CN102216400B - 可辐射固化涂料 - Google Patents
可辐射固化涂料 Download PDFInfo
- Publication number
- CN102216400B CN102216400B CN200980145009.9A CN200980145009A CN102216400B CN 102216400 B CN102216400 B CN 102216400B CN 200980145009 A CN200980145009 A CN 200980145009A CN 102216400 B CN102216400 B CN 102216400B
- Authority
- CN
- China
- Prior art keywords
- butyl
- ethyl
- methyl
- methylimidazole
- ammonium
- 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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- 239000011248 coating agent Substances 0.000 title claims abstract description 64
- 239000000463 material Substances 0.000 title claims abstract description 19
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- -1 4-octyl group Chemical group 0.000 claims description 196
- 150000002500 ions Chemical class 0.000 claims description 72
- 239000000203 mixture Substances 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 239000003795 chemical substances by application Substances 0.000 claims description 26
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- 230000001235 sensitizing effect Effects 0.000 claims description 23
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 19
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- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
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- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims description 9
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- 229910052736 halogen Inorganic materials 0.000 claims description 9
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- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 8
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 claims description 8
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 6
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
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- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 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
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
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- 229910052751 metal Inorganic materials 0.000 claims description 4
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- 239000000654 additive Substances 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
- CDIWYWUGTVLWJM-UHFFFAOYSA-N 1,3,4-trimethylimidazol-1-ium Chemical compound CC1=C[N+](C)=CN1C CDIWYWUGTVLWJM-UHFFFAOYSA-N 0.000 claims description 2
- MCMFEZDRQOJKMN-UHFFFAOYSA-N 1-butylimidazole Chemical compound CCCCN1C=CN=C1 MCMFEZDRQOJKMN-UHFFFAOYSA-N 0.000 claims description 2
- NUUDMTGMAZJCBY-UHFFFAOYSA-N 1-decyl-3-methyl-2h-imidazole Chemical compound CCCCCCCCCCN1CN(C)C=C1 NUUDMTGMAZJCBY-UHFFFAOYSA-N 0.000 claims description 2
- BJDVEYLUFYKDIQ-UHFFFAOYSA-N 3-methyl-2-oxopentanal Chemical compound CCC(C)C(=O)C=O BJDVEYLUFYKDIQ-UHFFFAOYSA-N 0.000 claims description 2
- UASQKKHYUPBQJR-UHFFFAOYSA-N 4-decylbenzenesulfonic acid Chemical compound CCCCCCCCCCC1=CC=C(S(O)(=O)=O)C=C1 UASQKKHYUPBQJR-UHFFFAOYSA-N 0.000 claims description 2
- LLCHQRKZFHWNRT-UHFFFAOYSA-N C(C)C1=C(C([N+](C)(C)CCCCCCCCCCCCCCCC)(CC)CC)C=CC=C1 Chemical compound C(C)C1=C(C([N+](C)(C)CCCCCCCCCCCCCCCC)(CC)CC)C=CC=C1 LLCHQRKZFHWNRT-UHFFFAOYSA-N 0.000 claims description 2
- XBFZNCSEYRABGK-UHFFFAOYSA-N CCCCCCCCCCCCCCCC[N+](C)(C)C.CN(C)C Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C)C.CN(C)C XBFZNCSEYRABGK-UHFFFAOYSA-N 0.000 claims description 2
- RNCYIAWLGISVQR-UHFFFAOYSA-N benzyl-ethyl-di(propan-2-yl)azanium Chemical compound CC[N+](C(C)C)(C(C)C)CC1=CC=CC=C1 RNCYIAWLGISVQR-UHFFFAOYSA-N 0.000 claims description 2
