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US 6,099,122 AGranted
Process for the functionalization of surfaces
AssigneeCIBA Vision Corporation
InventorsPeter Chabrecek, Dieter Lohmann
Life of this patent
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Abstract
The present invention describes a novel coating process that comprises the use of a functional photoinitiator, or a macroinitiator derived therefrom, in a cascade of process steps, wherein, on the one hand, a functional photoinitiator or a macroinitiator derived therefrom is covalently bonded to a carrier and, on the other hand, an oligomer or polymer forming a new surface layer is covalently bonded to the functional photoinitiator, or to the carrier modified by a functional photoinitiator, via functional groups that are co-reactive with isocyanate groups. The invention relates also to novel intermediates that are carriers to which functional photoinitiators that contain free isocyanate groups are bonded.
Claims17
A process for the multi-stage coating of a surface, which comprises, on the one hand, covalently bonding a functional photoinitiator containing at least one isocyanate group, or a macroinitiator derived therefrom, to a carrier and, on the other hand, covalently bonding an oligomer or polymer, forming a new surface layer, to the functional photoinitiator or to the carrier modified by a functional photoinitiator via functional groups that are co-reactive with isocyanate groups, wherein said process comprises the following steps:
- (a) reacting an oligomer or polymer containing groups that are co-reactive with isocyanate groups with a functional photoinitiator of formula Ia or Ib to form a macroinitiator, the isocyanate group of the photoinitiator forming a covalent bond with one of the co-reactive groups of the oligomer or polymer,
- (b) applying a thin layer of the macroinitiator so obtained to a surface containing suitable groups that are co-reactive with radicals;
- (c) irradiating the coated surface with UV light of a suitable wavelength, there being produced by radical (.alpha.-cleavage in the macroinitiator benzoyl-like radicals that form a covalent bond with the co-reactive groups of the surface;
- wherein formulae Ia and Ib are as follows:
- ##STR48## wherein Y is O, NH or NR.sub.1A ;
- Y, is O;
- Y.sub.2 is --O--, --O--(O)C--, --C(O)--O-- or --O--C(O)--O--;
- each n independently of the others is 0 or 1;
- R is H, C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.12 alkoxy or C.sub.1 -C.sub.12 alkylNH--;
- R.sub.1 and R.sub.2 are each independently of the other H, linear or branched C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 hydroxyalkyl or C.sub.6 -C.sub.10 aryl, or
- two groups R.sub.1 --(Y.sub.1).sub.n -- together are --(CH.sub.2).sub.x --, or
- the groups R.sub.1 --(Y.sub.1).sub.n -- and R.sub.2 --(Y.sub.1).sub.n -- together are a radical of the formula ##STR49## R.sub.3 is a direct bond or linear or branched C.sub.1 -C.sub.8 alkylene that is unsubstituted or substituted by --OH and/or optionally interrupted by one or more groups --O--, --O--C(O)-- or --O--C(O)--O--;
- R.sub.4 is branched C.sub.3 -C.sub.18 alkylene, unsubstituted or C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy-substituted C.sub.6 -C.sub.10 arylene, or unsubstituted or C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy-substituted C.sub.7 -C.sub.18 -aralkylene, unsubstituted or C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy-substituted C.sub.3 -C.sub.8 cycloalkylene, unsubstituted or C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy-substituted C.sub.3 -C.sub.8 cycloalkylene-C.sub.y H.sub.2y - or unsubstituted or C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy-substituted-C.sub.y H.sub.2y -(C.sub.3 -C.sub.8 cycloalkylene)-C.sub.y H.sub.2y --;
