AU726375B2 - Photoactivatable nitrogen-containing bases based on alpha-ammonium ketones, iminium ketones or amidinium ketones and aryl borates - Google Patents
Photoactivatable nitrogen-containing bases based on alpha-ammonium ketones, iminium ketones or amidinium ketones and aryl borates Download PDFInfo
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- AU726375B2 AU726375B2 AU64972/98A AU6497298A AU726375B2 AU 726375 B2 AU726375 B2 AU 726375B2 AU 64972/98 A AU64972/98 A AU 64972/98A AU 6497298 A AU6497298 A AU 6497298A AU 726375 B2 AU726375 B2 AU 726375B2
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- arh
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- alkyl
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- -1 amidinium ketones Chemical class 0.000 title claims description 228
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title claims description 5
- 150000002576 ketones Chemical class 0.000 title description 8
- 239000000203 mixture Substances 0.000 claims description 53
- 150000001875 compounds Chemical class 0.000 claims description 46
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 229920000058 polyacrylate Polymers 0.000 claims description 25
- 238000000576 coating method Methods 0.000 claims description 23
- 229920000642 polymer Polymers 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 claims description 18
- 229920000647 polyepoxide Polymers 0.000 claims description 17
- 229920000728 polyester Polymers 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 239000000758 substrate Substances 0.000 claims description 13
- 229920001577 copolymer Polymers 0.000 claims description 12
- 239000003822 epoxy resin Substances 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 125000001188 haloalkyl group Chemical group 0.000 claims description 10
- 229920001228 polyisocyanate Polymers 0.000 claims description 10
- 239000005056 polyisocyanate Substances 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 7
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical compound CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000001725 pyrenyl group Chemical group 0.000 claims description 7
- 238000006467 substitution reaction Methods 0.000 claims description 7
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 6
- 238000007259 addition reaction Methods 0.000 claims description 6
- 150000008064 anhydrides Chemical group 0.000 claims description 6
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 239000012948 isocyanate Substances 0.000 claims description 6
- 150000002513 isocyanates Chemical class 0.000 claims description 6
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 6
- 125000005561 phenanthryl group Chemical group 0.000 claims description 6
- 125000001791 phenazinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 6
- 229920005989 resin Polymers 0.000 claims description 6
- 239000011347 resin Substances 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 5
- 125000005493 quinolyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 4
- 238000006555 catalytic reaction Methods 0.000 claims description 4
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 125000003838 furazanyl group Chemical group 0.000 claims description 4
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 125000002346 iodo group Chemical group I* 0.000 claims description 4
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 4
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- 150000004658 ketimines Chemical class 0.000 claims description 4
- 150000002894 organic compounds Chemical class 0.000 claims description 4
- 125000005327 perimidinyl group Chemical group N1C(=NC2=CC=CC3=CC=CC1=C23)* 0.000 claims description 4
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims description 4
