CN1128799C - 基于α-氨基烯烃的可被光活化的含氮碱 - Google Patents
基于α-氨基烯烃的可被光活化的含氮碱 Download PDFInfo
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- CN1128799C CN1128799C CN98803471A CN98803471A CN1128799C CN 1128799 C CN1128799 C CN 1128799C CN 98803471 A CN98803471 A CN 98803471A CN 98803471 A CN98803471 A CN 98803471A CN 1128799 C CN1128799 C CN 1128799C
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- Prior art keywords
- formula
- phenyl
- compound
- base
- alkyl
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- 238000006555 catalytic reaction Methods 0.000 claims abstract description 8
- -1 tetrafluoroborate Chemical compound 0.000 claims description 96
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
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- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 6
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 24
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 13
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
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- 239000000463 material Substances 0.000 description 12
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
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- 239000000853 adhesive Substances 0.000 description 9
- 230000001070 adhesive effect Effects 0.000 description 9
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 8
- FTWUXYZHDFCGSV-UHFFFAOYSA-N n,n'-diphenyloxamide Chemical compound C=1C=CC=CC=1NC(=O)C(=O)NC1=CC=CC=C1 FTWUXYZHDFCGSV-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
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- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 239000011253 protective coating Substances 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
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- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
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- OARRHUQTFTUEOS-UHFFFAOYSA-N safranin Chemical compound [Cl-].C=12C=C(N)C(C)=CC2=NC2=CC(C)=C(N)C=C2[N+]=1C1=CC=CC=C1 OARRHUQTFTUEOS-UHFFFAOYSA-N 0.000 description 1
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- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008117 stearic acid 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
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
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- 125000003944 tolyl group Chemical group 0.000 description 1
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- KKFOMYPMTJLQGA-UHFFFAOYSA-N tribenzyl phosphite Chemical compound C=1C=CC=CC=1COP(OCC=1C=CC=CC=1)OCC1=CC=CC=C1 KKFOMYPMTJLQGA-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- OAUXBAZCEXSXGL-UHFFFAOYSA-M triphenyl(phenylsulfanylmethyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CSC1=CC=CC=C1 OAUXBAZCEXSXGL-UHFFFAOYSA-M 0.000 description 1
- HHBXWXJLQYJJBW-UHFFFAOYSA-M triphenyl(propan-2-yl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C(C)C)C1=CC=CC=C1 HHBXWXJLQYJJBW-UHFFFAOYSA-M 0.000 description 1
- NBGQQOBCTPJEFE-ZUQRMPMESA-M triphenyl-[(e)-3-phenylprop-2-enyl]phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C\C=C\C1=CC=CC=C1 NBGQQOBCTPJEFE-ZUQRMPMESA-M 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
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 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
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- 238000005406 washing Methods 0.000 description 1
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- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
-
- 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
- G03F7/0046—Photosensitive materials with perfluoro compounds, e.g. for dry lithography
-
- 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
-
- 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
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/037—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polyamides or polyimides
-
- 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
- G03F7/075—Silicon-containing compounds
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Abstract
本发明涉及一种分子量低于1000,含有至少一个式(I)结构单位的有机化合物,其中R1为可吸收波长范围为200到650nm的光线而使相邻的碳-氮键解离的芳基或杂芳基。该化合物为碱催化反应的光引发剂。本发明还涉及包含具有式(I)结构单位的化合物的碱-聚合或交联组合物,进行光化学诱导的方法,进行碱催化反应的方法,以及该化合物作为碱催化反应光引发剂的用途。
Description
本发明涉及可经光化学转化成为脒衍生物的α-氨基烯烃,涉及其制备方法以及涉及脒衍生物的光化学制备方法。本发明的另一主题涉及包含上述α-氨基烯烃的碱-可聚合的或可交联的组合物,一种利用光化学诱导,碱-催化反应的方法,和α-氨基烯烃作为碱-催化反应光引发剂的用途。
碱的光解以及与这些碱有关的光聚合反应已被描述,用于制备各种类型的对光不稳定的化合物,例如氨基甲酸酯(Cameron等,美国专利5 545 509及其引用的参考文献;Cameron和Frechet,J.Am.Chem.Soc.(1991)113,4303),α-酮基氨基甲酸酯(Cameron等,J.Am.Chem.Soc.(1996),118,12925),O-酰基肟(Tsunooka等,J.Polymer Sci.:Part A:Polymer Chem.(1994),32,2177),甲酰胺(Nishikubo等,Polym.J.(1993)25,421;idem,J.Polymer Sci.:Part A:Polymer Chem.(1993),31,3013),共-胺配合物(C.Kutal等,J.Electrochem.Soc.(1987),134,2280)。