- R.sub.5 independently has the same definitions as R.sub.4 or is linear C.sub.3 -C.sub.18 alkylene;
- R.sub.1A is lower alkyl;
- x is an integer from 3 to 5;
- y is an integer from 1 to 6;
- R.sub.a and R.sub.b are each independently of the other H, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 cycloalkyl, benzyl or phenyl;
- with the provisos that n in the groups --(Y.sub.1).sub.n --R.sub.1 is 0 when R.sub.2 is H;
- that not more than two Y.sub.1 of the --(Y.sub.1).sub.n -- groups are 0 and n in the other --(Y.sub.1).sub.n -- groups is 0;
- and that n in the group --(Y.sub.2).sub.n -- is 0 when R.sub.3 is a direct bond;
- and wherein also X is bivalent --O--, --NH--, --S--, lower alkylene or ##STR50## Y.sub.10 is a direct bond or --O(CH.sub.2)y-- wherein y is an integer from 1 to 6 and the terminal CH.sub.2 group of which is linked to the adjacent X in formula (Ib);
- R.sub.100 is H, C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.12 alkoxy, C.sub.1 -CalkylNH-- or --NR.sub.1A R.sub.1B wherein R.sub.1A is lower alkyl and R.sub.1B is H or lower alkyl;
- R.sub.101, is linear or branched lower alkyl, lower alkenyl or aryl-lower alkyl;
- R.sub.102 independently of R.sub.101, has the same definitions as R.sub.101, or is aryl, or
- R.sub.101, and R.sub.102 together are, --(CH.sub.2).sub.m -- wherein m is an integer from 2 to 6;
- R.sub.103 and R.sub.104 are each independently of the other linear or branched lower alkyl that may be substituted by C.sub.1 -C.sub.4 alkoxy, or aryl-lower alkyl or lower alkenyl;
- or
- R.sub.103 and R.sub.104 together are --(CH.sub.2),.--Y.sub.11 --(CH.sub.2).sub.z -- wherein Y.sub.11 is a direct bond, --O--, --S-- or --NR.sub.1B --, and R.sub.1B is H or lower alkyl and each z independently of the other is an integer from 2 to 4.
26 more elements
A process for the multi-stage coating of a surface, which comprises, on the one hand, covalently bonding a functional photoinitiator containing at least one isocyanate group, or a macroinitiator derived therefrom, to a carrier and, on the other hand, covalently bonding an oligomer or polymer, forming a new surface layer, to the functional photoinitiator or to the carrier modified by a functional photoinitiator via functional groups that are co-reactive with isocyanate groups, wherein said process comprises the following steps:
- (a) where applicable providing the surface of a base material with functional groups that are co-reactive with isocyanate groups, for example OH, NH.sub.2 or COOH, by suitable chemical or physical pre-treatment, for example plasma treatment;
- (b) covering the surface containing groups that are co-reactive with isocyanate groups with a functional photoinitiator of formula Ia or Ib, the isocyanate group of the photoinitiator forming a covalent bond with the surface;
- (c) covering the surface modified by a photoinitiator with a thin layer of a vinylic monomer containing at least one isocyanate group or a mixture, of vinyl monomers containing such a monomer,
- (d) irradiating the coated surface with UV light of a suitable wavelength, there being produced a graft (co)polymer containing isocyanate, groups that is covalently bonded to the surface;
- (e) applying to the surface so modified an oligomer or polymer containing groups that are co-reactive with isocyanate groups;