- 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
- 238000001035 drying Methods 0.000 claims description 2
- 230000005670 electromagnetic radiation Effects 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
- 229940015043 glyoxal Drugs 0.000 claims description 2
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- 239000010985 leather Substances 0.000 claims description 2
- 239000002649 leather substitute Substances 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- MTKJRUNLKOGMRG-UHFFFAOYSA-N n,n-dimethylmethanamine;ethanamine Chemical compound CCN.CN(C)C MTKJRUNLKOGMRG-UHFFFAOYSA-N 0.000 claims description 2
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 claims description 2
- 239000004745 nonwoven fabric Substances 0.000 claims description 2
- 239000000758 substrate Substances 0.000 claims description 2
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- 238000000465 moulding Methods 0.000 claims 1
- 239000000049 pigment Substances 0.000 description 31
- 239000000975 dye Substances 0.000 description 30
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 22
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 21
- 150000003254 radicals Chemical class 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 239000002585 base Substances 0.000 description 12
- 229910052760 oxygen Inorganic materials 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
- 235000010290 biphenyl Nutrition 0.000 description 10
- 239000001301 oxygen Substances 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 9
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 241000723346 Cinnamomum camphora Species 0.000 description 8
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- 229960000846 camphor Drugs 0.000 description 8
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- 239000000945 filler Substances 0.000 description 8
- 239000001327 prunus amygdalus amara l. extract Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 7
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 7
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
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- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 6
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
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- 150000003457 sulfones Chemical class 0.000 description 6
- LUMIAJYHNYFZLD-UHFFFAOYSA-N 4-(chloromethyl)triazine Chemical compound ClCC1=CC=NN=N1 LUMIAJYHNYFZLD-UHFFFAOYSA-N 0.000 description 5
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- 125000002091 cationic group Chemical group 0.000 description 3
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- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical group CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 3
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- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
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- 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
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Classifications
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- 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
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/029—Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
-
- 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
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
Abstract
本发明涉及包含新型光敏引发剂的可辐射固化涂料及其用途。
Description
本发明涉及包含新型光敏引发剂的可辐射固化涂料及其用途。
本发明使用双组分IR光敏引发剂体系作为光敏引发剂,其包含至少一种敏化剂染料(还称为敏化剂)和至少一种自由基引发剂(还称为共引发剂)。
