MXPA99007895A - PHOTOACTIVATABLE NITROGEN-CONTAINING BASES BASED ON&agr;-AMMONIUM KETONES, IMINIUM KETONES OR AMIDINIUM KETONES AND ARYL BORATES - Google Patents
PHOTOACTIVATABLE NITROGEN-CONTAINING BASES BASED ON&agr;-AMMONIUM KETONES, IMINIUM KETONES OR AMIDINIUM KETONES AND ARYL BORATESInfo
- Publication number
- MXPA99007895A MXPA99007895A MXPA/A/1999/007895A MX9907895A MXPA99007895A MX PA99007895 A MXPA99007895 A MX PA99007895A MX 9907895 A MX9907895 A MX 9907895A MX PA99007895 A MXPA99007895 A MX PA99007895A
- Authority
- MX
- Mexico
- Prior art keywords
- carbon atoms
- arh
- alkyl
- compound
- phenyl
- Prior art date
Links
- 150000002576 ketones Chemical class 0.000 title abstract description 10
- 150000001642 boronic acid derivatives Chemical class 0.000 title description 7
- -1 amidinium ketones Chemical class 0.000 claims abstract description 206
- 239000000203 mixture Substances 0.000 claims abstract description 53
- 238000000034 method Methods 0.000 claims abstract description 20
- 238000002360 preparation method Methods 0.000 claims abstract description 20
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 88
- 229910052739 hydrogen Inorganic materials 0.000 claims description 64
- 150000001875 compounds Chemical class 0.000 claims description 52
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 238000000576 coating method Methods 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 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 23
- 229920000642 polymer Polymers 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 18
- 229920000647 polyepoxide Polymers 0.000 claims description 17
- 229920000728 polyester Polymers 0.000 claims description 16
- 125000001188 haloalkyl group Chemical group 0.000 claims description 15
- 125000001544 thienyl group Chemical group 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 125000000304 alkynyl group Chemical group 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 229920001577 copolymer Polymers 0.000 claims description 12
- 239000003822 epoxy resin Substances 0.000 claims description 12
- 239000000758 substrate Substances 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 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
- 229920001228 polyisocyanate Polymers 0.000 claims description 10
- 239000005056 polyisocyanate Substances 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 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
- 150000001252 acrylic acid derivatives Chemical class 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
- 238000006467 substitution reaction Methods 0.000 claims description 7
- 238000007259 addition reaction Methods 0.000 claims description 6
- 150000008064 anhydrides Chemical group 0.000 claims description 6
- 150000004945 aromatic hydrocarbons 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
- 229920005989 resin Polymers 0.000 claims description 6
- 239000011347 resin Substances 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 150000001728 carbonyl compounds Chemical class 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
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000005605 benzo group Chemical group 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 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
- 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
- 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
- 238000000465 moulding Methods 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 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
- 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
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 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
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 claims description 4
- 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 3
- 125000003700 epoxy group Chemical group 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000011368 organic material Substances 0.000 claims description 3
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims description 3
- 229920001296 polysiloxane Polymers 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
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 2
- 150000004893 oxazines Chemical class 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
- 150000001412 amines Chemical class 0.000 abstract description 9
- 150000002466 imines Chemical class 0.000 abstract description 4
- 150000003839 salts Chemical class 0.000 abstract description 4
- 150000001409 amidines Chemical class 0.000 abstract description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 58
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 30
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
- 238000004458 analytical method Methods 0.000 description 18
- 150000003254 radicals Chemical class 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
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000011248 coating agent Substances 0.000 description 14
- 101150041968 CDC13 gene Proteins 0.000 description 13
- 239000007983 Tris buffer Substances 0.000 description 13
- 239000010410 layer Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000011230 binding agent Substances 0.000 description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 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
- 238000001723 curing Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 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
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 238000007639 printing Methods 0.000 description 7
- 239000000047 product 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
- 239000002253 acid Substances 0.000 description 6
- 239000012964 benzotriazole Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 229920000570 polyether Polymers 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000004814 polyurethane Substances 0.000 description 5
- 229920002635 polyurethane Polymers 0.000 description 5
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical group OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 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
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 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
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- MLSKXPOBNQFGHW-UHFFFAOYSA-N methoxy(dioxido)borane Chemical compound COB([O-])[O-] MLSKXPOBNQFGHW-UHFFFAOYSA-N 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
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000011253 protective coating Substances 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
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 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
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 150000002334 glycols Chemical class 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 150000004694 iodide salts Chemical class 0.000 description 3
- 239000004611 light stabiliser Substances 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000000123 paper Substances 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000011241 protective layer Substances 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- PHBVXHIVWULVNF-UHFFFAOYSA-N (4-fluorophenoxy)boronic acid Chemical class OB(O)OC1=CC=C(F)C=C1 PHBVXHIVWULVNF-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- UCJDCGANFAKTKA-UHFFFAOYSA-N 2,4-dimethyl-1,3,5-triazine Chemical compound CC1=NC=NC(C)=N1 UCJDCGANFAKTKA-UHFFFAOYSA-N 0.000 description 2
- ONTODYXHFBKCDK-UHFFFAOYSA-N 2-(2,4-dimethylphenyl)-1,3,5-triazine Chemical compound CC1=CC(C)=CC=C1C1=NC=NC=N1 ONTODYXHFBKCDK-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- VVHFXJOCUKBZFS-UHFFFAOYSA-N 2-(chloromethyl)-2-methyloxirane Chemical compound ClCC1(C)CO1 VVHFXJOCUKBZFS-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 2
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 description 2
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 150000004729 acetoacetic acid derivatives Chemical class 0.000 description 2
- WEVYAHXRMPXWCK-FIBGUPNXSA-N acetonitrile-d3 Chemical compound [2H]C([2H])([2H])C#N WEVYAHXRMPXWCK-FIBGUPNXSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 238000005815 base catalysis Methods 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical group C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 230000001680 brushing effect Effects 0.000 description 2
- 229940043232 butyl acetate Drugs 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical class OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- 238000005530 etching Methods 0.000 description 2
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 2
- PLAHQMWSZPRDKI-UHFFFAOYSA-N hexoxyboronic acid Chemical compound CCCCCCOB(O)O PLAHQMWSZPRDKI-UHFFFAOYSA-N 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- UKJARPDLRWBRAX-UHFFFAOYSA-N n,n'-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexane-1,6-diamine Chemical compound C1C(C)(C)NC(C)(C)CC1NCCCCCCNC1CC(C)(C)NC(C)(C)C1 UKJARPDLRWBRAX-UHFFFAOYSA-N 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 238000007645 offset printing Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- ZQBAKBUEJOMQEX-UHFFFAOYSA-N phenyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000033458 reproduction Effects 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 229940096522 trimethylolpropane triacrylate Drugs 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 238000003466 welding Methods 0.000 description 2
- OUBISKKOUYNDML-UHFFFAOYSA-N (2,2,6,6-tetramethylpiperidin-4-yl) 2-[bis[2-oxo-2-(2,2,6,6-tetramethylpiperidin-4-yl)oxyethyl]amino]acetate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CN(CC(=O)OC1CC(C)(C)NC(C)(C)C1)CC(=O)OC1CC(C)(C)NC(C)(C)C1 OUBISKKOUYNDML-UHFFFAOYSA-N 0.000 description 1
- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical class OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 description 1
- HQEPZWYPQQKFLU-UHFFFAOYSA-N (2,6-dihydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC(O)=C1C(=O)C1=CC=CC=C1 HQEPZWYPQQKFLU-UHFFFAOYSA-N 0.000 description 1
- ATLWFAZCZPSXII-UHFFFAOYSA-N (2-octylphenyl) 2-hydroxybenzoate Chemical compound CCCCCCCCC1=CC=CC=C1OC(=O)C1=CC=CC=C1O ATLWFAZCZPSXII-UHFFFAOYSA-N 0.000 description 1
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- PDLPMGPHYARAFP-UHFFFAOYSA-N (3-hydroxy-2-phenylphenyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C=1C(O)=CC=CC=1C(=O)C1=CC=CC=C1 PDLPMGPHYARAFP-UHFFFAOYSA-N 0.000 description 1
- KBQNNOCVJFDHSC-UHFFFAOYSA-N (3-methylphenoxy)boronic acid Chemical class CC1=CC=CC(OB(O)O)=C1 KBQNNOCVJFDHSC-UHFFFAOYSA-N 0.000 description 1
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 1
- GOZHNJTXLALKRL-UHFFFAOYSA-N (5-benzoyl-2,4-dihydroxyphenyl)-phenylmethanone Chemical compound OC1=CC(O)=C(C(=O)C=2C=CC=CC=2)C=C1C(=O)C1=CC=CC=C1 GOZHNJTXLALKRL-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
- VYMPLPIFKRHAAC-UHFFFAOYSA-N 1,2-ethanedithiol Chemical compound SCCS VYMPLPIFKRHAAC-UHFFFAOYSA-N 0.000 description 1
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 description 1
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical group CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- VOBUAPTXJKMNCT-UHFFFAOYSA-N 1-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound CCCCCC(OC(=O)C=C)OC(=O)C=C VOBUAPTXJKMNCT-UHFFFAOYSA-N 0.000 description 1
- IHYBZJJHCMSCOF-UHFFFAOYSA-N 1-propoxyethanol Chemical compound CCCOC(C)O IHYBZJJHCMSCOF-UHFFFAOYSA-N 0.000 description 1
- ZMVJNUHXICCZAH-UHFFFAOYSA-N 10-oxo-10-(2,2,6,6-tetramethyl-1-octoxypiperidin-3-yl)oxydecanoic acid Chemical compound CCCCCCCCON1C(C)(C)CCC(OC(=O)CCCCCCCCC(O)=O)C1(C)C ZMVJNUHXICCZAH-UHFFFAOYSA-N 0.000 description 1
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 1
- GXURZKWLMYOCDX-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O.OCC(CO)(CO)CO GXURZKWLMYOCDX-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- 125000005808 2,4,6-trimethoxyphenyl group Chemical group [H][#6]-1=[#6](-[#8]C([H])([H])[H])-[#6](-*)=[#6](-[#8]C([H])([H])[H])-[#6]([H])=[#6]-1-[#8]C([H])([H])[H] 0.000 description 1
- HWRLEEPNFJNTOP-UHFFFAOYSA-N 2-(1,3,5-triazin-2-yl)phenol Chemical class OC1=CC=CC=C1C1=NC=NC=N1 HWRLEEPNFJNTOP-UHFFFAOYSA-N 0.000 description 1
- OXEMYLNXNAJPGY-UHFFFAOYSA-N 2-(2,2-diphenylpropoxy)ethyl prop-2-enoate Chemical compound C(C=C)(=O)OCCOCC(C)(C1=CC=CC=C1)C1=CC=CC=C1 OXEMYLNXNAJPGY-UHFFFAOYSA-N 0.000 description 1
- FJJLBQYSVLDVRU-UHFFFAOYSA-N 2-(4-methylphenyl)-1,3,5-triazine Chemical compound C1=CC(C)=CC=C1C1=NC=NC=N1 FJJLBQYSVLDVRU-UHFFFAOYSA-N 0.000 description 1
- DAXRGSDCXVUHEW-UHFFFAOYSA-N 2-(benzhydrylamino)ethanol Chemical compound C=1C=CC=CC=1C(NCCO)C1=CC=CC=C1 DAXRGSDCXVUHEW-UHFFFAOYSA-N 0.000 description 1
- ZMWRRFHBXARRRT-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=CC(N2N=C3C=CC=CC3=N2)=C1O ZMWRRFHBXARRRT-UHFFFAOYSA-N 0.000 description 1
- LHPPDQUVECZQSW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-ditert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=CC=CC3=N2)=C1O LHPPDQUVECZQSW-UHFFFAOYSA-N 0.000 description 1
- IYAZLDLPUNDVAG-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 IYAZLDLPUNDVAG-UHFFFAOYSA-N 0.000 description 1
- VQMHSKWEJGIXGA-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-6-dodecyl-4-methylphenol Chemical compound CCCCCCCCCCCCC1=CC(C)=CC(N2N=C3C=CC=CC3=N2)=C1O VQMHSKWEJGIXGA-UHFFFAOYSA-N 0.000 description 1
- FJGQBLRYBUAASW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)phenol Chemical class OC1=CC=CC=C1N1N=C2C=CC=CC2=N1 FJGQBLRYBUAASW-UHFFFAOYSA-N 0.000 description 1
- SZCFDTYKNQJQKT-UHFFFAOYSA-N 2-(oxiran-2-ylmethoxy)-6-oxabicyclo[3.1.0]hexane Chemical compound C1CC2OC2C1OCC1CO1 SZCFDTYKNQJQKT-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- XORJNZNCVGHBDZ-UHFFFAOYSA-N 2-[2-(6-oxabicyclo[3.1.0]hexan-2-yloxy)ethoxy]-6-oxabicyclo[3.1.0]hexane Chemical compound C1CC2OC2C1OCCOC1C2OC2CC1 XORJNZNCVGHBDZ-UHFFFAOYSA-N 0.000 description 1
- DBYBHKQEHCYBQV-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-dodecoxyphenol Chemical compound OC1=CC(OCCCCCCCCCCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(C)=CC=2)C)=N1 DBYBHKQEHCYBQV-UHFFFAOYSA-N 0.000 description 1
- LSNNLZXIHSJCIE-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-tridecoxyphenol Chemical compound OC1=CC(OCCCCCCCCCCCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(C)=CC=2)C)=N1 LSNNLZXIHSJCIE-UHFFFAOYSA-N 0.000 description 1
- WPMUMRCRKFBYIH-UHFFFAOYSA-N 2-[4,6-bis(2-hydroxy-4-octoxyphenyl)-1,3,5-triazin-2-yl]-5-octoxyphenol Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C1=NC(C=2C(=CC(OCCCCCCCC)=CC=2)O)=NC(C=2C(=CC(OCCCCCCCC)=CC=2)O)=N1 WPMUMRCRKFBYIH-UHFFFAOYSA-N 0.000 description 1
- HHIVRACNDKRDTF-UHFFFAOYSA-N 2-[4-(2,4-dimethylphenyl)-6-(2-hydroxy-4-propoxyphenyl)-1,3,5-triazin-2-yl]-5-propoxyphenol Chemical compound OC1=CC(OCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(OCCC)=CC=2)O)=N1 HHIVRACNDKRDTF-UHFFFAOYSA-N 0.000 description 1
- IOOMXAQUNPWDLL-UHFFFAOYSA-N 2-[6-(diethylamino)-3-(diethyliminiumyl)-3h-xanthen-9-yl]-5-sulfobenzene-1-sulfonate Chemical compound C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=C(S(O)(=O)=O)C=C1S([O-])(=O)=O IOOMXAQUNPWDLL-UHFFFAOYSA-N 0.000 description 1
- OJPDDQSCZGTACX-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)anilino]ethanol Chemical compound OCCN(CCO)C1=CC=CC=C1 OJPDDQSCZGTACX-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- AWEVLIFGIMIQHY-UHFFFAOYSA-N 2-ethylhexyl 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OCC(CC)CCCC)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O AWEVLIFGIMIQHY-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 1
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 1
- AIBRSVLEQRWAEG-UHFFFAOYSA-N 3,9-bis(2,4-ditert-butylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP1OCC2(COP(OC=3C(=CC(=CC=3)C(C)(C)C)C(C)(C)C)OC2)CO1 AIBRSVLEQRWAEG-UHFFFAOYSA-N 0.000 description 1
- SSADPHQCUURWSW-UHFFFAOYSA-N 3,9-bis(2,6-ditert-butyl-4-methylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound CC(C)(C)C1=CC(C)=CC(C(C)(C)C)=C1OP1OCC2(COP(OC=3C(=CC(C)=CC=3C(C)(C)C)C(C)(C)C)OC2)CO1 SSADPHQCUURWSW-UHFFFAOYSA-N 0.000 description 1
- YLUZWKKWWSCRSR-UHFFFAOYSA-N 3,9-bis(8-methylnonoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound C1OP(OCCCCCCCC(C)C)OCC21COP(OCCCCCCCC(C)C)OC2 YLUZWKKWWSCRSR-UHFFFAOYSA-N 0.000 description 1
- PZRWFKGUFWPFID-UHFFFAOYSA-N 3,9-dioctadecoxy-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound C1OP(OCCCCCCCCCCCCCCCCCC)OCC21COP(OCCCCCCCCCCCCCCCCCC)OC2 PZRWFKGUFWPFID-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- SAEZGDDJKSBNPT-UHFFFAOYSA-N 3-dodecyl-1-(1,2,2,6,6-pentamethylpiperidin-4-yl)pyrrolidine-2,5-dione Chemical compound O=C1C(CCCCCCCCCCCC)CC(=O)N1C1CC(C)(C)N(C)C(C)(C)C1 SAEZGDDJKSBNPT-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- JGLYXLCIDZQOEW-UHFFFAOYSA-N 4,4,4-triphenylbutoxyboronic acid Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(CCCOB(O)O)C1=CC=CC=C1 JGLYXLCIDZQOEW-UHFFFAOYSA-N 0.000 description 1