- (f) a covalent bond being formed by the oligomer or polymer with the isocyanate groups of the graft (co)polymer;
- wherein formulae Ia and Ib are as follows:
- ##STR56## wherein Y is O, NH or NR.sub.1A ;
- Y, is O;
- Y.sub.2 is --O--, --O--(O)C--, --C(O)--O-- or --O--C(O)--O--;
- each n independently of the others is 0 or 1;
- R is H, C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.12 alkoxy or C.sub.1 -C.sub.12 alkylNH--;
- R.sub.1 and R.sub.2 are each independently of the other H, linear or branched C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 hydroxyalkyl or C.sub.6 -C.sub.10 aryl, or
- two groups R.sub.1 --(Y.sub.1).sub.n -- together are --(CH.sub.2).sub.x --, or
- the groups R.sub.1 --(Y.sub.1).sub.n -- and R.sub.2 --(Y.sub.1).sub.n -- together are a radical of the formula ##STR57## R.sub.3 is a direct bond or linear or branched C.sub.1 -C.sub.8 alkylene that is unsubstituted or substituted by --OH and/or optionally interrupted by one or more groups --O--, --O--C(O)-- or --O--C(O)--O--;
- R.sub.4 is branched C.sub.3 -C.sub.18 alkylene, unsubstituted or C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy-substituted C.sub.6 -C.sub.10 arylene, or unsubstituted or C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy-substituted C.sub.7 -C.sub.18 -aralkylene, unsubstituted or C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy-substituted C.sub.3 -C.sub.8 cycloalkylene, unsubstituted or C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy-substituted C.sub.3 -C.sub.8 cycloalkylene-C.sub.y H.sub.2y - or unsubstituted or C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy-substituted-C.sub.y H.sub.2y -(C.sub.3 -C.sub.8 cycloalkylene)-C.sub.y H.sub.2y --;
- R.sub.5 independently has the same definitions as R.sub.4 or is linear C.sub.3 -C.sub.18 alkylene;
- R.sub.1A is lower alkyl;
- x is an integer from 3 to 5;
- y is an integer from 1 to 6;
- R.sub.a and R.sub.b are each independently of the other H, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 cycloalkyl, benzyl or phenyl;
- with the provisos that n in the groups --(Y.sub.1).sub.n --R.sub.1 is 0 when R.sub.2 is H;
- that not more than two Y.sub.1 of the --(Y.sub.1).sub.n -- groups are 0 and n in the other --(Y.sub.2).sub.n -- groups is 0;
- and that n in the group --(Y.sub.2).sub.n -- is 0 when R.sub.3 is a direct bond;
- and wherein also X is bivalent --O--, --NH--, --S--, lower alkylene or ##STR58## Y.sub.10 is a direct bond or --O(CH.sub.2).sub.y -- wherein y is an integer from 1 to 6 and the terminal CH.sub.2 group of which is linked to the adjacent X in formula (Ib);
- R.sub.100 is H, C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.12 alkoxy, C.sub.1 -CalkylNH-- or --NR.sub.1A R.sub.1B wherein R.sub.1A is lower alkyl and R.sub.18 is H or lower alkyl;
- R.sub.101, is linear or branched lower alkyl, lower alkenyl or aryl-lower alkyl;
- R.sub.102 independently of R.sub.101, has the same definitions as R.sub.101, or is aryl;
- or
- R.sub.101, and R.sub.102 together are, --(CH.sub.2).sub.m -- wherein m is an integer from 2 to 6;
- R.sub.103 and R.sub.104 are each independently of the other linear or branched lower alkyl that may be substituted by C.sub.1 -C.sub.4 alkoxy, or aryl-lower alkyl or lower alkenyl;
- or
- R.sub.103 and R.sub.104 together are --(CH.sub.2),.--Y.sub.11 --(CH.sub.2).sub.z -- wherein Y.sub.11 is a direct bond, --O--, --S-- or --NR.sub.1B, and R.sub.1B is H or lower alkyl and each z independently of the other is an integer from 2 to 4.