花青染料由花青阳离子和相应阴离子构成。它可为单独的阴离子或内部的阴离子;换句话说,使得该阴离子基团化学连接至花青阳离子。通常它们在其制备过程中以简单盐如卤化物、四氟硼酸盐、高氯酸盐或甲苯磺酸盐得到。迄今为止还未公开具有含长链烷基或烷基取代芳基的阴离子的花青染料。花青染料可市购。
阳离子花青染料常以其烷基-和芳基磺酸盐、硫酸盐、氯化物、碘化物等的形式使用。
本发明敏化剂选择以选择阴离子为特征的苯乙烯系花青阳离子。
苯乙烯系花青阳离子例如由US 6,110,987已知。其中公开的用于苯乙烯系花青阳离子如结构2、5、10、11、12和13的所述阴离子为卤离子并且作为磺酸根,仅公开了苯磺酸根、对甲苯磺酸根和甲基磺酸根。作为敏化剂,这些在涂料中仅具有低溶解性。
同样适用于EP 915136B1、EP 1069163A1和EP 1002817B1的苯乙烯系花青阳离子,在其中的结构1、3、4和6-9的每种情况下,以卤离子、高氯酸根或四苯基硼酸根的盐得到。作为阴离子的萘磺酸根被描述为其它敏化剂的抗衡离子。
同样适用于EP 879829B1(=US 6,165,686)的敏化剂。
EP 1170339A2公开了具有含有偶氮基的有机金属配合物的苯乙烯系花青阳离子。
V.S.Jolly、P.I.Ittyerah和K.P.Sharme在Orient.J.Chem.17(2),275-278,2001中公开了呈其碘化物形式的苯乙烯系花青阳离子。
由EP 1091247A2,段落[0109]-[0111]已知,将长链脂族磺酸根作为花青阳离子的抗衡离子。
例如由WO 2006/058731已知长链磺酸根作为阴离子。然而,暴露之后,其中作为花青阳离子所公开的敏化剂具有有色性,其尤其在清漆中是破坏性的。
本发明的目的是提供可辐射固化涂料用敏化剂,其在暴露时显示出有效地全固化,固化后具有低有色性水平并且在可辐射固化涂料中显示出良好的溶解性。
该目的借助可辐射固化涂料用敏化剂体系(A)实现,该体系包含式(I)的苯乙烯系阳离子D+和作为抗衡离子的阴离子An-:
其中,
R1、R5、R6、R7和R8可各自独立地为氢、C1-C18烷基或C1-C18烷氧基,
R1可额外为卤素,优选溴,
R2、R3和R4可各自独立地为C1-C18烷基,
R9和R10可各自独立地为未取代或被芳基、烷基、芳氧基、烷氧基、杂原子和/或杂环取代的C1-C18烷基、C6-C12芳基或C5-C12环烷基,
R11可为C5-C18烷基,
R12可为C1-C18烷基。
其中定义如下:
任选被芳基、烷基、芳氧基、烷氧基、杂原子和/或杂环取代的C1-C18烷基例如为甲基、乙基、丙基、异丙基、正丁基、仲丁基、叔丁基、戊基、己基、庚基、辛基、2-乙基己基、2,4,4-三甲基戊基、癸基、十二烷基、十四烷基、十七烷基、十八烷基、1,1-二甲基丙基、1,1-二甲基丁基、1,1,3,3-四甲基丁基、苄基、1-苯基乙基、2-苯基乙基、α,α-二甲基苄基、二苯甲基、对甲苯基甲基、1-(对丁基苯基)乙基、对氯苄基、2,4-二氯苄基、对甲氧基苄基、间乙氧基苄基、2-氰基乙基、2-氰基丙基、2-甲氧基羰基乙基、2-乙氧基羰基乙基、2-丁氧基羰基丙基、1,2-二(甲氧基羰基)乙基、2-甲氧基乙基、2-乙氧基乙基、2-丁氧基乙基、二乙氧基甲基、二乙氧基乙基、1,3-二氧戊环-2-基、1,3-二氧戊环-2-基、2-甲基-1,3-二氧戊环-2-基、4-甲基-1,3-二氧戊环-2-基、2-异丙氧基乙基、2-丁氧基丙基、2-辛氧基乙基、氯甲基、2-氯乙基、三氯甲基、三氟甲基、1,1-二甲基-2-氯乙基、2-甲氧基异丙基、2-乙氧基乙基、丁基硫代甲基、2-十二烷基硫代乙基、2-苯基硫代乙基、2,2,2-三氟乙基、2-羟基乙基、2-羟基丙基、3-羟基丙基、4-羟基丁基、6-羟基己基、2-氨基乙基、2-氨基丙基、3-氨基丙基、4-氨基丁基、6-氨基己基、2-甲基氨基乙基、2-甲基氨基丙基、3-甲基氨基丙基、4-甲基氨基丁基、6-甲基氨基己基、2-二甲基氨基乙基、2-二甲基氨基丙基、3-二甲基氨基丙基、4-二甲基氨基丁基、6-二甲基氨基己基、2-羟基-2,2-二甲基乙基、2-苯氧基乙基、2-苯氧基丙基、3-苯氧基丙基、4-苯氧基丁基、6-苯氧基己基、2-甲氧基乙基、2-甲氧基丙基、3-甲氧基丙基、4-甲氧基丁基、6-甲氧基己基、2-乙氧基乙基、2-乙氧基丙基、3-乙氧基丙基、4-乙氧基丁基或6-乙氧基己基,
未取代或被芳基、烷基、芳氧基、烷氧基、杂原子和/或杂环取代的C5-C18烷基例如为戊基、己基、庚基、辛基、2-乙基己基、2,4,4-三甲基戊基、癸基、十二烷基、十四烷基、十七烷基、十八烷基、1,1-二甲基丙基、1,1-二甲基丁基、1,1,3,3-四甲基丁基,
任选被芳基、烷基、芳氧基、烷氧基、杂原子和/或杂环取代的C6-C12芳基例如为苯基、甲苯基、二甲苯基、α-萘基、β-萘基、4-联苯基、氯苯基、二氯苯基、三氯苯基、二氟苯基、甲基苯基、二甲基苯基、三甲基苯基、乙基苯基、二乙基苯基、异丙基苯基、叔丁基苯基、十二烷基苯基、甲氧基苯基、二甲氧基苯基、乙氧基苯基、己氧基苯基、甲基萘基、异丙基萘基、氯萘基、乙氧基萘基、2,6-二甲基苯基、2,4,6-三甲基苯基、2,6-二甲氧基苯基、2,6-二氯苯基、4-溴苯基、2-或4-硝基苯基、2,4-或2,6-二硝基苯基、4-二甲基氨基苯基、4-乙酰基苯基、甲氧基乙基苯基或乙氧基甲基苯基,
任选被芳基、烷基、芳氧基、烷氧基、杂原子和/或杂环取代的C5-C12环烷基例如为环戊基、环己基、环辛基、环十二烷基、甲基环戊基、二甲基环戊基、甲基环己基、二甲基环己基、二乙基环己基、丁基环己基、甲氧基环己基、二甲氧基环己基、二乙氧基环己基、丁基硫代环己基、氯环己基、二氯环己基、二氯环戊基或者饱和或不饱和双环体系如降冰片烷基或降冰片烯基。
基团R1、R5、R6、R7和R8各自独立地优选为氢或C1-C4烷基,更优选氢、甲基或乙基,非常优选氢或甲基,尤其是氢。
在本说明书中C1-C4烷基为甲基、乙基、丙基、异丙基、正丁基、仲丁基或叔丁基,优选甲基、乙基或正丁基,更优选甲基或乙基,非常优选甲基。
基团R1优选位于吲哚环上5或6位。
基团R5、R6、R7和R8中优选至少两个为氢,更优选至少3个,非常优选所有4个为氢。
基团R2可优选为C1-C4烷基,更优选甲基或乙基,非常优选乙基。
基团R3和R4可各自独立地优选为甲基或乙基,更优选乙基。在一个优选的实施方案中,两个基团R3和R4是相同的。
基团R9和R10各自独立地优选为未取代或被芳基、烷基、芳氧基、烷氧基、杂原子和/或杂环取代的C1-C18烷基,更优选甲基、乙基、正丙基、2-羟基乙基、2-羟基丙基、2-氯乙基、2-氰基乙基、2-乙酰氧基乙基、环己基或环戊基,非常优选甲基、乙基、2-羟基乙基、2-氯乙基和2-氰基乙基,尤其是甲基、乙基和2-氰基乙基。
在一个可能的实施方案中,基团R9和R10可形成连接的链,例如1,5-亚戊基、1,4-亚丁基或3-氧杂-1,5-亚戊基。
在另一可能的实施方案中,基团R9和R8和/或R6和R10可形成连接的链,例如1,2-亚乙基或1,3-亚丙基。此时优选基团R9和R8以及基团R6和R10均形成链,更优选在每种情况下链长相同。
基团R11例如为线性或支化烷基,优选线性烷基。优选1-戊基、1-己基、2-乙基-1-己基、1-辛基、1-壬基、1-癸基、1-十一烷基、1-十二烷基或1-十四烷基。特别优选1-己基、1-辛基、1-癸基、1-十二烷基或1-十四烷基。
基团R12可例如为甲基、乙基、正丁基、正己基、正辛基、正癸基或正十二烷基,优选甲基、乙基、正丁基或正十二烷基,更优选甲基、乙基或正十二烷基。
苯乙烯系花青阳离子D+优选选自如下个体:
*编号2;R9+R8:1,3-亚丙基,R10+R6:1,3-亚丙基
优选阴离子An-为式(II)基团,更优选正辛基磺酸根,正癸基磺酸根或正十二烷基磺酸根以及4-烷基苯磺酸根(其中烷基由6-12个碳原子构成)如4-己基苯磺酸根、4-辛基苯磺酸根、4-癸基苯磺酸根或4-十二烷基苯磺酸根。就此所述产物还可以以原则上已知的方式为技术产物,其显示出具有不同长度的不同烷基的分布。特别优选4-正十二烷基苯磺酸根作为An-。
敏化剂优选以与具有缔合抗衡离子1/xcatx+的式(IV)共引发剂(B)的混合物使用:
其中
x为1或2,
cat为阳离子,
z1、z2、z3和z4各自独立地为0或1,
z1+z2+z3+z4之和为0、1、2或3,优选0、1或2,更优选0或1,非常优选0,