- HPFWYRKGZUGGPB-UHFFFAOYSA-N 4,6-dichloro-n-(2,4,4-trimethylpentan-2-yl)-1,3,5-triazin-2-amine Chemical compound CC(C)(C)CC(C)(C)NC1=NC(Cl)=NC(Cl)=N1 HPFWYRKGZUGGPB-UHFFFAOYSA-N 0.000 description 1
- WXQZLPFNTPKVJM-UHFFFAOYSA-N 4-[(4-hydroxycyclohexyl)methyl]cyclohexan-1-ol Chemical compound C1CC(O)CCC1CC1CCC(O)CC1 WXQZLPFNTPKVJM-UHFFFAOYSA-N 0.000 description 1
- HDPBBNNDDQOWPJ-UHFFFAOYSA-N 4-[1,2,2-tris(4-hydroxyphenyl)ethyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)C(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 HDPBBNNDDQOWPJ-UHFFFAOYSA-N 0.000 description 1
- FROCQMFXPIROOK-UHFFFAOYSA-N 4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]benzene-1,3-diol Chemical compound CC1=CC(C)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(O)=CC=2)O)=N1 FROCQMFXPIROOK-UHFFFAOYSA-N 0.000 description 1
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical class NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 1
- YWVFNWVZBAWOOY-UHFFFAOYSA-N 4-methylcyclohexane-1,2-dicarboxylic acid Chemical compound CC1CCC(C(O)=O)C(C(O)=O)C1 YWVFNWVZBAWOOY-UHFFFAOYSA-N 0.000 description 1
- ZCILGMFPJBRCNO-UHFFFAOYSA-N 4-phenyl-2H-benzotriazol-5-ol Chemical compound OC1=CC=C2NN=NC2=C1C1=CC=CC=C1 ZCILGMFPJBRCNO-UHFFFAOYSA-N 0.000 description 1
- CZWLNLPFOCRODM-UHFFFAOYSA-N 4-phenylbutoxyboronic acid Chemical compound OB(O)OCCCCC1=CC=CC=C1 CZWLNLPFOCRODM-UHFFFAOYSA-N 0.000 description 1
- DBOSBRHMHBENLP-UHFFFAOYSA-N 4-tert-Butylphenyl Salicylate Chemical compound C1=CC(C(C)(C)C)=CC=C1OC(=O)C1=CC=CC=C1O DBOSBRHMHBENLP-UHFFFAOYSA-N 0.000 description 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
- YIROYDNZEPTFOL-UHFFFAOYSA-N 5,5-Dimethylhydantoin Chemical compound CC1(C)NC(=O)NC1=O YIROYDNZEPTFOL-UHFFFAOYSA-N 0.000 description 1
- OQAPYXJOOYQXDV-UHFFFAOYSA-N 5,5-dimethyl-3-[2-(oxiran-2-ylmethoxy)propyl]-1-(oxiran-2-ylmethyl)imidazolidine-2,4-dione Chemical compound C1OC1COC(C)CN(C(C1(C)C)=O)C(=O)N1CC1CO1 OQAPYXJOOYQXDV-UHFFFAOYSA-N 0.000 description 1
- UWSMKYBKUPAEJQ-UHFFFAOYSA-N 5-Chloro-2-(3,5-di-tert-butyl-2-hydroxyphenyl)-2H-benzotriazole Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O UWSMKYBKUPAEJQ-UHFFFAOYSA-N 0.000 description 1
- SVLTVRFYVWMEQN-UHFFFAOYSA-N 5-methylcyclohex-3-ene-1,2-dicarboxylic acid Chemical compound CC1CC(C(O)=O)C(C(O)=O)C=C1 SVLTVRFYVWMEQN-UHFFFAOYSA-N 0.000 description 1
- NJCDRURWJZAMBM-UHFFFAOYSA-N 6-phenyl-1h-1,3,5-triazin-2-one Chemical compound OC1=NC=NC(C=2C=CC=CC=2)=N1 NJCDRURWJZAMBM-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- NWEAIBRKHPNJIJ-UHFFFAOYSA-N 8-acetyl-3-dodecyl-7,7,9,9-tetramethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione;n'-[2-(3-aminopropylamino)ethyl]propane-1,3-diamine Chemical compound NCCCNCCNCCCN.O=C1N(CCCCCCCCCCCC)C(=O)NC11CC(C)(C)N(C(C)=O)C(C)(C)C1 NWEAIBRKHPNJIJ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241001550224 Apha Species 0.000 description 1
- ADAHGVUHKDNLEB-UHFFFAOYSA-N Bis(2,3-epoxycyclopentyl)ether Chemical compound C1CC2OC2C1OC1CCC2OC21 ADAHGVUHKDNLEB-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- 229920001174 Diethylhydroxylamine Polymers 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- 238000005967 Finkelstein reaction Methods 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910001218 Gallium arsenide Inorganic materials 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 238000006000 Knoevenagel condensation reaction Methods 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 238000006845 Michael addition reaction Methods 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- OGDAMSGMJREIQA-UHFFFAOYSA-N O.O.B(OC1=CC=C(C=C1)F)(O)O Chemical compound O.O.B(OC1=CC=C(C=C1)F)(O)O OGDAMSGMJREIQA-UHFFFAOYSA-N 0.000 description 1
- FMLYEBRADICKTC-UHFFFAOYSA-N OB(O)OC1=CC=CC=C1.N.N Chemical class OB(O)OC1=CC=CC=C1.N.N FMLYEBRADICKTC-UHFFFAOYSA-N 0.000 description 1
- JQNURTYSNZCZQY-UHFFFAOYSA-N OP(O)OP(O)O.C(C)(C)(C)C1=C(C=CC=C1)C(O)C(CO)(CO)CO Chemical compound OP(O)OP(O)O.C(C)(C)(C)C1=C(C=CC=C1)C(O)C(CO)(CO)CO JQNURTYSNZCZQY-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 1
- 206010034960 Photophobia Diseases 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- QYTDEUPAUMOIOP-UHFFFAOYSA-N TEMPO Chemical group CC1(C)CCCC(C)(C)N1[O] QYTDEUPAUMOIOP-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 238000003848 UV Light-Curing Methods 0.000 description 1
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 1
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 1
- MSILJOYZYPRFDK-UHFFFAOYSA-N [4-[4-(sulfanylmethyl)phenoxy]phenyl]methanethiol Chemical compound C1=CC(CS)=CC=C1OC1=CC=C(CS)C=C1 MSILJOYZYPRFDK-UHFFFAOYSA-N 0.000 description 1
- BEIOEBMXPVYLRY-UHFFFAOYSA-N [4-[4-bis(2,4-ditert-butylphenoxy)phosphanylphenyl]phenyl]-bis(2,4-ditert-butylphenoxy)phosphane Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(C=1C=CC(=CC=1)C=1C=CC(=CC=1)P(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C BEIOEBMXPVYLRY-UHFFFAOYSA-N 0.000 description 1
- HHFMFWAFQGUGOB-UHFFFAOYSA-N [5-(4-tert-butylbenzoyl)-2,4-dihydroxyphenyl]-(4-tert-butylphenyl)methanone Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)C1=CC(C(=O)C=2C=CC(=CC=2)C(C)(C)C)=C(O)C=C1O HHFMFWAFQGUGOB-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000000320 amidine group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 1
- RSOILICUEWXSLA-UHFFFAOYSA-N bis(1,2,2,6,6-pentamethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)N(C)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(C)C(C)(C)C1 RSOILICUEWXSLA-UHFFFAOYSA-N 0.000 description 1
- GOJOVSYIGHASEI-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) butanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CCC(=O)OC1CC(C)(C)NC(C)(C)C1 GOJOVSYIGHASEI-UHFFFAOYSA-N 0.000 description 1
- XITRBUPOXXBIJN-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 XITRBUPOXXBIJN-UHFFFAOYSA-N 0.000 description 1
- ZEFSGHVBJCEKAZ-UHFFFAOYSA-N bis(2,4-ditert-butyl-6-methylphenyl) ethyl phosphite Chemical compound CC=1C=C(C(C)(C)C)C=C(C(C)(C)C)C=1OP(OCC)OC1=C(C)C=C(C(C)(C)C)C=C1C(C)(C)C ZEFSGHVBJCEKAZ-UHFFFAOYSA-N 0.000 description 1
- AJCHRUXIDGEWDK-UHFFFAOYSA-N bis(ethenyl) butanedioate Chemical compound C=COC(=O)CCC(=O)OC=C AJCHRUXIDGEWDK-UHFFFAOYSA-N 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 125000004799 bromophenyl group Chemical group 0.000 description 1
- OCWYEMOEOGEQAN-UHFFFAOYSA-N bumetrizole Chemical compound CC(C)(C)C1=CC(C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O OCWYEMOEOGEQAN-UHFFFAOYSA-N 0.000 description 1
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- DCBIXTBHCUSRQQ-UHFFFAOYSA-N butanedioic acid;hexane-1,6-diol Chemical compound OCCCCCCO.OC(=O)CCC(O)=O DCBIXTBHCUSRQQ-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920006217 cellulose acetate butyrate Polymers 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- VYXSBFYARXAAKO-WTKGSRSZSA-N chembl402140 Chemical compound Cl.C1=2C=C(C)C(NCC)=CC=2OC2=C\C(=N/CC)C(C)=CC2=C1C1=CC=CC=C1C(=O)OCC VYXSBFYARXAAKO-WTKGSRSZSA-N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- 229940120693 copper naphthenate Drugs 0.000 description 1
- SEVNKWFHTNVOLD-UHFFFAOYSA-L copper;3-(4-ethylcyclohexyl)propanoate;3-(3-ethylcyclopentyl)propanoate Chemical compound [Cu+2].CCC1CCC(CCC([O-])=O)C1.CCC1CCC(CCC([O-])=O)CC1 SEVNKWFHTNVOLD-UHFFFAOYSA-L 0.000 description 1
- VNZQQAVATKSIBR-UHFFFAOYSA-L copper;octanoate Chemical compound [Cu+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O VNZQQAVATKSIBR-UHFFFAOYSA-L 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 238000007766 curtain coating Methods 0.000 description 1
- 239000011353 cycloaliphatic epoxy resin Substances 0.000 description 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- BOXSCYUXSBYGRD-UHFFFAOYSA-N cyclopenta-1,3-diene;iron(3+) Chemical class [Fe+3].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 BOXSCYUXSBYGRD-UHFFFAOYSA-N 0.000 description 1
- WTVNFKVGGUWHQC-UHFFFAOYSA-N decane-2,4-dione Chemical compound CCCCCCC(=O)CC(C)=O WTVNFKVGGUWHQC-UHFFFAOYSA-N 0.000 description 1
- 125000002704 decyl 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])* 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- URSLCTBXQMKCFE-UHFFFAOYSA-N dihydrogenborate Chemical compound OB(O)[O-] URSLCTBXQMKCFE-UHFFFAOYSA-N 0.000 description 1
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000005805 dimethoxy phenyl group Chemical group 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000004662 dithiols Chemical class 0.000 description 1
- 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 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000001652 electrophoretic deposition Methods 0.000 description 1
- 238000009713 electroplating Methods 0.000 description 1
- 238000007590 electrostatic spraying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- FYIBGDKNYYMMAG-UHFFFAOYSA-N ethane-1,2-diol;terephthalic acid Chemical compound OCCO.OC(=O)C1=CC=C(C(O)=O)C=C1 FYIBGDKNYYMMAG-UHFFFAOYSA-N 0.000 description 1
- BLCTWBJQROOONQ-UHFFFAOYSA-N ethenyl prop-2-enoate Chemical compound C=COC(=O)C=C BLCTWBJQROOONQ-UHFFFAOYSA-N 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical class CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000011152 fibreglass Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- NZYMWGXNIUZYRC-UHFFFAOYSA-N hexadecyl 3,5-ditert-butyl-4-hydroxybenzoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NZYMWGXNIUZYRC-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000001469 hydantoins Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 125000003387 indolinyl group Chemical class N1(CCC2=CC=CC=C12)* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002497 iodine compounds Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 208000013469 light sensitivity Diseases 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- FDZZZRQASAIRJF-UHFFFAOYSA-M malachite green Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](C)C)C=C1 FDZZZRQASAIRJF-UHFFFAOYSA-M 0.000 description 1
- 229940107698 malachite green Drugs 0.000 description 1
- 125000002960 margaryl 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])[H] 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- UJRDRFZCRQNLJM-UHFFFAOYSA-N methyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OC)=CC(N2N=C3C=CC=CC3=N2)=C1O UJRDRFZCRQNLJM-UHFFFAOYSA-N 0.000 description 1
- VRBLLGLKTUGCSG-UHFFFAOYSA-N methyl 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OC)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O VRBLLGLKTUGCSG-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 description 1
- 229960000907 methylthioninium chloride Drugs 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 125000001421 myristyl 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])[H] 0.000 description 1
- ZJFPXDGPJMHQMW-UHFFFAOYSA-N n,n'-bis[3-(dimethylamino)propyl]oxamide Chemical compound CN(C)CCCNC(=O)C(=O)NCCCN(C)C ZJFPXDGPJMHQMW-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- DARUEKWVLGHJJT-UHFFFAOYSA-N n-butyl-1-[4-[4-(butylamino)-2,2,6,6-tetramethylpiperidin-1-yl]-6-chloro-1,3,5-triazin-2-yl]-2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CC1(C)CC(NCCCC)CC(C)(C)N1C1=NC(Cl)=NC(N2C(CC(CC2(C)C)NCCCC)(C)C)=N1 DARUEKWVLGHJJT-UHFFFAOYSA-N 0.000 description 1
- BLBLVDQTHWVGRA-UHFFFAOYSA-N n-butyl-3-[4-[4-(butylamino)-1,2,2,6,6-pentamethylpiperidin-3-yl]-6-chloro-1,3,5-triazin-2-yl]-1,2,2,6,6-pentamethylpiperidin-4-amine Chemical compound CCCCNC1CC(C)(C)N(C)C(C)(C)C1C1=NC(Cl)=NC(C2C(N(C)C(C)(C)CC2NCCCC)(C)C)=N1 BLBLVDQTHWVGRA-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- ZMVMYBGDGJLCHV-UHFFFAOYSA-N n-methyl-4-[[4-(methylamino)phenyl]methyl]aniline Chemical compound C1=CC(NC)=CC=C1CC1=CC=C(NC)C=C1 ZMVMYBGDGJLCHV-UHFFFAOYSA-N 0.000 description 1
- HKUFIYBZNQSHQS-UHFFFAOYSA-N n-octadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCCCC HKUFIYBZNQSHQS-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- RNVAPPWJCZTWQL-UHFFFAOYSA-N octadecyl 3,5-ditert-butyl-4-hydroxybenzoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 RNVAPPWJCZTWQL-UHFFFAOYSA-N 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- XQAABEDPVQWFPN-UHFFFAOYSA-N octyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OCCCCCCCC)=CC(N2N=C3C=CC=CC3=N2)=C1O XQAABEDPVQWFPN-UHFFFAOYSA-N 0.000 description 1
- DMFXLIFZVRXRRR-UHFFFAOYSA-N octyl 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OCCCCCCCC)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O DMFXLIFZVRXRRR-UHFFFAOYSA-N 0.000 description 1
- 125000001117 oleyl 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])=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])[H] 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 150000002917 oxazolidines Chemical class 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 229930184652 p-Terphenyl Natural products 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl 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])[H] 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000002958 pentadecyl 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])[H] 0.000 description 1
- 229940059574 pentaerithrityl Drugs 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000005008 perfluoropentyl group Chemical group FC(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)* 0.000 description 1
- 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 description 1
- 229960000969 phenyl salicylate Drugs 0.000 description 1
- ZPNJBTBYIHBSIG-UHFFFAOYSA-N phenyl-(2,2,6,6-tetramethylpiperidin-4-yl)methanone Chemical compound C1C(C)(C)NC(C)(C)CC1C(=O)C1=CC=CC=C1 ZPNJBTBYIHBSIG-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001603 poly (alkyl acrylates) Polymers 0.000 description 1
- 229920002755 poly(epichlorohydrin) Polymers 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229940068886 polyethylene glycol 300 Drugs 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920001289 polyvinyl ether Polymers 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 238000007763 reverse roll coating Methods 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 229940043267 rhodamine b Drugs 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 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
- 229960004889 salicylic acid Drugs 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 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
- 238000003860 storage Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
- YEOUFHBJWTZWCZ-UHFFFAOYSA-M sulforhodamine G Chemical compound [Na+].C=12C=C(C)C(NCC)=CC2=[O+]C=2C=C(NCC)C(C)=CC=2C=1C1=CC=C(S([O-])(=O)=O)C=C1S([O-])(=O)=O YEOUFHBJWTZWCZ-UHFFFAOYSA-M 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- WAWBMJIRULKJPO-UHFFFAOYSA-N tetraethylazanium borate Chemical compound [O-]B([O-])[O-].CC[N+](CC)(CC)CC.CC[N+](CC)(CC)CC.CC[N+](CC)(CC)CC WAWBMJIRULKJPO-UHFFFAOYSA-N 0.000 description 1
- 125000006337 tetrafluoro ethyl group Chemical group 0.000 description 1
- 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
- NZNAAUDJKMURFU-UHFFFAOYSA-N tetrakis(2,2,6,6-tetramethylpiperidin-4-yl) butane-1,2,3,4-tetracarboxylate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CC(C(=O)OC1CC(C)(C)NC(C)(C)C1)C(C(=O)OC1CC(C)(C)NC(C)(C)C1)CC(=O)OC1CC(C)(C)NC(C)(C)C1 NZNAAUDJKMURFU-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 150000004897 thiazines Chemical class 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 125000004862 thiobutyl group Chemical group 0.000 description 1
- 125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 description 1
- 125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 description 1
- 125000004035 thiopropyl group Chemical group [H]SC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 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
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- 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
- JODJRDDQVZMRIY-UHFFFAOYSA-N trityloxyboronic acid Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OB(O)O)C1=CC=CC=C1 JODJRDDQVZMRIY-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
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
Abstract
This invention relates to&agr;-ammonium ketones, iminium ketones or amidinium ketones in the form of their tetraaryl- or triarylalkylborate salts which can be photochemically converted into amines, imines or amidines as well as to a process for their preparation. This invention also relates to base-polymerisable or cross-linkable compositions comprising these&agr;-ammonium ketones, iminium ketones or amidinium ketones in the form of their tetra- or triarylalkylborate salts, to a process for carrying out photochemically induced, base-catalysed reactions as well as to their use as photoinitiators for base-catalysed reactions.