30 more elements
A film comprising (a) a base material and (b) a covalently bonded thin layer on the surface, consisting of (b1) constituents that are derived from at least one photoinitiator of formula Ia or Ib and (b2) a polymer of an olefin that is covalently bonded to isocyanate groups of constituent (b1) via groups that are co-reactive with isocyanate groups, wherein formulae Ia and Ib are as follows:
- ##STR59## wherein Y is O, NH or NR.sub.1A ;
- Y, is O;
- Y.sub.2 is --O--, --O--(O)C--, --C(O)--O-- or --O--C(O)--O--;
- each n independently of the others is 0 or 1;
- R is H, C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.12 alkoxy or C.sub.1 -C.sub.12 alkylNH--;
- R.sub.1 and R.sub.2 are each independently of the other H, linear or branched C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 hydroxyalkyl or C.sub.6 -C.sub.10 aryl, or
- two groups R.sub.1 --(Y.sub.1).sub.n -- together are --(CH.sub.2).sub.x --, or
- the groups R.sub.1 --(Y.sub.1).sub.n -- and R.sub.2 --(Y.sub.1).sub.n -- together are a radical of the formula ##STR60## R.sub.3 is a direct bond or linear or branched C.sub.1 -C.sub.8 alkylene that is unsubstituted or substituted by --OH and/or optionally interrupted by one or more groups --O--, --O--C(O)-- or --O--C(O)--O--;
- R.sub.4 is branched C.sub.3 -C.sub.18 alkylene, unsubstituted or C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy-substituted C.sub.6 -C.sub.10 arylene, or unsubstituted or C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy-substituted C.sub.7 -C.sub.18 -aralkylene, unsubstituted or C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy-substituted C.sub.3 -C.sub.8 cycloalkylene, unsubstituted or C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy-substituted C.sub.3 -C.sub.8 cycloalkylene-C.sub.y H.sub.2y - or unsubstituted or C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy-substituted-C.sub.y H.sub.2y -(C.sub.3 -C.sub.8 cycloalkylene)-C.sub.y H.sub.2y --;
- R.sub.5 independently has the same definitions as R.sub.4 or is linear C.sub.3 -C.sub.18 alkylene;
- R.sub.1A is lower alkyl;
- x is an integer from 3 to 5;
- y is an integer from 1 to 6;
- R.sub.a and R.sub.b are each independently of the other H, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 cycloalkyl, benzyl or phenyl;
- with the provisos that n in the groups --(Y.sub.1).sub.n --R.sub.1 is 0 when R.sub.2 is H;
- that not more than two Y.sub.1 of the --(Y.sub.1).sub.n -- groups are 0 and n in the other --(Y.sub.1).sub.n -- groups is 0;
- and that n in the group --(Y.sub.2).sub.n -- is 0 when R.sub.3 is a direct bond;
- and wherein also X is bivalent --O--, --NH--, --S--, lower alkylene or ##STR61## Y.sub.10 is a direct bond or --O--(CH.sub.2).sub.y -- wherein y is an integer from 1 to 6 and the terminal CH.sub.2 group of which is linked to the adjacent X in formula (Ib);
- R.sub.100 is H, C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.12 alkoxy, C.sub.1 -CalkylNH-- or --NR.sub.1A R.sub.1B wherein R.sub.1A is lower alkyl and R.sub.1B is H or lower alkyl;
- R.sub.101, is linear or branched lower alkyl, lower alkenyl or aryl-lower alkyl;
- R.sub.102 independently of R.sub.101, has the same definitions as R.sub.101, or is aryl, or
- R.sub.101, and R.sub.102 together are, --(CH.sub.2).sub.m -- wherein m is an integer from 2 to 6;
- R.sub.103 and R.sub.104 are each independently of the other linear or branched lower alkyl that may be substituted by C.sub.1 -C.sub.4 alkoxy, or aryl-lower alkyl or lower alkenyl;
- or
- R.sub.103 and R.sub.104 together are --(CH.sub.2),.--Y.sub.11 --(CH.sub.2).sub.z -- wherein Y.sub.11 is a direct bond, --O--, --S-- or --NR.sub.1B --, and R.sub.1B is H or lower alkyl and each z independently of the other is an integer from 2 to 4.