链烯的光化学分子内γ-氢消去反应是已知的,但是,到目前为止,没有文献详细描述羰基化合物的相应反应(参见V.SreedharaRao,A.K.Chandra,J.Photochem.Photobial.A Chem.101(1996),189及其引用的参考文献)。链烯的相应的热反应却有更详细的描述,例如,J.-L.Ripoll,Y.Vallée in Synthesis(1993),659及其引用的参考文献。
现已令人惊奇地发现,当暴露于可见或UV光下时,其中包含式(I)的结构单位的某些α-氨基烯烃会释放脒基。该脒基的碱性足以激发大量碱催化反应,特别是聚合反应。该化合物具有很高的敏感性,通过选择取代基R1,其吸收谱可在很宽的范围内变化。
这类化合物使得可以制备具有很长储存期的带有可碱催化的低聚物或单体的所谓的一釜系统。聚合反应例如在见光之后即被引发。该系统中可含有或不含溶剂,因为该化合物可不受影响地溶于单体或低聚物中。活性催化剂仅在见光之后形成。这些具有碱催化的低聚物或单体的系统可用于各种用途,如涂饰,涂料,模制化合物或光刻法复制。
R1表示的芳基或杂芳基符合Hückel4n+2规则。
通过选择R1表示的芳基或杂芳基,最大吸收可在很宽范围内变化,该化合物的光敏性可从UV迁移至日光区。
其中式(I)结构单位包含式(II)化合物的有机化合物优选其中R1为可吸收波长范围为200到650nm的光线,并因此解离相邻的碳氮键的芳基或杂芳基;R2和R3各自独立地为氢,C1-C18烷基,C3-C18链烯基,C3-C18炔基或苯基,如果R2为氢或C1-C18烷基,R3还可为-CO-R14,其中R14为C1-C18烷基或苯基;R5为C1-C18烷基或NR15R16;R4,R6,R7,R15和R16各自独立地为氢或C1-C18烷基;或R4和R6一起形成C2-C12亚烷基桥或R5和R7,R4和R6,各自独立地,分别形成C2-C12亚烷基桥或,如果R5为NR15R16,R16和R7一起形成C2-C12亚烷基桥;R17为氢,C1-C18烷基;R18为氢,C1-C18烷基或由C1-C18烷基,乙烯基,C3-C18链烯基,C3-C18炔基,C1-C18卤代烷基,苯基,NO2,OH,CN,OR10,SR10,C(O)R11,C(O)OR12或卤素取代的苯基;以及R10,R11和R12为氢或C1-C18烷基。
各基团中具有至多18个碳原子的烷基可为直链或支链烷基,如甲基,乙基,丙基,异丙基,正丁基,仲丁基,异丁基,叔丁基,2-乙基丁基,正戊基,异戊基,1-甲基戊基,1,3-二甲基丁基,正己基,1-甲基己基,正庚基,异庚基,1,1,3,3-四甲基丁基,1-甲基庚基,3-甲基庚基,正辛基,2-乙基己基,1,1,3-三甲基己基,1,1,3,3-四甲基戊基,壬基,癸基,十一烷基,1-甲基十一烷基,十二烷基,1,1,3,3,5,5-六甲基己基,十三烷基,十四烷基,十五烷基,十六烷基,十七烷基,十八烷基。优选具有1到12,特别是1到6个碳原子的烷基。
具有3到18个碳原子的链烯基,可为直链或支链基团,如丙烯基,2-丁烯基,3-丁烯基,异丁烯基,正-2,4-戊二烯基,3-甲基-2-丁烯基,正-2-辛烯基,正-2-十二烯基,异十二烯基,油基,正-2-十八烯基或正-4-十八烯基。优选具有3到12,特别是3到6个碳原子的链烯基。
具有3到18个碳原子的炔基,可为直链或支链基团,如丙炔基,2-丁炔基,3-丁炔基,正-2-辛炔基或正-2-十八炔基。优选具有3到12,特别是3到6个碳原子的炔基。
C2-C12亚烷基桥的例子为亚乙基,亚丙基,亚丁基,亚戊基,亚己基,亚庚基,亚辛基,亚壬基,亚癸基,亚十一烷基或亚十二烷基。
优选的式(II)化合物为其中R1为苯基,萘基,菲基,蒽基,芘基,5,6,7,8-四氢-2-萘基,5,6,7,8-四氢-1-萘基,噻吩基,苯并[b]噻吩基,萘并[2,3-b]噻吩基,噻嗯基,二苯并呋喃基,苯并吡喃基,占吨基,噻吨基,(夹)氧硫蒽基(phenoxathiinyl),吡咯基,咪唑基,吡唑基,吡嗪基,嘧啶基,哒嗪基,中氮茚基,异吲哚基,吲哚基,吲唑基,嘌呤基,喹嗪基,异喹啉基,喹啉基,2,3-二氮杂萘基,1,5-二氮杂萘基,喹喔啉基,喹唑啉基,1,2-二氮杂萘基,喋啶基,卡唑基,β-咔啉基,菲啶基,吖啶基,白啶基,菲咯啉基,吩嗪基,异噻唑基,吩噻嗪基,异噁唑基,呋咱基,三联苯基,氐基,芴基或吩噁嗪基,这些基团是未取代的或被下列基团取代一次或多次:C1-C18烷基,C3-C18链烯基,C3-C18炔基,C1-C18卤代烷基,NO2,NR8R9,N3,OH,CN,OR10,SR10,C(O)R11,C(O)OR12或卤素,或者R1为式A或B基团 R8,R9,R10,R11和R12为氢或C1-C18烷基;R13为C1-C18烷基,C2-C18链烯基,C2-C18炔基,C1-C18卤代烷基,NO2,NR8R9,OH,CN,OR10,SR10,C(O)R11,C(O)OR12或卤素;以及n为0或1,2或3。C1-C18烷基,C3-C18链烯基和C3-C18炔基的实例如前所述。
卤素为氟,氯,溴或碘。
C1-C18卤代烷基的例子为完全或部分卤代的C1-C18烷基。这里的卤素为氟,氯,溴或碘。例子为单-到十氟戊基,单-到八氟丁基,单-到六氟丙基,单-到四氟乙基和单-到二氟甲基的位置异构体以及相应的氯,溴和碘代化合物。优选全氟烷基。例子为全氟戊基,全氟丁基,全氟丙基,全氟乙基,特别是,三氟甲基。
NR8R9氨基的例子为相应的单烷基氨基或二烷基氨基,如甲氨基,乙氨基,丙氨基,丁氨基,戊氨基,己氨基,十八烷氨基,二甲氨基,二乙氨基,二丙氨基,二异丙氨基,二-正-丁氨基,二-异丁氨基,二戊氨基,二己氨基或二-十八氨基。其他二烷基氨基为其中两个基团各自独立为直链或支链烷基的二烷基氨基,例如甲乙氨基,甲基-正丙基氨基,甲基异丙基氨基,甲基-正丁基氨基,甲基异丁基氨基,乙基异丙基氨基,乙基-正丁基氨基,乙基异丁基氨基,乙基叔丁基氨基,异丙基-正丁基氨基或异丙基异丁基氨基。
具有至多18个碳原子的烷氧基OR10为支链或直链基团,如甲氧基,乙氧基,丙氧基,异丙氧基,正丁氧基,异丁氧基,戊氧基,异戊氧基,己氧基,庚氧基,辛氧基,癸氧基,十四烷氧基,十六烷氧基或十八烷氧基。优选具有1到12,特别是1到8,例如1到6个碳原子的烷氧基。
硫代烷基SR10的例子为硫代甲基,硫代乙基,硫代丙基,硫代丁基,硫代戊基,硫代己基,硫代庚基,硫代辛基或硫代十八烷基,烷基部分可以是直链或支链。
基团R1的例子为苯基,萘基,菲基,蒽基,联苯基,芘基,5,6,7,8-四氢-2-萘基,5,6,7,8-四氢-1-萘基,噻吩基,苯并[b]噻吩基,萘并[2,3-b]噻吩基,thiathrenyl,二苯并呋喃基,苯并吡喃基,占吨基,噻吨基,phenoxathiinyl,吡咯基,咪唑基,吡唑基,吡嗪基,嘧啶基,哒嗪基,中氮茚基,异吲哚基,吲哚基,吲唑基,嘌呤基,喹嗪基,异喹啉基,喹啉基,2,3-二氮杂萘基,1,5-二氮杂萘基,喹喔啉基,喹唑啉基,1,2-二氮杂萘基,喋啶基,卡唑基,β-咔啉基,菲啶基,吖啶基,白啶基,菲咯啉基,吩嗪基,异噻唑基,吩噻嗪基,异噁唑基,呋咱基,二联苯,三联苯基,氐基,芴基,吩噁嗪基,甲氧基苯基,2,4-甲氧基苯基,2,4,6-三甲氧基苯基,3,4,5-三甲氧基苯基,溴苯基,甲苯基,二甲苯基,米基,硝基苯基,二甲氨基苯基,二乙氨基苯基,氨基苯基,二氨基苯基,硫代甲基苯基,1-萘基,2-萘基,1-苯氨基-4-萘基,1-甲基萘基,2-甲基萘基,1-甲氧基-2-萘基,2-甲氧基-1-萘基,1-二甲氨基-2-萘基,1,2-二甲基-4-萘基,1,2-二甲基-6-萘基,1,2-二甲基-7-萘基,1,3-二甲基-6-萘基,1,4-二甲基-6-萘基,1,5-二甲基-2-萘基,1,6-二甲基-2-萘基,1-羟基-2-萘基,2-羟基-1-萘基,1,4-二羟基-2-萘基,7-菲基,1-蒽基,2-蒽基,9-蒽基,3-苯并[b ]噻吩基,5-苯并[b]噻吩基,2-苯并[b]噻吩基,4-二苯并呋喃基,4,7-二苯并呋喃基,4-甲基-7-二苯并呋喃基,2-占吨基,8-甲基-2-占吨基,3-占吨基,2-phenoxathiinyl,2,7-phenoxathiinyl,2-吡咯基,3-吡咯基,5-甲基-3-吡咯基,2-咪唑基,4-咪唑基,5-咪唑基,2-甲基-4-咪唑基,2-乙基-4-咪唑基,2-乙基-5-咪唑基,3-吡唑基,1-甲基-3-吡唑基,1-丙基-4-吡唑基,2-吡嗪基,5,6-二甲基-2-吡嗪基,2-中氮茚基,2-甲基-3-异吲哚基,2-甲基-1-异吲哚基,1-甲基-2-吲哚基,1-甲基-3-吲哚基,1,5-二甲基-2-吲哚基,1-甲基-3-吲唑基,2,7-二甲基-8-嘌呤基,2-甲氧基-7-甲基-8-嘌呤基,2-喹嗪基,3-异喹啉基,6-异喹啉基,7-异喹啉基,异喹啉基,3-甲氧基-6-异喹啉基,2-喹啉基,6-喹啉基,7-喹啉基,2-甲氧基-3-喹啉基,2-甲氧基-6-喹啉基,6-2,3-二氮杂萘基,7-2,3-二氮杂萘基,1-甲氧基-6-2,3-二氮杂萘基,1,4-二甲基-6-2,3-二氮杂萘基,1,8-二氮杂萘-2-基,2-喹喔啉基,6-喹喔啉基,2,3-二甲基-6-喹喔啉基,2,3-二甲氧基-6-喹喔啉基,2-喹唑啉基,7-喹唑啉基,2-二甲氨基-6-喹唑啉基,1,2-二氮杂萘-3-基,1,2-二氮杂萘-6-基,1,2-二氮杂萘-7-基,3-甲氧基-1,2-二氮杂萘-7-基,2-喋啶基,6-喋啶基,7-喋啶基,6,7-二甲氧基-2-喋啶基,2-卡唑基,3-卡唑基,9-甲基-2-卡唑基,9-甲基-3-卡唑基,β-咔啉-3-基,1-甲基-β-咔啉-3-基,1-甲基-β-咔啉-6-基,3-菲啶基,2-吖啶基,3-吖啶基,2-白啶基,1-甲基-5-白啶基,5-菲咯啉基,6-菲咯啉基,1-吩嗪基,2-吩嗪基,3-异噻唑基,4-异噻唑基,5-异噻唑基,2-吩噻嗪基,3-吩噻嗪基,10-甲基-3-吩噻嗪基,3-异噁唑基,4-异噁唑基,5-异噁唑基,4-甲基-3-呋咱基,2-吩噁嗪基或10-甲基-2-吩噁嗪基。
特别优选的R1为苯基,萘基,芘基,噻吨基,thiathrenyl或吩噻嗪基,这些基团是未取代的或被下列基团取代一次可多次:C1-C18烷基,C1-C18卤代烷基,NR8R9,CN,NO2,N3,SR10或OR10,或者R1为上述式A或B基团。
更特别优选的化合物为其中R1为苯基,芘基或萘基化合物,其中的苯基,芘基或萘基未被取代或被下列基团取代一次或多次:CN,NR8R9,NO2,CF3,SR10或OR10,或者R1为上述式A或B基团。
非常优选的R1为苯基,4-氨基苯基,4-甲硫基苯基,4-三氟甲基苯基,4-硝基苯基,2,4,6-三甲氧基苯基,2,4-二甲氧基苯基,萘基,蒽基,芘基或上述式A或B基团。
优选的R2和R3各自独立地为氢或C1-C6烷基。同样优选的R4和R6一起形成C2-C6亚烷基桥。