Description
BASES CONTAINING PHOTOACTIVE NITROGEN, BASED ON CETONAS-AMMONIUM, CETONAS IMINION OR AMIDINIO CETONAS AND ARIL BORATOS The present invention relates to a-ammonium ketones, iminium ketones or amidinium ketones in the form of their salts tetraaril- or triarilaquilboratos that can be photochemically converted in amines, imines or amidines, as well as a procedure for their preparation. This invention also relates to crosslinkable or polymerizable base compositions, which comprise these α-ammonium ketones, iminium ketones or amidinium ketones in the form of their tetra- or triarylalkyl borate salts, to a process for carrying out photochemically induced, base-catalyzed reactions , as well as its use as photoinitiators for base catalyzed reactions. The photolytic breakdown of specific a-amino ketones into radicals and their photopolymerization of olefinically unsaturated monomers or oligomers has been known for a long time, and is described, for example, in EP-A-284,561. In addition to radically polymerizable oligomers or monomers, base catalysable systems have been described in particular for photolithographic processes. These systems require a photoinitiator that releases a base upon exposure to light, D. R. MacKean et al., Polym. Mater. Sci. Eng. (1992), 66, 237-238, for example, reports the photo-structured polyimide using specific carbamates as photoinitiators. In J. of Polymer Science: Polym. Chem. Ed., Vol.
12, 2943-2951 (1974), Ko et al. Report BF4 ~ salts containing α-ammonium ketones which, upon exposure to light, decompose into radicals with a-rupture, but which do not form any free amine and are therefore inadequate as latent bases. J. Chem. Soc. (C), 1971, 1863-1869 discloses bromine salts of α-ammonium ketones which upon exposure to light result in protonated amines and which are therefore inadequate as latent bases. In Chem. Mater. 1996, 8, 1360-1362, Neckers et al., Recently reported novel systems for photostructures based on polymeric ammonium phenylborates containing mobile benzophenone groups in the polymer structure. Surprisingly, it has now been found that certain α-ammonium ketones, iminium ketones or amidinium ketones in the form of their tetraaryl- or triarylalkyl borate salts, release an amine, imine or amidine group upon exposure to visible light or UV light. These groups are sufficiently basic to initiate a large number of base catalysable reactions, in particular polymerization reactions. These compounds are highly sensitive and through the selection of the substitution pattern, the absorption spectrum can be varied over a wide range. These compounds make it possible to prepare so-called one-pot systems with base-catalysable oligomers or monomers having an extremely long shelf life. A polymerization reaction, for example, starts only after exposure to light. The systems can be formulated with little or no solvent, since the compounds can be dissolved in the monomers or oligomers, without being affected. The active catalyst is formed only after exposure to light. These systems can be used for numerous purposes such as for finishes, coatings, molding compounds or photolithographic reproductions. This invention provides compounds of the formula (I)
where m is 1 or 2 and corresponds to the number of positive charges of the cation; x is phenyl, naphthyl, phenanthryl, anthracyl, pyrenyl,
,6,7,8-tetrahydro-2-naphthyl, 5,6,7,8-tetrahydro-1-naphthyl, thienyl, benzo [b] thienyl, naphtho [2,3-b] thienyl, thiarenyl, dibenzofuryl, chromenyl, xanthenyl, thioxanthyl, phenoxyntinyl, pyrrolyl, imidazolyl, pyrazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolizinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolizinyl, isoquinolyl, quinolyl, phthalazinyl, naftriridinyl, quinoxalinyl, quinazolinyl, cinolinyl, pteridinyl, carbazolyl, β-carbolinyl, phenanthridinyl, acridinyl, perimidinyl, phenanthrolinyl, phenazinyl, isothiazolyl, phenothiazinyl, isoxazolyl, furazanyl, terphenyl, stilbenyl, fluorenyl or phenoxazinyl, these radicals are unsubstituted or mono - or polysubstituted by alkyl with 1 to 18 carbon atoms, alkenyl with 3 to 18 carbon atoms, alkynyl with 3 to 18 carbon atoms, haloalkyl with 1 to 18 carbon atoms, N02, NR6R7, N3, OH, CN, OR8, C (0) R9, C (O) OR10 or halogen, or Rx is a radical of formula A or B
(B); R2 * R3 and R each independently are hydrogen, alkyl with 1 to 18 carbon atoms, alkenyl with 3 to 18 carbon atoms, alkynyl with 3 to 18 carbon atoms, or phenyl, or R2 and R3 and / or R4 and R3 each forms independently of the other, an alkylene bridge with haloalkyl having 2 to 12 carbon atoms; or R2, R3, R4 together with the linking nitrogen atom are a phosphazene base of the P17 P2 < t / 4 > or a group of the structural formula
(a), (b), (c), (d), (e), (f) or (g)
where k e 1 each independently of the other is a number of
2 to 12;
R5, R6, R7, R8, R9 and? O are hydrogen or alkyl having 1 to 18 carbon atoms; or Rs and R? together with the linking carbon atoms are a benzocyclopentanone radical; Rn is alkyl with 1 to 18 carbon atoms, alkenyl with
2 to 18 carbon atoms, alkynyl with 2 to 18 carbon atoms, haloalkyl with 1 to 18 carbon atoms, N02, NR6R7, N3, OH, CN, OR8, C (0) R9, C (O) OR10 or halogen; and n is 0 or 1, 2 or 3; R12, Ri3 and Ri4 are phenyl or other aromatic hydrocarbon, these radicals are unsubstituted or mono- or polysubstituted by alkyl having 1 to 18 carbon atoms, alkenyl with 3 to 18 carbon atoms, alkynyl with 3 to 18 carbon atoms, haloalkyl with 1 to 18 carbon atoms, N02, NR6R7, N3, OH, CN, OR8, C (0) R9, C (O) OR10 or halogen; R1S is alkyl having 1 to 18 carbon atoms, phenyl or other aromatic hydrocarbon, the phenyl and aromatic hydrocarbon radicals are unsubstituted or mono- or polysubstituted by alkyl having 1 to 18 carbon atoms, alkenyl having 3 to 18 carbon atoms, alkynyl with 3 to 18 carbon atoms, haloalkyl with 1 to 18 carbon atoms, N02, NR6R7, N3, OH, CN, 0R8, C (0) R9; C (O) OR10 or halogen, or
R ?? is a radical .R - X-B; 12 * 3; and X is alkylene with 1 to 20 carbon atoms, alkylene 2 to
carbon atoms, which is interrupted by -O-, -S- or NR8 or X is
The absorption maximum can be varied within a wide range through the selection of the aromatic or heteroaromatic Rx and the respective borate anion and in this way the photosensitivity of the compounds can be shifted from the UV region to that of daylight. Alkyl in the various radicals having up to 18 carbon atoms, is a branched or unbranched radical such as methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, 2-ethyl-butyl, n-pentyl, isopentyl, 1-methylpentyl, 1,3-dimethylbutyl, n-hexyl, 1-methylhexyl, n-heptyl, isoheptyl, 1,1,3,3-tetramethylbutyl, 1-methylheptyl, 3-methylheptyl, n- octyl, 2-ethylhexyl, 1, 1,3-trimethyl-ilhexyl, 1,1,3,3-tetramethylpentyl, nonyl, decyl, undecyl, 1-methylundecyl, dodecyl, 1, 3, 3, 5, 5-hexamethylhexyl , tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl. Preference is given to alkyl having 1 to 12, especially 1 to 6, carbon atoms. Alkenyl having 3 to 18 carbon atoms is a branched or unbranched radical such as propenyl, 2-butenyl, 3-butenyl, isobutenyl, n-2, 4-pentadienyl, 3-methyl-2-butenyl, n-2 octenyl, n-2-dodecinyl, iso-dodecenyl, oleyl, n-2-octadecenyl or n-4-octadecenyl. Preference is given to alkenyl having 3 to 12, especially 3 to 6, carbon atoms. Alkynyl having 3 to 18 carbon atoms is a branched or unbranched radical such as propynyl (-CH2-C = CH), 2-butynyl, 3-butynyl, n-2-octynyl, or n-2-octadecynyl. Preference is given to alkynyl having 3 to 12, especially 3 to 6, carbon atoms. The alkylene bridge with 2 to 12 carbon atoms is ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene or dodecylene. Halogen is fluorine, chlorine, bromine or iodine. Typical examples of alkyl halo with 1 to 18 carbon atoms comprise total or partially halogenated alkyl. An illustrative example is the positional isomers of mono- to deca-fluoropentyl, mono- to octafluorobutyl, mono- to hexafluoropropyl, mono- to tetrafluoroethyl and mono- a difluoromethyl and also the corresponding chlorine, bromine and iodine compounds. Preference is given to perfluorinated alkyl radicals. Examples of these are perfluoropentyl, perfluorobutyl, perfluoropropyl, perfluoroethyl and in particular trifluoromethyl. Example of the group NR8R9 amino are the respective monoalkyl or dialkylamino groups such as methylamino, ethylamino, propylamino, butylamino, pentylamino, hexylamino, octadecylamino, dimethylamino, diethylamino, dipropylamino, diisopropylamino, di-n-butylamino, di-isobutylamino, dipentylamino, dihexylamino or dioctadecylamine. Additional dialkylamino groups are those in which the two radicals independently are branched or unbranched, for example, methylethylamino, methyl-n-propylamino, methylisopropylamino, methyl-n-butylamino, methylisobutylamino, ethylisopropylamino, ethyl-n-butylamino, ethylisobutylamino , ethyl-tert-butylamino, isopropyl-n-butylamino or isopropylisobutylamino. The OR10 alkoxy group having up to 18 carbon atoms is a branched or unbranched radical such as methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, pentoxy, isopentoxy, hexoxy, heptoxy, octoxy, decyloxy, tetradecyloxy, hexadecyloxy or octadecyloxy. Preference is given to alkoxy having 1 to 12, especially 1 to 8, for example 1 to 6 carbon atoms. Examples of the thioalkyl group SR10 are thiomethyl, thioethyl, thiopropyl, thiobutyl, thiopentyl, thiohexyl, thioheptyl, thiocotyl or thiooctadecyl, it being possible for the alkyl radicals to be linear or branched. Aromatic hydrocarbons such as may be present in the novel compounds (R13, Ri4 or R15) may contain, for example, one or more, preferably 1 or 2, hetero atoms. Suitable hetero atoms for example are N, O, P or S, preferably N or O. Typical examples of aromatic hydrocarbons are: phenyl, α- and β-naphthyl, stilbenyl, biphenyl, o-, m-, p-terphenyl, tri-phenylphenyl, binaphthyl, anthracyl, phenanthryl, pyrenyl, furan-2-yl or furan-3-thiophen-2-yl or thiophen-3-yl, pyridin-2-yl, pyridin-3-yl or pyridin-4- ilo, quinolyl or isoquinolyl. . Examples of R? they are phenyl, naphthyl, phenanthryl, anthracyl, pyrenyl, 5, 6, 7, 8-tetrahydro-2-naphthyl, 5,6,7,8-tetrahydro-1-naphthyl, thienyl, benzo [b] thienyl, naphtho [2 , 3-b] thienyl, thiarenyl, dibenzofuryl, chromenyl, xanthenyl, phenoxyntinyl, pyrrolyl, imidazolyl, pyrazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolizinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolizinyl, isoquinolyl, quinolyl, phthalazinyl, naphidinyl, quinoxalinyl, quinazolinyl, cimolinyl, pteridinyl, carbazolyl, β-carbolinyl, phenanedrinyl, acridinyl, perimidinyl, phenanthrolinyl, phenazinyl, isothiazolyl, phenotriazinyl, isoxazolyl, furazanyl, biphenyl, sty-benyl, terphenyl, fluorenyl, phenoxazinyl, methoxyphenyl, 2-4 dimethoxyphenyl, 2,4,6-trimethoxyphenyl, bromophenyl, tolyl, xylyl, mesityl, nitrophenyl, dimethylaminophenyl, diethylaminophenyl, aminophenyl, diaminophenyl, 1-naphthyl, 2-naphthyl, 1-phenylamino-4-naphthyl, 1-methylnaphthyl, 2- methylnaphthyl, l-methoxy-2-naphthyl, 2-methoxy-l-naf lime, 1-dimethylamino-2-naphthyl, 1,2-dimethyl-4-naphthyl, 1,2-dimethyl-6-naphthyl, 1,2-dimethyl-7-naphthyl, 1,3-dimethyl-6-naphthyl, 1, 4-dimethyl-6-naphthyl, 1,5-dimethyl-2-naphthyl, 1,6-dimethyl-2-naphthyl, 1-hydroxy-2-naphthyl, 1-hydroxy-1-naphthyl, 1,4- dihydroxy-2-naphthyl, 7-phenanthryl, 1-anthryl, 2-anthryl, 9-anthryl, 3-benzo [b] thienyl, 5-benzo [b] thienyl, 2-benzo [b] thienyl, 4-dibenzofuryl, 4,7-dibenzofuryl, 4-methyl-7-dibenzofuryl, 2-xanthenyl, 8-methyl-2-xanthenyl, 3-xanthenyl, 2-phenoxathiinyl, 2,7-phenoxathiinyl, 2-pyrrolyl, 3-pyrrolyl, 5- methyl-3-pyrrolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 2-methyl-4-imidazolyl, 2-ethyl-4-imidazolyl, 2-ethyl-5-imidazolyl, 3-pyrazolyl, 1-methyl- 3-pyrazolyl, l-propyl-4-pyrazolyl, 2-pyrazinyl, 5,6-dimethyl-2-pyrazinyl, 2-indolizinyl, 2-methyl-3-isoindolyl, 2-methyl-l-isoindolyl, l-methyl-2-indolyl, 1-methyl-3-indolyl, 1,5-dimethyl-2-indolyl, l-methyl-3-indazolyl, 2,7-dimethyl-8 nyl, 2-methoxy-7-methyl-8-nyl, 2-quinolizinyl, 3-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, isoquinolyl, 3-methoxy-6-isoquinolyl, 2-quinolyl, 6-quinolyl, -quinolyl, 2-methoxy-3-quinolyl, 2-methoxy-6-quinolyl, 6-phthalazinyl, 7-phthalazinyl, 1-methoxy-6-phthalazinyl, 1,4-dimethoxy-6-phthalazinyl, 1,8-naph riridin-2-yl, 2-quinoxalinyl, 6-quinoxalinyl, 2,3-dimethyl-6-quinoxalinyl, 2,3-dimethoxy-6-quinoxalinyl, 2-quinazolinyl, 7-quinazolinyl, 2-dimethylamino-6 -quinazolinyl, 3-cinolinyl, 6-cinolinyl, 7-cinolinyl, 3-methoxy-7-cinolinyl, 2-pteridinyl, 6-pteridinyl, 7-pteridinyl, 6,7-dimethoxy-2-pteridinyl, 2-carbazolyl, 3-carbazolyl, 9-methyl-2-carbazolyl, 9-methyl-3-carbazolyl, β-carbolin-3-yl, l-methyl-β-carbolin-3-yl, methyl-β-carbolin-6-yl, 3-phenanthridinyl, 2-acridinyl, 3-acridinyl, 2-perimidinyl, l-methyl-5-perimidinyl, -phenanthrolinyl, 6-phenanthroline, 1-phenazinyl, 2-phenazinyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 2-phenothiazinyl, 3-phenothiazinyl, 10-methyl-3-phenothiazinyl, 3-isoxazolyl, 4-isoxazolyl , 5-isoxazolyl, 4-methyl-3-furazanyl, 2-phenoxazinyl or 10-methyl-2-phenoxazinyl.
