、例えばベンジルジメチルケタールである。
合成を、ガラスブリッジによって結合された、本質的に2つのジャケット付容器(250ml及び2500ml)から成るLabvision(R)実験室用自動装置(Laborautomation)中で実施した。両容器には、インペラー式ガラス攪拌機(Impellerglasruehrer)、阻流板(Stromstoerer)及びサーモスタットが備えられていた。250ml容器中での回転数は350rpmであり、2500ml容器中の回転数は250rpmであった。
Vielsmeier-Haack−ホルミル化:
窒素洗浄装置、還流冷却器及びKPG攪拌機を有する四つ口フラスコ250ml中に、ジメチルホルムアミド8g及び2−[(2−シアノエチル)−m−トリルアミノ]−エチル酢酸エステルを装入した。5℃〜10℃で、オキシ塩化リン6gを10分で滴加した。その後、室温に加温し、70℃で5.5時間、攪拌し、かつ一晩中、攪拌下で冷却させた。その後、メチル−t−ブチルエーテル200mlを添加し、かつ氷水浴で冷却し、かつ5分かけて最大10℃までで、酢酸ナトリウム17gと水70mlからの溶液を滴加した。それから室温にて相分離が行われた。有機相を水で洗浄し、その後、飽和炭酸水素ナトリウム溶液で洗浄し、硫酸ナトリウム上で乾燥させ、回転蒸発器で濃縮した。。
攪拌子を有するエルレンマイヤーフラスコ500ml中に、メタノール120ml及び2−[(2−シアノエチル)(4−ホルミル-3−メチルフェニル)アミノ]エチル酢酸エステル8.7gを装入した。それに加えて、水40mlと炭酸ナトリウム3.4gを添加し、そして一晩中、室温で攪拌した。翌朝、濾過分離し、そして母液をpH7に調節した。回転蒸発器を用いて、メタノールをこの溶液から除去し、ジクロロメタンで3回抽出し、合一された有機相を硫酸ナトリウム上で乾燥させた。真空中での有機溶媒の除去後に、3−[(4−ホルミル−3−メチルフェニル)(2−ヒドロキシエチル)アミノ]プロピオンニトリル6.6g(収率90%)を得た。
窒素洗浄装置、還流冷却器及びKPG攪拌機を有する四つ口フラスコ250ml中で、3−[(4−ホルミル−3−メチルフェニル)(2−ヒドロキシエチル)アミノ]プロピオンニトリル3.2g及び1−エチル−2,3,3−トリメチルインドリウムヨージド4.2gを、トルエン20ml及びn−ブタノール6ml中に懸濁させ、105℃に加熱し、2時間、攪拌した。一晩かけて、室温に冷却し、そして得られた懸濁液を濾過分離した。濾過ケークを、トルエン及びメチル−t−ブチルエーテルで洗浄し、そして真空中で50℃にて乾燥させた。2−((E)−2−{4−[(2−シアノエチル)(2−ヒドロキシエチル)アミノ]−2−メチルフェニル}ビニル)−1−エチル−3,3−ジメチル−3H−インドリウムヨージド6.7g(収率95%)が赤色の固体として得られた。
攪拌子を有するエルレンマイヤーフラスコ1000ml中で、2−((E)−2−{4−[(2−シアノエチル)(2−ヒドロキシエチル)アミノ]−2−メチルフェニル}ビニル)−1−エチル−3,3−ジメチル−3H−インドリウムヨージドをジクロロメタン300ml中に溶解させ、水100ml中のドデシルベンゼンスルホン酸ナトリウム2.1gと混ぜ、そして室温にて3時間、攪拌した。その後、相分離が行われ、有機相を硫酸ナトリウム上で乾燥させ、濾過分離し、真空中で濃縮及び乾燥させた。
このためにサンドウィッチ試験体を、覆いを取り外すことによって開き、塗膜を、場合により金属スパチュラで擦ることによって、以下の通り、その硬度に関して評価した:"なお液状"、"硬化した−しかし軟質"、"硬質"。同様に、残色の度合いを硬化後に評価した。その際、実施例1及び2に記載される、いくつかの色素を使用した際に、該色素の対イオンがヨージドである場合、対イオンが長鎖アルキル基で置換されたアリールスルホネートである場合より多くの残色が塗料中に留まることがわかった。例えば、前出の表からの番号16及び19の色素を有する塗料は、硬化後に、ほとんど無色であった。それに対して、相応するヨージドは、なお僅かに淡青色もしくは僅かに赤色を帯びていた。
シアニンカチオンは、対イオンとしてEP1091247A2から公知であるアルキルスルホネートアニオンを有するものと比較して、対イオンとして式(II)の長鎖アルキル基で置換されたアリールスルホネートと高められた光活性を示す。
Claims (11)
- 式(I)
R 5 、R6、R7及びR8は、そのつど互いに無関係に、水素、C1〜C18−アルキル又はC1〜C18−アルキルオキシ、
R1は、水素、C 1 〜C 18 −アルキル、C 1 〜C 18 −アルキルオキシ又はハロゲン、
R2、R3及びR4は、そのつど互いに無関係に、C1〜C18−アルキル、
R9及びR10は、そのつど互いに無関係に、場合によりアリール、アルキル、アリールオキシ、アルキルオキシ、ヘテロ原子及び/又は複素環によって置換されたC1〜C18−アルキル、C6〜C12−アリール又はC5〜C12−シクロアルキル、
を意味する]のスチリル系カチオンD+