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims description 4
- 125000005954 phenoxathiinyl group Chemical group 0.000 claims description 4
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims description 4
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 3
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000003700 epoxy group Chemical group 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 238000000465 moulding Methods 0.000 claims description 3
- 239000011368 organic material Substances 0.000 claims description 3
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 claims description 2
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 150000004893 oxazines Chemical class 0.000 claims description 2
- 125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 claims description 2
- 239000004925 Acrylic resin Substances 0.000 claims 2
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims 1
- 231100000489 sensitizer Toxicity 0.000 claims 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 26
- 238000005481 NMR spectroscopy Methods 0.000 description 24
- 150000003254 radicals Chemical class 0.000 description 19
- 238000004458 analytical method Methods 0.000 description 18
- 239000000178 monomer Substances 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000002585 base Substances 0.000 description 14
- BJFLSHMHTPAZHO-UHFFFAOYSA-N benzotriazole Chemical compound [CH]1C=CC=C2N=NN=C21 BJFLSHMHTPAZHO-UHFFFAOYSA-N 0.000 description 12
- 239000012964 benzotriazole Substances 0.000 description 12
- 239000011248 coating agent Substances 0.000 description 11
- 239000010410 layer Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000011230 binding agent Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 150000001649 bromium compounds Chemical class 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 229920000570 polyether Polymers 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical group [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 229910002091 carbon monoxide Inorganic materials 0.000 description 5
- 238000001723 curing Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- 238000000016 photochemical curing Methods 0.000 description 5
- 239000004814 polyurethane Substances 0.000 description 5
- 229920002635 polyurethane Polymers 0.000 description 5
- 238000007639 printing Methods 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 150000001642 boronic acid derivatives Chemical class 0.000 description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
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- 150000002170 ethers Chemical class 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 230000035945 sensitivity Effects 0.000 description 4
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 4
- 239000002023 wood Substances 0.000 description 4
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 3
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 3
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
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- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- RGQAIWXLKWWUPY-UHFFFAOYSA-N tris(3,5-dichloro-2,4,6-trimethylphenyl)methoxyboronic acid Chemical compound CC1=C(Cl)C(C)=C(Cl)C(C)=C1C(OB(O)O)(C=1C(=C(Cl)C(C)=C(Cl)C=1C)C)C1=C(C)C(Cl)=C(C)C(Cl)=C1C RGQAIWXLKWWUPY-UHFFFAOYSA-N 0.000 description 1
- NLNLETVNYOUACV-UHFFFAOYSA-N tris(3-chlorophenyl)methoxyboronic acid Chemical compound C=1C=CC(Cl)=CC=1C(C=1C=C(Cl)C=CC=1)(OB(O)O)C1=CC=CC(Cl)=C1 NLNLETVNYOUACV-UHFFFAOYSA-N 0.000 description 1
- TVWXXIOKTYINMH-UHFFFAOYSA-N tris(3-fluorophenyl)methoxyboronic acid Chemical compound C=1C=CC(F)=CC=1C(C=1C=C(F)C=CC=1)(OB(O)O)C1=CC=CC(F)=C1 TVWXXIOKTYINMH-UHFFFAOYSA-N 0.000 description 1
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 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