优选的R17为氢或C1-C4烷基,优选的R18为氢,C1-C4烷基或苯基。
特别优选的式(II)化合物是那些其中R1为苯基,萘基或芘基,它们未被取代或被下列基团取代一次或多次:CN,NR8R9,NO2,CF3,SR10或OR10,或者R1为上述式A或B基团。n为0,R8,R9,R10和R13为氢或C1-C6烷基;R2和R3为氢或C1-C6烷基;R4,R6和R7各自独立地为氢或C1-C6烷基;R5为C1-C6烷基或NR15R16,其中R15和R16为氢或C1-C6烷基;或R4和R6一起形成C2-C6亚烷基桥;或R4和R6,R5和R7各自独立地分别形成C2-C6亚烷基桥或,如果R5为NR15R16,R16和R7一起形成C2-C6亚烷基桥;R17为氢或C1-C4烷基;以及R18为氢,C1-C4烷基或苯基。
特别优选的式(II)有机化合物是那些其中R1为苯基或萘基,它们未被取代或被下列基团取代一次或多次:CN,NR8R9,NO2,CF3,SR10或OR10,或者R1为噻蒽基,芴基或噻吨基,或R1为式A基团n为0,R8,R9和R10为氢或C1-C6烷基;R2和R3为氢或C1-C6烷基;R4和R6一起形成C2-C6亚烷基桥;R5和R7一起形成C2-C6亚烷基桥;R17为氢;以及R18为氢,C1-C4烷基。
本发明还提供了制备含有式(I)结构单位的如上所述的化合物的方法,该方法包括,第一步,使含有式(III)结构单位的化合物与含有式(IV)结构单位的化合物反应其中卤素为F,Cl,Br或I,R1定义如权利要求1,第二步,使用鏻(PR4 +)盐与由此得到的反应产物进行Wittig反应。
优选的制备式(II)化合物的方法包括使式(V)化合物其中基团R4,R5,R6和R7定义如上,包括优选定义,与式(VI)化合物反应其中基团R1,R2和R3定义如上,包括优选定义,卤素为F,Cl,Br或I,第二步中,使用式(VIII)鏻(PR4 +)盐
R17R18CH-P(苯基)3 +X-(VIII),其中R17和R18定义如上,包括优选定义,X为F,CI,Br,I或四氟硼酸根,与由此得到的反应产物进行Wittig反应。
适当的Wittig试剂(鏻(PR4+)盐)为市场上可得到的,例如,Lancaster Chemical Catalogue,Appendix1,pagesA2-A6中所述的那些。例子为:甲基三苯基溴化鏻,甲基三苯基碘化鏻,乙基三苯基氯化鏻,乙基三苯基溴化鏻,乙基三苯基碘化鏻,正丙基三苯基溴化鏻,正丁基三苯基氯化鏻,正丁基三苯基溴化鏻,异丁基三苯基溴化鏻,正戊基三苯基溴化鏻,异戊基三苯基溴化鏻,正己基三苯基溴化鏻,正庚基三苯基溴化鏻,正辛基三苯基溴化鏻,正壬基三苯基溴化鏻,正癸基三苯基溴化鏻,正十一烷基三苯基溴化鏻,正十二烷基三苯基溴化鏻,正十四烷基三苯基溴化鏻,正十六烷基三苯基溴化鏻,三甲基甲硅烷基三苯基碘化鏻,2-二甲氨基乙基三苯基溴化鏻,2-氯乙基三苯基溴化鏻,2-羟基乙基三苯基溴化鏻,3-溴丙基三苯基溴化鏻,4-溴丁基三苯基溴化鏻,2-(1,3-二噁烷-2-基)乙基三苯基溴化鏻,环丙基甲基三苯基溴化鏻,4-羧基丁基三苯基溴化鏻,4-乙酯基丁基三苯基溴化鏻,4-戊烯基三苯基溴化鏻,5-己烯基三苯基溴化鏻,3-苯基丙基三苯基溴化鏻,亚乙基二(三苯基溴化鏻),亚丙基二(三苯基溴化鏻),亚丁基二(三苯基溴化鏻),亚戊基二(三苯基溴化鏻),异丙基三苯基碘化鏻,2-丁基三苯基溴化鏻,2-戊基三苯基溴化鏻,环丙基三苯基溴化鏻,环戊基三苯基溴化鏻,环己基三苯基溴化鏻,环庚基三苯基溴化鏻,烯丙基三苯基氯化鏻,烯丙基三苯基溴化鏻,2-甲基烯丙基三苯基氯化鏻,3-甲基烯丙基三苯基氯化鏻,3,3-二甲基烯丙基三苯基溴化鏻,2-亚丁基-1,4-二(三苯基氯化鏻),肉桂基三苯基氯化鏻,肉桂基三苯基溴化鏻,炔丙基三苯基溴化鏻,苄基三苯基氯化鏻,苄基三苯基溴化鏻,苄基三苯基碘化鏻,2-甲基苄基三苯基氯化鏻,2-甲基苄基三苯基溴化鏻,3-甲基苄基三苯基氯化鏻,4-甲基苄基三苯基氯化鏻,4-甲基苄基三苯基溴化鏻,2-羟基苄基三苯基溴化鏻,4-甲氧基苄基三苯基氯化鏻,4-乙氧基苄基三苯基溴化鏻,4-丁氧基苄基三苯基溴化鏻,4-氟苄基三苯基氯化鏻,4-氯苄基三苯基氯化鏻,4-溴苄基三苯基溴化鏻,4-氰基苄基三苯基氯化鏻,4-甲酯基苄基三苯基溴化鏻,2-硝基苄基三苯基溴化鏻水合物,4-硝基苄基苄基三苯基溴化鏻,邻二甲苯基二(三苯基溴化鏻),对二甲苯基二(三苯基氯化鏻),对二甲苯基二(三苯基溴化鏻),1-萘基甲基三苯基氯化鏻,二苯甲基三苯基氯化鏻,羟甲基三苯基氯化鏻,甲氧基甲基三苯基氯化鏻,氯甲基三苯基碘化鏻,甲硫基甲基三苯基氯化鏻,苯基硫甲基三苯基氯化鏻,1,3-二噻烷-2-基三苯基氯化鏻,甲酰基甲基三苯基氯化鏻,乙酰基甲基三苯基溴化鏻,苯甲酰甲基三苯基溴化鏻,α-甲基苯甲酰甲基三苯基溴化鏻,甲酯基甲基三苯基氯化鏻,甲酯基甲基三苯基溴化鏻,乙酯基甲基三苯基氯化鏻,乙酯基甲基三苯基溴化鏻,1-乙酯基乙基三苯基溴化鏻,4-(三苯基鏻)丁烯酸甲酯溴化物,1-乙酯基乙基三苯基鏻四氟硼酸盐,氰基甲基三苯基氯化鏻,2-(三苯基正膦基亚基)琥珀酸酐,9-芴基三苯基溴化鏻,乙烯基三苯基溴化鏻,或1,2-亚乙烯基(三苯基溴化鏻)。
式(V)化合物与式(VI)化合物的反应可按本身已知的方式进行。优选地,可使用溶剂或溶剂混合物,例如,烃类如苯,甲苯,二甲苯,等,卤代烃如二氯甲烷,氯仿,四氯化碳,氯苯,等,醇类如甲醇,乙醇,乙二醇单甲醚,等,和醚类如乙醚,二丁基醚,乙二醇二甲醚,等,及其混合物。
该反应可选择性地在从-10℃到100℃的温度范围内进行,优选的反应温度为10℃到50℃。
Wittig反应可以常规方式进行。优选使用溶剂或溶剂混合物,例如,烃类如苯,甲苯,二甲苯,等,卤代烃如二氯甲烷,氯仿,四氯化碳,氯苯,等,醇类如甲醇,乙醇,乙二醇单甲醚,等,和醚类如乙醚,二丁基醚,乙二醇二甲醚,等,及其混合物。
该反应可在从-10℃到100℃的温度范围内进行,优选的反应温度为10℃到70℃。
在本发明光活性碱的制备过程中,可能生产异构体混合物。可通过技术人员熟悉的常规方法加以分离。另一方面,可直接使用所得到的异构体混合物作为光活性碱。
本发明还提供了制备式(VII)化合物的方法其中基团R4,R5,R6和R7定义如上,包括优选定义,该方法包括将式(II)化合物其中基团R1,R2,R3,R4,R5,R6R7,R17和R18定义如上,包括优选定义,暴露于波长为200nm到650nm的光线下。该反应优选在溶剂或溶剂混合物中进行。式(II)化合物的浓度优选地被调节至所有光线实际上都吸收于反应容器中。
反应溶液优选地被搅拌,如果需要,在此暴露于光线的过程中可将其冷却。
合适的溶剂如上所述。
按照本发明,含有式(I)结构单位的有机化合物可用作光活性碱。
本发明还提供了一种组合物,其中包括A)至少一种含有式(I)结构单位的化合物和B)至少一种可进行碱催化的加成或取代反应的有机化合物。
优选的是上述的式(II)有机化合物。
碱催化的加成或取代反应可用低分子量化合物(单体),低聚物,聚合化合物或这些化合物的混合物进行。可使用新的光引发剂由单体和低聚物/聚合物进行的反应的例子为Knoevenagal反应或Michael加成反应。
其中组分B)为阴离子催化的可聚合的或可交联的有机材料的组合物特别重要。该有机材料可为单-或多官能化的的单体,低聚物或聚合物。
特别优选的低聚物/聚合物系统为涂料工业中的常规粘合剂。
碱催化粘合剂的例子为:a)具有烷氧基硅烷或烷氧基硅氧烷侧基的丙烯酸酯共聚物,例如US-A-4,772,672或US-A-4,444,974所述的聚合物;b)含有含羟基的聚丙烯酸酯,聚酯,和/或聚醚和脂族或芳族聚异氰酸酯的二组分系统;c)含有官能化的聚丙烯酸酯和聚环氧化物的二组分系统,其中聚丙烯酸酯含有羧基和酸酐基;d)含有氟-修饰的或硅氧烷-修饰的含羟基的聚丙烯酸酯,聚酯,和/或聚醚和脂族或芳族聚异氰酸酯的二组分系统;e)含有(聚)酮亚胺和脂族或芳族聚异氰酸酯的二组分系统;f)含有(聚)酮亚胺和不饱和丙烯酸酯树脂或乙酰乙酸酯树脂或α-丙烯酰氨基甲基甘醇酸甲酯的二组分系统;h)含有(聚)酮亚胺和含酸酐基的聚丙烯酸酯,或不饱和聚丙烯酸酯树脂或聚异氰酸酯的二组分系统;i)含有环氧基-官能基的聚丙烯酸酯和含羧基的或含氨基的聚丙烯酸酯的二组分系统;l)基于烯丙基缩水甘油基醚的聚合物;m)含有(聚)醇和(聚)异氰酸酯的二组分系统;n)含有α,β亚乙基化的不饱和羰基化合物和其中含有活化的CH2基的聚合物的二组分系统,其中活化的CH2基既可存在于主链也可存在于侧链,例如,EP-B-0 161 697中的(聚)丙二酸酯基。其他具有活化的CH2基的化合物为(聚)乙酰乙酸酯和(聚)氰基乙酸酯。
其中特别优选的碱催化粘合剂为:b)含有含羟基的聚丙烯酸酯,聚酯,和/或聚醚和脂族或芳族聚异氰酸酯的二组分系统;c)含有官能化的聚丙烯酸酯和聚环氧化物的二组分系统,其中聚丙烯酸酯含有羧基和酸酐基;i)含有环氧基-官能基的聚丙烯酸酯和含羧基的或含氨基的聚丙烯酸酯的二组分系统;m)含有(聚)醇和(聚)异氰酸酯的二组分系统;和n)含有α,β亚乙基化的不饱和羰基化合物和其中含有活化的CH2基的聚合物的二组分系统,其中活化的CH2基既可存在于主链也可存在于侧链。
含有α,β亚乙基化的不饱和羰基化合物和(聚)丙二酸酯的二组分系统,及其制备,描述于EP-B-0 161 687中。丙二酸酯基既可存在于聚氨基甲酸乙酯,聚酯,聚丙烯酸酯,环氧树脂,聚酰胺或聚乙烯聚合物的主链也可存在于其侧链。例如丙烯酸或甲基丙烯酸酯和酰胺。酯基中也可能存在另外的羟基。也可为二酯或三酯。典型的例子为己二醇二丙烯酸酯或三羟甲基三丙烯酸酯。除丙烯酸外,也可使用其他酸及其酯或酰胺,如丁烯酸或肉桂酸。
在碱催化剂的作用下,在室温下,系统中的组分相互反应,生成适于各种用途的交联的涂料系统。由于其良好的气候适应性,它可用于,例如,外墙涂料,如果需要,可加入UV吸收剂和其他光稳定剂使其稳定。