及び対イオンとして、4−ヘキシルベンゼンスルホネート、4−オクチルベンゼンスルホネート、4−デシルベンゼンスルホネート及び4−ドデシルベンゼンスルホネートから成る群から選択されるアニオンAn-からの、放射線硬化性被覆材料用の増感剤系(A)。 - 前記基R9及びR10が、そのつど互いに無関係に、場合によりアリール、アルキル、アリールオキシ、アルキルオキシ、ヘテロ原子及び/又は複素環によって置換されたC1〜C18−アルキルであることを特徴とする、請求項1記載の増感剤系。
- 前記基R9及びR10が、そのつど互いに無関係に、メチル、エチル、n−プロピル、2−ヒドロキシエチル、2−ヒドロキシプロピル、2−クロロエチル、2−シアンエチル、2−アセトキシエチル、シクロヘキシル及びシクロペンチルから成る群から選択されていることを特徴とする、請求項1記載の増感剤系。
- 請求項1から4までのいずれか1項記載の式An- D + の少なくとも1つの成分(A)、及び
対イオン1/x Katx+を有する少なくとも1つの成分(B)、その際、該対イオン 1 / x Kat x+ は、テトラ−n−オクチルアンモニウム、テトラメチルアンモニウム、テトラエチルアンモニウム、テトラ−n−ブチルアンモニウム、トリメチルベンジルアンモニウム、トリメチルセチルアンモニウム、トリエチルベンジルアンモニウム、トリ−n−ブチルベンジルアンモニウム、トリメチルエチルアンモニウム、トリ−n−ブチルエチルアンモニウム、トリエチルメチルアンモニウム、トリ−n−ブチルメチルアンモニウム、ジイソプロピルジエチルアンモニウム、ジイソプロピルエチルメチルアンモニウム、ジイソプロピルエチルベンジルアンモニウム、N,N−ジメチルピペリジニウム、N,N−ジメチルモルホリニウム、N,N−ジメチルピペラジニウム及びN−メチルジアザビシクロ[2.2.2]オクタンから成る群から選択されている、を含有する混合物。 - 請求項1から4までのいずれか1項記載の式An - D + の少なくとも1つの成分(A)、及び
対イオン 1 / x Kat x+ を有する少なくとも1つの成分(B)、その際、該対イオン 1 / x Kat x+ は、1−メチルイミダゾリウム、1−ブチルイミダゾリウム、1,3−ジメチルイミダゾリウム、1,2,3−トリメチルイミダゾリウム、1−n−ブチル−3−メチルイミダゾリウム、1−エチル−3−メチルイミダゾリウム、1,3,4,5−テトラメチルイミダゾリウム、1,3,4−トリメチルイミダゾリウム、2,3−ジメチルイミダゾリウム、1−ブチル−2,3−ジメチルイミダゾリウム、3,4−ジメチルイミダゾリウム、2−エチル−3,4−ジメチルイミダゾリウム、3−メチル−2−エチルイミダゾリウム、3−ブチル−1−メチルイミダゾリウム、3−エチル−1−メチルイミダゾリウム、3−ブチル−1−エチルイミダゾリウム、3−ブチル−1,2−ジメチルイミダゾリウム、1,3−ジ−n−ブチルイミダゾリウム、3−ブチル−1,4,5−トリメチルイミダゾリウム、3−ブチル−1,4−ジメチルイミダゾリウム、3−ブチル−2−メチルイミダゾリウム、1,3−ジブチル−2−メチルイミダゾリウム、3−ブチル−4−メチルイミダゾリウム、3−ブチル−2−エチル−4−メチルイミダゾリウム、3−ブチル−2−エチルイミダゾリウム、1−メチル−3−オクチルイミダゾリウム及び1−デシル−3−メチルイミダゾリウムから成る群から選択されている、を含有する混合物。 - 式An- D + の成分(A)と、対イオン1/x Katx+を有する成分(B)との質量比が、1:1〜1:5であることを特徴とする、請求項5又は6記載の混合物。
- − 請求項1から4までのいずれか1項記載の式An- D + の少なくとも1つの成分(A)、
− 請求項5から7までのいずれか1項記載の対イオン1/x Katx+を有する少なくとも1つの成分(B)、
− 場合により少なくとも1つの溶媒(C)、
− 少なくとも1つの結合剤(D)、
− 場合により少なくとも1つの反応希釈剤(E)、
− 場合により少なくとも1つのUV光開始剤(F)、
− 場合により少なくとも1つの着色剤(G)及び
− 場合によりさらなる一般的な塗料添加剤(H)
を含有する放射線硬化性被覆材料。 - 請求項8記載の放射線硬化性被覆材料を、10〜1000μmの厚さで、被覆されるべき物体に施与し、場合により乾燥させ、引き続き、700〜900nmの波長領域の電磁放射線による照射によって照射することを特徴とする、基材の被覆方法。
- 木材、紙、ボール紙、板紙、織物、皮革、皮革代用品、不織布、プラスチック表面、ガラス、セラミック、鉱物建築材料、金属又は被覆金属を被覆するための、請求項8記載の放射線硬化性被覆材料の使用。
- 自動車のクリアコート又はトップコートとして、又は、自動車のクリアコート又はトップコート中での、あるいは、塗料、工業塗料、コイル被覆、成形材料、注型材料又は歯科用材料中での、請求項8記載の放射線硬化性被覆材料の使用。