Where R1 and R5 together with the linking carbon atoms form a benzocyclopentanone radical, this means structures as follows
Typical examples of phosphazene bases of the type Px, P2 or P < t / 4 > They are
wherein the phosphazene bases can be linked by imine nitrogen, as well as by one of the tertiary nitrogen atoms to the CH2 group of the ketone. The phosphazene phases are preferably linked by one of the tertiary nitrogen atoms to the CH2 group of the ketone. Rx preferably is phenyl, naphthyl, phenanthryl, anthracyl, pyrenyl, 5, 6, 7, 8-tetrahydro-2-naphthyl, 5,6,7,8-tetrahydro-1-naphthyl, thienyl, benzo [b] thienyl, naphth [2., 3-b] thienyl, thiarenyl, dibenzofuryl, chromenyl, xanthenyl, thioxanthyl, phenoxyantiinyl, pyrrolyl, imidazolyl, pyrazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolizinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolizinyl, isoquinolyl, quinolyl , phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinolinyl, pteridinyl, carbazolyl, β-carbolinyl, phenanthridinyl, acridinyl, perimidinyl, phenanthrolinyl, phenazinyl, isothiazolyl, phenothiazinyl, isoxazolyl, furazanyl, terphenyl, stilbenyl, fluorenyl or phenoxazinyl, these radicals are unsubstituted or mono- or polysubstituted by alkyl with 1 to 18 carbon atoms, alkenyl with 3 to 18 carbon atoms, alkynyl with 3 to 18 carbon atoms, haloalkyl with 1 to 18 carbon atoms, N02, NRfaR- / 7 N3, OH, CN, 0R8, C (0) R9, C (O ) OR10 or halogen; or Rx is a radical of formula A or B
or R1 and R5 together with the linking carbon atoms are a benzocyclopentanone radical. Preferably Rx is particularly phenyl, naphthyl, pyrenyl, thioxanthyl or phenothiazinyl, these radicals are unsubstituted or mono- or polysubstituted by alkyl with 1 to 18 carbon atoms, haloalkyl with 1 to 18 carbon atoms, NR6R7, CN, N02 , SR8 or OR8, R2, R3 and R preferably each independently are hydrogen, alkyl having 1 to 18 carbon atoms or R2 and R3 and / or R4 and R3 each independently of the other form an alkylene bridge with 2 to 12 carbon atoms, or R2, R3, R4 together with the bonding nitrogen atom are a group of the structural formulas (a), (b), (c), (d), (e), (f), (g), as indicated above, or a phosphazene base of the type Px, P2 or P < t / 4>. Each of k and 1 independently of the other, is a number of 2 to 12, preferably a number from 2 to 6. Particularly preferred compounds are those wherein R2, R3 and R4, each independently of the other, are alkyl with 1 to 18 carbon atoms. arbono or R2, R3, R4 together with the nitrogen atom form a group of the structural formula (a), (b), (c), (d) or (e) as indicated above. R12, Ri3, Ri4 are preferably phenyl, biphenyl, naphthyl, anthracyl or phenanthryl, these radicals are unsubstituted or mono- or polysubstituted by alkyl with 1 to 18 carbon atoms, haloalkyl with 1 to 18 carbon atoms, N02, OH , CN, OR8 or halogen and R15 is alkyl with 1 to 18 carbon atoms or phenyl which is unsubstituted or mono- or polysubstituted with alkyl having 1 to 18 carbon atoms, haloalkyl with 1 to 18 carbon atoms, N02, OH , CN, OR8 or halogen. Suitable borate anions for the nitrogenous base cation in the compounds of formula I are also to be found among others in US 4772530, GB 2307474, GB 2307473, GB2307472, EP775706. Illustrative examples are triphenylbutylborate, trifenylhexylborate, triphenylmethylborate, dimesitylphenylmethylborate or dimesitylphenylbutylborate, di (bromo-mesityl) phenyl-methylborate or di (bromomesityl) phenylbutylborate, tris (3-fluorophenyl) exilborate, tris (3-fluorophenyl) methylborate or tris (3 - fluorophenyl) butylborate, dichloro-dimethyl-phenylmethylborate or dichloromesit-ilphenylbutylborate, tris (dichlorosityl) methylborate, tris (3-chlorophenyl) exilborate, tris (3-chlorophenyl) methylborate or tris (3-chlorofenyl) butyl-borate, tris (3-bromo-phenyl)-exoborate, tris (3-bromfenyl) methylborate or tris (3-bromo-phenyl) butylborate, tris (3,5-dif luorofenyl) hexylborate, dimesitylbifenyl-butylborate, dimesitilnaf, tylmethylborate or dimesitilnafylbutyl-ilborate, di (o-tolyl) -9-anthracyl methylborate, or di (o-tolyl) -9-anthracylbutylborate, dimesityl-9-f enantrilf enylborate or dimesityl-9-f enantrilf enyl-butylborate or
The preparation of these anions is described in the aforementioned publications. The preparation of the bromides or iodides of the novel compounds of the formula I is carried out, for example, by the methods described by A. Padwa, W.
Eisenhardt, R. Gruber and D. Pashayan in J. Am. Chem. Soc., 93, 6998 (1971) or by T. Laird and H. Williams, J. Chem. Soc.
(C), 3467 (1971). The borates are obtained from there in an analogous way. The reaction can be carried out in a manner known per se. It is also useful to use a solvent or mixture of solvents, for example hydrocarbons (benzene, toluene, xylene), halogenated hydrocarbons (methylene chloride, chloroform, carbon tetrachloride, chlorobenzene), alkanols (methanol, ethanol, 2-methoxy-ethanol) and ethers (diethyl ether, dibutyl ether, 1,2-dimethoxyethane) or mixtures thereof. The reaction is conveniently carried out in the temperature range from -10 ° C to + 100 ° C. It is preferably carried out in the range of 10 ° C to 50 ° C. This invention also provides a process for the preparation of the compounds of the formula I, which comprises reacting in a first step, a nitrogenous base of the formula II NR2R3R4 (II) with an a-halogen ketone of the formula III
Halogen CH (II) O with a compound of the formula IV
(IV) or and in a second step, reacting the compounds of the formula IV, with a compound of the formula V
to the compound of formula I, wherein halogen is bromine or iodine, and M is Na, K or ammonium and R1 (R2, R4, R5, R? 2 / L13, R1 and R15 have the meanings and meanings previously established This invention also relates to a composition comprising A) at least one compound of the formula (I), and B) at least one organic compound that is capable of a base catalyzed addition reaction or substitution reaction. The substitution reaction or base catalyzed addition reaction can be carried out with low molecular weight compounds (monomers), with oligomers, with polymeric compounds or with a mixture of these compounds. Examples of reactions that can be carried out with both monomers and oligomers / polymers using the novel photoinitiators are the Knoevenagel reaction or the Michael addition reaction.
Particularly important compositions are those in which component B) is an anionically polymerizable or crosslinkable organic material. The organic material may be in the form of mono- or polyfunctional monomers, oligomers or polymers. Particularly preferred oligomeric / polymeric systems are binders or coating systems as is usual in the coating industry. Examples of these binders or base catalysable coating systems are: a) acrylate copolymers having alkoxysilane or alkoxysiloxane side groups, for example the polymers described in US-A 4,772,672 or US-A 4,444,974; b) two-component systems comprising polyacrylates containing hydroxyl groups, polyesters and / or polyethers and aliphatic or aromatic polyisocyanates; c) two-component systems comprising functional polyacrylates and a polyepoxide, wherein the polyacrylate contains carboxyl or anhydride groups; d) two-component systems comprising polyacrylates, polyesters and / or polyethers containing hydroxyl group modified with silicone or modified with fluorine and aliphatic or aromatic polyisocyanates; e) two component systems comprising (poly) ketimines and aliphatic or aromatic polyisocyanates;
f) two-component systems comprising (poly) ketimines and unsaturated acrylate resins or acetoacetate or methyl a-acrylamidomethylglycolate resins; h) two-component systems comprising (poly) oxazolidines and polyacrylates containing anhydride groups or unsaturated acrylate resins or polyisocyanates; i) two-component systems comprising polyacrylates containing epoxy and polyacrylates containing carboxyl group; 1) polymers based on allyl glycidyl ether; m) two-component systems comprising a (poly) alcohol and a (poly) isocyanate; n) two-component systems comprising an α, β-ethylenically unsaturated carbonyl compound and a polymer containing activated CH 2 gr, it being possible for the activated CH 2 gr to be present either in the main chain or in the secondary chain or in both, as described for example in EP-B-0 161 697 for gr
(poly) malonate. Other compounds having activated CH2 groups are (poly) acetoacetates and (poly) cyanoacetates. Among these base-catalysable binders, particular preference is given to the following: b) two-component systems comprising polyacrylates, polyesters and / or polyethers containing hydroxyl groups and aliphatic or aromatic polyisocyanates; c) two-component systems comprising functional polyacrylates and a polyepoxide, wherein the polyacrylate contains carboxyl or anhydride groups; i) two-component systems comprising polyacrylates containing epoxy and polyacrylates containing carboxyl group; m) two-component systems comprising a (poly) alcohol and a (poly) isocyanate; and n) two-component systems comprising an α, β-ethylenically unsaturated carbonyl compound and a polymer containing activated CH 2 groups, it being possible for the activated CH 2 groups to be present, either in the main chain or in the secondary chain or both as it is described, for example, in EP-B-0 161 697 for (poly) malonate groups. Other compounds having activated CH2 groups are (poly) acetoacetates and (poly) cyanoacetates. Two-component systems comprising a α, β-ethylenically unsaturated carbonyl compound and a
(poly) malonate, and its preparation are described in EP-B-0 161
687. The malonate group can be connected here in a polyurethane, polyester, polyacrylate, epoxy resin, polyamide or polyvinyl polymer, either in the main chain or in a secondary chain. The O, β-ethylenically unsaturated carbonyl compound employed can be any double bond activated by a carbonyl group. Examples are esters or amides of acrylic acid or methacrylic acid. In the ester groups, it is also possible that additional hydroxyl groups are present. Diesters and triesters are also possible. Typical examples are hexandiol diacrylate or trimethylol propane triacrylate. Instead of acrylic acid, it is also possible to use other acids and their esters or amides such as crotonic acid or cinnamic acid. Under base catalysis, the components of the system react with each other at room temperature to form an interlocking coating system that is suitable for numerous applications. Due to their good resistance to inherent weathering, they are suitable for example for outdoor applications as well and can, if required, be additionally stabilized by UV absorbers and other light stabilizers. Other systems suitable as component B) in the novel compositions are epoxy systems. Epoxy resins which are suitable for preparing novel, curable mixtures comprising epoxy resins as component B) are those which are customary in epoxy resin technology, examples of these epoxy resins are:
I) Polyglycidyl and poly (β-methylglycidyl) esters, which are obtained by reacting a compound having at least two carboxyl groups in the molecule with epichlorohydrin or β-methylepichlorohydrin. The reaction is carried out judiciously in the presence of bases. Since the compound has at least two carboxyl groups in the molecule, it is possible to use aliphatic polycarboxylic acids. Examples of these polycarboxylic acids are oxalic, succinic, glutaric, adipic, pimelic, suberic, azelaic or dimerized or trimerized linoleic acid. However, it is also possible to use cycloaliphatic polycarboxylic acids such as tetrahydrophthalic acid, 4-methyltetrahydrophthalic acid, hexahydrophthalic acid or 4-methylhexahydrophthalic acid. Further aromatic polycarboxylic acids may be used such as phthalic, isophthalic or terephthalic acid. II) Polyglycidyl or poly (β-methylglycidyl) ethers, which are obtained by reacting a compound having at least two free alcoholic hydroxyl groups and / or phenolic hydroxyl groups with epichlorohydrin or β-methylepichlorohydrin, under alkaline conditions or in the presence of a Acidic catalyst with subsequent alkaline treatment. Glycidyl ethers of this type are derived, for example, from acyclic alcohols such as ethylene glycol, diethylene glycol and poly (oxyethylene) higher glycols, propan-1,2-diol or poly (oxypropylene) glycols, propan-1,3-diol, bu t an-1,4-diol, poly (oxy-tetramethylene) glycols , pentan-1, 5-diol, hexan-1,6-diol, hexan-2,4,6,6-triol, glycerol, 1,1-trimethylolpropane, pentaerythritol, sorbitol and polyepichlorohydrins. They are also derived, for example, from cycloaliphatic alcohols such as 1, 4-c ichexandimet anol, bis (4-hydroxycyclohexyl) -methane or 2,2-bis (4-hydroxycyclohexyl) -panoid, or possess aromatic nuclei such as N, N- bis (2-hydroxyethyl) aniline op, p'-bis (2-hydroxyethylamino) -diphenylmethane. The glycidyl ethers may also be derived from mononuclear phenols such as resorcinol or hydroquinone, or are based on polynuclear phenols such as bis (4-hydroxyphenyl) methane, 4,4'-di-idroxybiphenyl, bis (4-hydroxyphenyl) sulfone, 1,1 , 2,2-tetrakis (4-hydroxyphenyl) ethane, 2,2-bis (4-hydroxyphenyl) propane, 2,2-bis (3,5-dibromo-4-hydroxyphenyl) -propane and novolaks obtained when condensing aldehydes such as formaldehyde, acetaldehyde, chloral or furfuraldehyde, with phenols such as phenol or with phenols whose nuclei are replaced by chlorine atoms or alkyl groups with 1 to 9 carbon atoms, examples are 4-chlorophenol, 2-methylphenol or 4-tert-butylphenol or by condensation with bisphenols, those of the type specified above. III) Poly (N-glycidyl) compounds which are obtained by dehydrochlorination of the reaction products of epichlorohydrin with amines containing at least two active hydrogens bound with amino nitrogen. These amines, for example, are aniline, n-butylamine, bis (4-aminophenyl) -methane, m-xylylenediamine or bis (4-methylaminophenyl) methane. The poly (N-glycidyl) compounds also include triglycidyl isocyanurate, N, N'-diglycidyl derivatives of cycloalkylene ureas such as ethylene urea or 1,3-propylene urea and diglycidyl derivatives of hydantoins such as 5,5-dimethylhydantoin. IV) Poly (S-glycidyl) compounds or, for example, di-S-glycidyl derivatives which are obtained from dithiols such as ethane-1,2-dithiol or bis (4-mercaptomethylphenyl) ether. V) Cycloaliphatic epoxy resins for example bis (2, 3-epoxycyclopentyl) ether, 2,3-epoxy-cyclopentyl glycidyl ether, 1,2-bis (2,3-epoxycyclopentyloxy) ethane or 3,4-epoxycyclohexyl-methyl-3 '4' -epoxycyclohexanecarboxylate. However, it is also possible to use epoxy resins where the 1,2-epoxide groups are connected to different heteroatoms and / or functional groups; These compounds include, for example, the N, N, 0-triglycidyl derivative of 4-aminophenol, the glycidyl ether, the glycidyl ester of salicylic acid, N-glycidyl-N '- (2-glycidyloxypropyl) -5,5-dimethylhydantoin or glycidyloxy-1,3-bis (5,5-dimethyl-1-glycidylhydantoin-3-yl) -panode. Mixtures of epoxy resins can also be used as component B). A composition wherein component B) is an epoxy resin or a mixture of different epoxy resins, therefore also conforms to this invention. The compositions comprise the photoinitiator, component A), preferably in an amount of 0.01 to 10% by weight based on component B). In addition to the photoinitiator, component A), the photopolymerizable mixtures may include different additives. Examples of these are thermal inhibitors that are intended to prevent premature polymerization, such as hydroquinone, hydroquinone derivatives, p-methoxyphenol, β-naphthol or sterically hindered phenols, such as 2,6-di (tert-butyl) -p-cresol , for example. To increase storage stability in the dark, it is possible for example to use copper compounds, such as copper naphthenate, stearate or octoate, phosphorus compounds such as triphenylphosphine, tributylphosphine, triethyl phosphite, triphenyl phosphite or tribenzyl phosphite, compounds of quaternary ammonium, such as tetramethylammonium chloride or trimethylbenzylammonium chloride, or hydroxylamine derivatives such as N-diethylhydroxylamine. To exclude atmospheric oxygen during polymerization, it is possible to add paraffin or similar wax-like substances that, due to their lack of solubility in the polymer, migrate to the surface at the beginning of the polymerization, where they form a transparent surface layer that prevents the entry of air It is also possible to apply an oxygen impermeable layer. Light stabilizers, which may be added in a small amount, are UV absorbers, such as those for example of the hydroxyphenylbenzotriazole, hydroxyphenylbenzophenone, oxalamide or hydroxyphenyl-s-triazine type. Individual compounds or mixtures of these compounds can be used with or without the use of sterically hindered amines (HALS). Illustrative examples of these UV absorbers and light stabilizers are the following: 1. 2- (2'-Hydroxyphenyl) benzotriazoles. for example 2- (2'-hydroxy-5 • -methylphenyl), -1, 2- (3 ', 5'-di-tert-butyl-2'-hydroxyphenyl) benzotriazole, 2-5'-tert-butyl- 2 '-hydroxyphenyl) benzotriazole, 2- (2'-hydroxy-5' - (1,1,3,3-tetramethylbutyl) phenyl) benzotriazole, 2- (3 ', 5'-di-tert-butyl-2' -hydroxyphenyl) -5-chloro-benzotriazole, 2- (3'-tert-butyl-2'-hydroxy-5'-methylphenyl) -5-chloro-benzotriazole, 2- (3'-sec-butyl-5 '- tert-butyl-2 '-hydroxy-enyl) -benzotriazole, 2- (2'-hydroxy-4'-octyl-oxy-enyl) -benzotriazole, 2- (3', 5'-di-tert-amyl-2'-hydroxyphenyl) -benzotriazole, 2- (3 ', 5'-bis- (OI, a-dimethylbenzyl) -2'-hydroxy-f-enyl) benzotriazole, a mixture of 2- (3'-tert-butyl-2'-hydroxy- 5 '- (2-Octyloxycarbonylethyl) phenyl) -5-chloro-benzotriazole, 2- (3'-tert-butyl-5' - [2- (2-ethylhexyloxy) carbonylethyl] -2-hydroxyphenyl) -5-chloro- benzotriazole, 2- (3'-tert-butyl-2'-hydroxy-5 '- (2-methoxycarbonylethyl) phenyl) -5-chloro-benzotriazole, 2- (3'-er-but i 1-2' -hydroxy) - 5 '- (2-methoxycarbonylethyl) phenyl) benzotriazole, 2- (3'-tert-butyl-2'-hydroxy-5' - (2-octyloxycarbonyl-ethyl) phenyl) benzotriazole, 2- (3'-tert-butyl) -5 '- [2- (2-ethexyloxy) carbonylethyl] -2'-hydroxy-f-enyl) benzotriazole, 2- (3'-dodecyl-2'-hydroxy-5'-methylphenyl) -benzotriazole and 2- (3'-tert-butyl-2'-hydroxy-5 '- (2-isooctyloxycarbonylethyl) f-enylbenzotriazole, 2,2'-methylenebis [4- (1,1,3,3-tetramethylbutyl) -6-benzotriazole-2 -ilf enol]; the transesterification product of 2- [3'-tert-butyl-5 '- (2-methoxycarbonylethyl) -2'-hydroxyphenyl] -2H-benzotriazole with polyethylene glycol 300; [R-CH2CH2-COO (CH2) 3] 2- where R =
3 '-tert-butyl-4' -hydroxy-5'-2H-benzotriazol-2-ylfenyl. 2. 2-Hydroxybenzofenones, for example the 4-hydroxy, 4-methoxy, 4-octyloxy, 4-decyloxy, 4-dodecyloxy, 4-benzyloxy, 4, 2 ', 4' -trihydroxy and 2'-hydroxy derivatives 4, 4'-dimethoxy.