新的组合物其他合适的组分B)为环氧系统。环氧树脂适于制备新的,可处理的混合物,其中作为组分B)的环氧树脂为环氧树脂技术中常规的环氧树脂,例子为:I)通过分子中具有至少两个羧基的化合物与表氯醇或β-甲基表氯醇反应得到的聚缩水甘油基和聚(β-甲基缩水甘油基)酯。该反应可在碱存在下进行。上述分子中具有至少两个羧基的化合物可能使用脂族多羧酸。多羧酸的例子为草酸,琥珀酸,戊二酸,己二酸,庚二酸,辛二酸,壬二酸或二聚或三聚亚油酸。但是,也可使用环脂族多羧酸,如四氢邻苯二甲酸,4-甲基四氢邻苯二甲酸酐,六氢邻苯二甲酸或4-甲基六氢邻苯二甲酸。另外,也可使用芳族多羧酸,如邻苯二甲酸,间苯二甲酸或对苯二甲酸。II)通过分子中具有至少两个游离的醇羟基或酚羟基的化合物与表氯醇或β-甲基表氯醇反应得到的聚缩水甘油基和聚(β-甲基缩水甘油基)醚,该反应可在碱性条件下进行,或在酸催化剂存在下进行,随后用碱处理。用于生成这类缩水甘油基醚的原料为,例如,无环醇,如乙二醇,二甘醇和高聚(氧乙烯基)二醇,丙烷-1,2-二醇和聚(氧丙烯基)二醇,丙烷-1,3-二醇,丁烷-1,4-二醇,聚(氧丁烯基)二醇,戊烷-1,5-二醇,己烷-1,6-二醇,己烷-2,4,6-三醇,甘油,1,1,1-三羟甲基丙烷,季戊四醇,山梨醇,以及聚表氯醇。但是,它们的原料也可为,例如,脂环醇,如1,4-环己烷二甲醇,二(4-羟基环己基)甲烷或2,2-二(4-羟基环己基)丙烷,或者具有芳香核的醇,如N,N-(而-羟基乙基)苯胺或p,p’-二(2-羟基乙氨基)二苯基甲烷。缩水甘油基醚的也可由,例如,单核酚,如间苯二酚或对苯二酚,核苯酚,如二(4-羟基苯基)甲烷,4,4’-二羟基联苯二(4-羟基苯基)砜,1,1,2,2-四(4-羟基苯基)乙烷,2,2-二(4-羟基苯基)丙烷,2,2-二(3,5-二溴-4-羟基苯基)丙烷以及通过醛,如甲醛,乙醛,氯醛或糠醛与酚,如苯酚,或其核被氯原子或C1-C9烷基取代的酚,例如4-氯苯酚,或4-叔丁基苯酚,或上述类型的二苯酚缩合的酚醛清漆衍生。III)通过使表氯醇与含至少两个胺的氢原子的胺的反应产物脱氯化氢得到的聚(N-缩水甘油基)化合物。这些胺为,例如,苯胺,正丁基胺,二(4-氨基苯基)甲烷,碱二甲苯二胺或二(4-甲氨基苯基)甲烷。但是,聚(N-缩水甘油基)化合物也可包括三缩水甘油基异氰酸酯,环亚烷基脲的N,N’-二缩水甘油基衍生物,如亚乙基脲或1,3-亚丙基脲,以及乙内酰脲的二缩水甘油基衍生物,如5,5-二甲基乙内酰脲。IV)聚(S-缩水甘油基)化合物,例如由二硫醇如乙烷-1,2-二硫醇或二(4-巯基甲基苯基)醚衍生的二-S-缩水甘油基衍生物。V)环脂族环氧树脂,例如二(2,3-环氧环戊基)醚,2,3-环氧环戊基缩水甘油基醚,1,2-二(2,3-二环氧环戊基氧)乙烷或3,4-环氧环己基甲基3’,4’-环氧环己烷羧酸酯。选择性地,环氧树脂中的1,2-环氧基可连接在不同的杂原子和/或官能基上;这样的化合物包括,例如,4-氨基苯酚的N,N,O-三缩水甘油基衍生物,水杨酸的缩水甘油基醚缩水甘油基酯,N-缩水甘油基-N’(2-缩水甘油基氧丙基)-5,5-二甲基乙内酰脲或2-缩水甘油基氧-1,3-二5,5,-二甲基-1-缩水甘油基乙内酰脲-3-基)丙烷。
环氧树脂混合物也可用作组分B)。
因此,本发明组合物也包括作为组分B)的环氧树脂或不同的环氧树脂混合物。
该组合物包含光引发剂,组分A),优选基于组分B)的量为0.01到10%(重量)。
除光引发剂,组分A)外,光致聚合混合物还可包括各种添加剂。例如,防止过早聚合的热抑制剂,如氢醌,氢醌衍生物,对甲氧基苯酚,β-萘酚或立体受阻酚如2,6-二(叔丁基)-对甲苯酚。为了提高暗储存稳定性,例如,可使用铜化合物,如环烷酸,硬脂酸或辛酸铜,磷化合物,如三苯膦,三丁基膦,三乙基亚磷酸酯,三苯基亚磷酸酯或三苄基亚磷酸酯,季铵化合物,如氯化四甲铵或氯化三甲基苄基铵,或羟胺衍生物,如N-二乙基-羟胺。为了在聚合时排斥空气中的氧,可加入石蜡或相似的蜡状物质,这些物质在聚合物中的溶解度低,可在聚合开始时迁移至表面形成透明的表面层以防止空气的进入。同样,也可使用氧-不渗透层。也可加入少量光稳定剂,例如,UV吸收剂,如羟苯基苯并三唑,羟苯基-二苯酮,草酰胺或或羟苯基-s-三嗪类。在有或没有立体受阻胺(HALS)的情况下,既可使用单个上述化合物,也可使用其混合物。
UV吸收剂和光稳定剂的例子如下。1.2-(2’-羟基苯基)苯并三唑,例如2-(2’-羟基-5’-甲基苯基)苯并三唑,2-(3’,5’-二-叔丁基-2’-羟基苯基)苯并三唑,2-(5’-叔丁基-2’-羟基苯基)苯并三唑,2-(2’-羟基-5’-(1,1,3,3-四甲基丁基)苯基)苯并三唑,2-(3’,5’-二叔丁基-2’-羟基苯基)-5-氯苯并三唑,2-(3’-叔丁基-2’-羟基-5’-甲基苯基)-5-氯苯并三唑,2-(3’-仲丁基-5’叔丁基-2’-羟基苯基)苯并三唑,2-(2’-羟基-4’-辛氧基苯基)苯并三唑,2-(3’,5’-二叔戊基-2’-羟基苯基)苯并三唑,2-(3’,5’-二(α,α-二甲基苄基)-2’-羟基苯基)苯并三唑,2-(3’-叔丁基-2’-羟基-5’-(2-辛氧羰基乙基)苯基)-5-氯苯并三唑,2-(3’-叔丁基-5’-[2-(2-乙基己氧)羰基乙基]-2’-羟基苯基)-5-氯苯并三唑,2-(3’-叔丁基-2’-羟基-5’-(2-甲氧羰基乙基)苯基)-5-氯苯并三唑,2-(3’-叔丁基-2’-羟基-5’-(2-甲氧羰基乙基)苯基)苯并三唑,2-(3’-叔丁基-2’-羟基-5’-(2-辛氧羰基乙基)苯基)苯并三唑,2-(3’-叔丁基-5’-[2-(2-乙基已氧)羰基乙基]-2’-羟基苯基)苯并三唑,2-(3’-十二烷基-2’-羟基-5’-甲基和苯基)苯并三唑和2-(3’-叔丁基-2’-羟基-5’-(2-异辛基氧羰基乙基)苯基)苯并三唑的混合物,2,2’-亚甲基二[4-(1,1,3,3-四甲基丁基)-6-苯并三唑-2-基苯酚];2-[3’-叔丁基-5’-(2-甲氧羰基乙基)-2’-羟基苯基)苯并三唑与聚乙二醇300的酯交换产物;[R-CH2CH2-COO(CH2)3]2-其中R=3’-叔丁基-4’-羟基-5’-2H-苯并三唑-2-基苯基。2.2-羟基二苯酮,例如4-羟基,4-甲氧基,4-辛氧基,4-癸氧基,4-十二烷氧基,4-苄氧基,4,2’,4’-三羟基和2’-羟基-4,4’-二甲氧基衍生物。3.取代和未取代的苯甲酸酯,例如4-叔丁基苯基水杨酸酯,苯基水杨酸酯,辛基苯基水杨酸酯,二苯甲酰基间苯二酚,二(4-叔丁基苯甲酰基)间苯二酚,苯甲酰基间苯二酚,3,5-二叔丁基-4-羟基苯甲酸2,4-二叔丁基苯基酯,3,5-二叔丁基-4-羟基苯甲酸十六烷基酯,3,5-二叔丁基-4-羟基苯甲酸十八烷基酯,和3,5-二叔丁基-4-羟基苯甲酸2-甲基-4,6-二叔丁基苯基酯。4.丙烯酸酯,例如α-氰基-β,β-二苯基丙烯酸乙基或异辛基酯,α-甲酯基肉桂酸甲基酯,α-氰基-β-甲基-对甲氧基肉桂酸甲基和丁基酯,α-甲酯基对甲氧基肉桂酸甲基酯和N-(β-甲酯基-β-氰基乙烯基)-2-甲基二氢吲哚。5.立体受阻胺,如二(2,2,6,6-四甲基哌啶基)癸二酸酯,二(2,2,6,6-四甲基哌啶基)琥珀酸酯,二(1,2,2,6,6-五甲基哌啶基)癸二酸酯,二(1,2,2,6,6-五甲基哌啶基)正丁基-3,5-二叔丁基-4-羟基苄基丙二酸酯,1-羟乙基-2,2,6,6-四甲基-4-羟基哌啶和琥珀酸的缩合产物,N,N’-二(2,2,6,6-四甲基-4-哌啶基)亚己基二胺和4-叔辛基氨基-2,6-二氯-1,3,5-一均一三嗪的缩合产物,三(2,2,6,6-四甲基-4-哌啶基)次氯基三乙酸酯,四(2,2,6,6-四甲基-4-哌啶基)-1,2,3,4-丁四酸酯,1,1’-(1,2-乙烷二基)-二(3,3,5,5-四甲基哌嗪酮),4-苯甲酰基-2,2,6,6-四甲基哌啶,4-硬脂酰氧基-2,2,6,6-四甲基哌啶,二(1,2,2,6,6-五甲基哌啶基)2-正丁基-2-(2-羟基-3,5-二叔丁基苄基)丙二酸酯,3-正辛基-7,7,9,9-四甲基-1,3,8-三氮杂螺[4.5]癸-2,4-二酮,二(1-辛氧基-2,2,6,6-四甲基哌啶基)癸二酸酯,二(1-辛氧基-2,2,6,6-四甲基哌啶基)琥珀酸酯,N,N’-二(2,2,6,6-四甲基-4-哌啶基)亚己基二胺和4-吗啉基-2,6-二氯-1,3,5-三嗪的缩合产物,2-氯-4,6-二(4-正丁基氨基-2,2,6,6-四甲基哌啶基)-1,3,5-三嗪和1,2-二(3-氨基丙氨基)乙烷的缩合产物,2-氯-4,6-二(4-正丁基氨基-1,2,2,6,6-五甲基哌啶基)-1,3,5-三嗪和1,2-二(3-氨基丙氨基)乙烷的缩合产物,8-乙酰基-3-十二烷基-7,7,9,9-四甲基-1,3,8-三氮杂螺[4.5]癸-2,4-二酮,3-十二烷基-1-(2,2,6,6-四甲基-4-哌啶基)吡咯烷-2,5-二酮,3-十二烷基-1-(1,2,2,6,6-五甲基-4-哌啶基)吡咯烷-2,5-二酮。6.草酰胺,例如4,4’-二辛氧基-N,N’-草酰二苯胺,2,2’-二乙氧基-N,N’-草酰二苯胺,2,2’-二辛氧基-5,5’-二叔丁基-N,N’-草酰二苯胺,2,2’-二-十二烷氧基-5,5’-二叔丁基-N,N’-草酰二苯胺,2-乙氧基-2’-乙基-N,N’-草酰二苯胺,N,N’-二(3-二甲氨基丙基)草酰胺,2-乙氧基-5-叔丁基-2’-乙基-N,N’-草酰二苯胺,及其与2-乙氧基-2’-乙基-5,4’-二叔丁基-N,N’-草酰二苯胺的混合物,邻-和对-甲氧基和邻-和对-乙氧基-取代的N,N’-草酰二苯胺的混合物。7.2-(2-羟基苯基)-1,3,5-三嗪,例如2,4,6-三(2-羟基-4-辛氧基苯基)-1,3,5-三嗪,2-(2-羟基-4-辛氧基苯基)-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪,2-(2,4-二羟基苯基)-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪,2,4-二(2-羟基-4-丙氧基苯基)-6-二(2,4-二甲基苯基)-1,3,5-三嗪,2-(2-羟基-4-辛氧基苯基)-4,6-二(4-甲基苯基)-1,3,5-三嗪,2-(2-羟基-4-十二烷氧基苯基)-4,6-二(2,4二甲基苯基)-1,3,5-三嗪,2-[2-羟基-4-(2-羟基-3-丁氧基丙氧基)苯基]-4,6-二(2,4二甲基苯基)-1,3,5-三嗪,2-[2-羟基-4-(2-羟基-3-辛氧基丙氧基)苯基]-4,6-二(2,4二甲基苯基)-1,3,5-三嗪,2-[4-十二/十三烷氧基-(2-羟丙基)氧-2-羟基苯基]-4,6-二(2,4二甲基苯基)-1,3,5-三嗪。8.亚磷酸酯和膦酸酯,例如三苯基亚磷酸酯,二苯基烷基亚磷酸酯,苯基二烷基亚磷酸酯,三(壬基苯基)亚磷酸酯,三-十二烷基亚磷酸酯,三-十八烷基亚磷酸酯,二-十八烷基季戊四醇二亚磷酸酯,三(2,4-二叔丁基苯基)亚磷酸酯,二异癸基季戊四醇二亚磷酸酯,二(2,4-二叔丁基苯基)季戊四醇二亚磷酸酯,二(2,6-二叔丁基-4-甲基苯基)季戊四醇二亚磷酸酯,二-异癸氧基季戊四醇二亚磷酸酯,二(2,4-二叔丁基-6-甲基苯基)季戊四醇二亚磷酸酯,二(2,4,6-三叔丁基苯基)季戊四醇二亚磷酸酯,三-十八烷基山梨醇三亚磷酸酯,四(2,4-二-叔丁基苯基)-4,4’-亚联苯基二膦酸酯,6-异辛氧基-2,4,8,10-四-叔丁基-12H-二苯并[d,g]-1,3,2-dioxaphosphocin,6-氟-2,4,8,10-四-叔丁基-12H-二苯并[d,g]1,3,2-dioxaphosphocin,二(2,4-二叔丁基-6-甲基苯基)甲基亚磷酸酯,二(2,4-二叔丁基-6-甲基苯基)乙基亚磷酸酯。
其他添加剂的例子为:填料和增强剂,例如碳酸钙,硅酸盐,玻璃纤维,玻璃珠,石棉,滑石,高岭土,云母,硫酸钡,金属氧化物和氢氧化物,碳黑,石墨,木粉和其他天然物质的粉末或纤维,合成纤维。其他添加剂,如增塑剂,润滑剂,乳化剂,颜料,流变添加剂,催化剂,均化剂,荧光增白剂,耐火剂,抗静电剂,发泡剂。