Y1、Y2、Y3和Y4各自独立地为O、S或NR17,
R13、R14、R15和R16各自独立为C1-C18烷基,C2-C18烷基,其未间隔或被一个或多个氧和/或硫原子间隔和/或被一个或多个取代或未取代的亚氨基间隔,或为C6-C12芳基,C5-C12环烷基或5-7元含氧、氮和/或硫原子的杂环,其中所述基团各自可被芳基、烷基、芳氧基、烷氧基、杂原子和/或杂环取代,
R17为氢、C1-C18烷基或C6-C12芳基,
条件是基团R13-R16中至少一个为C1-C18烷基,并且基团R13-R16中至少一个为C6-C12芳基,其中在每种情况下所述基团可被芳基、烷基、芳氧基、烷氧基、杂原子和/或杂环取代。
Y1、Y2、Y3和Y4彼此独立地各自优选为氧或NR17,更优选氧。
R17优选氢或C1-C4烷基。
R13、R14、R15和R16在每种情况下优选彼此独立地为C1-C18烷基、C6-C12芳基或C5-C12环烷基,更优选C1-C18烷基和C6-C12芳基,非常优选选自甲基、乙基、丙基、异丙基、正丁基、仲丁基、叔丁基、戊基、己基、庚基、辛基、2-乙基己基、2,4,4-三甲基戊基、癸基、十二烷基、十四烷基、十七烷基、十八烷基、1,1-二甲基丙基、1,1-二甲基丁基、1,1,3,3-四甲基丁基、苄基、1-苯基乙基、2-苯基乙基、α,α-二甲基苄基、二苯甲基、对甲苯基甲基、1-(对丁基苯基)乙基、苯基、甲苯基、二甲苯基、α-萘基、β-萘基、4-联苯基、甲基苯基、二甲基苯基、三甲基苯基、乙基苯基、二乙基苯基、异丙基苯基、叔丁基苯基和十二烷基苯基,特别是选自甲基、乙基、丙基、正丁基、己基、辛基、2-乙基己基、十二烷基、苄基、2-苯基乙基、苯基、甲苯基、α-萘基和β-萘基,尤其是选自甲基、乙基、正丙基、正丁基、苄基、苯基和甲苯基。
根据本发明,基团R13-R16中至少一个为C1-C18烷基且至少一个为C6-C12芳基;优选至少一个为C1-C18烷基,至少一个为C6-C12芳基且另外两个同样选自C1-C18烷基和C6-C12芳基;更优选至少一个为C1-C18烷基且至少两个为C6-C12芳基;非常优选一个为C1-C18烷基且三个为C6-C12芳基。
可辐射固化涂料中敏化剂染料(A)的量由技术人员选择以得到涂料的充足光固化。通常,小于5重量%的量是充足的。证明特别合适的量相对于该涂料所有组分之和为0.05-4重量%,优选0.1-3重量%,更优选0.2-2.5重量%,非常优选0.3-2.0重量%。根据本发明,必须保证加入的敏化剂染料完全溶于涂料中。
该敏化剂染料在涂料中的溶解性优选为至少0.2重量%,更优选至少0.5重量%,非常优选至少1.0重量%,例如至少2重量%。
根据本发明,本发明混合物同样包含组分(B),其包含式(IV)的阴离子硼化合物。
这些阴离子硼化合物具有作为抗衡离子的带x个正电荷的阳离子catx+。这类阳离子可例如为碱金属、碱土金属或铵离子,例如Mg2+、Li+、Na+或K+,但优选为铵离子。
对本发明而言,铵离子为离子化合物,其包含至少一种四取代的氮原子,其中取代基选自C1-C18烷基和C6-C12芳基,优选为烷基。两个或更多个取代基还可连接并形成环使得季氮原子为5-7元环的一部分。
铵阳离子的实例为四正辛基铵、四甲基铵、四乙基铵、四正丁基铵、三甲基苄基铵、三甲基十六烷基铵、三乙基苄基铵、三正丁基苄基铵、三甲基乙基铵、三正丁基乙基铵、三乙基甲基铵、三正丁基甲基铵、二异丙基二乙基铵、二异丙基乙基甲基铵、二异丙基乙基苄基铵、N,N-二甲基哌啶N,N-二甲基吗啉N,N-二甲基哌嗪或N-甲基二氮杂双环[2.2.2]辛烷。优选的烷基铵离子为四辛基铵、四甲基铵、四乙基铵离子和四正丁基铵离子,特别优选四辛基铵离子和四正丁基铵离子,尤其优选四正丁基铵离子。
包含环体系的铵离子的实例为甲基化、乙基化、正丁基化、十六烷基化或苄基化的哌嗪、哌啶、咪唑、吗啉、奎宁环、喹啉、吡啶或三亚乙基二胺。
在一个优选的实施方案中,阴离子硼化合物的阳离子catx+为描述于WO 2008/058885A2,第16页第30行至第25页第29行的那类阳离子。由此这些段落构成本发明公开内容的一部分。
特别优选那些阳离子catx+选自1-甲基咪唑1-丁基咪唑1,3-二甲基咪唑1,2,3-三甲基咪唑1-正丁基-3-甲基咪唑1-乙基-3-甲基咪唑1,3,4,5-四甲基咪唑1,3,4-三甲基咪唑2,3-二甲基咪唑1-丁基-2,3-二甲基咪唑3,4-二甲基咪唑2-乙基-3,4-二甲基咪唑3-甲基-2-乙基咪唑3-丁基-1-甲基咪唑3-乙基-1-甲基咪唑3-丁基-1-乙基咪唑3-丁基-1,2-二甲基咪唑1,3-二正丁基咪唑3-丁基-1,4,5-三甲基咪唑3-丁基-1,4-二甲基咪唑3-丁基-2-甲基咪唑1,3-二丁基-2-甲基咪唑3-丁基-4-甲基咪唑3-丁基-2-乙基-4-甲基咪唑3-丁基-2-乙基咪唑1-甲基-3-辛基咪唑和1-癸基-3-甲基咪唑
本发明另外提供可用作光敏引发剂的组分(A)和(B)的混合物:
本发明混合物包含:
-至少一种如上所示的式An-Cya+的组分(A),和
-至少一种优选具有抗衡离子1/xcatx+的式(IV)的组分(B)。
合适的锍盐例如描述于DE-A119730498,特别是其中第3页,第28-29行中,由此将该段落详细引入本发明公开内容作为参考。
这些盐优选为下式的盐:
其中
R18和R19各自为任选取代的芳基,和
R20为任选取代的烷基、任选取代的链烯基、任选取代的脂环族基团、任选取代的芳基或任选取代的芳烷基,和AnA-为阴离子。
特别优选三苯基锍、二苯基茴香基锍、二苯基(4-甲苯基)锍、二苯基(4-氟苯基)锍、二苯基[4-(苯基硫)苯基)锍、二苯基苄基锍、二苯基(4-氯苄基)锍、二苯基(4-溴苄基)锍、二苯基(4-氰基苄基)锍、二(4-叔丁基苯基)苄基锍、二茴香基(4-溴苯基)锍、二苯基苯甲酰甲基锍、二苯基(4-氯苯甲酰甲基)锍、二苯基(4-氰基苯甲酰甲基)锍、二苯基烯丙基锍、二苯基甲磺酰基锍、二苯基对甲苯磺酰基甲基锍、二苯基(二甲基锍基甲基)锍和二苯基[4-(二苯基锍基苯基]锍。
优选的阴离子AnA-为BF4 -、PF6 -、AsF6 -、SbF6 -、CIO4 -、CI-、Br-、四苯基硼酸根、四(五氟苯基)硼酸根、苯磺酸根阴离子、对甲苯磺酸根阴离子和三氟甲烷磺酸根阴离子。
这些盐优选为下式的盐:
R21-I+-R22AnB-
其中R21和R22为任选取代的芳基且AnB-为阴离子。
优选的阴离子AnB-为BF4 -、PF6 -、AsF6 -、SbF6 -、CIO4 -、CI-、Br-、四苯基硼酸根、四(五氟苯基)硼酸根、苯磺酸根阴离子、对甲苯磺酸根阴离子和三氟甲烷磺酸根阴离子。
合适的砜例如描述于DE-A119730498,特别是其中第4页,第1-12行中,由此将该段落详细引入本发明公开内容作为参考。
这些砜优选为下式的砜:
其中R23为任选取代的芳基且基团R24各自为卤原子。
对本说明书而言,卤素包含氟、氯、溴和碘,优选氯和溴,更优选氯。
特别优选三氯甲基苯基砜、三溴甲基苯基砜、三氯甲基4-氯苯基砜、三溴甲基4-硝基苯基砜、2-三氯甲基苯并噻唑砜、2,4-二氯苯基三氯甲基砜、2-甲基-4-氯苯基三氯甲基砜和2,4-二氯苯基三溴甲基砜。
合适的过氧化物例如描述于DE-A119730498,特别是其中第4页,第13-24行中,由此将该段落详细引入本发明公开内容作为参考。
这些过氧化物优选为下式的过氧化物:
其中
R25为任选取代的芳基,和
R26为任选取代的烷基、任选取代的芳基或任选取代的苯甲酰基,优选为式R25-(CO)-的烷基。
特别优选过氧化苯甲酰、过氧化2,4-二氯苯甲酰、叔丁基过氧化苯甲酸酯、二(叔丁基过氧)间苯二甲酸酯、二(叔丁基过氧)对苯二甲酸酯、二(叔丁基过氧)邻苯二甲酸酯、2,5-二甲基二(苯甲酰基过氧)己烷和3,3′,4,4′-四(叔丁基过氧羰基)二苯甲酮。
合适的吡啶N-氧化物例如描述于DE-A119730498,特别是其中第3页,第44-62行中,由此将该段落详细引入本发明公开内容作为参考。
这些N-氧化物优选为下式的N-氧化物:
其中R27、R28、R29、R30和R31彼此独立地各自为氢原子、卤原子、氰基、任选取代的烷基、任选取代的烷氧基或任选取代的芳基,R32为任选取代的烷基,AnC-为阴离子。