3. Esters of substituted and unsubstituted benzoic acids, such as for example 4-tert-butyl phenyl salicylate, phenyl salicylate, octylphenyl salicylate, dibenzoyl resorcinol, bis (4-tert-butylbenzoyl) resorcinol, benzoyl resorcinol, 2,4-di-ter- butyl-phenyl-3,5-di-tert-butyl-4-hydroxybenzoate, hexadecyl-3,5-di-tert-butyl-4-hydroxybenzoate, octadecyl-3,5-di-tert-butyl-4-hydroxy-benzoate, -methyl-4,6-di-tert-butylphenyl-3,5-di-tert-butyl-4-hydroxy-benzoate. 4_. Acrylates, for example ethyl a-cyano-β, β-diphenylacrylate, isooctyl a-cyano-β, β-diphenylacrylate, methyl α-carbomethoxy-cinnamate, methyl α-cyano-β-methyl-p-methoxy-cinnamate, butyl a -cyano-ß-methyl-p-methoxy-cinnamate, methyl a-carbomethoxy-p-methoxy-cinnamate and N- (β-carbomethoxy-β-cyanovinyl) -2-methylindoline. 5. Sterically hindered amines, for example bis (2,2,6,6-tetramethyl-4-piperidyl) sebacate, bis (2,2,6,6-tetramethyl-4-piperidyl) succinate, bis (1, 2, 2, 6, 6-pentamethyl-4-piperidyl) -sebacate, bis (l, 2,2,6,6-pentamethyl-4-piperidyl) n-butyl-3,5-di-tert-butyl-4-idroxybenzylmalonate , the condensate of 1- (2-hydroxyethyl) -2,6,6-tetramethyl-4-hydroxypiperidine and succinic acid, the condensate of N, N'-bis (2, 2, 6,6-tetramethyl- 4-piperidyl) hexa-methylenediamine and 4-tert-octylamino-2,6-dichloro-1,3,5-triazine, tris (2, 2, 6, 6-tetramethyl-4-piperidyl) nitrilotriacetate, tetrakis- (2 , 2,6,6-tetramethyl-4-piperidyl) -1,2,3,4-butane-tetracarboxylate, 1,1 '- (1,2-ethanedyl) -bis (3,3,5,5,5-tetramethylpiperazinone ), 4-benzoyl-2,2,6,6-tetramethylpiperidine, 4-stearyloxy -2,6,6,6-tetramethyl-piperidine, bis (1,2-, 2,6,6-pentamethylpiperidyl) -2-n -butyl-2- (2-hydroxy-3,5-di-tert-butylbenzyl) malonate, 3-n-octyl-7,7,9,9-tetramethyl-1,3,8-triazaspiro [4. 5] decan-2, 4-dione, bi s (1-octyloxy-2, 2, 6, 6-tetramethylpiperidyl) sebacate, bis (1-octyloxy-2,6,6,6-tetramethylpiperidyl) succinate, Condensate of N, N'-bis (2, 2, 6,6-tetramethyl-4-piperidyl) hexamethylenediamine and 4-morpholin-2,6-dichloro-1,3,5-triazine, the condensate of 2-chloro- 4, 6-bis (4-n-butylamino-2, 2,6,6-tetramethylpiperidyl) -1,3,5-triazine and 1,2-bis (3-amino-propylamino) ethane, the condensate of 2- chloro-4,6-di- (4-n-butylamino-1,2,2,6,6-pentamethylpiperidyl) -1,3,5-triazine and 1,2-bis (3-amino-propylamino) ethane 8-acetyl-3-dodecyl-7,7,9,9-tetramethyl-1,3,8-triazaspiro [4.5] decan-2,4-dione, 3-dodecyl- (2,2,6,6) -tetramethyl-4-piperidyl) pyrrolidin-2,5-dione, 3-dodecyl-1- (1,2,2,6,6-pentamethyl-4-piperidyl) pyrrolidin-2, 5-dione. 6. Oxamides, for example 4,4'-dioctyloxyoxanilide, 2,2'-diethoxy-oxanilide, 2,2'-dioctyloxy-5,5'-di-tert-butoxyanilide, 2,2'-didodecyloxy-5, 5 '-di-tert-butoxyanilide, 2-ethoxy-2'-eti loxanyl ida, N, N' -bis (3-dimethylaminopropyl) oxamide, 2-ethoxy-5-tert-butyl-2-ethoxyanilide and its mixture with 2 -ethoxy-2'-ethyl-5,4'-di-tert-butoxyanilide, mixtures of o- and p-methoxy disubstituted oxanilides and mixtures of disubstituted o- and p-ethoxy oxanilides. 7. 2- (2-Hydroxyphenyl) -1,3,5-triazines, for example 2,4,6-tris (2-hydroxy-4-octyloxyphenyl) -1,3,5-triazine, 2- (2-hydroxy) 4-octyloxyphenyl) -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine, 2- (2,4-dihydroxyphenyl) -4,6-bis (2,4-dimethylphenyl) -1 , 3, 5-triazine, 2,4-bis (2-hydroxy-4-propyl-oxyphenyl) -6- (2,4-dimethylphenyl) -1,3,5-triazine, 2- (2-hydroxy) -4 -octyloxyphenyl) -4,6-bis (4-methylphenyl) -1,3,5-triazine, 2- (2-hydroxy-4-dodecyloxyphenyl) -4,6-bis (2,4-dimethyl-phenyl) - 1,3,5-triazine, 2- (2-hydroxy-4-tridecyloxyphenyl) -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine, 2- [2-hydroxy-4- (2-hydroxy-3-butyloxy-propoxy) phenyl] -4,6-bis (2,4-dimethyl) -1, 3,5-triazine, 2- [2-hydroxy-4- (2-hydroxy-3-octyloxy-propyloxy) phenyl] -4,6-bis (2,4-dimethyl) -1,3,5-triazine , 2- [4- (dodecyloxy / tridecyloxy-2-hydroxypropoxy) -2-hydroxy-phenyl] -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine. 8. Phosphites and phosphonites, for example triphenyl phosphite, diphenyl alkyl phosphites, phenyl dialkyl phosphites, tris (nonylphenyl) phosphite, trilauryl phosphite, trioctadecyl phosphite, distearyl pentaerythritol diphosphite, tris (2,4-di-tert-butylphenyl) phosphite, diisodecyl penta-erythritol diphosphite, bis (2,4-di-tert-butylphenyl) pentaerythritol diphosphite, bis (2,6-di-tert-butyl-4-methylphenyl) -pentaerythritol diphosphite, diisodecyloxypentaerythritol diphosphite, bis (2, 4-di) -tert-butyl-6-methylphenyl) pentaerythritol diphosphite, bis (2,4,6-tris (tert-butyl-phenyl) pentaerythritol diphosphite, tristearyl sorbitol triphosphite, tetrakis (2,4-di-tert-butyl-phenyl) - 4, 4 '-biphenylene diphosphonite, 6-isooctyloxy-2, 4,8,10-tetra-tert-butyl-12H-dibenz - [d, g] -1,3, 2-dioxaphosphozin, 6-fluoro-2, 4.8, 10-tetra-tert-butyl-12-methyl-dibenz- [d, g] -1, 3, 2-dioxaphosphozin, bis (2,4-di-tert-foutyl-6-methylphenyl) methyl phosphite , bis (2,4-di-tert-butyl-6-methylphenyl) ethyl phosphite, illustrative examples of additional additives are: Fillers and reinforcing agents, for example calcium carbonate, silicates, glass fibers, glass beads, asbestos, talc, kaolin, mica, barium sulfate, metal oxides and hydroxides, carbon black, graphite, wood sawdust and flours or fibers of other natural products, synthetic fibers. Other additives, for example plasticizers, lubricants, emulsifiers, pigments, rheology additives, catalysts, flow control agents, optical brighteners, flameproofing agents, antistatic agents and blowing agents.
In addition to the additives indicated above, it is also possible that additional coinitiators are present. In general, these are dyes that improve the total quantum yield for example by energy transfer or transfer to electrons. Examples of suitable dyes which can be added as coinitiators are triarylmethanes, for example malachite green, indolines, thiazines, for example methylene blue, xanthones, thioxanthones, oxazines, acridines or phenazines, for example safranin and rhodamines of the formula
wherein R is alkyl or aryl; and R 'is hydrogen, an alkyl or aryl radical, for example Rhodamine B, Rhodamine 6G or Violamine R, and also Sulforhodamine B or Sulforhodamine G. Preference is given to thioxanthones, oxazine, acridines, phenazines and rhodamines. Bleaching combinations with borates are also convenient in this connection, as described among others in US 4772530, GB 2307474, GB 2307473, GB 2307472 and EP 775706.