22 more elements
A contact lens comprising (a) a transparent organic base material and (b) a covalenty bonded thin layer on the surface, consisting of (b1) constituents that are derived from at least one photoinitiator of formula Ia or Ib and (b2) a polymer of an olefin that is covalenty bonded to isocyanate groups of constituent (b1) via groups that are co-reactive with isocyanate groups, wherein formulae Ia and Ib are as follows:
- ##STR62## wherein Y is O, NH or NR.sub.1A ;
- Y, is O;
- Y.sub.2 is --O--, --O--(O)C--, --C(O)--O-- or --O--C(O)--O--;
- each n independently of the others is 0 or 1;
- R is H, C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.12 alkoxy or C.sub.1 -C.sub.2 alkylNH--;
- R.sub.1 and R.sub.2 are each independently of the other H, linear or branched C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 hydroxyalkyl or C.sub.6 -C.sub.10 aryl, or
- two groups R.sub.1 --(Y.sub.1).sub.n -- together are --(CH.sub.2).sub.x --, or
- the groups R.sub.1 --(Y.sub.1).sub.n -- and R.sub.2 --(Y.sub.1).sub.n -- together are a radical of the formula ##STR63## R.sub.3 is a direct bond or linear or branched C.sub.1 -C.sub.8 alkylene that is unsubstituted or substituted by --OH and/or optionally interrupted by one or more groups --O--, --O--C(O)-- or --O--C(O)--O--;
- R.sub.4 is branched C.sub.3 -C.sub.18 alkylene, unsubstituted or C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy-substituted C.sub.6 -C.sub.10 arylene, or unsubstituted or C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy-substituted C.sub.7 -C.sub.18 -aralkylene, unsubstituted or C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy-substituted C.sub.3 -C.sub.8 cycloalkylene, unsubstituted or C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy-substituted C.sub.3 -C.sub.8 cycloalkylene-C.sub.y H.sub.2y - or unsubstituted or C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy-substituted-C.sub.y H.sub.2y -(C.sub.3 -C.sub.8 cycloalkylene)-C.sub.y H.sub.2y --;
- R.sub.5 independently has the same definitions as R.sub.4 or is linear C.sub.3 -C.sub.18 alkylene;
- R.sub.1A is lower alkyl;
- x is an integer from 3 to 5;
- y is an integer from 1 to 6;
- R.sub.a and R.sub.b are each independently of the other H, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 cycloalkyl, benzyl or phenyl;
- with the provisos that n in the groups --(Y.sub.1).sub.n --R.sub.1 is 0 when R.sub.2 is H;
- that not more than two Y.sub.1 of the --(Y.sub.1).sub.n -- groups are 0 and n in the other --(Y.sub.1).sub.n -- groups is 0;
- and that n in the group --(Y.sub.2).sub.n -- is 0 when R.sub.3 is a direct bond;
- and wherein also X is bivalent --O--, --NH--, --S--, lower alkylene or ##STR64## Y.sub.10 is a direct bond or --O--(CH.sub.2)y-- wherein y is an integer from 1 to 6 and the terminal CH.sub.2 group of which is linked to the adjacent X in formula (Ib);
- R.sub.100 is H, C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.12 alkoxy, C.sub.1 -CalkylNH-- or --NR.sub.1A R.sub.1B wherein R.sub.1A is lower alkyl and R.sub.1B is H or lower alkyl;
- R.sub.101, is linear or branched lower alkyl, lower alkenyl or aryl-lower alkyl;
- R.sub.102 independently of R.sub.101, has the same definitions as R.sub.101, or is aryl, or
- R.sub.101, and R.sub.102 together are, --(CH.sub.2).sub.m -- wherein m is an integer from 2 to 6;
- R.sub.103 and R.sub.104 are each independently of the other linear or branched lower alkyl that may be substituted by C.sub.1 -C.sub.4 alkoxy, or aryl-lower alkyl or lower alkenyl;
- or
- R.sub.103 and R.sub.104 together are --(CH.sub.2),.--Y.sub.11 --(CH.sub.2).sub.z -- wherein Y.sub.11 is a direct bond, --O--, --S-- or --NR.sub.1B --, and R.sub.1B is H or lower alkyl and each z independently of the other is an integer from 2 to 4.