特别优选N-甲氧基吡啶N-乙氧基吡啶N-甲氧基-2-甲基吡啶N-甲氧基-3-甲基吡啶N-乙氧基-2-甲基吡啶N-乙氧基-3-甲基吡啶N-甲氧基-4-溴吡啶N-甲氧基-3-溴吡啶N-甲氧基-2-溴吡啶N-乙氧基-4-溴吡啶N-乙氧基-3-溴吡啶N-乙氧基-2-溴吡啶N-乙氧基-4-氯吡啶N-乙氧基-3-氯吡啶N-乙氧基-2-氯吡啶N-甲氧基-4-甲氧基吡啶N-甲氧基-3-甲氧基吡啶N-甲氧基-2-甲氧基吡啶N-乙氧基-4-甲氧基吡啶N-乙氧基-3-甲氧基吡啶N-乙氧基-2-甲氧基吡啶N-甲氧基-4-苯基吡啶N-甲氧基-3-苯基吡啶N-甲氧基-2-苯基吡啶N-乙氧基-4-苯基吡啶N-乙氧基-3-苯基吡啶N-乙氧基-2-苯基吡啶N-甲氧基-4-氰基吡啶N-乙氧基-4-氰基吡啶N,N′-二甲氧基-4,4′-联吡啶N,N′-二乙氧基-4,4′-联吡啶N,N′-二甲氧基-2,2′-联吡啶和N,N′-二乙氧基-2,2′-联吡啶
优选的阴离子AnC-为BF4 -、PF6 -、AsF6 -、SbF6 -、CIO4 -、CI-、Br-、四苯基硼酸根、四(五氟苯基)硼酸根、苯磺酸根阴离子、对甲苯磺酸根阴离子和三氟甲烷磺酸根阴离子。
合适的卤甲基三嗪例如描述于DE-A119730498,特别是其中第4页,第25-40行中,由此将该段落详细引入本发明公开内容作为参考。
这些卤甲基三嗪优选为下式的卤甲基三嗪:
其中R33、R34和R35彼此独立地各自为三卤甲基、任选取代的烷基、任选取代的链烯基或任选取代的芳基,条件是至少一个基团为三卤甲基。
特别优选2,4,6-三(三氯甲基)-s-三嗪、2,4,6-三(三溴甲基)-s-三嗪、2,4-二(二氯甲基)-6-三氯甲基-s-三嗪、2-丙酰基-4,6-二(三氯甲基)-s-三嗪、2-苯甲酰基-4,6-二(三氯甲基)-s-三嗪、2-(4-氰基苯基-4,6-二(三氯甲基)-s-三嗪、2-(4-硝基苯基)-4,6-二(三氯甲基)-s-三嗪、2-(4-氯苯基-4,6-二(三氯甲基)-s-三嗪、2-(4-枯烯基)-4,6-二(三氯甲基)-s-三嗪、2-(4-氨基苯基)-4,6-二(三氯甲基)-s-三嗪、2,4-二(4-甲氧基苯基)-6-三氯甲基、2,4-二(3-氯苯基)-6-三氯甲基-s-三嗪、2-(4-甲氧基苯乙烯基(三氯甲基)-s-三嗪、2-(4-氯苯乙烯基)-4,6-二(三氯甲基)-s-三嗪、2-(4-氨基苯基)-4,6-二(三氯甲基)-s-三嗪、2,4-二(4-甲氧基苯基)-6-三氯甲基-s-三嗪、2,4-二(3-氯苯基)-6-三氯甲基-s-三嗪、2-(4-甲氧基苯乙烯基)-4,6-二(三氯甲基)-s-三嗪、2-(4-氯苯乙烯基)-4,6-二(三氯甲基)-s-三嗪、2-(4-氨基苯乙烯基)-4,6-二(二氯甲基)-s-三嗪、2-(4′-甲氧基-1′-萘基)-4,6-二(三氯甲基)-s-三嗪和2-(6′-硝基-1′-萘基)-4,6-二(三氯甲基)-s-三嗪。
该混合物可另外包含至少一种溶剂(C)。这些可例如为酯类如乙酸丁酯或乙酸乙酯,芳族或(环)脂族烃类如二甲苯、甲苯或庚烷,酮类如丙酮、异丁基甲基酮、甲基乙基酮或环己酮,醇类如乙醇、异丙醇、单-或低聚乙二醇或丙二醇,单-或二醚化的乙二醇醚或丙二醇醚,乙二醇醚乙酸酯如甲氧基丙基乙酸酯,环状醚类如四氢呋喃,酰胺如二甲基甲酰胺或N-甲基吡咯烷酮和/或例如水。
优选的本发明混合物由以下组分构成:
-至少一种如上所示的式An-Cya+的组分(A),
-至少一种优选具有抗衡离子1/xcatx+的式(IV)的组分(B),和
-合适的话至少一种溶剂(C)。
在一个优选的实施方案中,所用本发明混合物不含溶剂(C)。
在本发明混合物中,式An-Cya+的组分(A)与具有抗衡离子1/xcatx+的式(IV)的组分(B)的重量比优选为1∶1-1∶5,更优选1∶1-1∶4,非常优选1∶2-1∶4。
本发明混合物高度溶于涂料中。阴离子的选择和阳离子上取代基的选择可影响溶解性。在花青或式(II)或(III)阴离子上作为取代基的较长烷基链通常也会得到较好的溶解性。
本发明敏化剂染料通常在400-650nm的波长范围中具有最大吸收。技术人员可以以原则上已知的方式通过选择花青阳离子上的取代基从而影响该敏化剂染料的最大吸收。
用于光固化的IR辐射可为宽谱带辐射如来自发光二极管(LED)、卤素灯、Xe灯等。它也可为窄谱带辐射或可为特定波长的激光辐射。特别合适的激光器为在IR范围中发射的已知激光器,其中实例为半导体二极管激光器。该辐射可以以连续或脉冲形式,例如以闪光的形式提供。
本发明另外提供包含本发明混合物的可辐射固化涂料。
这种涂料通常包含以下组分:
-至少一种如上所示的式An-Cya+的组分(A),
-至少一种优选具有抗衡离子1/xcatx+的式(IV)的组分(B),
-合适的话至少一种溶剂(C),
-至少一种基料(D),
-合适的话至少一种反应性稀释剂(E),
-合适的话至少一种UV光敏引发剂(F),
-合适的话至少一种色料(G),和
-合适的话其它典型涂料添加剂(H)。
基料(D)为具有自由基聚合性烯属不饱和基团的化合物。可辐射固化材料优选每1000g可辐射固化化合物包含0.001-12mol,更优选0.1-8mol,非常优选0.5-7mol可辐射固化烯属不饱和基团。
合适的可辐射固化化合物,例如包括(甲基)丙烯酸系化合物、乙烯基酰胺、不饱和聚酯(例如基于马来酸或富马酸)或马来酰亚胺/乙烯基醚体系。
优选(甲基)丙烯酸酯化合物如聚酯(甲基)丙烯酸酯、聚醚(甲基)丙烯酸酯、氨基甲酸酯(甲基)丙烯酸酯、环氧(甲基)丙烯酸酯、碳酸酯(甲基)丙烯酸酯、聚硅氧烷(甲基)丙烯酸酯和丙烯酸化聚丙烯酸酯。
优选至少40mol%,更优选至少60mol%的可辐射固化烯属不饱和基团为(甲基)丙烯酸系基团。
可辐射固化化合物可例如呈在有机溶剂或例如水中的溶液形式,或呈水分散体或粉末形式。
优选那些可辐射固化化合物,因此还有那些可辐射固化材料,其在室温下为流体。然而,以熔体或粉末(粉末涂料)形式施用可辐射固化化合物或涂料也可能是有利的。可辐射固化材料优选包含小于20重量%,尤其是小于10重量%的有机溶剂和/或水。优选它们不含溶剂和水(即100%体系)。此时优选可避免干燥步骤。
反应性稀释剂(E)例如为(甲基)丙烯酸与具有1-20个碳原子的醇的酯,其中实例为(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸丁酯、(甲基)丙烯酸2-乙基己基酯、丙烯酸2-羟基乙基酯、丙烯酸4-羟基丁基酯、丙烯酸二氢二环戊二烯基酯,乙烯基芳族化合物,其中实例为苯乙烯和二乙烯基苯,α,β-不饱和腈,其中实例为丙烯腈和甲基丙烯腈,α,β-不饱和醛,其中实例为丙烯醛和甲基丙烯醛,乙烯基酯,其中实例为乙酸乙烯酯和丙酸乙烯酯,卤化烯属不饱和化合物,其中实例为氯乙烯和偏二氯乙烯,共轭的不饱和化合物,其中实例为丁二烯、异戊二烯和氯丁二烯,单不饱和化合物,其中实例为乙烯、丙烯、1-丁烯、2-丁烯和异丁烯,环状单不饱和化合物,其中实例为环戊烯、环己烯和环十二碳烯、N-乙烯基甲酰胺、烯丙基乙酸、乙烯基乙酸,具有3-8个碳原子的单烯属不饱和羧酸及其水溶性碱金属、碱土金属或铵盐,例如:丙烯酸、甲基丙烯酸、二甲基丙烯酸、乙基丙烯酸、马来酸、柠康酸、亚甲基丙二酸、巴豆酸、富马酸、中康酸和衣康酸,N-乙基基吡咯烷酮,N-乙烯基内酰胺,其中实例为N-乙烯基己内酰胺,N-乙烯基-N-烷基酰胺或N-乙烯基酰胺如N-乙烯基乙酰胺、N-乙烯基-N-甲基甲酰胺和N-乙烯基-N-甲基乙酰胺,或乙烯基醚,其中实例为甲基乙烯基醚、乙基乙烯基醚、正丙基乙烯基醚、异丙基乙烯基醚、正丁基乙烯基醚、仲丁基乙烯基醚、异丁基乙烯基醚、叔丁基乙烯基醚、4-羟基丁基乙烯基醚及其混合物。
在本说明书中(甲基)丙烯酸表示甲基丙烯酸和丙烯酸,优选丙烯酸。
作为UV光敏引发剂(F),可使用技术人员已知的那些光敏引发剂,其中实例为描述于“Advances in Polymer Science”,第14卷,Springer Berlin1974或K.K.Dietliker,Chemistry and Technology of UV and EBFormulation for Coatings,Inks and Paints,第3卷;Photoinitiators for FreeRadical and Cationic Polymerization,P.K.T.Oldring(Eds.),SITATechnology Ltd,London中的那些。与该IR光敏引发剂相反,UV光敏引发剂基本通过λ=200-700nm,更优选λ=200-500nm,非常优选λ=250-400nm的波长范围的光激发。