In addition to the base-catalysable binders (curable) described above, component B), the composition can also include other binders equally. It is possible to use, for example, additional olefinically unsaturated compounds. The unsaturated compounds may include one or more olefinic double bonds. They may be low molecular mass (monomeric) or high molecular mass (oligomeric). Examples of monomers having a double bond are alkyl acrylates or L-hydroxyalkyl acrylates or alkyl methacrylates or hydroxyalkyl methacrylates, such as ethyl, butyl, 2-ethylhexyl or 2-hydroxyethyl acrylate, isobornyl acrylate, methyl methacrylate or ethyl methacrylates. Silicone acrylates are also of interest. Additional examples are acrylonitrile, acrylamide, methacrylamide, N-substituted (meth) acrylamides, vinyl esters such as vinyl acetate, vinyl ethers such as isobutyl vinyl ether, styrene, alkyl- and halostyrene, N-vinylpyrrolidone, vinyl chloride or vinylidene chloride. . Examples of monomers having several double enalces are the diacrylates of ethylene glycol, propylene glycol, neopentyl glycol, hexamethylene glycol or bisphenol A, 4,4'-bis (2-acryloyl-oxyethoxy) diphenylpropane, trimethylolpropane triacrylate, pentaerythritol triacrylate or pentaerythritol tetraacrylate, vinyl acrylate, divinyl benzene, divinyl succinate, diallyl phthalate, triaryl phosphate, triaryl isocyanurate or tris (2-acryloylethyl) isocyanurate. Examples of polyunsaturated compounds of higher molecular mass (oligomers) are acrylated epoxy resins, acrylated polyesters or polyesters containing vinyl ether groups or epoxy groups, polyurethanes and polyethers. Additional examples of unsaturated oligomers are unsaturated polyester resins which are primarily prepared from maleic acid, phthalic acid and one or more diols and have molecular weights of about 500 to 3000. In addition, it is also possible to employ vinyl ether monomers and oligomers and also oligomers terminated with maleate with polyester, polyurethane, polyether, polyvinyl ether and epoxy main chains. In particular, combinations of oligomers and polymers that carry vinyl ether are as described in WO 90/01512 and are very convenient. Copolymers of vinyl ether and monomers functionalized with maleic acid are also convenient. Unsaturated oligomers of this type can also be referred to as prepolymers. Particularly suitable examples are esters of ethylenically unsaturated carboxylic acids and polyols or polyepoxides and polymers having ethylenically unsaturated groups in the chain or in side or side groups, such as polyesters, polyamides and polyurethanes and their unsaturated copolymers, alkyd resins, butadiene copolymers and polybutadiene, copolymers of isoprene and polyisoprene, copolymers and polymers having (meth) acrylic groups in secondary chains and mixtures of one or more of these polymers. If in addition, these monomers are used, oligomers / polymers curable by radicals, then it is judicious to add an additional photoinitiator that dissociates into radicals. These photoinitiators are known and produced industrially. Examples are benzophenone, benzophenone derivatives, acetophenone, acetophenone derivatives, for example a-hydroxycycloalkyl phenyl ketones, dialkoxyacetophenones, a-hydroxy- or a-aminoacetophenones, 4-aroyl-1,3-dioxolanes, benzoyl alkyl ethers and benzyl ketals, monoacyl phosphine oxides, bisacylphosphine oxides, ferrocenium compounds or titanocenes. Examples are given in EP-A-284 561. Polymer systems of this type, wherein curing / entanglement is carried out by different mechanisms are also referred to as hybrid systems. It is also possible to add non-reactive binders to novel compositions, which is particularly judicious if the photopolymerizable compounds are liquids or viscous substances. The amount of the non-reactive binder for example may be 5-95%, preferably 10-90% and in particular 40-90% by weight based on the total solids content. The selection of the non-reactive binder is made according to the field of use and with the properties required for this use, such as the possibility for development in aqueous and organic solvent systems, substrates adhesion and sensitivity to oxygen. Examples of suitable binders are polymers having a molecular weight of about 5,000-2,000,000, preferably 10,000-1,000,000. Examples are homo- and copolymeric acrylates and methacrylates, for example copolymers of methyl methacrylate / ethyl acrylate / methacrylic acid, poly (alkyl methacrylates), poly (alkyl acrylates); cellulose esters and ethers such as cellulose acetate, cellulose acetate butyrate, methyl cellulose, ethyl cellulose; polyvinyl butyral, polyvinyl formal, cyclized rubber, polyethers such as polyethylene oxide, polypropylene oxide, polytetrahydrofuran; polystyrene, polycarbonate, polyurethane, chlorinated polyolefins, polyvinyl chloride, copolymers of vinyl chloride / vinylidene chloride, copolymers of vinylidene chloride with acrylonitrile, methyl methacrylate and vinyl acetate, polyvinyl acetate, copolymer (ethylene vinyl acetate), polymers such as polycaprolactam and poly (hexamethylene adipamide) and polyesters such as poly (ethylene glycol terephthalate) and poly (hexamethylene glycol succinate). Additionally, the invention provides a method for carrying out base catalyzed reactions comprising exposing light with a wavelength of 200 nm to 650 nm, a novel composition as described above. In some cases, it may be advantageous to carry out heating during or after exposure to light. In this way it is possible in many cases to accelerate the entanglement reaction. The light sensitivity of the novel compositions generally extends from about 200 nm through the UV region and into the infrared region (about 20,000 nm, in particular 1200 nm) and therefore extends over a very wide range. Convenient radiation comprises for example sunlight or light from artificial light sources. Therefore, a large number of very different types of light sources can be used. Both point sources and flat radiators (mats or lamp benches) are convenient. Examples are carbon arc lamps, xenon arc lamps, mercury lamps of medium pressure, high pressure and low pressure, if desired adulterated with metal halides (metal halogen lamps) metal vapor lamps excited by microwaves, excimer lamps, superactinic fluorescent tubes, fluorescent lamps, incandescent argon lamps, electronic flashing lamps, high intensity lamps or photographic projectors, electron beams and X-rays, which are produced by synchrotrons or laser plasma. The distance between the lamp and the substrate according to the invention to be exposed may vary depending on the application and the type and / or lamp energy, for example between 2 and 150 cm. Laser light sources, for example excimer lasers, are also particularly suitable. Laser in the visible region or in the IR region can also be used. The high sensitivity of the novel materials and the possibility of adapting a colorant as a co-initiator to the laser line is very advantageous here. By this method it is possible to produce printed circuits in the electronics industry, lithographic offset printing plates or relief printing plates and also photographic recording or recording materials. The novel compositions can be used for various purposes, for example as printing inks, as transparent coatings, as white paints, for example for wood or metal, as coating materials, among others for paper, wood, metal or plastic, as coatings in dust, such as coatings curable with daylight, to mark buildings and roads, for photographic reproduction processes, for holographic recording materials, for image recording processes or for the production of printing plates that can be revealed using organic solvents or aqueous alkaline media, for the production of masks for stencil printing, or dental filling materials, such as adhesives including pressure sensitive adhesives, such as laminating resins, as mordant protective layers or permanent protective layers and as welding masks for electronic circuits, for the production of article s three-dimensional by mass curing (UV curing in transparent molds) or by the stereolithography process, as described for example in U.S. Pat. No. 4,575,330, for the preparation of composite materials (for example styrenic polyesters which may contain glass fibers and / or other fibers and other auxiliaries (and other thick layer compositions, for the coating or encapsulation of electronic components, or as coatings for optical fibers) In paint systems, it is common to use mixtures of a prepolymer with polyunsaturated monomers that also contain a monosaturated monomer.The prepolymer here is primarily responsible for the properties of the coating film and varying it allows the worker to dexterously in the specialty it influences the properties of the cured film.The polyunsaturated monomer functions as an interlayer which makes the coating film insoluble.The monounsaturated monomer functions as a reactive diluent through which the viscosity is reduced without the need to use a solvent. unsaturated polyester, pri Usually used are used in two-component systems in conjunction with a mono-unsaturated monomer, preferably styrene. For photoresistors, one-component specific systems are frequently used, for example polymaleimides, polyhalcondes or polyimides as described in DE-A-2 308 830. The novel photocurable compositions are suitable for example as coating materials for substrates of all types, they are examples are wood, textiles, paper, ceramics, glass, plastics such as polyesters, polyethylene terephthalate, polyolefins or cellulose acetate, especially in the form of films and also metals such as Al, Cu, Ni, Fe, Zn, Mg or Co and GaAs , Si or Si02, in which it is the intention to apply a protective coating or by an image-like exposure of an image. The substrates can be coated by applying a liquid composition, a solution or suspension to the substrate. The selection of the solvent and the concentration depend predominantly on the time of composition and the coating process. The solvent must be inert; in other words, it should not undergo any chemical reaction with the components and should be able to be removed again after the coating operation in the drying process. Examples of suitable solvents are ketones, ethers and esters, such as methyl ethyl ketone, isobutyl methyl ketone, cyclopentanone, cyclohexanone, N-methylpyrrolidone, dioxane, tetrahydrofuran, 2-methylethoxyethanol, 2-ethoxyethanol, 1-methoxy-2-propanol, 1 , 2-dimethoxyethane, ethyl acetate, n-butyl acetate and ethyl 3-ethoxypropionate. Using known coating processes, the solution is uniformly applied to a substrate, for example by spin coating, dip coating, spatula coating, curtain coating, brushing or brushing, spraying especially by electrostatic spraying and reverse roll coating, and by electrophoretic deposition. It is also possible to apply the photosensitive layer to a temporary flexible support and then to coat final acetate for example a circuit board with copper coating by layer transfer by lamination. The amount applied (layer thickness) and the nature of the substrate (layer support) are functions of the desired field of application. The range of layer thicknesses generally comprises values from about 0.1 μm to more than 100 μm. The novel radiation-sensitive compositions can also be subjected to image exposure. In this case, they are used as negative protective layers. They are suitable for electronic components (electroplating protective coatings, etching protective coatings and welding protective coatings), for the production of printing plates, such as offset printing plates, flexographic and relief printing plates or stencil printing plates, for the production of marking seals and can be used for etching molded articles or as protective micro-layers in the production of integrated circuits. There is a wide range of variation correspondingly in the possible layer supports and in the processing conditions of the coated substrates. The term "image-like" exposure refers to both exposure through a photomask containing a predetermined pattern, for example a slide, exposure by a laser beam moving under computer control, for example on the substrate surface coated and in this way generates an image and irradiation with electron beams controlled by computer. Following the exposure as an image of the material and before development, it may be advantageous to carry out a brief heat treatment, where only the exposed parts are thermally cured. The temperatures employed in general are 50-150 ° C and preferably 80-130 ° C; The duration of the term treatment in general is between 0.25 and 10 minutes. An additional field of use for light curing is that of metal coatings, for example the surface coating of metal panels and tubes, cans or bottle caps and curing in polymer coatings, for example of floor or wall coverings, based on PVC Examples of the curing of paper coatings is the colorless varnishing of labels, recording linings or book covers. This invention also relates to the use of a compound of the formula I
as photoinitiator for addition reactions or photochemically induced base-catalyzed substitution reactions, in particular for curing molded articles, made from composite compositions, wherein R1 # R2, R3, R4, R5, R12, R13, R14, R15 and m has the preferred meanings and meanings set forth above. Another subject of this invention is the aforementioned use for the preparation of coatings, molded articles or photo-structured layers. The compound usually consists of a self-supporting matrix material, for example a fiberglass cloth, or else for example vegetable fibers [see K.-P. Mieck, T. Reussmann in Kunststoffe 85 (1995), 366-370], which is impregnated with the light-cured formulation. The molded articles made from materials produced with the novel compounds reach a high level of mechanical stability and strength. The novel compounds can also be used as light curing agents in molding, impregnation and coating compositions, such as described in EP-A-7086. These compositions, for example, are gel-coating resins, which are subjected to strict requirements regarding their curing activity and resistance to yellowing and to fiber-reinforced molded articles such as light diffusion panels that are planar or have longitudinal or transverse corrugation. . Examples and preferences of substitution reactions or base catalyzed addition reactions were established above. In other aspects, this invention relates to a coated substrate that has been covered on at least one surface with a composition as described above and to a process for the photographic production of relief images, wherein a coated substrate is subjected to Exposure in image fashion and then the unexposed areas are removed with a solvent. Of particular interest in this context is the aforementioned exposure by means of a laser beam. This invention also relates to the use of novel compounds for the preparation of coatings, molding compositions or photo-structured layers.
In other of these aspects, this invention relates to novel interlaced or polymerized compositions. The following examples illustrate the invention in more detail. As in the remainder of the description and in the claims, parts and percentages are given by weight unless stated otherwise. If alkyl or alkoxy radicals having more than three carbon atoms are indicated without reference to their isomeric form, then the respective n-isomers are intended. The following abbreviations are used in Examples: "Ph" for phenyl, "Me" for methyl, "Et" for ethyl, He for hexyl, "Ar" for aryl, "DMSO" for di-me-tyl sulfoxide, "U.V." for ultraviolet spectrum, "I.R." for infrared spectrum, "H NMR" for hydrogen nuclear magnetic resonance spectrum (indication of displacement values in ppm), "13C NMR, for carbon nuclear magnetic resonance spectrum (indication of displacement values in ppm) Examples A: Preparation of the bromides and iodides General procedure A nitrogenous base equivalent is stirred in diethyl ether at room temperature.An equivalent of a solution of the corresponding a-bromoketone in toluene is added and the reaction mixture is stirred by one hour The precipitated bromide is filtered, washed with diethyl ether and the solvent is removed under vacuum, yielding the product with yields of 80 to 90% In the examples, the extinction coefficients e denote the molar extinction coefficients in unit 1 / mol cm Example Al
Analysis for C 14 H 22 NO Br: calculated: C 56.01; H 7.39; N 4.67; Br 26.61. Found: C 56.02; H 7.34; N 4.45; Br 26.82. U.V. (CHC13) max. at 255 nm (e 13300). X H NMR (CDC13): 8.03 (2H, d, ArH), 7.38 (1 H, t, ArH), 7.23
(2H, m, ArH), 5.20 (2H, s, CH2), 3.69 (6H, q, CH2CH3) and 1.16
(9H, t, CH2CH3). Example A2
U.V. (CHC13) max. at 294 nm (e 16800) * H NMR (CDCl 3): 8.37 (2H, d, ArH), 7.00 (2H, d, ArH), 5.44 (2H, s, CH2), 3.88 (9H, qys, CH2CH3 and OCH3 ) and 1.41 (9H, t, CH2CH3) Example A3
U.V. (MeOH) max. at 261 nm (e 12800). H NMR (CDCl 3): 8.63 (2H, d, ArH), 8.30 (2H, d, ArH), 5.84 (2H, s, CH2), 3.86 (6H, q, CH2CH3) and 1.41 (9H, t, CH2CH3) . Example A4
U.V. (CHCI3) max. at 243 nm (e 3000) and 305 nm (e 24000).
X H NMR (CDCl 3): 8.41 (2 H, d, Ar H), 7.74 (2 H, d, Ar H), 7.58
(2H, d, ArH), 7.44 (3H, m, ArH), 5.57 (2H, s, CH2), 3.87
(6H, q, CH2CH3) and 1. 42 (9H, t, CH2CH3). E j us A5
Br U.V. (H20) max. at 252 nm (e 14100). H NMR (D20): 8.01 (2H, d, ArH), 7.79 (ΔH, t, ArH), 7.6 ((2H, t, ArH), 3.81 (6H, t, NCH2) and 3.31 (6H, t, NCH2 Example A6
Analysis for C15H21N2OBr: calculated C 55.39; H 6.51; N 8.61; Br 24.57; found: C 55.11; H 6.59; N
8. 70; Br 24.65. U.V. (CHC13) max. at 259 nm (e 14000). X H NMR (CDCl 3): 8.15 (2H, d, ArH), 7.50 (ΔH, t, ArH), 7.37
(2H, t, ArH), 6.03 (ÍH, q, CH), 3.99 (3H, t, NCH2), 3.85 (3H, t, NCH2), 3.14 (6H, m, NCH2) and 1.59 (3H, d, CH3). Example A7
O ^ feti Q- 2Br- O
U.V. (H20) max. at 254 nm (e 28200). X H NMR (DzO): 8.01 (4H, d, ArH), 7.80 (2H, t, ArH), 7.62 (4H, t, ArH) and 4.50 (12H, s, NCH2). Example A8 U.V. (MeOH) max. at 256 nm (e 23500). H NMR (D20): 8.07 (4H, d, ArH), 7.82 (2H, t, ArH), 7.66
(4H, t, ArH), 5.74 (2H, q, CH), 4.53 (6H, m, NCH2), 4.30 (6H, m, NCH2) and 1.85 (6H, d, CH3). Example A9
U.V. (CD3CN) max. to 245 (e 14600) and 281 (e 1500). X H NMR (DMSO): 9.06 (H, S, Ar H), 8.05 (2 H, d, Ar H), 7.80-7.60 (5 H, m, Ar H), 6.06 (2 H, s, CH 2) and 3.95 (3 H, s, NCH3). AlO example
H NMR (CDC13): 8.07 (2H, d, ArH), 7.63 (1H, t, ArH), 7.50 (2H, t, ArH), 5.57 (2H, s, CH2), 3.67 (4H, m, NCH2) and 3.5-1.3 (12H, m, CH2). Example All X H NMR (CDC13): 8.02 (2 H, d, Ar H), 7.61 (H, t, Ar H), 7.48 (2 H, t, Ar H), 5.33 (2 H, s, CH 2). 3.84 (2H, t, NCH2), 3.67 (4H, m, NCH2), 3.14 (2H, m, CH2) and 2.3-2.1 (4H, m, CH2). Example A12
U.V. (CHCI3) max. at 297 nm (e 22000). H NMR (CDC13): 8.08 (2H, d, ArH), 7.67 (2H, d, ArH), 7.54 (2H, d, ArH), 7.37 (3H, m, ArH), 5.37 (2H, s, CH2) , 3.84 (2H, t, NCH2), 3.54 (4H, m, NCH2), 3.11 (2H, m, CH2) and 2.3-2.1 (4H, m, CH2). Example A13
Br
a H NMR (CDCl 3): 8.57 (H, s, Ar H), 8.07 (2 H, d, Ar H), 7.64-7.50 (6 H, m, Ar H), 4.96 (2 H, s, CH 2), 3.94 (2 H, t, NCH2), 3.82 (2H, t, NCH2), 3.65 (4H, t, CH2), 3.45-3.30 (6H, m, CH2) and 2.4-2.1 (6H, m, CH2). Example Al4
U.V. (CHCI3) max. at 245 nm (e 30500), 291 nm (e 22300), 371 nm (e 17500) and 403 nm (e 14900). X H NMR (CDCl 3): 9.10 (1 H, d, Ar H), 8.66 (1 H, d, Ar H), 8.3-7.8 (7 H, m, Ar H), 5.56 (2 H, s, CH 2), 3.85 (2 H, t, NCH2), 3.57 (2H, t, NCH2), 3.23 (2H, t, CH2) and 2.4-2.1 (6H, m, CH2). The a-iodoketones are prepared from commercially available a-bromoketones by a Finkelstein reaction. The iodides are prepared in analogy to the bromides described above. Example A15"Analysis for C ^ H ^ NO!: Calculated: C 43.30, H 5.29, N 4.59, 1 41.59, found: C 43.32, H 5.22, N 4.59, 1 41.82, UV (CHC13) max at 246 nm (e 25800 ). * H NMR (CD3CN): 8.00 (2H, d, ArH), 7.70 (H, t, ArH), 7.57 (2H, t, ArH), 5.18 (2H, s, CH2) and 3.37 (9H, s) , CH3) Example Al6
U.V. (CHC13) max. at 249 nm (e 18900). X H NMR (CDCl 3): 8.19 (2 H, d, Ar H), 7.58 (H, t, Ar H), 7.43
(2H, t, ArH), 5.25 (2H, s, CH2), 3.82 (6H, q, CH2CH3) and 1.34
(9H, t, CH2CH3). Example A17
U.V. (CHCI3) max. at 245 nm (e 10300) and 295 nm (e 18100). H NMR (CDCl 3): 8.25 (2H, d, ArH), 6.93 (2H, d, ArH), 5.20 (2H, s, CH2), 3.82 (9H, qys, CH2CH3 and 0CH3) and 1.37 (9H, t, CH2CH3).
Example Al 8
H NMR (CDCl 3): 8.59 (2 H, d, Ar H), 8.32 (2 H, d, Ar H), 5.68 (2 H, s, CH 2), 3.86 (6 H, q, CH 2 CH 3) and 1.44 (9 H, t, CH 2 CH 3) . Example Al 9
U.V. (CHC13) max. at 244 nm (e 11100) and 305 nm (e 23400). H NMR (CDCl 3): 8.38 (2 H, d, Ar H), 7.72 (2 H, d, Ar H), 7.57 (2 H, d, Ar H), 7.42 (3 H, m, Ar H), 5.40 (2 H, s, CH 2) , 3.88 (6H, q, CH2CH3) and 1.42 (9H, t, CH2CH3). Example A20
U.V. (MeOH) max. at 249 nm (e 14900). X H NMR (D 20): 8.00 (2H, d, ArH), 7.78 (1H, t, ArH), 7.64 (2H, t, ArH), 3.81 (6H, t, NCH2) and 3.31 (6H, t, NCH2) .
Example A21
Analysis for C22H26N20212: calculated: C 43.73; H 4.34; N 4.64; 1 42.00. found: C 43.29; H 4.24; N 4.29; 1 41.82. U.V. (MeOH) max. at 252 nm (e 28400). H NMR (DMSO): 8.04 (4H, d, ArH), 7.79 (2H, t, ArH), 7.64 (4H, t, ArH), 5.55 (4H, s, CH2) and 4.31 (12H, s, NCH2) . Example A22
U.V. (CH3CN) max. to 246 (e 27400). X H NMR (DMSO): 9.03 (H, s, Ar H), 8.05 (2 H, d, Ar H), 7.80-7.60 (5 H, m, Ar H), 6.04 (2 H, s, CH 2) and 3.95 (3 H, s, NCH3). Example A23
or rT ^ .N '.
