Functionalized photoinitiators, derivatives and macromers therefrom and their use
AssigneeNovartis AG
InventorsPeter Chabrecek, Kurt Dietliker, Dieter Lohmann
Life of this patent
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Abstract
The present invention relates to α-aminoacetophenones functionalized with organic diisocyanates, which can be used as reactive photoinitiators; to oligomers and polymers to which such functionalized α-aminoacetophenones are bonded; to α-aminoacetophenones having unsaturated polymerizable side-chain; to dimeric and trimeric photoinitiators; to the use of such photoinitiators; to materials coated with such photoinitiators; and to the use of the functionalized α-aminoacetophenones for modifying surfaces.
Claims4
A contact lens comprising an oligomer or polymer having H-active groups —OH and/or —NH— bonded to the oligomer or polymer backbone, optionally via a bridge group, or having H-active —NH— groups bonded in the oligomer or polymer backbone, the H atoms of which H-active groups are partly or completely substituted by a radical of formula IV
- wherein X is bivalent —O—, —NH—, —S—, alkylene having up to 8 carbon atoms or
- Y is a direct bond or —O—(CH2)n— wherein n is an integer from 1 to 6 and the terminal CH2 group of which is linked to the adjacent X in formula (I);
- R is H, C1-C12 alkyl, C1-C12 alkoxy, C1-C12 alkylNH- or —NR1AR1B wherein R1A is alkyl having up to 8 carbon atoms and R1B is H or alkyl having up to 8 carbon atoms;
- R1 is linear or branched alkyl having up to 8 carbon atoms, alkenyl having from 2 to 8 carbon atoms or aryl-alkyl having up to 8 carbon atoms in the alkyl moiety;
- R2 independently of R1 has the same definitions as R1 or is aryl, or
- R1 and R2 together are —(CH2)m— wherein m is an integer from 2 to 6;
- R3 and R4 are each independently of the other linear orbranched alkyl having up to 8 carbon atoms that may be substituted by C1-C4 alkoxy, or aryl-alkyl having up to 8 carbon atoms in the alkyl moiety or alkenyl having from 2 to 8 carbon atoms;
- or
- R3 and R4 together are —(CH2)z—Y—(CH2)z— wherein the two valences are each attached to the N-atom, Y1 is a direct bond, —O—, —S— or —NR1B—, and R1B is H or alkyl having up to 8 carbon atoms and z is independently of the other an integer from 2 to 4;
- and
- R5 is branched C3-C18alkylene, unsubstituted or C1-C4alkyl- or C1-C4 alkoxy-substituted C6-C10 arylene, or unsubstituted or C1-C4 alkyl- or C1-C4 alkoxy-substituted C7-C18 aralkylene, unsubstituted or C1-C4alkyl- or C1-C4 alkoxy-substituted C13-C24-arylenealkylenearylene, unsubstituted or C1-C4 alkyl- or C1-C4alkoxy-substituted C3-C8-cycloalkylene, unsubstituted or C1 -C4 alkyl- or C1-C4 alkoxy-substituted C3-C8cycloalkylene-CyH2y— or unsubstituted or C1-C4 alkyl- or C1-C4 alkoxy-substituted —CyH2y—(C3-C8-cycloalkylene)-CyH2y—, wherein y is an integer from 1 to 6.
A process for modifying surfaces of a contact lens or ophthalmic moulded article that contain H-active HO-, HS-, HN-C1-C6alkyl groups or —NH2— groups, comprising the steps of
- a) applying to the substrate a thin layer of a photoinitiator of at least one compound of formula (I):
- wherein X is bivalent —O—, —NH—, —S—, alkylene having up to 8 carbon atoms, or
- Y is a direct bond or —O—(CH2)n— wherein n is an integer from 1 to 6 and the terminal CH2 group of which is linked to the admacent X in formula (I);
- R is H, C1-C12alkyl, C1-C12alkoxy, C1-C12 alkylNH- or —NR1AR1B wherein R1A is alkyl having up to 8 carbon atoms and R1B is H or alkyl having up to 8 carbon atoms;
- R1 is linear or branched alkyl having up to 8 carbon atoms, alkenyl having from 2 to 8 carbon atoms or aryl-alkyl having up to 8 carbon atoms in the alkyl moiety;
- R2 independently of R1 has the same definitions as R1 or is aryl, or
- R1 and R2 together are —(CH2)m— wherein m is an integer from 2 to 6;
- R3 and R4 are each independently of the other linear or branched alkyl having up to 8 carbon atoms that may be substtuted by C1-C4 alkoxy, or aryl-alkyl having up to 8 carbon atoms in the alkyl moiety or alkenyl having from 2 to 8 carbon atoms;
- or R3 and R4 together are —(CH2)z—Y1—(CH2)z— wherein the two valences are each attached to the N-atom, Y1 is a direct bond, —O—, —S— or —NR1B—, and R1B is H or alkyl having up to 8 carbon atoms and z is independently of the other an integer from 2 to 4;
- R5 is branched C3-C18 alkylene, unsubstituted or C1-C4 alkyl- or C1-C4 alkoxy-substituted C6-C10arylene, or unsubstituted or C1-C4alkyl- or C1-C4 alkoxy-substituted C7-C18 aralkylene, unsubstituted or C1-C4 alkyl- or C1-C4 alkoxy-substituted C13-C24arylene-alkylenearylene, unsubstituted or C1-C4 alkyl- or C1-C4 alkoxy-substituted C3-C8cycloalkylene, unsubstituted or C1-C4alkyl- or C1-C4 alkoxy-substituted C3-C8cycloalkylene-CyH2y— or unsubstituted or C1-C4 alkyl- or C1-C4 alkoxy-substituted —CyH2y—(C3-C8cycloalkylene)- CyH2y—, wherein y is an integer from 1 to 6;
- and
- D is an isocyanato group;
- b) heating the coated material and washing off the excess photoinitiator,
- c) applying a thin layer of a photo-polymerisable ethylenically unsaturated substance to the substrate surface provided with said photoinitiator, and
- d) irradiating the layer containing the ethylenically unsaturated substance optionally with UV radiation.
Dependencies are inferred from the claim text.