Photoactivatable nitrogen-containing bases based on α-ammonium ketones, iminium ketones or amidinium ketones and aryl borates
AssigneeCiba Specialty Chemical Corporation
InventorsVéronique Hall-Goulle, Sean Colm Turner, Allan Francis Cunningham
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Abstract
This invention relates to α-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 crosslinkable compositions comprising these α-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.
Claims18
A compound of formula (I)
- m is 1 or 2 and corresponds to the number of positive charges of the cation;
- R1 is 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, thianthrenyl, dibenzofuryl, chromenyl, xanthenyl, thioxanthyl, phenoxathiinyl, pyrrolyl, imidazolyl, pyrazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolizinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolizinyl, isoquinolyl, quinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, pteridinyl, carbazolyl, b-carbolinyl, phenanthridinyl, acridinyl, perimidinyl, phenanthrolinyl, phenazinyl, isothiazolyl, phenothiazinyl, isoxazolyl, furazanyl, terphenyl, stilbenyl, fluorenyl or phenoxazinyl, these radicals being unsubstituted or mono- or polysubstituted by C1-C18alkyl, C3-C18alkenyl, C3-C18alkynyl, C1-C18haloalkyl, NO2, NR6R7, N3, OH, CN, OR8, SR8, C(O)R9, C(O)OR10 or halogen, or R1 is a radical of formula A or B
- R2, R3 and R4 are each independently of one another hydrogen, C1-C18alkyl, C3-C18alkenyl, C3-C18alkynyl or phenyl, or R2 and R3 and/or R4 and R3 form each independently of one another a C2-C12alkylene bridge;
- or R2, R3, R4, together with the linking nitrogen atom, are a phosphazene base of the P1, P2, P <t/4> type or a group of the structural formula (a), (b), (c), (d), (e), (f) or (g)
- k and l are each independently of the other a number from 2 to 12;
- R5, R6, R7, R8, R9 and R10 are hydrogen or C1-C18alkyl;
- or
- R5 and R1, together with the linking carbon atoms, are a benzocyclopentanone radical;
- R11, is C1-C18alkyl, C2-C18alkenyl, C2-C18alkynyl, C1-C18haloalkyl, NO2, NR6R7, OH, CN, OR8, SR8, C(O)R9, C(O)OR10 or halogen;
- and
- n is 0 or 1, 2 or 3;
- R12, R13 and R14 is phenyl or another aromatic hydrocarbon, these radicals being unsubstituted or mono- or polysubstituted by C1-C18alkyl, C3-C18alkenyl, C3-C18alkynyl, C1-C18haloalkyl, NO2, OH, CN, OR8, SR8, C(O)R9, C(O)OR10 or halogen;
- R15 is C1-C18alkyl, phenyl or another aromatic hydrocarbon, the radicals phenyl and aromatic hydrocarbon being unsubstituted or mono- or polysubstituted by C1-C18alkyl, C3-C18alkenyl, C3-C18alkynyl, C1-C18haloalkyl, NO2, OH, CN, OR8, SR8, C(O)R9, C(O)OR10 or halogen, or R15 is a radical
- X is C1-C20alkylene, C2-C20alkylene which is interrupted by —O—, —S— or NR8, or X is
- provided that, if R12, R13, R14 and R15 are each phenyl,
- R2, R3 and R4 are not simultaneously methyl and
- R2, R3 and R4 together with the linking nitrogen are not
Dependencies are inferred from the claim text.