Analysis for C15H17N201: calculated: C 48.93; H.65; N 7.61; 1 34.46. found: C 48.89; H 4.60; N 7.34; 1 34.48. U.V. (CH3CN) max. at 257 (e 20500), 289 nm (e 26200) and 364
(e 7000). H NMR (DMSO): 8.18 (2H, d, ArH), 8.03 (2H, d, ArH), 7.76.
(1H, t, ArH), 7.64 (2H, d, ArH), 7.12 (2H, d, ArH), 5.96
(2H, s, CH2) and 3.23 (6H, s, NCH3). Example A24
Analysis for C20H42N7OP21: calculated: C 41.03; H 7.23; N
16. 75/1 21.68. found: C 40.62 / H 7.49 / N 17.10 / 1 21.56. Example A25
OR
U.V. (CHC13) max. at 245 nm (e 9500), 288 nm (e 23500) and 366 nm (e 4100).
H NMR (CDCl 3): 7.98 (2H, d, ArH), 6.92 (2H, d, ArH), 5.35 (2H, s, CH2), 3.81 (3H, s, OCH3), 3.65 (4H, m, NCH2) and 3.5-1.3 (12H, m, CH2). Example A26
, U.V. (CHCI3) max. at 247 nm (e 9800) and 287 nm (e 19500). H NMR (CDC13): 7.97 (2H, d, ArH), 6.95 (2H, d, ArH), 5.14 (2H, s, CH2), 3.85 (5H, m, NCH2 and OCH3), 3.55 (4H, m, NCH2), 3.10 (2H, m, NCH2) and 2.4-2.2 (4H, m, CH2). Example A27
l.R. (KBr): 1690 cm-1, 1665 cm "1 (C = 0). H NMR (CDC13): 8.72 (ΔH, s, ArH), 8.02 (2H, m, ArH),
7. 85 (2H, m, ArH), 7.56 (2H, m, ArH), 5.45 (2H, s, CH2), 3.84
(2H, t, NCH2), 3.58 (4H, m, NCH2), 3.17 (2H, m, CH2) and 2.3-2.1 (4H, m, CH2). Example A28: l.R. (KBr): 1695 cm "1, 1665 was" 1 (C = 0), 1640 cm-1. X H NMR (CDCl 3): 8.95 (H, d, Ar H), 8.43 (H, d, Ar H), 8.14
(ÍH, dd, ArH), 7.54 (4H, m, ArH), 5.42 (2H, s, CH2), 3.91
(2H, t, NCH2), 3.71 (2H, t, NCH2), 3.62 (2H, t, NCH2), 3.25 (2H, t, NCH2) and 2.4-2.2 (4H, m, CH2) '. Examples B: Preparation of borate salts General procedure for the preparation of tetraphenylborates One equivalent of the bromides is stirred in water at room temperature and one equivalent of an aqueous solution of sodium tetraphenyl borate is added. The precipitated tetraphenyl borate salt is isolated by filtration, washed with water and dried under vacuum, yielding the product in 95% yield.
Example Bl
BPh Analysis for C38H42NOB: calculated:: C 84.59 / H
7. 85 / N 2.60 / found: C 84.31 / H 8.18 / N 2.16. U.V. (CHC13) max. at 251 nm (e 18900). X H NMR (CDCl 3): 7.63 (3 HL, m, Ar H), 7.28 (lOH, m, Ar H), 6.94 (8 H, t, Ar H), 6.80 (4 H, t, Ar H), 3.78 (2 H, s, CH 2) , 2.81 (6H, q, CH2CH3) and 0.75 (9H, t, CH2CH3). 13 C NMR (CDCl 3): 189.93, 165.96, 165.17, 164.39, 163.61, 136.72,
135. 49, 133.99, 129.44, 128.43, 128.37, 128.24, 128.04,
127. 87, 127.81, 127.66, 127.48, 127.40, 127.37, 126.24,
126. 20, 126.16, 126.12, 122.27, 116.68, 58.60, 54.50 and
7. 41. Example B2
Analysis for C39H44N02B: calculated:: C 82.24 / H 7.79 / N 2.46 / found: C 82.05 / H 8.21 / N 2.24. 'H NMR (DMSO): 8.04 (2H, d, ArH), 7.16 (lOH, m, ArH), 6.93 (8H, t, ArH), 6.80 (4H, t, ArH), 5.09 (2H, s, CH2 ), 3.89 (3H, s, OCH3), 3.59 (6H, q, CH2CH3) and 1.20 (9H, t, CH2CH3). Example B3
Ph Analysis for C44H46NOB: calculated:: C 85.84 / H 7.53 / N 2.28 / found: C 85.86 / H 7.55 / N 2.04. X H NMR (DMSO): 8.15 (2 H, d, Ar H), 7.95 (2 H, d, Ar H), 7.81 (2 H, d, Ar H), 7.50 (3 H, m, Ar H), 7.17 (8 H, m, Ar H) , 6.93 (8H, t, ArH), 6.80 (4H, t, ArH), 5.21 (2H, s, CH2), 3.62 (6H, q, CH2CH3) and 1.25 (9H, t, CH2CH3). Example B4
Analysis for C35H36NOB: calculated:: C 84.50 / H 7.29 / N 2.82; found: C 84.52 / H 7.29 / N 2.64. X H NMR (DMSO): 7.99 (2 H, d, Ar H), 7.77 (H, t, Ar H), 7.63 (2 H, t, Ar H), 7.18 (8 H, m, Ar H), 6.93 (8 H, t, Ar H) , 6.79 (4H, t, ArH), 5.27 (2H, s, CH2) and 3.31 (9H, s, CH3). Example B5
Analysis for C 38 H 39 N 2 O B: calculated:: C 82.90 / H 7.14 / N 5.09; found: C 82.78 / H 7.12 / N 4.79.
H NMR (CD3COCD3): 8.02 (2H, d, ArH), 7.71 (ΔH, t, ArH), 7.58 (2H, t, ArH), 7.35 (8H, m, ArH), 6.92 (8H, m, ArH) , 6.77 (4H, m, ArH), 3.87 (6H, m, NCH2) and 3.33 (6H, m, NCH2). Example B6
Analysis for C70H66N2OB:: calculated: C 85.02 / H 6.73 / N
2. 83 / found: C 84.97 / H 6.60 / N 2.87. XH NMR (CD3COCD3): 8.00 (4H, d, ArH), 7.77 (2H, t, ArH), 7.60 (4H, t, ArH), 7.34 (16H, m, ArH), 6.93 (16H, m, ArH) , 6.78 (8H, m, ArH), 5.63 (2H, s, CH2) and 4.69 (12H, m, NCH2). Example B7
Analysis for C39H41NOB: calculated :: C 82.97 / H 7.32 / N
4. 96 / found: C 82.67 / H 7.11 / N 4.92. X H NMR (CD 3 COCD 3): 8.00 (2 H, d, Ar H), 7.67 (H, t, Ar H), 7.50 (2 H, t, Ar H), 7.22 (8 H, m, Ar H), 6.79 (8 H, m, Ar H) , 6.64 (4H, m, ArH), 5.45 (ÍH, q, CH), 3.83 (3H, m, NCH2), 3.57 (3H, m, NCH2), 3.16 (6H, m, NCH2) and 1.65 (3H, d, CH3).
Example B8
L? L NMR (CD3COCD3): 7.97 (4H, d, ArH), 7.66 (2H, t, ArH), 7.51 (4H, t, ArH), 7.22 (16H, m, ArH), 6.79 (16H, m, ArH), 6.65 (8H, m, ArH), 5.88 (2H, m, CH), 4.57 (6H, m, NCH2), 4.35 (6H, m, NCH2) and 1.78 (6H, m, CH3). Example B9
* H NMR (CDCl 3): 7.57 (2H, d, ArH), 7.5-6.8 (22H, m, ArH), 3.88 (3H, s, OCH3), 3.85 (2H, S, CH2), 3.23 (2H, m , CH2), 3.06 (3H, m, CH2), 2.87 (H, m, CH2), 2.53 (2H, t, CH2), 1.87 (2H, m, CH2) and 1.7-1.3 (6H, m, CH2) . BIO example
BPh,
Analysis for C 39 H 39 N 2 O B: calculated: C 83.27 / H 6.99; N 4.98; found: C 82.90; H 7.20; N 4.97. H NMR (C6D6): 7.78 (3H, m, ArH), 7.61 (5H, m, ArH), 7.15 (14H, m, ArH), 6.77 (3H, m, ArH), 3.35 (2H, s, CH2) , 2.22 (2H, q, CH2). , 1.8-1.0 (12H, m, CH2) and 0.23 (9H, t, CH3). Example Bll
Analysis for C40H43N2O2B: calculated: C 80.80; H 7.29; N, 4.71; found: C 81.01; H 7.29; N 4.62. U.V. (CH3CN) max. at 275 nm (e 20100). XH NMR (CDC13): 7.62 (2H, d, ArH), 7.5-6.8 (22H, m, ArH), 3.90 (3H, s, OCH3), 3.79 (2H, s, CH2), 3.51 (2H, t, CH2),
3. 17 (2H, t, CH2), 2.79 (2H, t, CH2), 2.53 (2H, t, CH2) and 1.86 (6H, m, CH2). Example B12
U.V. (CHC1X max at 243 nm (e 11800), 274 nm (e 14900) and 312 nm (e 9400).
X H NMR (CDC13): 7.88 (H, d, Ar H), 7.45 (8 H, m, Ar H), 6.94 (8 H, t, Ar H), 6.57 (H, d, Ar H), 6.41 (H, d, Ar H) , 4.07 (2H, s, CH2), 3.86 (3H, s, OCH3), 3.61 (3H, s, OCH3), 3.00 (2H, t, CH2), 2.65 (2LH, t, CH2), 2.56 (2H, t, CH2), 1.53 (2H, t, CH2) and 1.30 (6H, m, CH2). Example B13
Analysis for C45H43N2OB: calculated: C 84.63; H 6.79; N 4.39; found: C 84.50; H 6.84; N 4.35. XH NMR (CDC13): 7.7-6.7 (29H, m, ArH), 3.71 (2H, s, CH2), 3.08 (2H, t, NCH2), 2.72 (2H, t, NCH2) 253 (2H, t, NCH2 ) and 1.7-1.4 (6H, m, CH2). Example B14
Analysis for C43H41N.OB: calculated :: C 84.31; H 6.75; N 4.57; found: C 84.20; H 6.82; N 4.50. U.V. (CH3CN) max. at 250 nm (e 63000) and 284 nm (e 10100). X H NMR (CD 3 CN): 8.58 (H, s, Ar H), 8.00 (4 H, m, Ar H), 7.68 (2 H, m, Ar H), 7.27 (8 H, m, Ar H), 6.98 (8 H, m, Ar H) , 6.83 (4H, t, ArH), 5.04 (2H, s, CH2), 3.71 (2H, t, NCH2), 3.40 (4H, m, NCH2), 2.77 (2H, t, CH2) and 2.1-1.8 ( 6H, m, CH2). Example B15
U.V. (CHC13) max. at 246 nm (e 40700), 292 nm (e 21100), 374 nm (e 16600) and 406 nm (e 15600). Example B16
l.R. (KBr): 1695 cm "1 1680 cm" 1 (C = 0), 1665 cm "1, 1640 cm" 1. X H NMR (CD 3 COCD 3): 9.01 (ΔH, d, ArH), 8.54 (ΔH, d, ArH), 8.16 (1H, dd, ArH), 7.86 (ΔH, d, ArH), 7.78 (2H, dd, ArH) , 7.64 (HH, m, ArH), 7.35 (8H, m, ArH), 6.79 (4H, t, ArH), 5.18 (2H, s, CHX, 3.70 (2H, t, NCH2), 3.58 (2H, t , NCH2), 3.40 (2H, dd, NCH2) and 2.7-2.1 (6H, m, CH2) Preparation of the tetra (4-fluorophenyl) borate salts One equivalent of the bromides is stirred in water at room temperature and one equivalent of an aqueous solution of sodium tetra (4-fluorophenyl) borate dihydrate is added.The precipitated tetra (4-fluorophenyl) borate salt is isolated by filtration, washed with water and dried under vacuum to give the product in quantitative yield.
U.V. (CHC13) max. at 255 nm (e 16100). x? i NMR (CDC13): 7.81 (2H, d, ArH), 7.63 (ΔH, t, ArH), 7.45 (2H, t, ArH), 7.16 (8H, m, ArH), 6.67 (8H, m, ArH), 4.36 (2H, s, CH2), 3.32 (6H, q, CH2CH3) and 1.08 (9H, t, CH2CH3). 13C
NMR (C6D6): 162.34, 159.20, 137.61, 135.69, 129.57, 128.52,
128. 20, 127.88, 116.92, 54.67 and 7.44. Example B18
Analysis for C39H35N2OBF4: calculated: C 73.82; H 5.56; N 4.41; found: C 73.62; H 5.55; N 4.63. U.V. (CHCI3) max. at 246 nm (e 20700). XH NMR (C6Db): 7.74 (2H, d, ArH), 7.61 (8H, m, ArH), 7.34-7.15 (3H, m, ArH), 6.91 (8H, m, ArH), 4.09 (2H, s, CH2), 2.22 (2H, q, CH2), 1.8-1.0 (12H, m, CH2) and 0.23 (9H, t, CH3) 13C NMR (CDCl3): 197.79, 167.20, 163.43, 141.89, 139.85, 134.37, 133.53 , 117.48, 117.43, 117.19, 117.15, 64.01, 59.94, 51.83, 47.73, 35.70, 24.15 and 23.16. Preparation of tetra (2, 3,4,5,6-Pentafluorophenyl) borate salt One equivalent of the bromides is stirred in water at room temperature and one equivalent of a methanolic / aqueous solution (3/1) of tetra (2). , 3, 4, 5, 6 -pentafluorophenyl) borate tetraethylammonium, is added. The precipitated tetra (2,3,4,5,5-pentafluorophenyl) borate is isolated by filtration, washed with water and dried under vacuum giving the product with a 75% yield. Example B19
U.V. (CHC13) max. at 256 nm (e 12800). H NMR (CDC13): 7.85 (2H, d, ArH), 7.63 (1H, t, ArH), 7.44
(2H, t, ArH), 4.60 (2H, s, CH2), 3.52 (6H, q, CH2CH3) and 1.17
(9H, t, CH2CH3). Preparation of the tri (3-fluorophenyl) hexylborate salt An equivalent of the bromides is stirred in water at room temperature and one equivalent of a methanolic solution of tetramethyl ammonium tri (3-fluorophenyl) hexyl borate is added. The precipitated tri (3-fluorophenyl) hexyl borate salt is isolated by filtration, washed with water and dried in vacuo to give the product in 75% yield. Example B20
U.V. (CHC13) max. at 252 nm (e 17600). X H NMR (CDCl 3): 7.68 (3 H, m, Ar H), 7.49 (2 H, t, Ar H), 7.22 (3 H, d, Ar H), 6.99 (6 H, m, Ar H), 6.53 (3 H, m, Ar H) , 3.78 (2H, s, CH2), 2.99 (6H, q, CH2CH3) and 1.4-0.7 (22H, m, CH2 and
CH3). Example B21:
U.V. (CHCI3) max. Bei 257 nm (e 89900), 369 nm (e 6300) and 388 nm (e 5800). X H NMR (CDCl 3): 8.62 (δH, s, ArH), 8.11 (2H, m, ArH), 7.62-7.45 (6H, m, ArH), 7.08 (3H, m, ArH), 6.87 (6H, m, ArH), 6.41 (3H, m, ArH), 4.24 (2H, s, CH2), 3.44 (2H, t, NCH2), 3.15 (2H, t, NCH2), 3.04 (2H, t, NCH2), 2.51 ( 2H, t, CH2), 2.01-1.7 (4H, m, CHJ and 1.3-0.7 (13H, m, CH2 and CH3) Example B22:
U.V. (CHC13) max. at 256 nm (e 55600), 298 nm (e 11400) and 346 nm (e 2400). X H NMR (CDC13): 8.21 (1H, s, ArH), 8.01 (ΔH, d, ArH), 7.90 (2H, m, ArH), 7.81 (ΔH, d, ArH), 7.64 (2H, m, ArH) , 7.21 (3H, m, ArH), 6.94 (6H, m, ArH), 6.49 (3H, m, ArH), 4.16 (2H, S, CH2), 3.44 (2H, t, NCH2), 3.06 (2H, t, NCH2), 2.87 (2H, t, NCH2), 2.14 (2H, t, CH2), 2.0-1.7 (4H, m, CH2) and 1.3-0.7 (13H, m, CH_ and CH3). Example B23:
U.V. (CHCI3) max. at 246 nm (e 34800), 292 nm (e 24100), 371 nm (e 18500) and 404 nm (e 15800). X H NMR (CDCl 3): 9.16 (ΔI, d, ArH), 8.3-7.9 (8H, m, ArH), 7.3-6.8 (9H, m, ArH), 6.50 (3H, m, ArH), 4.32 (2H, s, CH2), 3.36 (2H, t, NCH,), 3.01 (2H, t, NCH2), 2.91 (2H, t, NCH2), 2.18 (2H, t, CH2), 2.0-1.7 (4H, m, CH2) and 1.3-0.6 (13H, m, CH2 and CH3). Example B24
XH NMR (CD3COCD3): 8.00 (4H, d, ArH), 7.77 (2H, t, ArH),
7. 60 (4H, t, ArH), 7.34 (16H, m, ArH), 6.93 (16H, m, ArH),
6. 78 (8H, m, "ArH), 5.63 (2H, s, CH2) and 4.69 (12H, m, NCH2),
7. 22 (3H, d, ArH), 6.99 (6H, m, ArH), 6.53 (3H, m, ArH),
3. 78 (2H, s, CH2), 2.99 (6H, q, CH2CH3) and 1.4-0.7 (22H, m, CH2 and CH3). Example B25
^? NMR (CDCl 3): 7.47 (2H, d, ArH), 7.0-6.4 (14H, m, ArH), 4.04 (2H, s, CH2), 3.69 (3H, s, OCH3), 3.16 (2H, m, CH2 ), 3.00 (3H, m, CH2), 2.85 (H, m, CH2), 2.62 (2H, m, CH2), 1.91 (2H, m, CH2) and 1.7-0.6 (19H, m, CH2). Example B26
U.V. (CHCI3) max. at 247 nm (e 24100). X H NMR (CDCl 3): 7.62 (3 H, m, Ar H), 7.44 (2 H, m, Ar H), 7.05 (3 H, m, Ar H), 6.86 (6 H, m, Ar H), 6.42 (3 H, m, Ar H) , 3.97 (2H, S, CH,), 2.62 (2H, t, NCH2), 2.50 (2H, t, NCH2), 2.33 (2H, t, NCH _,), 1.74 (2H, t, CH2), 1.29 ( 2H, m, CH2) and 1.15 (2H, m, CH2). Example B27
X H NMR (CDCl 3): 7.62 (2 H, d, Ar H), 7.08 (3 H, m, Ar H), 6.86 (8 H, m, Ar H), 6.42 (3 H, m, Ar H), 3.96 (2 H, s, CH 2) , 3.81 (3H, s, 0CH3), 3.30 (2H, t, CH2), '2.94 (2H, t, CH2), 2.75 (2H, t, CH2), 2.03 (2H, t, CH2), 1.76 (4H , m, CH2) and 1.3- 0.6 (13H, m, CH; and CH3). Preparation of tetra (3-methylphenyl) borate salt An equivalent of the bromides is stirred in dimethylformamide at room temperature and one equivalent of a solution of tetrakis (3-methylphenyl) borate cesium in dimethylformamide is added. The precipitated tetrakis (3-methylphenyl) borate salt is isolated by filtration, washed several times with water and dried under vacuum. Example B28
U.V. (CHC1J max at 245 nm (e 17200) and 298 nm (e 23000).