除上述添加剂外还可存在另外的共引发剂。通常,它们为可通过,例如,能量转移或电子转移的方式改进总量子场的染料。可作为共引发剂的合适的染料的例子为三芳基甲烷,例如孔雀绿,二氢吲哚,噻嗪,例如亚甲蓝,占吨酮,噻吨酮,噁嗪,吖啶或吩嗪,例如藏红,以及下式所示的若丹明其中R为烷基或芳基,R’为氢,烷基或芳基,例如若丹明B,若丹明6G或紫胺R,以及SulforhodamineB或SulforhodamineG。
其中优选噻吨酮,噁嗪,吖啶,吩嗪和若丹明。
同样合适的还有染料与硼酸盐的组合,例如,US4 772 530,GB2307 474,GB2 307 473,GB2 307 472和EP775 706中所述。
除上述可碱催化(硫化)的粘合剂,组分B)外,该组合物还可包括其他粘合剂。另外,还可包括烯类不饱和化合物。该不饱和化合物可含有一个或多个烯烃双键。它们的分子量可低(单体)可高(低聚物)。具有一个双键的单体的例子为烷基或羟基烷基丙烯酸酯或甲基丙烯酸酯,如丙烯酸甲酯,乙酯,丁基酯,2-乙基己基酯或2-羟基乙基酯,isbornylacrylate,甲基丙烯酸甲酯或甲基丙烯酸乙酯。丙烯酸硅氧烷基酯也是有用的。其他例子为丙烯腈,丙烯酰胺,甲基丙烯酰胺,N-取代的(甲基)丙烯酰胺,乙烯基酯如乙酸乙烯酯,乙烯基醚如异丁基乙烯基醚,苯乙烯,烷基-或卤代苯乙烯,N-乙烯基吡咯烷酮,氯乙烯或1,1-二氯乙烯。
具有两个或更多双键的单体的例子为乙二醇,丙二醇,新戊基二醇,己二醇或双酚A的二丙烯酸酯,4,4’-二(2-丙烯酰氧乙氧基)二苯基丙烷,三羟甲基三丙烯酸酯,季戊四醇三丙烯酸酯或四丙烯酸酯,丙烯酸乙烯酯,二乙烯基苯,琥珀酸二乙烯基酯,磷酸二烯丙基酯,磷酸三烯丙基酯,异氰酸三烯丙基酯或异氰酸三(2-丙烯酰乙基)酯。
分子量相对高的多不饱和化合物(低聚物)的例子为含丙烯酸的环氧树脂含丙烯酸的聚酯或含乙烯基醚基或环氧基的聚酯,聚氨基甲酸乙酯和聚醚。不饱和低聚物的其他例子为主要由马来酸,邻苯二甲酸和一种或多种二醇制备并且分子量约500到3000的不饱和聚酯树脂。另外,也可使用乙烯基醚单体和低聚物,以及马来酸酯封端的低聚物与聚酯,聚氨基甲酸乙酯,聚醚,聚乙烯基醚和环氧主链。特别地,乙烯基醚-官能基低聚物和WO90/01512所述的聚合物是非常合适的。而且,乙烯基醚和马来酸-官能基单体的共聚物也是合适的。这类不饱和低聚物也可为预聚物。
特别合适的例子为含烯基的不饱和羧酸与多元醇或聚环氧化物的酯,以及在主链或侧基上具有含烯基的不饱和基团的聚合物,如不饱和聚酯,聚酰胺和聚氨基甲酸乙酯及其共聚物,醇酸树脂,聚丁二烯和丁二烯共聚物,聚异戊二烯和异戊二烯共聚物具有(甲基)丙烯酸基侧链的聚合物和共聚物,以及一种或多种上述聚合物的混合物。
另外,如果使用自由基硫化的单体,低聚物/聚合物,可另外加入解离成自由基的光引发剂。这样的光引发剂是已知的并可工业生产。例子为二苯酮,二苯酮衍生物,苯乙酮,苯乙酮衍生物,例如α-羟基环烷基苯基酮,二烷氧基苯乙酮,α-羟基-或α-氨基苯乙酮,4-芳酰基-1,3-二噁烷,苯偶姻烷基醚和苯偶酰缩酮,单酰基膦氧化物,双酰基膦氧化物,二茂铁或titanocenes。
实例在EP-A-284 561中说明。可通过不同机理进行硫化/交联的这类聚合物系统也可称为杂合系统。
也可在上述新的组合物中加入非活性的粘合剂,特别是当光聚合化合物为液体或粘性固体时。基于所有固体总量,非活性粘合剂的量可为,例如,5-95%,优选10-90%,特别是40-90%(重量)。非活性粘合剂的选择可根据使用领域和该用途所需的性质,如在水和有机溶剂系统中的分散性,对基质的粘合性,以及对氧的敏感性进行。
合适的粘合剂为分子量约5000-2,000,000,优选10,000-1,000,000的聚合物。例子为:丙烯酸酯和甲基丙烯酸酯的单-或共聚物,例如甲基丙烯酸甲酯/丙烯酸乙酯/甲基丙烯酸共聚物,聚(甲基丙烯酸烷基酯),聚(丙烯酸烷基酯);纤维素酯和纤维素醚,如乙酸纤维素,乙酸丁酸纤维素,甲基纤维素,乙基纤维素;聚乙烯醇缩丁醛,聚乙烯醇缩甲醛,环化橡胶,聚醚如聚环氧乙烷,聚环氧丙烷,聚四氢呋喃;聚苯乙烯,聚碳酸酯,聚氨基甲酸乙酯,氯化聚烯烃,聚氯乙烯,乙烯基氯/亚乙烯基氯共聚物,亚乙烯基氯与丙烯腈,甲基丙烯酸甲酯和乙烯基乙酸酯的共聚物,乙烯基乙酸酯共聚物,(亚乙基/乙烯基乙酸酯)共聚物,聚合物如聚己内酰胺和聚(亚己基己二酰二胺)和聚酯如聚(乙二醇对苯二酸酯)和聚(己二醇琥珀酸酯)。
本发明还提供了一种进行碱催化反应的方法,其中包括用波长为200nm到650nm的光线照射上述组合物,该组合物包括A)至少一种具有式(I)结构单位的化合物其中R1为可吸收波长为200nm到650nm的光线并因此解离相邻的碳-氮键的芳基或杂芳基;和B)至少一种可进行碱催化反应的有机化合物。组分A)优选地为包括优选部分的上述式(II)有机化合物。
碱催化反应的例子和优选定义如上所述。
在某些情况下,在光照期间或之后,可优选地进行加热。在很多情况下,可以这种方式加速交联反应。
另外,上述制备涂料,模铸组合物或光结构层的方法也属于本发明。
上述新的组合物通常对约200nm到UV区直到红外区(约20,000nm,特别是1200nm)的光线敏感,也就是说,该范围很宽。合适的光线包括,例如,阳光或人工光源发出的光。因此,可使用大量不同类型光源。点光源和平板辐射器(lamp carpets)都是合适的。例子为碳弧光灯,氙弧光灯,中压-,高压-和低压汞灯,如果需要用金属卤化物激发(金属卤灯),微波激发的金属蒸汽灯,激态原子灯,超锕系元素荧光灯,荧光灯,白炽灯,电子闪光灯,摄影溢光灯,通过同步加速器或激光等离子体产生的电子束和X-射线。按照本发明,灯和基质之间的距离可根据用途和灯的类型和/或功率的不同,有很大的变化,例如2cm到150cm。特别适用的是激光光源,例如激态激光。也可使用可见区或IR区的激光。这里特别优选的是对激光光线高度敏感的新材料和可用作共引发剂的染料。通过该方法可生产电子工业中的印刷电路,平版胶印的印刷版或凸版印刷版,以及光显象记录材料。
新的组合物可用于各种目的,例如油墨,透明涂料,白漆,例如用于木材或金属的白漆,涂层材料,特别用于纸,木材,金属或塑料,粉末涂料,用于标记建筑和道路的日光固化涂料,用于照相复制,全息照相材料,用于图像记录或印刷版的生产,其中可使用有机溶剂或含水-碱性介质,用于生产筛网印刷的掩蔽剂,牙科填充材料,胶粘剂,包括压敏粘合剂,层压树脂,蚀刻防染剂或永久防染剂和用于电路的焊接掩蔽剂,用于通过质量固化(透明模具中的UV固化)或通过立体光刻法生产三维制品,例如,US专利N0.4 575 330所述,制备复合材料(例如苯乙烯聚酯,它可含有玻璃纤维和/或其他纤维和其他助剂)和其他薄层组合物,电子组分的涂层或密封,或光学纤维的涂层。
在表面涂层中,通常使用预聚物与也含有单不饱和单体的多不饱和单体的混合物。这里的预聚物主要与涂层膜的性质有关,技术人员已知它的变化对固化膜的性质的影响。多不饱和单体也可作为交联剂,这使涂层膜变得不易溶解。单不饱和单体也可作为活性稀释剂,因此不需要使用溶剂便可降低粘度。
不饱和聚酯树脂主要用于与单不饱和单体协同的二-组分系统,优选苯乙烯。特殊的单组分系统常用于抗光蚀剂,例如聚马来酰胺,聚查耳酮或聚酰亚胺,如DE-A-2 308 830所述。新的光固化组合物适于,例如,作为所有种类基质的涂层材料基质的例子为木材,织物,纸,陶瓷,玻璃,塑料如聚酯,聚对苯二甲酸乙二醇酯,聚烯烃或乙酸纤维素,特别是膜形式的材料,以及金属如Al,Cu,Ni,Fe,Zn,Mg或Co和GaAs,Si或SiO2,将其用于保护涂层,或通过图像曝光产生图像,也包括于本发明中。
通过在基质上使用液体组合物,溶液或悬浮液,可在基质上形成涂层。溶剂和浓度的选择主要取决于组合物的性质和涂敷方法。溶剂应该为惰性的,也就是说,不应该与组分有任何化学反应,涂敷结束后应该能以干燥的方法被除去。合适的溶剂的例子为酮,醚和酯,如甲基乙基酮,异丁基甲基酮,环戊酮,环己酮,N-甲基吡咯烷酮,二噁烷,四氢呋喃,2-甲氧基乙醇,2-乙氧基乙醇,1-甲氧基-2-丙醇,1,2-二甲氧基乙烷,乙酸乙酯,乙酸正丁基酯和3-乙氧基丙酸乙酯。使用已知的涂敷技术,例如,旋转涂敷,浸涂,刮涂,幕涂,刷涂,喷涂-特别是电喷-和反向辊涂,以及通过电泳沉积,可将该溶液均匀地涂敷于基质。也可将光敏感层用于暂时的,柔软的载体,然后通过层压层转移的方式涂敷于最终的基质,例如铜-镀过的电路板。
用量(层厚度)和基质(层载体)的性质取决于所使用的领域。层厚度通常为约0.1μm到超过100μm。
也可使用新的光线敏感组合物进行图像曝光。在这种情况下,它们用作负像防染剂。它们适用于电子学(电防染剂,蚀刻剂和焊接防染剂),适用于制备印刷版,如胶版印刷版,flexographic和凸版印刷版或筛网印刷版,适用于条纹标记,并可在集成电路的制备中用于化学研磨或用作微防染剂。相应地,载体和涂敷基质的工艺条件将在很宽的范围内变化。
术语“图像”曝光涉及含预定图案,例如载片,的光掩蔽物,通过,例如由计算机控制的激光束,在涂敷的基质的表面曝光,产生图像,同时也涉及用计算机控制的电子束曝光。材料图像曝光后以及显影前,可优选地进行短暂的热处理,仅使曝光部分热固化。温度通常为50-150℃,优选80-130℃;热处理的时间通常为0.25到10分钟。
使用光涂敷的另一领域是金属涂敷,例如金属板和管,容器或瓶盖的表面涂敷,以及聚合物涂层的,例如覆盖PVC的楼板和墙,的光固化。纸涂层光固化的例子为标签,唱片套或书皮的无色处理。
新化合物在固化复合组合物制备的预制图形中的用途同样是有用的。复合组合物由自载基质材料,例如玻璃纤维织物或植物纤维组成[cf.K.-P.Mieck,T.Reussmann in Kunststoffe85(1995),366-370],该材料被光固化制剂浸透。由含本发明化合物的复合组合物制备的预制图形具有很高的机械稳定性和阻力。如EP-A-7086中所述,本发明化合物也可在模制,浸渍和涂层组合物中用作光固化剂。这样的组合物的例子为高级涂层树脂,它的用途在于其固化活性和抵抗泛黄的性质,或增强纤维模制剂如平面或纵向或横向波纹光漫射板。
本发明还提供了上述含式(I)结构单位的化合物作为光化学诱导,碱催化加成或取代反应的光引发剂的用途。优选的含式(I)结构单位的化合物的例子,以及适于碱催化加成或取代反应的底物如上所述。
本发明还提供了至少一个表面涂敷了上述组合物的涂层基质,提供了照相产生浮雕图像的方法,其中包括将涂层基质图像曝光,然后用溶剂除去未曝光区域。特别令人感兴趣的是利用激光束曝光。本发明还提供了上述聚合的或交联的组合物。