根据本发明,这包含当暴露于光时释放自由基且能引发自由基反应如自由基聚合的那些光敏引发剂。
合适的实例包括氧化膦、二苯甲酮、α-羟基烷基芳基酮、噻吨酮、蒽醌、苯乙酮、苯偶姻和苯偶姻醚、缩酮、咪唑或苯甲酰甲酸和其混合物。
氧化膦例如为单-或二酰基氧化膦,例如如EP-A 7508、EP-A 57474、DE-A 19618720、EP-A 495751或EP-A 615980所述,其中实例为2,4,6-三甲基苯甲酰基二苯基氧化膦、2,4,6-三甲基苯甲酰基苯基次膦酸乙酯或二(2,6-二甲氧基苯甲酰基)-2,4,4-三甲基戊基氧化膦,
二苯甲酮例如为二苯甲酮、4-氨基二苯甲酮、4,4′-二(二甲基氨基)二苯甲酮、4-苯基二苯甲酮、4-氯二苯甲酮、米蚩酮、邻甲氧基二苯甲酮、2,4,6-三甲基二苯甲酮、4-甲基二苯甲酮、2,4-二甲基二苯甲酮、4-异丙基二苯甲酮、2-氯二苯甲酮、2,2′-二氯二苯甲酮、4-甲氧基二苯甲酮、4-丙氧基二苯甲酮或4-丁氧基二苯甲酮,
α-羟烷基芳基酮例如为1-苯甲酰基环己-1-醇(1-羟基环己基苯基酮)、2-羟基-2,2-二甲基苯乙酮(2-羟基-2-甲基-1-苯基丙-1-酮)、1-羟基苯乙酮、1-[4-(2-羟基乙氧基)苯基]-2-羟基-2-甲基-1-丙-1-酮或包含呈共聚形式的2-羟基-2-甲基-1-(4-异丙烯-2-基苯基)丙-1-酮的聚合物,
呫吨酮和噻吨酮例如为10-噻吨酮、噻吨-9-酮、呫吨-9-酮、2,4-二甲基噻吨酮、2,4-二乙基噻吨酮、2,4-二异丙基噻吨酮、2,4-二氯噻吨酮或氯呫吨酮,
蒽醌例如为β-甲基蒽醌、叔丁基蒽醌、蒽醌甲酸酯、苯并[de]蒽-7-酮、苯并[a]蒽-7,12-二酮、2-甲基蒽醌、2-乙基蒽醌、2-叔丁基蒽醌、1-氯蒽醌或2-戊基蒽醌,
苯乙酮类例如为苯乙酮、乙酰萘醌、苯戊酮、苯己酮、α-苯基苯丁酮、对吗啉基苯丙酮、二苯并环庚酮、4-吗啉基二苯甲酮、对二乙酰基苯、4′-甲氧基苯乙酮、α-四氢萘酮、9-乙酰基菲、2-乙酰基菲、3-乙酰基菲、3-乙酰基吲哚、9-芴酮、1-二氢茚酮、1,3,4-三乙酰基苯、1-萘乙酮、2-萘乙酮、2,2-二甲氧基-2-苯基苯乙酮、2,2-二乙氧基-2-苯基苯乙酮、1,1-二氯苯乙酮、1-羟基苯乙酮、2,2-二乙氧基苯乙酮、2-甲基-1-[4-(甲基硫)苯基]-2-吗啉基丙-1-酮、2,2-二甲氧基-1,2-二苯基乙-2-酮或2-苄基-2-二甲基氨基-1-(4-吗啉基苯基)丁-1-酮,
苯偶姻和苯偶姻醚例如为4-吗啉基脱氧苯偶姻、苯偶姻、苯偶姻异丁基醚、苯偶姻四氢吡喃醚、苯偶姻甲基醚、苯偶姻乙基醚、苯偶姻丁基醚、苯偶姻异丙基醚或7H-苯偶姻甲基醚;或
缩酮例如为苯乙酮二甲基缩酮、2,2-二乙氧基苯乙酮或偶苯酰缩酮如偶苯酰二甲基缩酮。
苯甲酰甲酸例如描述于DE-A 19826712、DE-A 19913353或WO98/33761。
可额外使用的光敏引发剂例如为苯甲醛、甲基乙基酮、1-萘甲醛、三苯基膦、三邻甲苯基膦或2,3-丁二酮。
通常混合物例如包含2-羟基-2-甲基-1-苯基丙-2-酮和1-羟基环己基苯基酮、二(2,6-二甲氧基苯甲酰基)-2,4,4-三甲基戊基氧化膦和2-羟基-2-甲基-1-苯基丙-1-酮、二苯甲酮和1-羟基环己基苯基酮、二(2,6-二甲氧基苯甲酰基)-2,4,4-三甲基戊基氧化膦和1-羟基环己基苯基酮、2,4,6-三甲基苯甲酰基二苯基氧化膦和2-羟基-2-甲基-1-苯基丙-1-酮、2,4,6-三甲基二苯甲酮和4-甲基二苯甲酮,或2,4,6-三甲基二苯甲酮和4-甲基二苯甲酮,以及2,4,6-三甲基苯甲酰基二苯基氧化膦。
在一个本发明优选的实施方案中,至少一种UV光敏引发剂存在于本发明涂料中。
对本说明书而言,所用色料(G)包括颜料和染料,优选颜料。
根据CDChemie Lexikon-第1.0版,Stuttgart/New York:Georg Thieme Verlag 1995,参考DIN 55943,颜料(G)为颗粒状的“基本不溶于施用介质中的有机或无机彩色或非彩色的色料”。
这里基本不溶指在25℃下溶解性小于1g/1000g施用介质,优选小于0.5g/1000g施用介质,更优选小于0.25g/1000g施用介质,非常优选小于0.1g/1000g施用介质,特别是小于0.05g/1000g施用介质。
在真正意义上颜料的实例包括吸收颜料和/或效应颜料,优选吸收颜料的任何所需体系。颜料组分的数目和选择不受任何限制。它们可例如以任意方式调整到具体要求如所需色彩效果。例如可将标准化漆混合物体系的所有颜料组分作为基础。
效应颜料是指显示片状结构并赋予表面涂料特定装饰性色彩效果的所有颜料。效应颜料例如为通常在车辆涂饰和工业涂料中采用的所有效应赋予性颜料。这种效应颜料的实例为纯金属颜料,例如铝、铁或铜颜料;光干涉颜料如二氧化钛涂覆的云母、氧化铁涂覆的云母、混合氧化物涂覆的云母(例如用二氧化钛和Fe2O3或二氧化钛和Cr2O3)、金属氧化物涂覆的铝或液晶颜料。
色彩赋予性吸收颜料例如为可在漆工业中使用的常规有机或无机吸收颜料。有机吸收颜料的实例为偶氮颜料、酞菁颜料、喹吖啶酮颜料和吡咯并吡咯颜料。无机吸收颜料的实例为氧化铁颜料、二氧化钛和炭黑。
染料同样为色料并且与颜料在其在施用介质中的溶解性上而不同,即它们在25℃下在施用介质中具有大于1g/1000g的溶解性。
染料的实例为偶氮、吖嗪、蒽醌、吖啶、花青、嗪、聚甲炔、噻嗪和三芳基甲烷染料。这些染料可以以碱性或阳离子染料、媒染料、直接染料、分散染料、显色染料、瓮染料、金属配合物染料、反应性染料、酸染料、硫染料、偶合染料或直接染料使用。
作为其它典型涂料添加剂(H),例如可使用抗氧化剂、稳定剂、活化剂(促进剂)、填料、抗静电剂、阻燃剂、增稠剂、触变剂、表面活性剂、粘度改进剂、增塑剂或螯合剂。
作为热后固化用促进剂,例如可使用辛酸锡、辛酸锌、月桂酸二丁基锡或二氮杂双环[2.2.2]辛烷。
此外,可加入一种或多种光化学和/或热活化性引发剂,其中实例为过氧二硫酸钾、过氧化二苯甲酰、过氧化环己酮、过氧化二叔丁基、偶氮二异丁腈、过氧化环己基磺酰乙酰、过碳酸二异丙基酯、过辛酸叔丁基酯或苯频哪醇,以及例如在80℃下具有大于100小时的半衰期的那些热活化性引发剂如过氧化二叔丁基、氢过氧化枯烯、过氧化二枯基、过苯甲酸叔丁酯、甲硅烷基化频哪醇(其可例如以商品名ADDID600由Wacker市购),或含羟基胺N-氧化物如2,2,6,6-四甲基哌啶-N-氧自由基、4-羟基-2,2,6,6-四甲基哌啶-N-氧自由基等。
其它合适引发剂的实例描述于“Polymer Handbook”,第二版,Wiley& Sons,New York。
除自由基(共)聚合性(共)聚合物以外,合适的增稠剂还包括常规有机和无机增稠剂如羟甲基纤维素或膨润土。
可使用的螯合剂的实例包括乙二胺乙酸和其盐以及β-二酮。
色彩惰性填料为下述所有物质/化合物:其一方面为色彩非活性-即,它们显示出几乎没有的内在吸收并具有类似于涂料介质的折射指数,另一方面能影响效应颜料在表面涂层,即施用的漆膜中的导向(平行排列)以及该涂层或涂料的性能如硬度或流变性。可使用的惰性物质/化合物在下文中以示例的方式给出,但不限制于这些实例的色彩惰性、拓扑影响填料的概念。满足定义的合适惰性填料可例如为透明或半透明填料或颜料如塑料颗粒、硅胶、钡白、硅藻土、滑石、碳酸钙、石灰、高岭土、硫酸钡、硅酸镁、硅酸铝、结晶二氧化硅、无定形二氧化硅、氧化铝。额外地,作为惰性填料可使用任何所需固体惰性有机颗粒如脲甲醛缩合物、微粒聚烯烃蜡和微粒酰胺蜡。惰性填料在每种情况下还可以以混合物使用。然而,优选在每种情况下仅使用一种填料。
合适的稳定剂通常包含UV吸收剂如草酰二苯胺、三嗪和苯并三唑和二苯甲酮。这些可单独或以与合适自由基清除剂一起使用,其中实例为位阻胺如2,2,6,6-四甲基哌啶、2,6-二叔丁基哌啶或其衍生物例如癸二酸二(2,2,6,6-四甲基-4-哌啶基)酯。稳定剂常以基于配制剂中所包含的固体组分为0.1-5.0重量%的量使用。
本发明混合物可用作IR活化性光敏引发剂并在涂料和漆体系中显示出比其中式(IV)硼酸根离子起花青阳离子的抗衡离子作用的现有技术IR光敏引发剂配制剂更好的溶解性。因此,一方面,该光敏引发剂可更均匀地分布在漆体系中并且无作为缺点的不溶性颗粒残留在随后的漆中,另一方面,获得更高光反应性。在现有技术的IR光敏引发剂中,由于不足的溶解性,该化合物在一定程度上以晶体在涂料中沉淀。