22 more elements
A film comprising (a) a base material and (b) a covalently bonded thin layer on the surface, consisting of (b) constituents that are derived from at least one photoinitiator of formula Ia or Ib, the constituents (b) still containing isocyanate groups in free form, wherein formulae Ia and Ib are as follows:
- ##STR65## wherein Y is O, NH or NR.sub.1A ;
- Y, is O;
- Y.sub.2 is --O--, --O--(O)C--, --C(O)--O-- or --O--C(O)--O--;
- each n independently of the others is 0 or 1;
- R is H, C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.12 alkoxy or C.sub.1 -C.sub.12 alkylNH--;
- R.sub.1 and R.sub.2 are each independently of the other H, linear or branched C.sub.1 C.sub.8 alkyl, C.sub.1 -C.sub.8 hydroxyalkyl or C.sub.6 -C.sub.10 aryl, or
- two groups R.sub.1 --(Y.sub.1).sub.n -- together are --(CH.sub.2).sub.x --, or
- the groups R.sub.1 --(Y.sub.1).sub.n -- and R.sub.2 --(Y.sub.1).sub.n -- together are a radical of the formula ##STR66## R.sub.3 is a direct bond or linear or branched C.sub.1 -C.sub.8 alkylene that is unsubstituted or substituted by --OH and/or optionally interrupted by one or more groups --O--, --O--C(O)-- or --O--C(O)--O--;
- R.sub.4 is branched C.sub.3 -C.sub.18 alkylene, unsubstituted or C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy-substituted C.sub.6 -C.sub.10 arylene, or unsubstituted or C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy-substituted C.sub.7 -C.sub.18 -aralkylene, unsubstituted or C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy-substituted C.sub.3 -C.sub.8 cycloalkylene, unsubstituted or C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy-substituted C.sub.3 -C.sub.8 cycloalkylene-C.sub.y H.sub.2y - or unsubstituted or C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy-substituted-C.sub.y H.sub.2y -(C.sub.3 -C.sub.8 cycloalkylene)-C.sub.y H.sub.2y --;
- R.sub.5 independently has the same definitions as R.sub.4 or is linear C.sub.3 -C.sub.18 alkylene;
- R.sub.1A is lower alkyl;
- x is an integer from 3 to 5;
- y is an integer from 1 to 6;
- R.sub.a and R.sub.b are each independently of the other H, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 cycloalkyl, benzyl or phenyl;
- with the provisos that n in the groups --(Y.sub.1).sub.n --R.sub.1 is 0 when R.sub.2 is H;
- that not more than two Y.sub.1 of the --(Y.sub.1).sub.n -- groups are 0 and n in the other --(Y.sub.1).sub.n -- groups is 0;
- and that n in the group --(Y.sub.2).sub.n -- is 0 when R.sub.3 is a direct bond;
- and wherein also X is bivalent --O--, --NH--, --S--, lower alkylene or ##STR67## Y.sub.10 is a direct bond or --O--(CH.sub.2)y-- wherein y is an integer from 1 to 6 and the terminal CH.sub.2 group of which is linked to the adjacent X in formula (Ib);
- R.sub.100 is H, C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.12 alkoxy, C.sub.1 -CalkylNH-- or --NR.sub.1A R.sub.1B wherein R.sub.1A is lower alkyl and R.sub.1B is H or lower alkyl;
- R.sub.101, is linear or branched lower alkyl, lower alkenyl or aryl-lower alkyl;
- R.sub.102 independently of R.sub.101, has the same definitions as R.sub.101, or is aryl, or
- R.sub.101, and R.sub.102 together are, --(CH.sub.2).sub.m -- wherein m is an integer from 2 to 6;
- R.sub.103 and R.sub.104 are each independently of the other linear or branched lower alkyl that may be substituted by C.sub.1 -C.sub.4 alkoxy, or aryl-lower alkyl or lower alkenyl;
- or
- R.sub.103 and R.sub.104 together are --(CH.sub.2),.--Y.sub.11 --(CH.sub.2).sub.z -- wherein Y.sub.11 is a direct bond, --O--, --S-- or --NR.sub.1B --, and R.sub.1B is H or lower alkyl and each z independently of the other is an integer from 2 to 4.