下列实施例用于说明本发明。实施例A:制备光引发剂一般制备方法a)将相应的α-溴代酮在甲苯中的溶液加入1,5-二氮杂双环[4.3.0]壬烷在甲苯中的溶液中,然后在室温下搅拌过夜。将反应混合物过滤,用软化水洗涤,并用MgSO4干燥。随后进一步真空干燥,以85%的产率得到相应的α-氨基酮。b)将甲基三苯基溴化磷和氨基钠在二氯甲烷中搅拌15分钟,然后加入a)中制备的α-氨基酮在二氯甲烷中的溶液,并将该混合物在室温下搅拌18小时。将该溶液过滤,真空浓缩滤液。得到α-氨基酮粗产物,产率65-85%。实施例中的摩尔消光系数ε的单位为l/mol cm。实施例A1R1=联苯基,R2=R3=H,R4/R6=-(CH2)3-,R5/R7=-(CH2)3-,R17=R18=H元素分析计算值C22H26N2:C82.97;H8.23;N8.80.实测值C82.83;H8.26;N8.59.U.V.(CHCl3)max.at 275nm(ε21600).I.R.(KBr)1625和1600cm-1(C=C).1H NMR(CDCl3);7.66-7.28(9H,m,ArH),5.51(1H,s,=CH),5.29(1H,s,=CH),3.83(1H,d,J 13.3Hz,NCH2C(CH2)Ph),3.07(3H,m,NCH2),2.89(1H,d,J 13.3Hz,NCH2C(CH2)Ph),2.38-1.12(10H,m,CH2).13C NMR(CDCl3):144.14,141.02,140.27,139.31,128.82,127.25,127.08,126.99,126.92,115.43,85.08,58.92,52.33,51.92,51.19,29.52,24.75 and 19.55.m/z(EI)318(M+)实施例A2R1=2-萘基,R2=R3=H,R4/R6=-(CH2)3-,R5/R7=-(CH2)3-,R17=R18=H元素分析计算值C20H24N2:C82.15;H8.27;N9.58.实测值C82.25;H8.25;N9.24.U.V.(CHCl3)max.at 247nm(ε35600)和287nm(ε8600).I.R.(KBr)1625和1595cm-1(C=C)。1H NMR(CDCl3):7.95(1H,s,ArH),7.85-7.65(4H,m,ArH),7.45-7.35(2H,m,ArH),5.58(1H,s,=CH),5.39(1H,s,=CH),3.88(1H,d,J 13.6Hz,NCH2C(CH2)Ph),3.07(3H,m,NCH2),2.97(1H,d,J 13.7Hz,NCH2C(CH2)Ph),2.44-1.45(10H,m,CH2).13C NMR(CDCl3):144.57,137.84,133.41,132.97,128.37,127.68,127.53,125.96,125.78,125.15,124.94,115.79,84.94,58.65,52.21,52.09,51.12,29.49,24.58 and 19.58.m/z(EI)292(M+).实施例A3R1=4-二乙氨基苯基,R2=R3=H,R4/R6=-(CH2)3-,R5/R7=-(CH2)3-。R17=R18=HU.V.(CHCl3)max.at 245nm(ε3700)和305nm(ε16100).I.R.(KBr)1610cm-1和1520cm-1(C=C).1H NMR(CDCl3):7.48(2H,d,ArH),6.58(2H,d,ArH),5.32(1H,s,=CH),5.05(1H,s,=CH),3.74(1H,d,J 13.1Hz,NCH2C(CH2)Ph),3.32(4H,q,J 7.1Hz,NCH2CH3),3.06(3H,M,NCH2),2.80(1H,d,J 13.1Hz,NCH2C(CH2)Ph),2.36 1.23(10H,m,CH2)and 1.13(6H,t,J 7.1Hz,CH3).13C NMR(CDCl3):147.21,143.63,131.43,127.36,111.34,110.07,84.21,59.02,52.30,51.81,51.24,44.40,29.42.24.75,19.53 and 12.71.m/z(EI)313(M+).实施例A4R1=4-硫甲基苯基,R2=R3=H,R4/R6=-(CH2)3-,R5/R7=-(CH2)3-,R17=R18=HU.V.(CHCl3)max.at 280nm(ε13800).I.R.(KBr)1670,1625和1595cm-1(C=C).1H NMR(CDCl3):7.48(2H,d,ArH),7.16(2H,d,ArH),5.41(1H,s,=CH),5.21(1H,s,=CH),3.74(1H,d,J 13.2Hz,NCH2C(CH2)Ph),3.05(3H,m,NCH2),2.83(1H,d,J 13.2Hz,NCH2C(CH2)Ph),2.44(3H,s,SCH3),2.30-1.4(10H,m,CH2).13C NMR(CDCl3):143.83,137.46,137.16,126.89,126.49,114.93,84.99,58.85,52.25,51.78,51.12,29.42,24.67,19.48 and 15.97.m/z(EI)288(M).实施例A5R1=苯基,R2=H,R3=CH3,R4/R6=-(CH2)3-,R5/R7=-(CH2)3-,R17=R18=H元素分析计算值C17H24N2:C79.64;H9.43;N10.93.实测值C79.64;H9.46;N10.75.U.V.(CHCl3)max.at 244nm(ε6700).I.R.(KBr)1630,1600和1575cm-1(C=C).1H NMR(CDCl3):7.50-7.17(5H,m,ArH),5.35(0.75H,s,=CH),5.24(0.25H,s,=CH),5.15(0.75H,s,=CH),5.10(0.25H,s,=CH),4.06(1H,q,J 6.8Hz,NCHCH3),2.94(3H,m,NCH2),2.63(1H,m,NCH2),2.2-1.2(9H,m,CH2),1.36(0.75H,d,J 7.0Hz,CH3)and 1.13(2.25H,d,J 6.8Hz,CH3).13C NMR(CDCl3):150.38,142.89,128.16,127.04,126.93,114.95(次要非对映体),114.48(主要非对映体),82.18(次要非对映体),82.03(主要非对映体),56.37,52.24,51.60,43.27,28.99(次要非对映体),28.73(主要非对映体),25.62(主要非对映体),25.14(主要非对映体),19.36 and 9.35.m/z(DCI)256(M+).实施例A6R1=4-联苯基,R2=H,R3=CH3,R4/R6=-(CH2)3-,R5/R7=-(CH2)3-。R17=R18=H.U.V.(CHCl3)max at 266nm(ε19200).I.R.(KBr)1625,1600,1580cm-1(C=C).1H NMR(CDCl3):7.49-7.14(9h,m ArH),5.29(0.8H,s,=CH),5.18(0.2H,s,=CH),5.05(0.8H,s=CH),5.00(0.2H,s=CH),4.00(1H,q,J 6.5Hz,NCHCH3),2.91(2H,m,NCH2).2.75(1H,m,NCH2),2.52(1H,m,NCH),2.1-1.2(9H,m,CH2)and 1.04(3H,d,J 6.8HzMCH3).13C NMR(CDCl3):150.00,141.80,141.18,139.88,128.83,128.74,127.46,127.33,127.11,127.02,126.90,126.85,114.51,82.18,57.33(次要非对映体),56.30(主要非对映体),52.28(主要非对映体),51.96(次要非对映体),51.63(主要非对映体),51.34(次要非对映体),46.18(次要非对映体),43.27(主要非对映体),29.10(次要非对映体),28.76(主要非对映体),25.64(次要非对映体),25.19(主要非对映体),19.36(主要非对映体),18.74(次要非对映体),15.35(次要非对映体),9.27(主要非对映体)m/z(EI)332(M+).实施例A7R1=1-萘基,R2=H,R3=CH3,R4/R6=-(CH2)3-,R5/R7=-(CH2)3-,R17=R18=HU.V.(CHCl3)max.at 271nm(ε26900)和280nm(6000).I.R.(KBr)1620,1590,1570cm-1(C=C).1H NMR(CDCl3):7.77-7.52(5H,m ArH),7.42-7.30(2H,m ArH),5.54(0.75H,s,=CH),5.40(0.25H,s,=CH),5.31(0.75H,s,=CH),5.29(0.25H,s,=CH),4.14(1H,q,J 6.8Hz,NCHCH3),2.87(3H,m,NCH2),2.62(1H,m,NCH),2.1-1.0(12H,m,CH2 and CH3).13C NMR(CDCl3):150.84,140.43,133.48,132.80,128.11,127.75,127.65,127.54,127.49,126.09,125.80,125.62,125.60,114.86,82.18(次要非对映体),81.95(主要非对映体),57.22(次要非对映体),56.33(主要非对映体),52.08(主要非对映体),51.89(次要非对映体),51.46(主要非对映体),51.28(次要非对映体),46.00(次要非对映体),43.41(主要非对映体),29.02(次要非对映体),28.78(主要非对映体),25.60(次要非对映体),25.00(主要非对映体),19.39(主要非对映体),19.07(次要非对映体),9.43.m/z(EI)306(M+).实施例A8R1=2-萘基,R2=H,R3=CH3,R4/R6=-(CH2)3-,R5/R7=-(CH2)3-,R17=R18=HU.V.(CHCl3)max.at 245(ε5660).I.R.(KBr)1625,1600,1570cm-1(C=C).1H NMR(CDCl3):7.83-7.72(4H,m ArH),7.60(1H,m ArH),7.47-7.24(2H,m ArH),5.46(0.75H,s,=CH),5.37(0.25H,s,=CH),5.25(075H,s,=CH),5.20(0.25H,s,=CH),4.20(1H,q,J 6.8Hz,NCHCH3),3.01-2.65(4H,m),2.18-1.43(9H,m)and 1.18(3H,d,J 6.8Hz,CH3)。13C NMR(CDCl3):150.81,140.45,133.49,132.81,128.12,127.53,125.77,125.62,125.48,114.88,82.18(次要非对映体),81.95(主要非对映体),56.32,52.07(主要非对映体),51.88(次要非对映体),51.45(主要非对映体),51.28(次要非对映体),43.40,29.08(次要非对映体),28.78(主要非对映体),25.41(次要非对映体),25.00(主要非对映体),19.39,9.45.m/z(EI)306(M+).