为实现改善的溶解性,将本发明混合物与可辐射固化化合物,即例如基料(D)和/或反应性稀释剂(E),或包含它们的配制剂如涂料、漆或漆配制剂共混。
IR光敏引发剂特别有利的是这种引发剂甚至在着色漆中能引发自由基聚合,因为颜料通常几乎不或根本不吸收活化性辐射,而颜料通常吸收和/或散射活化UV光敏引发剂所需的UV辐射,因此具有在涂料中的低渗透深度。因此本发明优选的实施方案在着色涂料中使用本发明混合物。
本发明另一有利的实施方案包括在具有高涂层厚度的涂料中使用本发明混合物。因此在一个优选的实施方案中,将该混合物用于显示出大于30μm,优选大于45μm,更优选大于60μm涂层厚度的涂料中。该涂层可具有至多300μm,优选至多250μm,更优选至多200μm的厚度。
当然还可施用更厚或更薄的涂层,例如10-1000μm。然而,在施用非常厚的涂料的情况下,必须辐照两次或更多次。
该可辐射固化涂料组合物可优选以简单方式例如通过喷雾、抹涂、涂布、刮涂、刷涂、滚压、辊涂、浇塑、浸渍、层压、反注塑或共挤出等施用到待涂覆制品上并且合适的话可干燥。
固化通过使用包含可见区和IR区,优选可见区,更优选波长范围为400-650nm的电磁辐射辐照进行。
在本发明的一个优选的实施方案中,辐照还可在缺氧下进行。为此,辐照的进行使得它在用IR辐射辐照时,使涂料暴露于小于18kPa的氧分压中。暴露时,相关区域为待涂覆且提供有可辐射固化涂料的制品的表面区域。优选氧分压不大于17kPa,更优选不大于15.3kPa,非常优选不大于13.5kPa,特别是不大于10kPa,尤其是不大于6.3kPa。
通常不需要完全缺氧,因此氧分压无需小于优选0.5kPa,更优选0.9kPa,非常优选1.8kPa,特别是2.5kPa。
在低氧分压下固化的一个察觉到的优点例如为改善的抗划伤性。
这种低氧分压可有利地通过用至少一种惰性气体稀释含氧氛围或用至少一种惰性气体,即在辐射固化条件下为非反应性的气体替换而得到。合适的惰性气体优选包括氮气、稀有气体、二氧化碳或燃烧气体。在进行辐射固化的氛围中,所述至少一种惰性气体的比例应大于80体积%,优选至少85体积%,更优选至少90体积%,非常优选至少95体积%,特别是至少98体积%。辐照可额外用覆盖有透明介质的涂料进行。透明介质例如为聚合物膜、玻璃或液体如水。特别优选辐照如WO 01/14483所述进行,由此将其整个内容引入作为参考。非常特别优选辐照以描述于DE-A119957900的方式进行,由此将其整个内容引入作为参考。
本发明涂料和漆配制剂尤其适用于涂覆基材如木材,优选松、冷杉、山毛榉、栎木或枫木,纸张,卡纸板,纸板,纺织品,皮革,皮革代用品,非织造物,塑料表面,优选SAN、PMMA、ABS、PP、PS、PC或PA(根据DIN7728的缩写),玻璃,陶瓷,矿物建材如水泥模制品和纤维-水泥板,或未涂覆或涂覆金属,优选塑料或金属,其也可例如呈板(箔或膜)的形式。为了储存或运输,包膜或未包膜金属也可例如加工为卷形物,称为卷材。金属涂层可包含常规底漆或阴极沉积涂料。
特别优选本发明涂料适用于户外施用或在包括暴露于日光中的优选建筑物或建筑物部件的施用中适用于内部涂料,以及飞机和车辆上的涂料。特别是将本发明涂料用作或用于汽车清漆和面漆中以及用于漆、尤其是圬工漆、工业涂料、卷材涂料、模塑配混料、浇塑配混料或牙科用配混料中。另外可将本发明混合物用于固化建材、瓦、砖块、人造石、刮板、抹灰和涂料(对于其涂层而言)。本发明涂料可有利地用于装饰性涂料,特别是涂覆家具、木块地面、层制品或地面覆盖物。
此外,可将本发明涂料用于印刷方法或用于生产印刷板,例如立体平版印刷、照相平版法、丝网印刷、胶印、平版印刷、凹版印刷或凸版印刷以及喷墨方法中。
如下实施例用于说明本发明性能,但不限制它。
在本说明书中,除非另有说明,“份”或“%”指“重量份”或“重量%”。
合成在自动Laboratory单元中进行,其基本由两个通过玻璃桥连接的夹套容器250ml和2500ml构成。这两种容器装有玻璃叶轮搅拌器、流体扰动器和恒温箱。在250ml容器中的转速为350rpm,而在2500ml容器中的转速为250rpm。
首先将100g二甲基甲酰胺(DMF)加入250ml容器中,加入100g N,N-二(氰基乙基)苯胺并用25.5g DMF进行漂洗。然后将恒温箱设置为20℃,并在40分钟内计量加入80g磷酰氯(POCl3)。在计量加料结束后,将批料加热到90℃并搅拌1小时。
在小容器中的加热操作过程中,在大容器中加入300g水并将恒温箱设置为40℃。在小容器中完全转化后,进行水解-缓慢打开小容器中的底部排放口并且温度为90℃的反应溶液通过玻璃桥流入装水的大容器。在约5分钟后,沉淀细浅黄色的固体。用10-15ml DMF漂洗小容器,并搅拌5分钟。然后在大容器中计量加入400g二乙基酮(DEK),并且在加料结束后,将内容物加热到70℃中。在70℃下在15分钟内用浓度为50%的氢氧化钠水溶液将pH调节为6.0。然后在70℃下搅拌1小时,然后进行相分离。废弃水相。将温度为70℃的有机相与88g 1,3,3-三甲基-2-亚甲基二氢吲哚(费舍尔碱)以200rpm快速混合,然后在6分钟内与52g浓硫酸混合。然后,将批料加热到100℃并将反应水通过蒸馏除去。在100℃下持续搅拌约1小时,在此过程中还蒸除反应水。此后将反应混合物冷却到90℃并加入184g十二烷基苯磺酸钠在800g水中的溶液(溶液温度:约60℃)。在70℃下持续搅拌约1.75小时。进一步相分离后,将有机相在减压下浓缩。
这得到330g(3个步骤内收率为92%)红色固体。
Vielsmeier-Haack甲酰化:
在250ml具有氮清洗器、回流冷却器和KPG搅拌器的四颈烧瓶中加入8g二甲基甲酰胺和8.6g 2-[(2-氰基乙基)间甲苯基氨基]乙基乙酸酯。在5-10℃下在10分钟内滴加6g磷酰氯。此后将混合物加热到室温,在70℃下搅拌5.5小时,在搅拌下冷却过夜。然后加入200ml甲基叔丁基醚并用冰水浴冷却混合物,并在5分钟内在不大于10℃温度下滴加17g乙酸钠和70ml水的溶液。然后在室温下相分离。将有机相用水洗涤,然后用饱和碳酸氢钠溶液洗涤,在硫酸钠上干燥并在旋转蒸发器上浓缩。
这得到8.7g(收率91%)2-[(2-氰基乙基)(4-甲酰基-3-甲基苯基)氨基]乙基乙酸酯。
乙酸酯去保护:
在500ml具有搅拌棒的Erlenmeyer烧瓶中加入120ml甲醇和8.7g2-[(2-氰基乙基)(4-甲酰基-3-甲基苯基)氨基]乙基乙酸酯。加入40ml水和3.4g碳酸钠,并将混合物在室温下搅拌过夜。第二天早晨将其过滤并将母液调节到pH 7。使用旋转蒸发器将甲醇从该溶液中除去,用二氯甲烷萃取三次,并在硫酸钠上干燥合并的有机相。在减压下除去有机溶剂而得到6.6g(收率90%)3-[(4-甲酰基-3-甲基苯基)(2-羟基乙基)氨基]丙腈。
缩合:
在250ml具有氮清洗器、回流冷却器和KPG搅拌器的四颈烧瓶中,将3.2g 3-[(4-甲酰基-3-甲基苯基)(2-羟基乙基)氨基]丙腈和4.2g 1-乙基-2,3,3-三甲基吲哚碘化物悬浮在20ml甲苯和6ml正丁醇中,将悬浮液加热到105℃并搅拌2小时。将其过夜冷却到室温并过滤所得悬浮液。用甲苯和甲基叔丁基醚洗涤滤饼,并在50℃,减压下干燥。
盐转化:
在1000ml具有搅拌棒的Erlenmeyer烧瓶中,将3g 2-((E)-2-{4-[(2-氰基乙基)(2-羟基乙基)氨基]-2-甲基苯基}乙烯基)-1-乙基-3,3-二甲基-3H-吲哚碘化物溶于300ml二氯甲烷中;加入2.1g在100ml水中的十二烷基苯磺酸钠,并将混合物在室温下搅拌3小时。然后进行相分离,并将有机相在硫酸钠上干燥,过滤,在减压下浓缩并干燥。
以与实施例2相同的方式,由相应的反应物制备以下染料:表编号5、6和7。
以与实施例2相同,但无需乙酸酯去保护的方式,由相应的反应物制备以下染料:表编号2、3、8、9、11、12和19。
以与实施例2的缩合和盐转化相同的方式,由相应的反应物制备以下染料:表编号1、4、13、14和15。
分别由(2-((E)-2-{4-[(2-氯乙基)乙基氨基]-2-甲基苯基}乙烯基)-1,3,3-三甲基-3H-吲哚氯化物(Astrazon红色6B,源于ABCR)和(2-((E)-2-{4-[(2-氯乙基)甲基氨基]苯基}乙烯基)-1,3,3-三甲基-3H-吲哚氯化物(Astrazon粉色FG,源于ABCR)开始,以与实施例2相同的方式进行盐转化得到表编号17和18。
