CA2281860C - Photoactivatable nitrogen-containing bases based on .alpha.-ammonium ketones, iminium ketones or amidinium ketones and aryl borates - Google Patents

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Publication number

CA2281860C

CA2281860C CA002281860A CA2281860A CA2281860C CA 2281860 C CA2281860 C CA 2281860C CA 002281860 A CA002281860 A CA 002281860A CA 2281860 A CA2281860 A CA 2281860A CA 2281860 C CA2281860 C CA 2281860C

Authority

CA

Canada

Prior art keywords

arh

compound

c18alkyl

phenyl

component system

Prior art date

1997-02-26

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

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• -1 amidinium ketones Chemical class 0.000 title claims abstract description 222
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title claims description 6
• 150000002576 ketones Chemical class 0.000 title abstract description 10
• 239000000203 mixture Substances 0.000 claims abstract description 54
• 238000000034 method Methods 0.000 claims abstract description 19
• 238000002360 preparation method Methods 0.000 claims abstract description 19
• 238000006555 catalytic reaction Methods 0.000 claims abstract description 6
• 150000001875 compounds Chemical class 0.000 claims description 52
• 229910052739 hydrogen Inorganic materials 0.000 claims description 36
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
• 229920000058 polyacrylate Polymers 0.000 claims description 25
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
• 238000000576 coating method Methods 0.000 claims description 23
• 150000002367 halogens Chemical class 0.000 claims description 22
• 229920000642 polymer Polymers 0.000 claims description 22
• 229910052736 halogen Inorganic materials 0.000 claims description 21
• 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 14
• 239000000758 substrate Substances 0.000 claims description 13
• 125000003118 aryl group Chemical group 0.000 claims description 12
• 239000011248 coating agent Substances 0.000 claims description 12
• 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
• 229920001228 polyisocyanate Polymers 0.000 claims description 12
• 239000005056 polyisocyanate Substances 0.000 claims description 12
• 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
• 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
• 150000004945 aromatic hydrocarbons Chemical class 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
• 238000006467 substitution reaction Methods 0.000 claims description 8
• 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 7
• 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 7
• 238000007259 addition reaction Methods 0.000 claims description 7
• 239000001257 hydrogen Substances 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
• 125000005561 phenanthryl group Chemical group 0.000 claims description 7
• 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 7
• 125000001725 pyrenyl group Chemical group 0.000 claims description 7
• 150000008064 anhydrides Chemical group 0.000 claims description 6
• 150000001728 carbonyl compounds Chemical class 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
• 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 6
• 229920005989 resin Polymers 0.000 claims description 6
• 239000011347 resin Substances 0.000 claims description 6
• 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
• 125000001246 bromo group Chemical group Br* 0.000 claims description 4
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 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
• 125000005842 heteroatom Chemical group 0.000 claims description 4
• 125000002883 imidazolyl 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
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 4
• 229910052760 oxygen Inorganic materials 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
• 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims description 4
• 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 4
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 4
• 125000003373 pyrazinyl group Chemical group 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
• 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 claims description 4
• 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
• 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
• 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
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
• WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 claims description 2
• 150000001768 cations Chemical class 0.000 claims description 2
• 150000002894 organic compounds Chemical class 0.000 claims description 2
• 150000004893 oxazines Chemical class 0.000 claims description 2
• 229910052698 phosphorus Inorganic materials 0.000 claims description 2
• 231100000489 sensitizer Toxicity 0.000 claims description 2
• 229910052708 sodium Inorganic materials 0.000 claims description 2
• 229910052717 sulfur Inorganic materials 0.000 claims description 2
• 239000004925 Acrylic resin Substances 0.000 claims 2
• 150000005846 sugar alcohols Polymers 0.000 claims 2
• WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims 1
• 230000000977 initiatory effect Effects 0.000 claims 1
• 125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 claims 1
• 150000001412 amines Chemical class 0.000 abstract description 9
• 150000003839 salts Chemical class 0.000 abstract description 6
• 150000002466 imines Chemical class 0.000 abstract description 3
• 150000001409 amidines Chemical class 0.000 abstract description 2
• 238000005481 NMR spectroscopy Methods 0.000 description 50
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 32
• 101150041968 CDC13 gene Proteins 0.000 description 26
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 26
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
• 229910052799 carbon Inorganic materials 0.000 description 22
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 19
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
• 238000004458 analytical method Methods 0.000 description 18
• 239000000178 monomer Substances 0.000 description 17
• 150000003254 radicals Chemical class 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
• 239000010410 layer Substances 0.000 description 10
• 238000005160 1H NMR spectroscopy Methods 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
• 150000001649 bromium compounds Chemical class 0.000 description 8
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
• 239000002253 acid Substances 0.000 description 7
• 125000000217 alkyl group Chemical group 0.000 description 7
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 7
• 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
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
• 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
• 150000007513 acids Chemical class 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
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
• 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
• UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 4
• BJFLSHMHTPAZHO-UHFFFAOYSA-N benzotriazole Chemical compound [CH]1C=CC=C2N=NN=C21 BJFLSHMHTPAZHO-UHFFFAOYSA-N 0.000 description 4
• 239000012964 benzotriazole Substances 0.000 description 4
• 235000010290 biphenyl Nutrition 0.000 description 4
• 239000004305 biphenyl 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
• 239000002131 composite material Substances 0.000 description 4
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• 150000002170 ethers Chemical class 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
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• 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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• BPEIXVCQIIITDB-UHFFFAOYSA-N 6,6,6-tris(3-fluorophenyl)hexoxyboronic acid Chemical compound C=1C=CC(F)=CC=1C(C=1C=C(F)C=CC=1)(CCCCCOB(O)O)C1=CC=CC(F)=C1 BPEIXVCQIIITDB-UHFFFAOYSA-N 0.000 description 3
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• 239000007864 aqueous solution Substances 0.000 description 3
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• 102000016870 Hexosaminidase B Human genes 0.000 description 2
• 108010053345 Hexosaminidase B Proteins 0.000 description 2
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