XH NMR (CDC13): 7.57 (5H, m, ArH), 7.43 (4H, m, ArH), 7.31
(4H, m, ArH), 7.21 (4H, m, ArH), 6.77 (4H, t, ArH), 6.57
(4H, d, ArH), 3.51 _ (2H, s, CH2), 3.02 (2H, t, CH2), 2.64
(2H, t, CHX, 2.49 (2H, t, CH,), 2.05 (12H, s, CH3) and 1.7-1.4 (9H, m, CH3) Example B29:
X H NMR (CDCl 3): 9.16 (1H, d, ArH), 8.38 (1H, d, ArH), 8.28- 8.03 (7H, m, ArH), 7.44 (4H, m, ArH), 7.21 (4H, m, ArH), 7.77 (4H, t, ArH),, 6.57 (4H, d, ArH), 3.51 (2H, s, CH2),
3. 02 (2H, t, CHJ, 3.64 (2H, t, CH2), 2.49 (2H, t, CHJ, 2.05 (12H, s, CH3) and 1.7-1.4 (9H, m, CH3) Example B30:
U.V. (CHC13) max. at 245 nm (e 31900) and 305 nm (e 41800). * H NMR (CDCl 3): 7.71-7.31 (20H, m, ArH), 6.86-6.57 (6H, m, ArH), 3.88 (2H, s, CHJ, 3.24 (2H, t, CHj, 2.87 (2H, t , CHJ, 2.62 (2H, t, CHJ, 2.05 (12H, s, CH3) and 2.4-1.5 (42H, m, CH2 and CH3) Examples of Application C Procedure for the addition of Michael initiated by UV with dimethylmalonate and n -butylacrylate The latent base (7.4 x 10"5 moles) and 2,2,6,6-tetramethyl-1-piperidinyloxy (7.4 x 10" 5 moles) are dissolved in a 1: 1 mixture of dimethylmalonate and n-butylacrylate ( 200 mg, 7.4 x 10"4 moles) This mixture is irradiated by a silica flask using a high pressure mercury vapor lamp (200 watt) at a distance of 30 cm. Example Cl A compound of Example B13 is used.After 2 hours of exposure to light, a 55% reaction is found and after 100 hours 100% is reacted Example C2 A compound of Example B30 is used. achieves entanglement by exposure to visible light Examples of Use D Base catalysis with oligomeric / polymeric compounds Example DI Preparation of urethane acrylate based on isophorone diisocyanate and 4-hydroxybutylacrylate. The reaction is carried out under nitrogen and all commercially available chemicals used are used without further purification. 1566.8 g (13.78 moles of NCO) of isophorone diisocyanate, 2.3 g of dibutyltin dilaurate,
2. 3 g of 2, 5-diter-butyl-p-cresol and 802.8 g of butylacetate are placed in a three-necked flask equipped with condenser and addition funnel. Dry nitrogen is bubbled through the reaction mixture and the temperature rises slowly to 60 ° C.
Subsequently, 1987 g (13.78 moles) of 4-hydroxybutylacrylate are added, the reaction solution is slowly heated to 80 ° C. The temperature is maintained at 80 ° C and the addition funnel is rinsed with butylacetate
(86.6 g). The reaction is observed by titration of the residual amount of isocyanate and is terminated when the isocyanate content is less than 0.2% based on the solid. The reaction product obtained has the following physical properties: Residual amount of 4-hydroxybutylacrylate: < 0.002%, based on the solid (HPLC analysis), color: < < Gardner 1, viscosity: 43 cPa s (20 ° C), solid: 79.3% (1 hour at 140 ° C), GPC data (polystyrene standard), Mn 778, Mw 796, d = 1.02.
. Preparation of a malonate polyester The reaction is carried out under nitrogen and all commercially available products are employed without further purification. In a reaction vessel equipped with a stirrer and condenser, 1045 g of 1.5 pentanediol, 1377.4 g of diethyl malonate and 242.1 g of xylene are carefully refluxed. The maximum temperature of the reaction mixture is 196 ° C while the temperature is maintained at 79 ° C in the condenser head. 862 g of ethanol in this manner are isolated by distillation corresponding to a reaction at 97.7%. Xylene is then stripped under vacuum at a temperature of 200 ° C. The polymer thus obtained has a solids content of 98.6%, a viscosity of 2710 mmPas and an acid number of 0.3 mg KOH / g, based on the solid. Mn is 1838, Mw is 3186, color is 175 on the APHA scale (process of the American Public Health Association, "Hazen color unit", ISO 6271). Cured with UV radiation 6.4 x 10"'moles of the photoinitiator of Example B28 are dissolved in a 1: 1 mixture of the above urethane acrylate and the polyester malonate (400 mg, total amount) This mixture is emptied into a glass plate at a 50 μm film and irradiated using a mercury vapor lamp with high pressure (200 W) at a distance of 30 cm.The film is tack-free after 30 minutes.
Claims (19)
- R2, R3 and R4 each independently are alkyl with 1 to 18 carbon atoms, alkenyl with 3 to 18 carbon atoms, alkynyl with 3 to 18 carbon atoms, or phenyl, or R2 and R3 and / or R4 and R3 each forms independently of the other, an alkylene bridge with 2 to 12 carbon atoms; or R2, R3, R4 together with the linking nitrogen atom are a phosphazene base of the type P1 # P2 < t / 4 > or a group of structural formula (a), (b), (c), (d), (e), (f) or (g) where k and 1 each independently of the other is a number from 2 to 12; Rs, R6 / R7, R8, R9 and R10 are hydrogen or alkyl with 1 to 18 carbon atoms; or R5 and Rx together with the linking carbon atoms are a benzocyclopentanone radical; RX1 is alkyl with 1 to 18 carbon atoms, alkenyl with 2 to 18 carbon atoms, alkynyl with 2 to 18 carbon atoms, haloalkyl with 1 to 18 carbon atoms, NO, NR6R7, OH, CN, OR8, SR8, C (0) R9, C (O) OR10 or halogen; and n is 0 or 1, 2 or 3; R12, R13 and R14 are phenyl or other aromatic hydrocarbon, these radicals are unsubstituor mono- or polysubstituby alkyl having 1 to 18 carbon atoms, alkenyl with 3 to 18 carbon atoms, alkynyl with 3 to 18 carbon atoms, haloalkyl with 1 to 18 carbon atoms, N02, OH, CN, OR8, SR8, C (0) R9, C (O) OR10 or halogen; R1S is alkyl having 1 to 18 carbon atoms, phenyl or other aromatic hydrocarbon, the phenyl and aromatic hydrocarbon radicals are unsubstituor mono- or polysubstituby alkyl having 1 to 18 carbon atoms, alkenyl having 3 to 18 carbon atoms, alkynyl with 3 to 18 carbon atoms, haloalkyl with 1 to 18 carbon atoms, N02, OH, CN, OR8, SR8, C (0) R9, C (O) OR10 or halogen, or R15 is a radical / and X is alkylene with 1 to 20 carbon atoms, alkylene 2 to 20 carbon atoms, which is interrupby -O-, -S- or NRP or X is provided that if R? : , R13, R14 and R15 are simultaneously phenyl, (a) R2, R3 and R "are not simultaneously methyl / and (b) R2, R3 and R4 together are not
- 2 . A compound according to claim 1, characterized in that Rx is phenyl, naphthyl, pyrenyl, thioxanthyl or phenothiazinyl, these radicals are alkyl with 1 to 18 carbon atoms, haloalkyl with 1 to 18 carbon atoms unsubstituor mono- or polysubstitu NR6R, CN, N02, SR8 or 0R-.
- 3. A compound according to claim 1, characterized in that R2, R3 and R4 each independently of the other is alkyl with 1 to 18 carbon atoms or R2 and R3 and / or R4 and R3 each independently of the other form an alkylene bridge with 2 to 12 carbon atoms / or R2, R3, R4 together with the nitrogen bonds are a group of the structural formulas (a), (b), (c), (d), (e), (f), (g), (h) or a phosphazene base of the type Px, P2 or P < t / 4 > .
- 4. A compound according to claim 1• characterized in that R2, R3 and R4 each independently of the other is alkyl with 1 to 18 carbon atoms, or R2, R3, R4 together with the nitrogen atom are a group of the structural formula (a), (b) , (c), (d) or (e).
- 5. A compound according to claim 1, characterized in that R12, R13, RX4 are phenyl, biphenylyl, naphthyl, anthracyl or phenanthryl, these radicals are unsubstituted or mono- or polysubstituted by alkyl with 1 to 18 carbon atoms, haloalkyl with 1 to 18 carbon atoms, N0_, OH, CN, 0R8 or halogen and R15 is alkyl with 1 to 18 carbon atoms or phenyl which is unsubstituted or mono- or polysubstituted by alkyl with 1 to 18 carbon atoms, haloquyl with 1 to 18 carbon atoms, N02, OH, CN, 0R8 or halogen.
- 6. A process for the preparation of a compound of the formula I, which comprises reacting in a first step, a nitrogenous base of the formula II NR2R3R4 (II) with an α-halogen ketone of the formula III Halogen CH R, (III) R5 O to a compound of formula IV (IV) and in a second step, reacting the compound of the formula IV with a compound of the formula V to the compound of formula I, wherein halogen is bromine or iodine, and M is Na, K or ammonium, and Rx, R2, R3, R4, R5, R12, R13, R14 and R15 have the meanings and preferred meanings claimed in claim 1.
- 7. A composition, characterized in that it comprises: A) at least one compound of the formula (I) and (B) at least one organic compound that is capable of a substitution reaction or addition reaction catalyzed by base .
- 8. A composition according to claim 7, characterized in that the component B) is an organic material crosslinkable or anionically polymerizable.
- 9. A composition according to claim 7, characterized in that component B) is one of the following systems: a) an acrylate copolymer having alkoxysilane or alkoxysiloxane side groups, b) a two component system comprising a polyester and / or polyacrylate containing hydroxyl group and an aliphatic or aromatic polyisocyanate, c) a two-component system comprising a polyepoxide and a functional polyacrylate, wherein the polyacrylate contains carboxyl or anhydride groups, d) a two-component system comprising a polyester or polyacrylate containing hydroxyl group modified with silicone or modified with fluorine and an aliphatic or aromatic polyisocyanate, e) a two-component system comprising a (poly) ketimine and an aliphatic or aromatic polyisocyanate, f) a two-component system comprising a (poly) ketimine and an unsaturated acrylate resin or an acetoacetate resin or methyl a-acrylamidomethylglycollate , h) a two component system comprising a (poly) oxazolidine and a polyacrylate containing anhydride groups, or an unsaturated acrylate resin or a polyisocyanate, i) a two component system comprising a polyacrylate containing epoxy group and a polyacrylate containing carboxyl group, 1) an allyl glycidyl ether-based polymer, m) a two-component system comprising a (poly) alcohol and a (poly) isocyanate, n) a two-component system comprising a carbonyl compound a, beta-ethylenically unsaturated and a compound containing activated CH2 groups.
- 10. A composition according to claim 7, characterized in that component B) is one of the following systems: b) a. a two-component system comprising a polyester and / or polyacrylate containing hydroxyl group and an aliphatic or aromatic polyisocyanate, c) a two-component system comprising a functional polyacrylate and a polyepoxide, wherein the polyacrylate contains carboxyl or anhydride groups, i ) a two-component system comprising a polyacrylate containing the epoxy group and a polyacrylate containing the carboxyl group, m) a two-component system comprising a (poly) alcohol and a (poly) isocyanate and n) a - two-component system comprising a carbonyl α, beta-ethylenically unsaturated compound and a compound containing activated CH 2 groups.
- 11. A composition according to claim 7, characterized in that the component B) is an epoxy resin or a mixture of different epoxy resins.
- 12. A composition according to claim 7, characterized in that component A is present in an amount of 0.01 to 10% by weight based on component B).
- 13. A composition according to claim 7, characterized in that it additionally comprises a sensitizer selected from the group consisting of thioxanthones, oxazines, acridines, phenazines and rhodamines.
- 14. A process for carrying out base catalyzed reactions, characterized in that it comprises exposing a composition according to claim 7, to light having a wavelength in the range of 200 nm to 650 nm.
- 15. A method according to claim 14, characterized in that it comprises heating the composition before or after exposure to light.
- 16. Use of an organic compound according to claim 1, as photoinitiator for addition reactions or photochemically induced base-catalyzed substitution reactions.
- 17. Use of an organic compound according to claim 1, as a photoinitiator for the preparation of coatings, molding compounds or photo-structured layers.
- 18. A coated substrate, at least coated on a surface with a composition according to claim 7.
- 19. A polymerized or interlaced composition according to claim 7.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH444/97 | 1997-02-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA99007895A true MXPA99007895A (en) | 2000-02-02 |
Family
ID=
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR100505529B1 (en) | Photoactivatable nitrogen-containing bases based on α-amino ketones | |
| CA2281860C (en) | Photoactivatable nitrogen-containing bases based on .alpha.-ammonium ketones, iminium ketones or amidinium ketones and aryl borates | |
| KR100527614B1 (en) | α-amino alkene compounds, a process for preparing said compound and a composition comprising said compound | |
| KR100938769B1 (en) | Photoactivable nitrogen bases | |
| US6489374B1 (en) | Photoactivatable bases containing nitrogen | |
| US6551761B1 (en) | Photoactivatable nitrogen-containing bases based on α-ammonium ketones, iminium ketones or amidinium ketones and aryl borates | |
| MXPA99007895A (en) | PHOTOACTIVATABLE NITROGEN-CONTAINING BASES BASED ON&agr;-AMMONIUM KETONES, IMINIUM KETONES OR AMIDINIUM KETONES AND ARYL BORATES | |
| MXPA99008508A (en) | PHOTOACTIVATABLE NITROGEN-CONTAINING BASES BASED ON&agr;-AMINO ALKENES |