实施例A9R1=2-噻蒽基,R2=H,R3=CH3,R4/R6=-(CH2)3-,R5/R7=-(CH2)3-,R17=R18=HU.V.(CHCl3)max.at 262nm(ε29800).I.R.(KBr)1625,1580cm-1(C=C).H NMR(CDCl3):7.47-7.17(7H,m ArH),5.32(0.9H,s,=CH),5.24(0.1H,s,=CH),5.15(0.9H,s,=CH),5.11(0.1H,s,=CH),4.00(1H,q,J 6.7Hz,NCHCH3),3.03-2.60(4H,m),2.26-1.16(9H,m)and 1.12(3H,d,J 6.7Hz,CH3).13C NMR(CDCl3):149.46,142.80,135.82,135.75,135.07,133.80,128.73,128.69,128.37,127.59,127.54,127.10,126.43,115.63(次要非对映体),115.10(主要非对映体),82.00(次要非对映体),81.80(主要非对映体),57.37(次要非对映体),56.25(主要非对映体),52.12(主要非对映体),51.83(次要非对映体),51.40(主要非对映体),51.21(次要非对映体),46.65(次要非对映体),43.26(主要非对映体),29.75(次要非对映体),28.81(主要非对映体),25.57(次要非对映体),25.03(主要非对映体),19.38(主要非对映体),18.27(次要非对映体),14.16(次要非对映体),9.21(主要非对映体).m/z(EI)394(M+).实施例A10R1=2-噻吨基,R2=H,R3=CH3,R4/R6=-(CH2)3-,R5/R7=-(CH2)3-,R17=R18=HU.V.(CHCl3)max.at 391nm(ε4000)和266nm(e28700).I.R.(KBr)1640,1592cm-1(C=C).1H NMR(DMSO-d6):8.49(1H,d,ArH),8.47(1H,d,ArH),7.89(1H,dd,ArH),7.85(1H,d,ArH),7.79(1H,d,ArH),7.77(1H,t,ArH),7.59(1H,t,ArH),5.51(0.9H,s,=CH),5.45(0.1H,s,=CH),5.26(0.9H,s,=CH),5.18(0.1H,s,=CH),4.19(1H,q,J 5Hz,NCHCH3),2.85-2.80(4H,m),2.10-1.19(9H,m)和1.16(3H,d,J 7Hz,CH3).13C NMR(CDCl3):178.8,149.2,140.6,136.5,135.75,134.9,132.9,131.7,129.1,128.3,128.0,126.8,126.6,126.1,115.3,81.1,55.1,51.5,50.5,42.5,28.0,24.5,19.0,8.5.m/z(EI)390(M+).实施例A11R1=3,4,5-三甲氧苯基,R2=H,R3=CH3,R4/R6=-(CH2)3-,R5/R7=-(CH2)3-,R17=R18=H元素分析计算值C20H30N2O3:C69.33;H8.73;N8.09.实测值C69.14;H8.71;N8.06.U.V.(CHCl3)max at 319nm(e1000)和250nm(e7100).I.R.(KBr)1681,1578cm-1(C=C).1H NMR(CDCl3):6.65(1.6H,s,ArH),6.51(0.4H,s,ArH),5.29(0.8H,s,=CH),5.24(0.2H,s,=CH),5.10(0.8H,s,=CH),5.06(0.2H,s,=CH),4.04(1H,q,J 6.8Hz,NCHCH3),3.81(9H,s,OCH3),2.98-2.79(3H,m),2.62(1H,m),2.18-1.17(9H,m)and 1.12(3H,d,J 6.7Hz,CH3).13C NMR(CDCl3):152.8,150.6,138.7,114.2,104.3,81.9,60.7,56.4,56.2,52.1,51.5,43.2,28.8,25.1,19.4,9.3.m/z(EI)346(M+).实施例A12R1=4-硫甲基苯基,R2=H,R3=CH3,R4/R6=-(CH2)3-,R5/R7=-(CH2)3-,R17=R18=H元素分析计算值C18H26N2S:C71.48;H8.66;N9.26;S10.60实测值C71.48;H8.60;N8.44;S10.47.U.V.(CHCl3)max.at 275nm(e14100).I.R.(KBr)1620,1593cm-1(C=C).1H NMR(CDCl3):7.43-7.14(4H,m,ArH),5.34(0.75H,s,=CH),5.22(0.25H,s,=CH),5.11(075H,s,=CH),5.06(0.25H,s,=CH),4.05(1H,q,J 6.7Hz,NCHCH3),3.06-2.59(4H,m),2.44(3H,s,SCH3),2.17-1.34(9H,m)and 1.12(3H,d,J 6.7Hz,CH3).13C NMR(CDCl3);149.7,139.7,136.8,127.5,127.4,126.6,126.4,114.1,82.0,56.2,52.2,51.6,51.3,43.2,28.7,25.2,19.3,9.2.m/z(EI)302(M+).实施例A13R1=2-芴基,R2=H,R3=CH3,R4/R6=-(CH2)3-,R5/R7=-(CH2)3-,R17=R18=HU.V.(CHCl3)max.at 281nm(ε19500).I.R.(KBr)1623,1611cm-1(C=C).1H NMR(CDCl3):7.78-7.23(7H,m,ArH),5.42(0.75H,s,=CH),5.32(0.25H,s,=CH),5.19(075H,s,=CH),5.14(0.25H,s,=CH),4.14(1H,q,J 6.5Hz,NCHCH3),3.88(2H,m,C9芴基),3.16-2.87(3H,m),2.68(1H,q,J 5.6Hz),2.20-1.24(9H,m)und 1.17(3H,d,J6.7Hz,CH3).13C NMR(CDCl3):150.8,143.5,143.1,141.7,140.7,126.7,126.4,125.8,1,125.0,123.5,119.8,119.5,114.8(次要非对映体),114.2(主要非对映体),82.2(次要非对映体),82.0(主要非对映体),57.3(次要非对映体),56.5(主要非对映体),52.1(主要非对映体),52.0(次要非对映体),51.5(次要非对映体),51.3(次要非对映体),45.7(次要非对映体),43.4(主要非对映体),37.0(C9芴基),29.0(次要非对映体),28.8(主要非对映体),25.7(次要非对映体),25.1(主要非对映体),19.4,9.5.m/z(EI)344(M+).实施例A14R1=苯基,R2=H,R3=CH3,R4/R6=-(CH2)3-,R5/R7=-(CH2)3-,R17=H,R18=CH3
1H NMR(CDCl3):7.31-7.10(5H,m ArH),5.70-5.50(1H,m,=CH),3.80(1H,m,NCHCH3),
2.94(3H,m,NCH2),2.61(1H,m,NCH),2.1-1.0(15H,m,CH2 and CH3).用途实施例B:单体化合物的碱催化实施例B1-B4
UV引发的Michael加成。
在石英容器中,将7.4×10-5mol光引发剂(潜在的脒碱)溶于丙二酸二甲基酯和丙烯酸正丁基酯的混合物中。将该混合物在30cm的距离用高压汞灯照射。以时间为函数检测其转化。结果列于表1。表1
用途实施例C:碱催化剂与低聚物/聚合物化合物实施例C1
实施例 | 实施例引发剂 | 经曝光时间后的%转化率 | ||||||
0min | 10min | 20min | 30min | 40min | 60min | 120min | ||
B1 | A1 | 0 | - | 6 | - | 38 | 68 | 100 |
B2 | A2 | 0 | - | 8 | - | 35 | 58 | 94 |
B3 | A4 | 0 | - | 16 | - | 50 | 75 | 100 |
B4 | A5 | 0 | 19 | 64 | 91 | 100 | ||
B5 | A6 | 0 | 31 | 67 | 81 | 89 | 94 | 100 |
B6 | A8 | 0 | 40 | 94 | 100 | |||
B7 | A9 | 0 | 56 | 89 | 94 | 100 | ||
B8 | A10 | 0 | 74 | 98 | 100 | |||
B9 | A11 | 0 | 7 | 60 | 88 | 100 | ||
B10 | A12 | 0 | 18 | 33 | 61 | 83 | 100 | |
B11 | A13 | 0 | 11 | 76 | 94 | 100 |
基于异佛尔酮二异氰酸酯和4-羟基丁基丙烯酸酯的丙烯酸脲烷酯的制备。
将1566.8g(13.78mol NCO)二异氰酸异佛尔酮酯,2.3g二月桂酸二丁基锡,2.3g 2,5-二叔丁基-对甲苯酚和802.8g乙酸丁酯装入一个装有冷凝器和滴定装置的三颈烧瓶中。在反应混合物中鼓入干燥氮气,将温度慢慢升至60℃。在反应溶液慢慢温热至80℃的同时,加入1987g(13.78mol)4-羟基丁基丙烯酸酯。将温度保持在80℃,用乙酸丁酯(86.6g)冲洗滴定装置。通过滴定剩余异氰酸酯的量检测反应,当基于固体总量,异氰酸酯的量低于0.2%时反应结束。得到的反应产物具有下列物理性质:残留4-羟基丁基丙烯酸酯:<0.002%(基于固体)(HPLC分析),颜色:《加纳尔色(Gardner)1,粘度:43cPa s(20℃),固体含量:79.3%(1小时,140℃),GPC值(聚苯乙烯标准):Mn778,Mw796,d=1.02。
丙二酸酯聚酯的制备
该反应在氮气氛下进行,所有市场上得到的化学品使用时无需进一步纯化。将1045g 1,5-戊二醇,1377.4g二乙基丙二酸酯和242.1g二甲苯在反应容器中小心地回流。反应混合物的最高温度为196℃,同时冷凝器顶端的温度保持在79℃。以这种方式蒸出862g乙醇,相应的转化率为97.7%。在200℃的温度下真空除去二甲苯。所得聚合物固体含量为98.6%,粘度为2710mPa,基于固体含量的酸量为0.3mgKOH/g。Mn为1838,Mw3186,颜色在APHA谱中为175(“Hazencolour number”-ISO 6271 of American Haelth Association)。用UV光固化
将(6.4×10-5mol)实施例A5光引发剂溶于1.3∶1的上述脲烷丙烯酸酯和丙二酸酯聚酯的混合物(总量400mg)中。将一张50μm厚的膜在玻璃板上拉展,用高压汞灯(200W)在30cm处对其照射。120分钟后聚合物膜不再粘手。