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
- C08F299/04—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyesters
- C08F299/0485—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyesters from polyesters with side or terminal unsaturations
- C08F299/0492—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyesters from polyesters with side or terminal unsaturations the unsaturation being in acrylic or methacrylic groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
-
- 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
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/52—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides selected from boron, aluminium, gallium, indium, thallium or rare earths
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerization Catalysts (AREA)
- Polymerisation Methods In General (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
- Epoxy Resins (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Luminescent Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH444/97 | 1997-02-26 | ||
| CH44497 | 1997-02-26 | ||
| PCT/EP1998/000846 WO1998038195A1 (en) | 1997-02-26 | 1998-02-14 | PHOTOACTIVATABLE NITROGEN-CONTAINING BASES BASED ON α-AMMONIUM KETONES, IMINIUM KETONES OR AMIDINIUM KETONES AND ARYL BORATES |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU6497298A AU6497298A (en) | 1998-09-18 |
| AU726375B2 true AU726375B2 (en) | 2000-11-02 |
Family
ID=4187172
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU64972/98A Ceased AU726375B2 (en) | 1997-02-26 | 1998-02-14 | Photoactivatable nitrogen-containing bases based on alpha-ammonium ketones, iminium ketones or amidinium ketones and aryl borates |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP1032576B1 (enExample) |
| JP (1) | JP4155603B2 (enExample) |
| KR (1) | KR100542419B1 (enExample) |
| AU (1) | AU726375B2 (enExample) |
| BR (1) | BR9807790B1 (enExample) |
| CA (1) | CA2281860C (enExample) |
| DE (1) | DE69839020T2 (enExample) |
| TW (1) | TW425399B (enExample) |
| WO (1) | WO1998038195A1 (enExample) |
| ZA (1) | ZA981556B (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE360629T1 (de) | 2001-10-17 | 2007-05-15 | Ciba Sc Holding Ag | Photoaktivierbare stickstoffbasen |
| EP1652870B1 (en) | 2003-08-06 | 2009-06-17 | Mitsubishi Gas Chemical Company, Inc. | Photocurable composition and coating composition |
| JP2008506826A (ja) * | 2004-07-21 | 2008-03-06 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | 光活性化方法及び逆転した２段階工程による触媒の使用 |
| CA2681201C (en) | 2007-04-03 | 2016-06-14 | Basf Se | Photoactivable nitrogen bases |
| KR101588912B1 (ko) * | 2008-03-31 | 2016-01-26 | 산아프로 가부시키가이샤 | 광염기 발생제 |
| TW201106101A (en) * | 2009-06-01 | 2011-02-16 | Fujifilm Electronic Materials | Chemically amplified positive photoresist composition |
| US8968868B2 (en) * | 2010-06-30 | 2015-03-03 | 3M Innovative Properties Company | Curable-on-demand composition comprising dual reactive silane functionality |
| JP6336398B2 (ja) * | 2011-12-29 | 2018-06-06 | スリーエム イノベイティブ プロパティズ カンパニー | オンデマンド型硬化性ポリシロキサンコーティング組成物 |
| JP5912946B2 (ja) * | 2012-01-11 | 2016-04-27 | 株式会社Adeka | 感光性樹脂組成物 |
| EP2829534B1 (en) | 2012-03-22 | 2019-10-09 | Adeka Corporation | Novel compound and photosensitive resin composition |
| JP5997041B2 (ja) * | 2012-12-26 | 2016-09-21 | 東京応化工業株式会社 | 感光性樹脂組成物 |
| JP5978138B2 (ja) * | 2013-01-22 | 2016-08-24 | 株式会社Adeka | 新規化合物及び感光性樹脂組成物 |
| KR102305831B1 (ko) | 2013-07-18 | 2021-09-27 | 세메다인 가부시키 가이샤 | 광경화성 조성물, 경화물 및 그의 제조 방법, 그리고 관련 제품 및 그의 제조 방법 |
| JP6409784B2 (ja) | 2013-12-13 | 2018-10-24 | セメダイン株式会社 | 接着性を有する光硬化性組成物 |
| JP6167089B2 (ja) * | 2014-03-27 | 2017-07-19 | 富士フイルム株式会社 | 感光性樹脂組成物、硬化膜、硬化膜の製造方法および半導体デバイス |
| MX375374B (es) | 2015-04-29 | 2025-03-06 | Bsn Medical Gmbh | Dispositivo de baño médico. |