借助如下加速测试评价光敏引发剂:
用于自由基聚合性漆基材料的测试介质由来自BASF SE,Ludwigshafen的丙烯酸酯类型:8863(基于乙氧基化的三羟甲基丙烷的聚醚丙烯酸酯)、PO 84F(基于烷氧基化的三羟甲基丙烷的胺改性聚醚丙烯酸酯)和8987(以在二丙烯酸己二醇酯中的溶液的基于六亚甲基二异氰酸酯的氨基甲酸酯丙烯酸酯)的三种不同市售含丙烯酸酯漆基材料构成。在测试下将光敏引发剂各自称重加入这些测试介质中并且尽可能均匀的溶解。所用标准浓度为0.5%敏化剂染料和1.5%共引发剂(B)(通常四氢硼酸盐,尤其是正丁基三苯基四氢硼酸盐)。掺入和产物的处理主要在无直接光辐照下进行。
然后以薄涂层将掺杂有光敏引发剂的漆基材料施用到玻璃载体上。将1-3滴掺杂漆基材料施用到玻璃载物片上,伴随放置两个间隔膜(约50μm),最后用另一玻璃载物片覆盖该液体;两个载物片借助两个夹子压在一起。然后暴露这些“夹心样品”。在固化涂层膜上测量并得到约56μm的膜厚。
由于这里研究的光敏引发剂体系具有特定光谱敏感性,卤素灯特别适用于掺杂漆基材料的上述样品的固化。在标准研究的情况下,使用载物片投射器(卤素灯)并将样品在定义的距离暴露定义的暴露次数。
对所有样品首先在质量上评价光固化的成功:这通过打开夹心样品,去除盖子并合适的话,通过用金属刮刀摩擦,如下:“仍为液体”,“固化但柔软”,“硬”评价涂层膜的硬度而进行。
还评价固化后残留色彩的程度。因此发现当使用如实施例1和2中所述的特定染料时,在其中染料的抗衡离子为碘离子比其中抗衡离子为长链烷基取代的芳基磺酸根的涂料中残留更多残留色彩。例如具有来自上表的染料16和19的涂料在固化后几乎为无色的。相反,相应的碘化物仍分别显示出轻微的浅蓝色或轻微的红色。
实施例3
与含有由EP 1091247A2已知的烷基磺酸根阴离子作为其抗衡离子的那些相比,具有被长链烷基取代的式(II)的芳基磺酸根作为抗衡离子的花青阳离子显示出增加的光活化性。
在用50W卤素灯辐照下,此测试得到具有50μm膜厚的清漆不粘手涂层需要数秒的时间。为此,制备花青阳离子与十二烷基磺酸根(根据EP1091247A2比较)或十二烷基苯磺酸根(本发明),市售可辐射固化涂料组分(PO84F,8863,8987,来自BASF AG,Ludwigshafen)的混合物并固化。
结果如下:
看出具有被长链烷基取代的芳基磺酸根作为其抗衡离子的的花青阳离子具有比十二烷基磺酸根达到该膜的不粘手固化的更短时间,因此显示出更大的光活能力。
Claims (15)
1.一种可辐射固化涂料用敏化剂体系(A),其包含式(I)的苯乙烯系阳离子D+和作为抗衡离子的阴离子An-:
所述阴离子An-选自4-己基苯磺酸根、4-辛基苯磺酸根、4-癸基苯磺酸根和4-十二烷基苯磺酸根,
其中,
R1、R5、R6、R7和R8可各自独立地为氢、C1-C18烷基或C1-C18烷氧基,R1可额外为卤素,
R2、R3和R4可各自独立地为C1-C18烷基,
R9和R10可各自独立地为未取代或被芳基、烷基、芳氧基、烷氧基、杂原子和/或杂环取代的C1-C18烷基、C6-C12芳基或C5-C12环烷基。
2.根据权利要求1的敏化剂体系,其中R1可额外为溴。
3.根据权利要求1或2的敏化剂体系,其中所述基团R9和R10各自独立地为未取代或被芳基、烷基、芳氧基、烷氧基、杂原子和/或杂环取代的C1-C18烷基。
4.根据权利要求1或2的敏化剂体系,其中所述基团R9和R10各自独立地选自甲基、乙基、正丙基、2-羟基乙基、2-羟基丙基、2-氯乙基、2-氰基乙基、2-乙酰氧基乙基、环己基和环戊基。
7.根据权利要求6的混合物,其中所述阳离子catx+选自1-甲基咪唑1-丁基咪唑1,3-二甲基咪唑1,2,3-三甲基咪唑1-正丁基-3-甲基咪唑1-乙基-3-甲基咪唑1,3,4,5-四甲基咪唑1,3,4-三甲基咪唑2,3-二甲基咪唑1-丁基-2,3-二甲基咪唑3,4-二甲基咪唑2-乙基-3,4-二甲基咪唑3-甲基-2-乙基咪唑3-丁基-1-甲基咪唑3-乙基-1-甲基咪唑3-丁基-1-乙基咪唑3-丁基-1,2-二甲基咪唑1,3-二正丁基咪唑3-丁基-1,4,5-三甲基咪唑3-丁基-1,4-二甲基咪唑3-丁基-2-甲基咪唑1,3-二丁基-2-甲基咪唑3-丁基-4-甲基咪唑3-丁基-2-乙基-4-甲基咪唑3-丁基-2-乙基咪唑1-甲基-3-辛基咪唑和1-癸基-3-甲基咪唑
8.根据权利要求6或7的混合物,其中所述式An-Cya+的组分(A)与具有抗衡离子1/xcatx+的组分(B)的重量比为1:1-1:5。
9.一种可辐射固化涂料,其包含如下组分:
-至少一种根据权利要求1-5中任一项的式An-Cya+的组分(A),
-至少一种根据权利要求6-8中任一项的具有抗衡离子1/xcatx+的组分(B),
-任选至少一种溶剂(C),
-至少一种基料(D),
-任选至少一种反应性稀释剂(E),
-任选至少一种UV光敏引发剂(F),
-任选至少一种色料(G),和
-任选其它典型涂料添加剂(H)。
10.一种涂覆基材的方法,其包括以10-1000μm的厚度将根据权利要求9的可辐射固化涂料施用至待涂覆制品上,任选干燥,然后用波长范围为700-900nm的电磁辐射辐照。
11.根据权利要求9的可辐射固化涂料在涂覆木材、纸张、纸板、纺织品、皮革、皮革代用品、非织造物、塑料表面、玻璃、陶瓷、矿物建材或包膜或未包膜金属中的用途。
12.根据权利要求11的用途,用于涂覆卡纸板。
13.根据权利要求9的可辐射固化涂料在漆、模塑配混料、浇塑配混料或牙科用配混料中的用途。
14.根据权利要求13的用途,在工业涂料或卷材涂料中的用途。
15.根据权利要求13的用途,作为或在汽车清漆和面漆中的用途。
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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 |
WO2013087112A1 (de) | 2011-12-15 | 2013-06-20 | Siemens Aktiengesellschaft | Verfahren zur herstellung eines glimmschutzes, schnellhärtendes glimmschutzsystem und elektrische maschine |
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 |
EP3234021A1 (en) * | 2014-12-17 | 2017-10-25 | Covestro Deutschland AG | Photopolymer comprising a new class of photo initiator |
US10470980B2 (en) * | 2015-03-31 | 2019-11-12 | Mitsui Chemicals, Inc. | Dental polymerizable monomers, compositions, adhesive dental materials and kits |
EP3112330A1 (en) * | 2015-06-29 | 2017-01-04 | Sociedad Industrial Pizarreno | Coloured fiber cement products and methods for the production thereof |
JP6603127B2 (ja) * | 2015-12-29 | 2019-11-06 | サンアプロ株式会社 | 感光性組成物 |
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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EP2356182A1 (de) | 2011-08-17 |
WO2010055050A1 (de) | 2010-05-20 |
KR101640216B1 (ko) | 2016-07-15 |
US20110230617A1 (en) | 2011-09-22 |
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