Claims (17)
1.一种分子量低于1000的有机化合物,其式为式(H)其中R1为苯基,萘基,菲基,蒽基,5,6,7,8-四氢-2-萘基,5,6,7,8-四氢-1-萘基,噻吩基,苯并[b]噻吩基,萘并[2,3-b]噻吩基,噻嗯基,占吨基,噻吨基,(夹)氧硫蒽基或芴基,这些基团未被取代或被下列基团取代一次或多次:C1-C18烷基,C1-C18卤代烷基,NR8R9,OH,OR10,SR10,或卤素,或者R1为式A基团;
R2和R3各自独立地为氢或C1-C18烷基;
R4和R6一起形成C2-C12亚烷基桥;
R5和R7一起形成C2-C12亚烷基桥;
R8,R9和R10为氢或C1-C18烷基;
R13为C1-C18烷基或卤素;
N是0或1,2或3;及
R17和R18为氢或C1-C18烷基。
2.权利要求1的有机化合物,其中R2和R3各自独立地为氢或C1-C6烷基。
3.权利要求1的有机化合物,其中R4和R6一起形成C2-C6亚烷基桥。
4.权利要求1的有机化合物,其中R5和R7形成C2-C6亚烷基桥。
5.权利要求1中式(II)有机化合物,其中
R1为苯基或萘基,它们未被取代或被下列基团取代一次或多次:NR8R9,CF3,SR10或OR10,或者R1为噻蒽基,芴基或噻吨基,或R1为式A基团
n为0以及R8,R9和R10为氢或C1-C6烷基;
R2和R3为氢或C1-C6烷基;
R4和R6一起形成C2-C6亚烷基桥;
R5和R7一起形成C2-C6亚烷基桥;
R17为氢;以及
R18为氢或C1-C4烷基。
6.一种制备式(H)化合物的方法,该方法包括使式(V)化合物与式(VI)化合物反应 式(V)化合物中R4,R5,R6及R7基团如权利要求1定义,式(VI)化合物中R1,R2及R3基团如权利要求1定义以及卤素是F,Cl,Br或I,以及第二步,使用式(VIII)的鏻盐与由此得到的反应产物进行Wittig反应,
R17R18CH-P(苯基)3 +X-(VIII),其中R17和R18如权利要求1定义,以及X是F,Cl,Br,I或四氟硼酸根。
8.一种组合物,其中包括
A)至少一种权利要求1的式(II)化合物和
B)至少一种可进行碱催化的加成或取代反应的有机化合物。
9.权利要求8的组合物,其中组分(B)为可阴离子聚合的或可交联的有机材料。
10.权利要求8的组合物,其中组分(B)为下列体系之一:
a)具有烷氧基硅烷或烷氧基硅氧烷侧基的丙烯酸共聚物;
b)含有含羟基的聚丙烯酸酯,聚酯和/或聚醚和脂族或芳族聚异氰酸酯的二组分体系;
c)含有官能化的聚丙烯酸酯和聚环氧化物的二组分体系,其中聚丙烯酸酯含有羧基,酸酐基;
d)含有氟-修饰的或硅氧烷-修饰的含羟基的聚丙烯酸酯,聚酯和/或聚醚和脂族或芳族聚异氰酸酯的二组分体系;
e)含有(聚)酮亚胺和脂族或芳族聚异氰酸酯的二组分体系;
f)含有(聚)酮亚胺和不饱和丙烯酸酯树脂或乙酰乙酸酯树脂或α-丙烯酰氨基甲基甘醇酸甲酯的二组分体系;
h)含有(聚)噁唑烷和含酸酐基的聚丙烯酸酯,或不饱和丙烯酸酯树脂或聚异氰酸酯的二组分体系;
i)含有环氧基-官能化的聚丙烯酸酯和含羧基的或含氨基的聚丙烯酸酯的二组分体系;
l)基于烯丙基缩水甘油基醚的聚合物;
m)含有(聚)醇和(聚)异氰酸酯的二组分体系;
n)含有α,β-烯化的不饱和羰基化合物和其中含有活化的CH2基的聚合物的二组分体系。
11.权利要求8的组合物,其中组分(B)为环氧树脂或不同环氧树脂的混合物。
12.权利要求8的组合物,其中基于组分B)的量,组分A)为0.01到10%(重量)。
13.权利要求8的组合物,其中还可包括选自噻吨酮类,噁嗪类,吖啶类,吩嗪类和若丹明的敏化剂。
14.一种进行碱催化反应的方法,其中包括用波长为200nm到650nm的光线照射权利要求8的组合物。
15.权利要求13的方法,其中包括在照射期间或照射后进行加热。
16.根据权利要求8的聚合的或交联的组合物。
17.权利要求14的方法,用于制备涂层,模制组合物或光构造层。
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US5204218A (en) * | 1990-06-19 | 1993-04-20 | Mitsubishi Denki Kabushiki Kaisha | Photosensitive resin composition |
US5534629A (en) * | 1987-03-26 | 1996-07-09 | Ciba-Geigy Corporation | α-aminoacetophenones as photoinitiators |
US5545509A (en) * | 1992-11-24 | 1996-08-13 | International Business Machines Corporation | Photoresist composition with photosensitive base generator |
-
1998
- 1998-03-07 BR BRPI9808899-8A patent/BR9808899B1/pt not_active IP Right Cessation
- 1998-03-07 CN CN98803471A patent/CN1128799C/zh not_active Expired - Fee Related
- 1998-03-07 KR KR10-1999-7008433A patent/KR100527614B1/ko not_active IP Right Cessation
- 1998-03-07 CA CA002283446A patent/CA2283446C/en not_active Expired - Fee Related
- 1998-03-07 DE DE69806739T patent/DE69806739T2/de not_active Expired - Lifetime
- 1998-03-07 EP EP98916901A patent/EP0970085B1/en not_active Expired - Lifetime
- 1998-03-07 AU AU70327/98A patent/AU720834B2/en not_active Ceased
- 1998-03-07 JP JP54008698A patent/JP4308326B2/ja not_active Expired - Fee Related
- 1998-03-07 WO PCT/EP1998/001346 patent/WO1998041524A1/en active IP Right Grant
- 1998-03-16 US US09/039,766 patent/US6087070A/en not_active Expired - Lifetime
- 1998-03-17 ZA ZA982233A patent/ZA982233B/xx unknown
- 1998-04-07 TW TW087105322A patent/TW466255B/zh not_active IP Right Cessation
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4772530A (en) * | 1986-05-06 | 1988-09-20 | The Mead Corporation | Photosensitive materials containing ionic dye compounds as initiators |
US5534629A (en) * | 1987-03-26 | 1996-07-09 | Ciba-Geigy Corporation | α-aminoacetophenones as photoinitiators |
US5028618A (en) * | 1988-07-28 | 1991-07-02 | Basf Aktiengesellschaft | Substituted imidazolylmethyloxiranes and substituted imidazolylpropenes, their preparation and fungicides containing them |
US5204218A (en) * | 1990-06-19 | 1993-04-20 | Mitsubishi Denki Kabushiki Kaisha | Photosensitive resin composition |
US5545509A (en) * | 1992-11-24 | 1996-08-13 | International Business Machines Corporation | Photoresist composition with photosensitive base generator |
Non-Patent Citations (1)
Title |
---|
J.AMER,CHEM SOC.VOL.113.NO.11 1991-01-01 J.F.CAMERON等人.PHOTOGENERATION,OF * |
Also Published As
Publication number | Publication date |
---|---|
JP4308326B2 (ja) | 2009-08-05 |
ZA982233B (en) | 1998-09-18 |
DE69806739D1 (de) | 2002-08-29 |
KR100527614B1 (ko) | 2005-11-15 |
CN1251103A (zh) | 2000-04-19 |
DE69806739T2 (de) | 2003-03-13 |
WO1998041524A1 (en) | 1998-09-24 |
AU7032798A (en) | 1998-10-12 |
CA2283446A1 (en) | 1998-09-24 |
CA2283446C (en) | 2008-05-06 |
BR9808899A (pt) | 2000-08-01 |
US6087070A (en) | 2000-07-11 |
AU720834B2 (en) | 2000-06-15 |
BR9808899B1 (pt) | 2009-12-01 |
EP0970085B1 (en) | 2002-07-24 |
KR20000076332A (ko) | 2000-12-26 |
TW466255B (en) | 2001-12-01 |
EP0970085A1 (en) | 2000-01-12 |
JP2001515500A (ja) | 2001-09-18 |
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