| CA2984044A1 (en) | 2015-04-29 | 2016-11-03 | Bsn Medical Gmbh | Steady-state no production via ph control |
| EP3395800B1 (en) | 2017-04-26 | 2021-11-03 | Henkel AG & Co. KGaA | Heterocyclic quaternary nitrogen compounds comprising a polymeric substituent and their use as a photolatent catalyst in curable compositions |
| WO2019206416A1 (en) | 2018-04-26 | 2019-10-31 | Henkel Ag & Co. Kgaa | A quaternary nitrogen compound for use as a latent catalyst in curable compositions |
| CN112805311A (zh) | 2018-08-28 | 2021-05-14 | 学校法人东京理科大学 | 固化性组合物、固化物和固化物的制造方法 |
| JP7731353B2 (ja) * | 2020-06-26 | 2025-08-29 | 株式会社Adeka | 化合物、開始剤、組成物、硬化物及び硬化物の製造方法 |
| KR20230029579A (ko) | 2020-06-26 | 2023-03-03 | 가부시키가이샤 아데카 | 조성물, 경화물 및 경화물의 제조 방법 |
| WO2025131912A1 (en) | 2023-12-22 | 2025-06-26 | Essilor International | Latent borate-ammonium or iminium salts as photo-activatable catalysts for polythiourethane based substrates |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0377321A2 (en) * | 1988-12-29 | 1990-07-11 | Fuji Photo Film Co., Ltd. | Photopolymerizable composition |
| JPH0770221A (ja) * | 1993-09-01 | 1995-03-14 | Toyo Ink Mfg Co Ltd | 重合性組成物およびその硬化物の製造方法 |
| JPH0770068A (ja) * | 1993-09-01 | 1995-03-14 | Toyo Ink Mfg Co Ltd | ピリジニウム錯体およびその用途 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09263063A (ja) * | 1996-01-22 | 1997-10-07 | Toyo Ink Mfg Co Ltd | 感エネルギー線画像形成用組成物、それを用いた画像形成媒体、および画像形成方法 |
| JPH09227854A (ja) * | 1996-02-26 | 1997-09-02 | Toyo Ink Mfg Co Ltd | 感エネルギー線酸発生剤、感エネルギー線酸発生剤組成物、硬化性組成物およびその硬化物 |
| JPH09241614A (ja) * | 1996-03-04 | 1997-09-16 | Toyo Ink Mfg Co Ltd | 感エネルギー線酸発生剤、感エネルギー線酸発生剤組成物、硬化性組成物およびその硬化物 |
| JPH09316117A (ja) * | 1996-06-03 | 1997-12-09 | Toyo Ink Mfg Co Ltd | 重合性組成物およびその硬化物 |
| JPH09328507A (ja) * | 1996-06-10 | 1997-12-22 | Toyo Ink Mfg Co Ltd | 重合開始剤、重合性組成物およびその硬化物 |
| JPH101508A (ja) * | 1996-06-17 | 1998-01-06 | Toyo Ink Mfg Co Ltd | 感活性線酸発生剤組成物、感応性組成物および画像記録用組成物 |
| JPH107709A (ja) * | 1996-06-24 | 1998-01-13 | Toyo Ink Mfg Co Ltd | 感エネルギー線活性剤組成物、それを用いた感応性組成物ならびに画像形成用組成物 |
-
1998
- 1998-02-14 DE DE69839020T patent/DE69839020T2/de not_active Expired - Lifetime
- 1998-02-14 AU AU64972/98A patent/AU726375B2/en not_active Ceased
- 1998-02-14 KR KR1019997007769A patent/KR100542419B1/ko not_active Expired - Fee Related
- 1998-02-14 JP JP53724898A patent/JP4155603B2/ja not_active Expired - Fee Related
- 1998-02-14 WO PCT/EP1998/000846 patent/WO1998038195A1/en not_active Ceased
- 1998-02-14 BR BRPI9807790-2A patent/BR9807790B1/pt not_active IP Right Cessation
- 1998-02-14 CA CA002281860A patent/CA2281860C/en not_active Expired - Fee Related
- 1998-02-14 EP EP98910669A patent/EP1032576B1/en not_active Expired - Lifetime
- 1998-02-25 ZA ZA981556A patent/ZA981556B/xx unknown
- 1998-03-10 TW TW087103457A patent/TW425399B/zh not_active IP Right Cessation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0377321A2 (en) * | 1988-12-29 | 1990-07-11 | Fuji Photo Film Co., Ltd. | Photopolymerizable composition |
| JPH0770221A (ja) * | 1993-09-01 | 1995-03-14 | Toyo Ink Mfg Co Ltd | 重合性組成物およびその硬化物の製造方法 |
| JPH0770068A (ja) * | 1993-09-01 | 1995-03-14 | Toyo Ink Mfg Co Ltd | ピリジニウム錯体およびその用途 |
Also Published As
| Publication number | Publication date |
|---|---|
| BR9807790B1 (pt) | 2010-05-18 |
| KR20000075701A (ko) | 2000-12-26 |
| AU6497298A (en) | 1998-09-18 |
| CA2281860C (en) | 2007-04-10 |
| TW425399B (en) | 2001-03-11 |
| DE69839020D1 (de) | 2008-03-06 |
| EP1032576A1 (en) | 2000-09-06 |
| EP1032576B1 (en) | 2008-01-16 |
| KR100542419B1 (ko) | 2006-01-11 |
| JP4155603B2 (ja) | 2008-09-24 |
| BR9807790A (pt) | 2000-02-15 |
| WO1998038195A1 (en) | 1998-09-03 |
| CA2281860A1 (en) | 1998-09-03 |
| DE69839020T2 (de) | 2009-03-19 |
| JP2001513765A (ja) | 2001-09-04 |
| ZA981556B (en) | 1998-08-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) |