Imide-linked polymeric photoinitiators
Imide-linked polymeric photoinitiators and compositions useful in the preparation of such polymeric photoinitiators and to the use of these polymers in, e.g., UV curable adhesives, UV curable coating compositions and UV curable encapsulants.
1 . An imide-linked photoinitiator selected from the group consisting of structure (I), (II), and (III):
wherein Q 1 and Q 2 are each a small molecule or polymer, wherein Q 1 and Q 2 can be the same or different and comprise one or more units of the following structure (IV) or (V):
wherein Z is a moiety that does not comprise an Ar group;
Ar is selected from the group consisting of
R is a linear or branched alkyl group, cycloalkyl, alkylenoxy, alkenyl or aryl group, an alkyl group containing a heteroatom or a carbonyl group;
R 1 is independently a linear or branched alkyl group, a cycloalkyl, an alkylenoxy, an alkenyl, an aryl group, an alkyl group containing a heteroatom, a carbonyl group, H, OR, NR 2 , SR, F, Cl, Br or I;
Y 1 is a linear or branched (C 1 to C 8 ) alkylene group or a bond;
L f is a functional linkage selected from the group consisting of an ether, an ester, an amide, a urethane, and a carbonate;
m=0 or 1; n=0 or 1; p=0 or 1; and x=1-100.
2 . The imide-linked photoinitiator of claim 1 , wherein each R is independently selected from linear or branched alkylene, cycloalkylene, alkylenoxy, alkenylene, arylene and alkylene which contains a heteroatom or a carbonyl group.
3 . The imide-linked photoinitiator of claim 1 , wherein Q 1 and Q 2 comprise units derived from the polymerization of one or more ethylenically unsaturated monomers selected from olefins, dienes, (meth)acrylic monomers, vinyl ethers, styrenic monomers and mixtures thereof.
4 . The imide-linked photoinitiator of claim 1 , wherein Q 1 and Q 2 are independently derived from styrene-butadiene-styrene (SBS); styrene-isoprene-styrene(SIS); poly(butadiene); random styrene-butadiene-styrene rubber (SBR); acrylate polymers containing pendant or backbone unsaturation; maleinized poly(butadiene), maleinized poly(isoprene), maleinized poly(styrene-b-butadiene-b-styrene), or maleinized poly(styrene-b-isoprene-styrene), maleinized poly(styrene-b-ethylene/butylene-b-styrene), maleinized poly(styrene-b-ethylene/propylene-b-styrene), styrene-co-maleic anhydride, maleic anhydride-co-ethyl vinyl ether, maleic anhydride-co-methyl vinyl ether, maleic anhydride-co-decene or an anhydride functional acrylic polymer.
5 . The imide-linked photoinitiator of claim 1 , wherein Z is an alkyl, a cycloalkyl or a polyether moiety.
6 . The imide-linked photoinitiator of claim 5 , wherein Q 1 and Q 2 are independently derived from maleinized poly(butadiene), maleinized poly(isoprene), maleinized poly(styrene-b-butadiene-b-styrene), or maleinized poly(styrene-b-isoprene-styrene), maleinized poly(styrene-b-ethylene/butylene-b-styrene), maleinized poly(styrene-b-ethylene/propylene-b-styrene), styrene-co-maleic anhydride, maleic anhydride-co-ethyl vinyl ether, maleic anhydride-co-methyl vinyl ether, maleic anhydride-co-decene, or an anhydride functional acrylic polymer.
7 . The imide-linked photoinitiator of claim 1 , wherein Q 1 and Q 2 are the same.
8 . The imide-linked photoinitiator of claim 1 , wherein Q 1 and Q 2 are maleinized poly(butadiene).
9 . The imide-linked photoinitiator of claim 1 , wherein Ar is a benzophenone derivative.
10 . The imide-linked photoinitiator of claim 1 , wherein Ar is a thioxanthone derivative.
11 . The imide-linked photoinitiator of claim 1 , wherein p is 1.
12 . The imide-linked photoinitiator of claim 1 , wherein m is 1.
13 . The imide-linked photoinitiator of claim 1 , wherein m is 0.
14 . The imide-linked photoinitiator of claim 1 , wherein m is 0; Y is an ethylene group; Q 1 and Q2 are derived from maleinized poly(butadiene), maleinized poly(isoprene), maleinized poly(styrene-b-ethylene/butylene-b-styrene), and maleinized poly(styrene-b-ethylene/propylene-b-styrene); and Ar is
15 . The imide-linked photoinitiator of claim 14 , wherein R 1 is H.
16 . The imide-linked photoinitiator of claim 1 , wherein m and n are 1; Y is an ethylene group; Q 1 and Q 2 are derived from maleinized poly(butadiene), maleinized poly(isoprene), maleinized poly(styrene-b-ethylene/butylene-b-styrene), and maleinized poly(styrene-b-ethylene/propylene-b-styrene); Ar is
and optionally, R 1 is H.
17 . The imide-linked photoinitiator of claim 16 , wherein R 1 is H.
18 . The imide-linked photoinitiator of claim 1 , which corresponds to a structure comprising the following repeating units in any order
wherein w, x, y, y′, y″ and z are integers from 1 to 100;
Z is either: (1) a moiety that does not comprise an Ar group as defined above or (2) an alkyl, a cycloalkyl or a polyether moiety.
19 . A photocurable composition comprising the imide-linked photoinitiator of claim 1 .