22 more elements
A contact lens comprising (a) a transparent organic base material and (b) a covalently bonded thin layer on the surface, consisting of (b) constituents that are derived from at least one photoinitiator of formula Ia or Ib, the constituents (b) still containing isocyanate groups in free form, wherein formulae Ia and Ib are as follows:
- ##STR68## wherein Y is O, NH or NR.sub.1A ;
- Y, is O;
- Y.sub.2 is --O--, --O--(O)C--, --C(O)--O-- or --O--C(O)--O--;
- each n independently of the others is 0 or 1;
- R is H, C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.12 alkoxy or C.sub.1 -C.sub.12 alkylNH--;
- R.sub.1 and R.sub.2 are each independently of the other H, linear or branched C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 hydroxyalkyl or C.sub.6 -C.sub.10 aryl, or
- two groups R.sub.1 --(Y.sub.1).sub.n -- together are --(CH.sub.2).sub.x --, or
- the groups R.sub.1 --(Y.sub.1).sub.n -- and R.sub.2 --(Y.sub.1).sub.n -- together are a radical of the formula ##STR69## R.sub.3 is a direct bond or linear or branched C.sub.1 -C.sub.8 alkylene that is unsubstituted or substituted by --OH and/or optionally interrupted by one or more groups --O--, --O--C(O)-- or --O--C(O)--O--;
- R.sub.4 is branched C.sub.3 -C.sub.18 alkylene, unsubstituted or C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy-substituted C.sub.6 -C.sub.10 arylene, or unsubstituted or C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy-substituted C.sub.7 -C.sub.18 -aralkylene, unsubstituted or C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy-substituted C.sub.3 -C.sub.8 cycloalkylene, unsubstituted or C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy-substituted C.sub.3 -C.sub.8 cycloalkylene-C.sub.y H.sub.2y - or unsubstituted or C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy-substituted-C.sub.y H.sub.2y -(C.sub.3 -C.sub.8 cycloalkylene-C.sub.y H.sub.2y --;
- R.sub.5 independently has the same definitions as R.sub.4 or is linear C.sub.3 -C.sub.18 alkylene;
- R.sub.1A is lower alkyl;
- x is an integer from 3 to 5;
- y is an integer from 1 to 6;
- R.sub.a and R.sub.b are each independently of the other H, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 cycloalkyl, benzyl or phenyl;
- with the provisos that n in the groups --(Y.sub.1).sub.n --R.sub.1 is 0 when R.sub.2 is H;
- that not more than two Y.sub.1 of the --(Y.sub.1).sub.n -- groups are 0 and n in the other --(Y.sub.1).sub.n -- groups is 0;
- and that n in the group --(Y.sub.2).sub.n -- is 0 when R.sub.3 is a direct bond;
- and wherein also X is bivalent --O--, --NH--, --S--, lower alkylene or ##STR70## Y.sub.10 is a direct bond or --O--(CH.sub.2)y-- wherein y is an integer from 1 to 6 and the terminal CH.sub.2 group of which is linked to the adjacent X in formula (Ib);
- R.sub.100 is H, C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.12 alkoxy, C.sub.1 -CalkylNH-- or --NR.sub.1A R.sub.1B wherein R.sub.1A is lower alkyl and R.sub.1B is H or lower alkyl;
- R.sub.101, is linear or branched lower alkyl, lower alkenyl or aryl-lower alkyl;
- R.sub.102 independently of R.sub.101, has the same definitions as R.sub.101, or is aryl, or
- R.sub.101, and R.sub.102 together are, --(CH.sub.2).sub.m -- wherein m is an integer from 2 to 6;
- R.sub.103 and R.sub.104 are each independently of the other linear or branched lower alkyl that may be substituted by C.sub.1 -C.sub.4 alkoxy, or aryl-lower alkyl or lower alkenyl;
- or
- R.sub.103 and R.sub.104 together are --(CH.sub.2),.--Y.sub.11 --(CH.sub.2).sub.z -- wherein Y.sub.11 is a direct bond, --O--, --S-- or --NR.sub.1B --, and R.sub.1B is H or lower alkyl and each z independently of the other is an integer from 2 to 4.
22 more elements
Dependencies are inferred from the claim text.