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PCT/EP2009/064967 WO2010055050A1 (de) | 2008-11-12 | 2009-11-11 | Strahlungshärtbare beschichtungsmassen |
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EP2450893A1 (de) * | 2010-11-08 | 2012-05-09 | Bayer MaterialScience AG | Photopolymer-Formulierung zur Herstellung holographischer Medien mit hoch vernetzten Matrixpolymeren |
US8632858B2 (en) * | 2011-02-14 | 2014-01-21 | Eastman Kodak Company | Methods of photocuring and imaging |
US10186924B2 (en) | 2011-12-15 | 2019-01-22 | Siemens Aktiengesellschaft | Method for producing a corona shield, fast-curing corona shield system, and electric machine |
EP2645540A1 (de) * | 2012-03-28 | 2013-10-02 | Siemens Aktiengesellschaft | Glimmschutzwerkstoff für eine elektrische Maschine |
WO2014051026A1 (ja) * | 2012-09-27 | 2014-04-03 | 富士フイルム株式会社 | インク組成物、インクジェット記録方法、印刷物、ビスアシルホスフィンオキシド化合物、及び、モノアシルホスフィンオキシド化合物 |
WO2016096639A1 (en) * | 2014-12-17 | 2016-06-23 | Covestro Deutschland Ag | Photopolymer comprising a new class of photo initiator |
JP6634071B2 (ja) | 2015-03-31 | 2020-01-22 | 三井化学株式会社 | 歯科材料用重合性モノマー、組成物、接着性歯科材料、及びキット |
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EP3336067A1 (en) * | 2016-12-19 | 2018-06-20 | Eternit GmbH | Coated fiber cement products and methods for the production thereof |
BR102021021638A2 (pt) * | 2021-10-28 | 2023-05-09 | Wekoamérica Latina Equipamentos Industriais Ltda. | Composição de aditivo em pó para cura uv, processo para preparar dita composição, processo de preparação de uma resina, tinta ou verniz em pó curável por radiação uv, resina, tinta ou verniz em pó curável por uv e uso de dita composição |
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JPH1081838A (ja) * | 1996-07-16 | 1998-03-31 | Showa Denko Kk | 光硬化性材料及びその硬化方法 |
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JP2001026728A (ja) * | 1999-07-13 | 2001-01-30 | Showa Denko Kk | 光硬化性路面標示用塗料組成物 |
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US20030054291A1 (en) * | 2001-03-28 | 2003-03-20 | Horst Berneth | Optical data storage medium containing a hemicyanine dye as the light-absorbing compound in the information layer |
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